Remote work brings many efficiencies, from eliminating commutes for employees to reducing real estate costs for organizations. However, having a remote workforce makes the times that the team gathers in person all the more important. Team offsites – dedicated, extended period of times where a team gathers outside of the office – may be the only time that remote employees engage in real life, and are prime opportunities for planning, reflecting, and bonding. Offsites are a big investment in both time and money… every team member is not only potentially traveling on planes, but also taking a break from their day-to-day tasks to participate in the offsite. Considering these costs, it’s important the team leaders put significant thought and planning into an offsite in order to get the most value out of it. 

Given this is such an important topic, I enlisted the help of my friend Kirsten Newbold-Knipp, a GTM exec who has led sales and marketing teams of 5-50 people at companies like FullStory, HubSpot and Bigcommerce. Our thinking is aligned on the value of offsites and I’ve included some of her best practices in this discussion.

The last several leadership teams I have been a part of operated remotely, and we developed best practices to make our offsites effective. This article is a tactical playbook to help you run a great team offsite. While the examples are often referencing startups and scaleups, many of the insights are applicable for division offsites at larger organizations as well.

1. Plan every detail in advance, including a logistics schedule

If we are paying to fly people all over the place, we better have done our homework first. This includes the housing, food, discussion topics, supplies, travel schedules, etc. You may be thinking, “this sounds like too much planning, we can just wing it.” The dilemma is that when you are on the ground, and team members are arriving in droves, things get chaotic. We don’t have time to figure out the food, or realize that someone didn’t get a room booked, on the fly. Instead, it is much more relaxing when everything is figured out ahead of time.

To facilitate this at my last company, our Operations Manager, Kirsten Alexander, and I would create an extensive shared document for each offsite that contained all of the details I described above. It included a couple of key sections:

• Flight schedules: a list of attendees, their flight number, arrival time, etc.
• Car details: did we rent a car? All of the rental information is in the doc.
• Car logistics: are 3 people arriving earlier? Have them travel together.
• Meals: where are we going for each meal? Include reservations.
• Groceries: if we are at an Airbnb, what groceries do we need? 
• Housing: what’s the address of the Airbnb? What’s the code to get in? 

From a business perspective, it’s also important to think through the session agenda, how much time is being allocated to each topic and who is responsible for leading each discussion. Consider creating a “logistics schedule” that walks through minute-by-minute how the offsite will go. Here is an example:

This level of granularity accomplishes a few things:

• It forces you to think through the plan in advance, and avoids scrambling last minute.
• It ensures clarity and transparency for every attendee.
• It provides guidelines for time management (though you don’t need to limit a discussion to the scheduled time if it is going particularly well).

2. Spread agenda responsibility amongst the team

I break an offsite into “sessions” as illustrated in the agenda above – similar to a conference. Each session may be a different discussion or strategic topic that we want to tackle as a team. Some might be very active (e.g. brainstorming) while others might be more focused on presentation and feedback. To start, you can gather input from the team (via a Google form or live discussion) on what topics they are most interested in, and then cross reference that with your own priorities for the offsite.

If you are the team leader, your instinct might be that you need to do everything to plan and run the offsite. Instead, split the responsibility amongst the team so each person may be in charge of moderating a certain topic or session. For example, in the agenda I shared above, Neil’s name is highlighted next to the “Competition Review” session we scheduled. As the owner of that session, he is responsible for:

• Planning the session: what are we discussing and aiming to get out of it?
• Creating materials: if we need slides, he creates and presents them.
• Moderating: keeping the conversation focused and taking notes.
• Following up: identifying next steps and coordinating with the team leader to ensure they are acted upon.

You may consider giving team members specific constraints in creating a session. For example: include lots of customer artifacts (e.g. call clips, webinar clips) or include an interactive element (team should get up on their feet at least once). Ideally, each team member has flexibility to build the session however they see fit.

Regardless of how flexible or specific you are in setting the guidelines for the sessions, by spreading the responsibility, the rest of the team will feel a sense of ownership for the offsite. Plus, this approach takes lots of work off the team leader’s plate!

3. Set expectations

Prior to the offsite and at the start, it’s crucial for the team leader to share context on why we have gathered, why this time is so valuable, and what we aim to get out of it. Some items to consider communicating:

• Share clear goals: everyone who is attending an offsite should have clarity on why it is being hosted and what the objectives are to achieve.
• Be prepared: create session materials in advance, not the night before.
• Review other’s session materials: if materials are prepared in advance, everyone should read them so they have context prior to each session.
• Plan for your day job: ensure that out-of-office plans are set so people that will be unavailable during the offsite have their jobs covered.
• Communicate with leaders’ teams: if this is a leadership offsite, ensure each leader communicates with their teams that they will be relatively unavailable during the offsite.

Kirsten confirmed how important having “pre-reads” are – i.e. prepared slides or session outlines that the team can review in advance. She highlighted that we want to avoid an offsite where much of the time is spent “being presented at.” Instead, the time is far more valuable when everyone comes in with context and can spend the offsite having strategic discussion, gaining clarity and reaching consensus. 

4. Make space for breaks, but protect the offsite time

One of the difficult parts of attending a team offsite is pulling away from one’s day-to-day responsibilities. This can be particularly difficult for leaders, whose teams may be relying on them for input. However, offsite time is special, it doesn’t happen that often, and needs to be protected. There are a few ways you can do this:

• Schedule 30-60 minute breaks every few hours of sessions
• Have a 60 minute lunch break 
• Include buffer time in the early evening before dinner
• Do “walk and talk” breaks – Kirsten found that her exec team loved these at a small offsite

During these breaks, the team leader can encourage the group to check in with colleagues, respond to critical messages, or take a call. However, outside of those time windows it’s important to enforce that the team’s focus needs to be at the offsite, and other matters should wait unless they are extremely time sensitive. Team members frequently taking calls and excusing themselves during sessions undermines the point of gathering everyone in person.

You can encourage cooperation by sharing the agenda ahead of time, so team members can schedule important calls during the breaks.

5. Consider the physical space for team bonding

Team offsites are important both for the clarity that they bring, and also the community that they build. A part of that community building is the space that the offsite is hosted in. As Kirsten pointed out, “CEOs realize that employees don’t want to just sit and stare at each other in a windowless conference room – today’s teams seek inspiration in both their personal and professional lives.” The right offsite space will depend on the size and culture of the team. For small, tight knit teams, a shared house (i.e. Airbnb) works well for a few reasons:

• It feels more relaxed and less “stuffy” than a hotel
• It often has private space for activities (e.g. a backyard with a firepit)
• It enables the team to eat breakfast and lunch at home, often saving time and cost

I recognize that for larger teams, a shared house becomes impractical. At one of Kirsten’s early-stage startups the exec team rented an entire bed and breakfast. This provides many of the benefits of a shared house, but ensures team members have more personal space and some privacy. Boutique hotels nearby a private meeting space could work well for teams at larger companies or even getting a block of hotel rooms and working with a local venue for more creative space is viable.

If you decide to go the Airbnb route, consider some of these variables:

• Does everyone have their own room with a private bath?
• How close is it to nearby restaurants? Ideally a 15 minute drive max.
• How close is it to the airport? Ideally a 30 minute drive max.
• Does the living room have ample seating?
• Does the living room have a large TV that can be used for presentations?
• Does it have outdoor hangout space? A firepit is a great social hub.
• Does it have a kitchen that you can use for cooking breakfast and lunch?
• Do you have access to the thermostat to ensure the room is comfortable?
• Does it have an interesting view (e.g. waterfront, near mountains, etc). This is certainly not required, but it is nice to have!

In addition to the physical space, also consider the geographic location. If it’s winter, the team may really appreciate an offsite in Miami. I try to vary the locations for each offsite both for novelty and to make things fair for the remote team that is traveling in from many different locations. If someone who lives in California has to fly to Miami for the offsite in Q1, they might really appreciate if Q2’s offsite is in Denver, a much shorter flight.

6. Don’t skimp on the food

This one is simple but important – stock up on food! For many team members, these offsites may be one of the few times they are traveling during that month/quarter, and the experience should feel like a treat.

Snacks

A high impact, low cost tactic is filling the kitchen or meeting space with great snacks. The offsite can be a time to indulge, and binge on some snacks they might not normally eat at home. Get the chips that aren’t the healthiest but everyone loves to occasionally eat. Those little things make a big difference. At my last company, we got frequent requests for “flaming hot cheetos,” an obviously guilty pleasure among members of our team!

Meals 

Outside of snacks, meals can be a mixture of catered in or taking the entire group to a restaurant. Be sure to make all reservations well in advance. “Consider team members who are vegetarians or who may have food allergies. Figure this out ahead of time so you aren’t scrambling during the offsite,” notes Kirsten. 

If possible, have lunch either cooked at home or catered in. This is beneficial for managing cost and maintaining focus. An offsite has a packed agenda, and having everyone out for a 1.5 – 2 hour lunch is not the best use of time. Instead, dinner is often the best time to take the team out, so it is less disruptive to a long day of sessions. 

I like to use dinners as the primary “going out” portion of a team offsite, whereas the other meals are functional to keep people fueled during an intense day of sessions. This is an opportunity for high impact – consider finding unique restaurants that will be memorable. With that said, be flexible. I was surprised that at a recent offsite for my leadership team, everyone was so exhausted at the end of the day of sessions that the vote was to actually order in rather than do a big dinner out. Just go with the flow!

7. Get the right supplies to keep the team focused

Be sure to think through what tools you may need for the offsite, because you don’t want to be running to the store during precious meeting time. These might include:

• Giant sticky white boards for brainstorming
• Access to a large screen TV
• Connectors to ensure laptops can stream slides / notes to that TV
• Sticky notes 
• Markers
• Notepads

In order to keep people focused, limit laptop usage, or request that everyone logs out of Slack and email, and only uses laptops for note taking. This time is precious, and we want to minimize distractions. Using pen and paper for certain activities can help do that. To be sure, it also may be most efficient to take notes digitally, and that can often be delegated to one person for each session. 

8. Don’t feel pressure to plan fancy events and experiences

Some team leaders and planners assume that an offsite needs to have “fancy / speciality” events or experiences in order to be valuable for the team. For example, at one of my team’s offsites, we took everyone to a cool indoor mini-golf course. It was one of the higher cost items on the offsite budget. When we surveyed the team afterwards, we found it was actually something they valued the least, and instead it was the time spent simply sitting around the backyard fire pit that they valued more.

This does not mean you shouldn’t consider a speciality event or experience as part of the offsite. Just keep in mind that the team is there to bond, build trust and get work done. Having good food and good spaces for people to talk tends to accomplish 90% of that goal.

Kirsten’s #1 goal for COVID-era offsites has been building community – in a world where many team members have never even met – that common bond makes everything else in a team easier. Even if everyone leaves the offsite not digesting any of the business content, but still builds trust and deeper bonds (i.e. a stronger community), the investment was well worth it. 

9. Summarize the key takeaways and lessons learned promptly

Attending a team offsite is like drinking from a firehose. So much information is being shared and discussed, so many conversations – it can be overwhelming. To ensure the conclusions reached during the offsite are not lost in the shuffle, it’s important to quickly organize all of the notes taken and call out action items.

At my recent offsites, we created one primary notes shared doc, and contributed all of the session notes into it. Then, often on the flight home, I go through those notes, pull out key takeaways, and create a summary at the top. I then send a follow up email to all attendees with a link to that document. 

Logistical Feedback

In addition to the business takeaways that may be included in that summary, consider writing down all of the lessons learned from running the offsite on the flight home while they are fresh in your mind. Everything from pros/cons of the lodging to what food was most popular to how accurate your scheduling was. These insights will be invaluable when you are planning the next offsite.

Finally, consider sending a post-offsite survey to all attendees to gather fresh feedback on their perspective of the event. This can include tactical items (e.g. was the food good?) to session feedback (e.g. which session was most impactful for you, and why?). 

10. Create a rhythm for offsites

As you start to plan more offsites, consider having them on a regular cadence. For a leadership team, quarterly is my preference. For other teams, at least twice a year tends to work well. Having offsites on a regular rhythm can also help the team plan, both for their personal travel and to ensure that events don’t overlap major projects / deadlines.

An important note – if the offsite includes folks in sales, be sure to not schedule it at the end of a sales period (e.g. the last week of the month or quarter), as this can add unnecessary stress to that team.

Bottom line

Team offsites are an increasingly important way to build culture and cohesion amongst a team that is remote or hybrid. Kirsten shared a fascinating stat about this: “74% of companies are already or are becoming hybrid/remote in the next 5 years.” Additionally, she noted that according to Amex Travel, team meetings are the fastest growing type of meeting, and the per attendee budget is growing at 73%. All this is to say that team offsites are a major line item, both in cost and time. It’s worth the effort to get the logistics and the content right. 

It is amazing how much traction a business can get on purely founder-led and word-of-mouth sales. Many companies go years, and reach significant milestones, before building a sales team, and those with product-led growth can go even longer. However, the “no sales team” approach often has a ceiling. At some point, growth may start to slow and flatten. Typically, the desire to build a sales team increases as a business wants to move up-market towards larger customers that bring more significant and secure revenue.

When that time comes, the company is ready to build a true go-to-market (GTM) motion powered by sales and marketing. This is where many entrepreneurs and operators make a common but critical mistake: we try to start doing sales before we have marketing.

At first glance, it often appears that we can “brute force” the sales process by hiring an individual, high-performing sales rep and just hitting the phones or cold emails. While this can yield some results, it is often a fool’s errand because that sales rep lacks the marketing and sales management support needed to be successful. So, why is it so tough to make sales work prior to having any marketing in place?

Lack of air cover

Without marketing, when a sales rep gets on the phone or sends an email to a prospect, they need to tell the entire story. They need to articulate what the problem is, why their product exists, and how it delivers value for that prospect. That is a lot of story to tell, and often, it may take a prospect hearing that story many times before it resonates enough for them to opt into a sales process.

Air cover refers to all of the “story telling” that marketing is doing before a lead ever reaches a sales rep. The education, the content, the ebooks, the webinars, the advertisements, the email campaigns. When this lead nurturing is done early, a prospect that is speaking to a sales rep is far more qualified to buy.

It is possible for the sales rep to attempt to do all of that education as part of their outreach process, but that is a lot of work, and slows them down from focusing on the other mechanics of a great sales process that they are likely more skilled at.

Lack of infrastructure

Often in early GTM teams, marketing takes ownership of infrastructure, i.e. the tools needed for a sales team to actually sell. This might include CRM, email sequencing, prospect data enrichment, lead routing, etc. As a company grows, this can be owned by a dedicated Revenue Ops function, but early on, I have found that it is typically the marketing leader who is technical enough to assemble that infrastructure (Ryan did a fantastic job with this at my last business, Crystal).

I am making a generalization here, but many people who are great at sales do not want to context switch into configuring systems. It is dangerous to assume that an early sales rep or sales leader will want to spend a lot of time in the technical trenches on RevOps infrastructure, rather than speaking to prospects.

Necessity for full cycle cold prospecting through close

Without marketing, we are expecting sales reps to do everything, from completely cold prospecting all the way through negotiation, close and handoff to Customer Success. Having sales generate their own leads can be done, but as described earlier, those leads are going to come in with no prior context or education about the product (i.e. nurturing) . Once again, this just requires more of a sales rep’s limited time and effort, likely increasing the sales cycle and spreading reps thin.

A Better Way

Now, let’s consider the scenario where marketing is in place prior to building a sales team, or at least in tandem with the early start of a sales team. If that happens, marketing can deliver several critical components that address the challenges above.

Collateral

It seems so simple, but dissatisfaction with collateral is often one of the top complaints of a sales team. The collateral is either out of date, not easy to access, or doesn’t cover certain sales objections that commonly occur. Marketing most often owns collateral, and it’s an area where the Marketing Leader must be in lock-step with the Sales Leader to understand what collateral is working, and what the biggest needs are.

When I led marketing at Netpulse, we created tremendous amounts of ebooks, infographics, webinars and other content to nurture leads and qualify them for demos with our sales team. Each time a new collateral piece was designed and published, our marketing team would send an email to the sales team that provided context on what the collateral was, when to use it, and where to find it. This email was always sent before we did any email campaigns to send the collateral to existing leads/opportunities in our CRM.

Also, an often overlooked step, collateral needs to be organized and easily usable, which is also often owned by marketing. HubSpot has great tools for uploading and inserting collateral into sales emails. Marketing needs to train and retrain sales reps on where to find the collateral and how it is organized. In larger organizations, that process may be owned by Sales Enablement.

Nurtured leads

Delivering a nurtured, qualified (even inbound) lead to a sales team is so much better than a cold list of emails or phone numbers. As I mentioned earlier, it is certainly possible for sales reps to just engage in cold outreach, but if that is done without a great web presence, without any relevant advertising, without any collateral that provides validation and social proof… It is going to be an uphill battle to win deals.

Proper infrastructure like CRM and marketing automation

To follow up on the challenge illustrated earlier, when marketing is in place prior to or just as a sales team is being built, you are more likely to end up with better infrastructure and tools for success. Do not underestimate the importance of getting this stuff right. Little things like leads getting assigned properly or demo requests not being lost in the shuffle are crucial for a sales team to operate well, and with a high degree of morale. Marketing is often a sales team’s best friend in making sure those operational components work well, prior to having a dedicated RevOps person.

Key Takeaway

Both sales and marketing are critical components of a GTM strategy, and I am not suggesting one is more or less important than the other. Instead, the key takeaway is that we need them both working in tandem, and the order of operations should be marketing first, then sales.

Frank Slootman may be one of the most effective tech CEOs of all time. He has written several books about his no-nonsense operating style, from growing Data Domain from tiny startup to billion dollar acquisition in the early aughts, to now leading Snowflake which had the largest software IPO ever in 2020. It’s no secret among my friends how much I admire Frank’s approach; in fact, some have started referring to me as “Sklootman” – a comical nod to our similar names.

Frank’s most recent book, Amp It Up, tells the story of his career and offers a plethora of guidance for anyone who is operating a growing business today. You can buy the book here, and below are my top takeaways and quotes.

1. Clearly define a priority

"Priority should ideally only be used as a singular word. The moment you have many priorities, you actually have none."

As with much of what Frank writes, it’s so simple, yet rarely executed well. We cannot prioritize when everything is a priority. This plagues so many organizations, from chasing the random whim of the CEO to overreacting to market news and quickly pivoting a strategy. The best run companies have a very small amount of clear priorities, and ruthlessly focus on executing them well, pushing everything else aside.

2. Eliminate vagueness

"Vagueness causes confusion, but clarity of thought and purpose is a huge advantage in business. Good leadership requires a never-ending process of boiling things down to their essentials. Spell out what you mean! If priorities are not clearly understood at the top, how distorted will they be down the line?"

As a team grows, good communication becomes among the most important traits of a leader. I saw this first hand as we grew Crystal — what was in my head was not necessarily in the heads of our customer success managers or product designers. I needed to constantly over-communicate and simplify messaging down to its essence to ensure everyone was on the same page. Often, the team won’t raise their hands and say "this is confusing" — they’ll just move forward, lacking the full context needed to be effective in their roles.

3. Apply pressure and set a rigorous pace

"Leaders set the pace. People sometimes ask to get back to me in a week, and I ask, why not tomorrow or the next day? Start compressing cycle times. We can move so much quicker if we just change the mindset… Apply pressure. Be impatient. Patience may be a virtue, but in business it can signal a lack of leadership. Nobody wants to swim in glue or struggle to get things done."

Frank often points out how much "slack in the line" there is on most teams. People will not default to move at the pace they are truly capable of, and as a result, many organizations are far less efficient than they could be. It’s important to tread the line between optimizing efficiency and triggering burnout on the team. We can do so by avoiding unnecessary deadlines that lack business value, and instead instilling a cultural value of bias towards quick action.

4. Act quickly to get the wrong people off the bus

"If you don’t act quickly to get the wrong people off the bus, you have no prayer of changing the overall trajectory. We often believe, naively, that we can coach struggling teammates to a better place. And sometimes we can, but those cases are rarer than we imagine… Younger me was too timid when confronting these situations. I learned over time that I was too slow in pulling the trigger, as were many of my colleagues. Then I started moving faster to replace people who were badly suited for their roles. And often not even catastrophically bad, just worse than the caliber of people we knew we could hire to replace them."

Speaking for younger entrepreneurs and operators, this is often the most challenging aspect of our jobs. It takes experience and practice to gain the confidence to quickly part ways with poor performing teammates. Most of us want to save face, avoid conflict, prevent turmoil on the team — so we wait. We hold back on feedback, or we over-coach, and hope that things will improve. Frank’s decades of experience are correct — most often, if your gut says you have the wrong person on the bus, you need to quickly make a change. Not doing so is a disservice to everyone else on the team, and to the underperforming person as well, since they might be more effective at a different company in a different role.

5. Align incentives with compensation

"Where alignment matters further is in incentive compensation. We pay everybody the same way on our executive team, and we have a very select, focused set of metrics that we pay bonuses on. Our sales exec does not get paid on a commission plan if the rest of us aren’t. Everybody knows what we are aiming for."

Organizations break down into unproductive fiefdoms, rife with politics, when each functional leader is incentivized to take different actions. The old adage "people do what you pay them to do" rings true — effective teams need incentive alignment, driven by their compensation. At Crystal, I implemented Frank’s feedback by basing every member of the leadership team’s variable compensation on the same metric: % ARR growth.

6. Avoid a “wait and see” posture

"If you have a sales force that’s stuck in the mud, don’t just complain about the staff’s failure to hit your targets and timeline. Ask lots of questions to figure out what’s wrong. Then take bold steps to mitigate the problem as soon as you understand it. You can’t simply take a “wait and see” posture while hoping the metrics will improve. You have to aggressively manage nonperformance, cut headcount if appropriate, or add headcount wherever you have the highest probability of converting sales potential to sales yield."

When something isn’t working, as leaders we are sometimes too slow to act, or devolve into aimless complaints without deeply investigating "why." Frank is referencing startup sales teams, which are a crucial component of a growth engine, and also notoriously difficult to get right. Inevitably, the sales team will get stuck, either with inability to build qualified pipeline, low conversion rate to closed opportunity, or a myriad of other issues. Frank’s point is to not just leave things as-is for very long, because it’s not likely to fix itself.

7. Be cautious with transactional employment

"There is a school of thought that employees should negotiate hard at every turn to maximize their long-term earnings. I personally never did that, and I didn’t need to. I didn’t want to have a relationship with my employers that felt purely transactional."

During late 2020 through 2021, the business world saw the phenomenon of "the great resignation" — i.e. large numbers of people quitting jobs and looking for greener pastures elsewhere, often lured by perhaps too good to be true compensation. The default mode many people take is to frequently switch roles, each time leveling up for higher compensation, or gathering other offers to push a current employer for an off-cycle raise. As Frank notes, there is nothing inherently wrong with that, but one may get better results by focusing more on the long term value they can deliver, going above and beyond, graciously accepting increased responsibility and then proving oneself before seeking a compensation adjustment.

8. Avoid distractions

"A great mission helps prevent distractions that dilute everyone’s focus. In every company I’ve ever encountered, distractions are a huge threat. They often become a major source of self-defeating behavior… Continually narrowing the mission aperture is key because companies have a natural tendency to lose focus over time. It’s incredibly easy for managers to react to every headline that crosses their email inbox, Slack, or social media feeds. If you turn your time and attention to the latest shiny object, regardless of how little it has to do with your mission, you are on the path to trouble."

Every company is bombarded with potential distractions and shiny objects, whether literally in an office, virtually on Slack, or strategically with potential acquisitions, expansions, new hires and product lines. Narrowing our focus to push aside everything that is not in alignment with our priority and mission is a hallmark of great execution. It’s also exceptionally difficult to do, because those shiny objections are, well, shiny. It takes discipline to say "no" and stick to the execution plan. I wrote an article about a similar topic to this point a couple of years ago.

9. Value execution above all

"Strategy can’t really be mastered until you know how to execute well. That’s why execution must be your first priority as a leader. Worrying about your organization’s strategy before your team is good at executing is pointless. Execution is hard, and great execution is scarce—which makes it another great source of competitive advantage."

Frank is an operational and execution-focused leader (which being similar, is perhaps why I respect his mentality). Boards and leadership teams can sit around a table all day debating strategy. However, what often matters is the quality and consistency with which the team executes. Great execution comes from strong internal communication, alignment on objectives, transparency on progress, and accountability for results.

10. Build a culture that attracts and repels

"If you succeed in building and protecting a strong culture, it will simultaneously attract people who admire the culture while repelling those who find it distasteful. That’s an intentional feature, not a bug."

Dharmesh Shah and the team at HubSpot created a now famous slide deck, the HubSpot culture code, that outlined their intentional approach to defining 5 cultural attributes. In one slide, Dharmesh writes, "we hire, reward, and release people based on the five attributes." Let’s be clear on what he is saying — HubSpot chooses who to promote and who to let go based on alignment with culture. This is similar to the point Frank makes in the quote above -- if an organization lives their cultural values, the right people will want to be in, and the wrong people will opt out. It’s when an organization has a poorly defined or poorly followed culture code that you end up with a team of people with misaligned values, rowing in opposite directions.

In writing this article, I limited myself to 10 quotes, but I wrote down perhaps 30+ as I read Amp It Up. I would highly recommend the book for any leader, and as always, take Frank’s approach, apply your values/spin, and make it your own.

One of the most important jobs for the Founder/CEO of an early stage startup is selling. We are talking to prospects, pitching the solution, gathering feedback, closing deals, and building the foundation of a sales process. When we start to see early success, our natural inclination is “This is working! Yes! If only we just could clone me so we could go faster…”

It’s at this point in the story where many founders make a critical mistake – a mistake I have personally made over and over again. We hire the “business hacker” – a hungry, ambitious, inexperienced person who we believe we can train in how to pitch, how to do cold outreach, and if they are good, scale from individual contributor to our future sales leader. We imagine that they will reduce our workload and enable us to sell more. Perhaps this person has some previous experience as a sales rep, but has never built a sales team or process from scratch themselves. Or, this person may have aspirations to be a founder – i.e., the “clone” that the CEO was hoping for.

While this strategy may sound good in theory, it rarely works. Here are the problems:

You aren’t as good at sales as you think

There may be nobody more qualified to pitch an early vision, garner excitement, and convince early adopters to buy into the cause than a Founder/CEO. In the earliest days, we are the best people to demonstrate momentum, and then attract others to join the team. However, there is a big difference between early adopter selling, and building a repeatable, predictable, scalable sales process.

Sales is both an art, science and skillset that just like anything else, gets better with practice. From handling sales objections, navigating complex enterprise org structures, to crafting effective sales commission compensation plans, most Founder/CEOs can “fake it until we make it” as sales people, but would probably end up on a performance improvement plan if we were held accountable to carrying a quota.

Sales reps need a lot of coaching to be effective

Sales is one of the most coaching-intensive functions of a company. There are a plethora of products designed to support sales coaching, from call recording software like Gong to (shameless plug) personality insights tools like Crystal. Being able to effectively coach sales reps is highly unique to the product and sales process they are working in, and is something that, just like the rest of sales, takes lots of practice and acquired skill. Even if you are able to ramp up on sales coaching, it will take up an exceptional amount of your time if you want your reps to be effective.

Being a functional leader makes it hard to also be the CEO

Hiring the business hacker (i.e. the “CEO clone”) requires training them up to be as effective as you are. The more time you are spending managing and training that first sales person, the less time you can zoom out to actually be the CEO (whether that means other leadership hiring, culture, vision, strategy, etc). The business hacker path keeps you tethered to the sales organization as the de facto Head of Sales until the person you hired can scale into a leader, which unfortunately is much less likely with someone that you are training from scratch.

When there are problems, it’ll be hard to diagnose what is wrong

In an early stage startup, so many things could throw a wrench in your team’s ability to sell effectively – lack of product market fit, not enough marketing, pricing/business model problems, and more. If you have someone with minimal sales experience in the role, when they inevitably struggle, it will be unclear why… is it because your product is just not ready to be sold, or is it that your salesperson doesn’t know how to sell? If you want to move fast and efficiently, you need to eliminate that ambiguity.

A better way

After falling into this trap too many times, I finally got it right at Crystal when we brought on Jamison Newall as our VP Sales. Jamison had worked his way up from rep to team lead to sales manager and director of sales. He had worked in similar sized organizations that had a similar B2B SaaS business model, and scaled their revenue exactly to where we were hoping to get in the next few years.

We brought Jamison to Crystal with a clear mandate: on day 1, and perhaps for the foreseeable future, he would be an individual contributor. His role was to personally sell, learn as he goes, and write the initial playbook for our sales process. He would need to prove things out by closing the first several deals using that playbook. Once we see that the early process is repeatable with Jamison doing it himself, he can then start hiring a team and transitioning from an individual contributor to a player-coach as we scale.

Fast forward about 18 months since we first hired Jamison, and we’ve nearly doubled our revenue, built a sales team of 8 people and learned a tremendous amount about how to go to market with our product. The results speak for themselves, and it’s now abundantly clear that hiring someone with experience and having them sell personally, write the playbook, and then build the team has several benefits:

You know that if they fail, it’s not likely because they are bad at sales

This is the most important benefit – clarity on what is working and what isn’t. As I mentioned earlier, by hiring someone with deep sales experience, you can more likely eliminate the variable of “my sales person doesn’t know how to sell” if things aren’t working, and tweak other elements of the product, marketing, business model, sales structure, etc.

You move much faster

When you bring on a senior, experienced salesperson on day 1, they can immediately get to work. You will need to walk them through how you have demoed the product in the past, but they will quickly write their own script that will likely be superior to yours. Additionally, hiring someone to start as an individual contributor even though they have management experience means when it is time to build the team, they already know what to do, as opposed to learning on your time. A good rule of thumb is that your first sales hire should be teaching you the best practices of selling, not the other way around.

Your put the right structure in place early

Similar to other functions, there are many components of "infrastructure" that go into building a sales team and process, from your demo pitch script to how your CRM is organized. A more senior salesperson will come in understanding the best practices and immediately start putting the right tools in place. There are a lot of decisions to be made early that have a trickle down effect in the future; for example, the pipeline stages used to track deals in your CRM and calculate sales forecasts. Getting this right early on will save you plenty of headaches later.

You don’t have to repeat the recruiting process by yourself

Finally, if you hire a proven sales person first, and they are successful, they will be far more qualified than you to drive the hiring process of the first sales reps. They know what to look for, and the type of rep that would be most likely to perform well with your product, deal size and sales cycle. Recruiting takes a ton of time, and at a minimum with someone more experienced, you don’t have to lead that recruiting process yourself.

Considering the clear benefits, why do so many early Founder/CEOs make the mistake of hiring the business hacker instead? It often comes down to a few reasons:

Hiring a senior person is intimidating – it looks easier to hire a rep / business hacker

I won’t deny it – hiring someone more senior will be harder. They will be more difficult to find, more difficult to interview and assess their skillset, and a greater risk of injecting new (often strong) opinions into the team. Additionally, you need to find someone willing to take the risk of leaving a leadership role to temporarily be an individual contributor, and then build a team in the future. Not every salesperson will be willing to take that risk, but someone that does will also likely thrive in the chaos of a fast-moving startup. However, the reality is that hiring senior people across all of the functional areas of your business is an important skill that every startup CEO needs to develop. I outlined my interview process for senior hires here.

A senior sales person is more expensive

No doubt about it – in the short run, hiring the business hacker would be significantly less expensive, in both cash and equity. However, the old adage “you get what you pay for, sometimes less, never more” rings true here. As long as you structure your comp plan to be a healthy mix of base and variable (ideally 50% and 50% respectively), you are limiting your downside risk. Paying a higher base for someone who knows what they are doing and can teach you how to build a great sales organization is well worth the investment.

You are giving up more control

One of the appealing notions of the business hacker is that the Founder/CEO still controls the sales process, delegating some of the blocking and tackling to this new hire. However, if you acknowledge that someone more experienced would do a better job at building a sales process and leading the future team than you could, giving up that control is worth it (and even beneficial).

With that said, I am not suggesting you give up full control on day 1. To the contrary, any new hire, including someone senior, needs to prove themselves early on and build trust before you give them full autonomy. Trust is earned by delivering tangible results. As I mentioned with our VP Sales, Jamison, it was only after he proved he could sell effectively himself with the sales process he created that we allocated the budget to hiring a sales team around him.

Considering the pros and cons outlined above, after much trial and error I have learned that it is far better to bring on a Jamison-like senior person as your first sales hire, let them prove out the sales model and then build a team. You’ll save time, save money in the long run, and grow your company faster.

I used to think of myself as an information junkie. I read every news article I could find, endlessly scrolled through social media, and took pride in staying “informed.” While I may have been informed, I was not happy. Instead, I was stressed and distracted.

Many of us consume information reactively — we read whatever is put in front of us by news feeds, daily emails, social media posts or articles shared by friends. By default, we just absorb whatever information comes our way. The problem is, not all of that information is beneficial. In fact, much of it is totally unnecessary, and merely distracts us from focusing on more impactful things that would better ourselves and enable us to grow.

Last year, I made a conscious decision to exert greater control over the information I take in. It meant a major shift in mindset, from trying to consume as much information as possible to being heavily selective on what information I will benefit from. It has meant a disciplined approach to not read every article, not scroll through social media, not listen to every podcast a friend sends and ultimately, consume less.

The results have been remarkable, though not surprising. I’m less stressed, less irritable and more focused on things that actually matter (e.g. growing my business, talking to close friends, etc). Here is a breakdown of the tactics I used to tame information overload:

1. Delete social media from your phone

We know that social media apps are designed by brilliant teams to be deeply addicting. Once they become ingrained in our lives, we tend to just open them on autopilot without even thinking about it (often literally hundreds of times per day). To be sure, there is still plenty of value in social media, but I found that when it was on my phone, I wasn’t consciously choosing when to engage in, I’d just always open it by default. So the simple solution: delete social media apps from your phone. You can still log into them from your desktop when needed. But this way, you have to make a conscious choice to login, rather than just opening them everytime you’re bored.

2. Hide social media news feeds

Even when I visited social media from my desktop browser, I felt the addictive pull to scroll. And scroll. And scroll. There’s a simple(ish) solution: hide the feeds. I wrote a basic Chrome Extension and installed another that hides the feed section of some social sites. Once installed, you can visit a social media site but the feed is empty. This way, if you want to go to someone’s profile, you need to do it manually using the search bar. This preserves some of the tactical benefit of being on social media while preventing the time-sucking mechanic of feed scrolling.

3. Turn off notifications

The average smartphone user has 80 apps on their phone, and many of them have permission to send notifications. That means on a constant basis, everytime we are trying to focus, our phone is screaming “hey look at me! LOOK AT ME!” The phone ends up controlling where your attention goes, and that is ridiculous. So I turned off all notifications, except for phone calls. When I want to check my texts, I can open up the Message app to do so. New email? Cool, I’ll read it when I am in the mode of checking my email. This gives the power back to you — you get to control when and how you allocate your team to incoming information on your phone.

4. Pick websites to block and install a blocker app

One of the biggest allures of social media and news is that it serves as a welcomed break when we are trying to accomplish something difficult. If I am working through a hard problem, or trying to write something mentally intensive, I feel the subconscious pull to just type in a news site and start reading. It’s easier than actually accomplishing the difficult task I was trying to complete. Needless to say, that behavior is a recipe for lacking focus. So, I built another simple Chrome Extension that blocks specific websites (it just replaces all of the content with a big message on the screen that reminds me to get back to focusing). Occasionally, I’ll cheat and turn off the Chrome Extension to read an article or visit Instagram, but that takes several clicks and forces me to think “is that actually a good use of my time?”

5. Close out of email during meetings

Have you ever been in a meeting, glanced at your phone or inbox, saw a stressful email, and then from that point forward you are just thinking about the contents of that email and no longer present in the meeting? It happens all of the time, and the antidote is straightforward: close out of your email inbox during meetings (and remove email notifications from your phone). I try to keep my inbox tabs closed and only open them when I am actually in the mode of responding to email, rather than obsessively checking or responding instantly.

6. Replace news apps with books

Last year, I was in a habit of reading multiple news apps every night before I went to bed. It was perhaps the worst way to prepare for a good night’s sleep. Much of those news articles weren’t teaching me anything I urgently needed to know… it was just an automatic consumption of new information. So I took a stand, deleted the news apps and shifted to books. As of May, I’ve read 30 books so far in 2021. With books, I get to choose exactly what I want to learn about. I get to go much deeper into a topic and I’m not bombarded with salacious headlines that are fun to click but aren’t healthy or necessary to read.

7. Pick specific articles that are most relevant

When you do read articles, be selective. That means saying no to perhaps 9 out of 10 articles that come your way, and instead focusing on just the most impactful ones. For example, I’ve found that FirstRound’s Review tends to have exceptional content, so I make time to read it.

8. Unsubscribe from most email newsletters

Finally, consider opting out of most email newsletters that are curating and choosing for you what information to consume. There are certainly some exceptions: I like James Clear’s weekly email and my friend Scott Morrow’s comprehensive weekly newsletter. Choose the ones that are best for you, and don’t be afraid to respectfully unsubscribe from the noise.

Bottom Line

When you give yourself the power to determine what information you are going to consume, it becomes a lot easier to focus on what you care about, and tune out the noise that tends to add negative value. I recognize that the tactics shared here will work differently for each of us (e.g. if you are in sales, closing out of your email is likely not advisable). Consider adding your own ideas in addition to this list to tame information overload in your life.

I run every weekday morning at 7:30am. I run the same route, at the same time, every day. I don’t have to think much about it, nor do I agonize over whether or not today is a good day for a run. I just show up and go.

Routines are a remarkable thing. When they work, much of the mental load needed to make decisions simply melts away. Routines are the manifestation of systems created to achieve your goals. In his book Atomic Habits, James Clear writes "you do not rise to the level of your goals, you fall to the level of your systems." Indeed, for many of us, establishing a system that creates a recurring routine is the best path to accomplishing a goal, whether it be staying in shape, writing in your blog or hitting your sales target.

Upon further reflection, I recognized many more examples of "routines" that help reduce mental load and ensure I am on top of my objectives as a startup leader. Here are the top 10 routines that I’ve found particularly beneficial:

1. Sunday evening planning for the week

Each Sunday afternoon or early evening, I make a list of my top priorities for the upcoming week. I call it my “weekly agenda” and I keep it open throughout the week, checking things off and making notes as I go. This routine ensures I never show up on Monday morning unsure of where I want to aim my focus. Of course, I can add to the list through the week, and use it later to help myself remember everything that I worked on (or didn’t get to).

2. Monday morning 9am leadership meeting

Our go-to-market leadership team at Crystal starts our week together every Monday at 9am. We don’t ever have to wonder “when will we all have time to go over things together?” because we know that everyone will show up first thing on Monday. I treat that meeting as sacred and strive to avoid any conflicting meetings during that time slot. While we’re all in different time zones, we keep 9am CT clear for this weekly kickoff.

3. Monday 3pm sales pipeline review

Each Monday afternoon, our VP Sales, Jamison, and I go through the sales pipeline, discuss potential blockers, analyze the forecast and review other key sales metrics. Jamison knows that Monday afternoons is when the forecast should be updated, and he has meetings with our Account Executives in advance to ensure everything is properly entered and categorized in our CRM. I never have to wonder “when can I go over the pipeline with Jamison?” and Jamison never has to wonder “when is Greg going to want to dig into the pipeline?” The routine ensures an accurate forecast at the start of every week.

4. Bi-weekly All Hands at 10am on the 1st and 15th

Twice per month, we gather our entire team together for an All Hands meeting. We always report the sales metrics in the first meeting of the month and progress on our quarterly company goals in the second meeting of the month. This routine answers the question “when will we next meet all together as a team?” or “when will we get transparent updates on how the company is performing?”

5. Friday functional check in with marketing (2pm) and customer success (3pm)

Each week at the same time and the same day, I meet with our leaders of marketing and customer success. We always have an agenda that is sent a few hours before, and always have action items that are sent right after. This routine ensures that time is always carved out at the end of the week to sync on progress and priorities in these functional areas. It answers the question “when can we discuss potential blockers in marketing?” without having to think about it. To be sure, we can (and do) meet ad hoc all the time throughout the week to handle tactical matters. But we also know that every Friday afternoon, we have a guaranteed time to check in on the big picture.

6. Monthly 1-1 with all direct reports

One-on-ones are an important management tool that are near universally recommended. While I meet with functional leaders at least weekly to talk about projects/tactics, we also have a 1-1 meeting at the end of every month to share feedback with each other, discuss career progression, coaching, etc. This routine ensures that every month in the last week, my team knows that we’ll have an opportunity to sit down together and discuss whatever is on their minds. They never have to think “I need to schedule a meeting with Greg to discuss X concern” because the routine ensures that meeting will happen every month.

7. Weekly customer engagement scorecard audit

This is a fairly new routine that our Head of Customer Success, Neil, and I implemented. At the beginning of each week, we check our dashboards and review product usage and engagement for key enterprise customers. We note in a spreadsheet any troubling trends, and each week Customer Success provides comments and action plans for any customer flagged for needing some assistance. This routine results in clarity and focus on one of our most important metrics (customer engagement with our product).

8. Monthly expense-by-vendor audit

It’s critical that we understand precisely how we’re applying our resources on a monthly basis. As I shared in this article, among other financial reports I run an expense-by-vendor summary every month, sort it from high to low, and hunt for any potential waste or opportunities to tighten our spend. When coupled with a strong cadence of financial budgeting and forecasting, this routine ensures that expenses don’t creep up and we have excellent clarity on what we’re spending.

9. Weekly written recap of plans, progress, problems

This routine has been a part of my professional life for nearly a decade: writing a brief recap of my progress for the week, problems encountered and plans for next week. It takes discipline, but this routine forces a reflection on what happened over the last week and an intentional planning of what I want to accomplish next week. I write these recaps on Friday or Sunday early evenings, and they help make routine #1 on this list easier.

10. Monthly calls with friends and peer leaders

A final routine that I’ve found tremendously beneficial is recurring monthly calls with friends and peer leaders. For years now, my friend Max Veggeberg (who runs a fantastic company, HomeWorks Energy) and I do a monthly call where we recap our businesses challenges, pick each other’s brains, and serve as a sounding board. We used to have a recurring calendar invite, but now the routine is so ingrained that around the last weekend of the month, one of us instinctively knows to text the other and schedule the call. It happens like clockwork because we built the routine. There’s little effort or mental load required.

Bottom line

Your routines may be totally different, but the concept still holds true: find things that are important and create a recurring cadence to make them a routine. It can be a meeting, a run or a review of a specific metric. When it happens consistently each period on a recurring basis, you’re more likely to stick with it and accomplish what you set out to do. Additionally, when others are involved, routines ensure clear communication and reduce ambiguity. It’s a win-win!

Effective founders and CEOs may spend as much as 50% of their time on recruiting. As the organization grows, most of the time gets spent hiring world-class functional leaders and other high-impact roles. The investment in time is usually worth it: when that “functional seat” is filled, the CEO can step out of the weeds and focus on the broader business.

Despite the heavy time investment, we often get it wrong. As much as 70% of new executives fail in the first 18 months. Making a bad senior hire is a costly mistake. A poor fit can permeate throughout an organization, contaminating everyone they collaborate with, spreading misaligned cultural values, taking the team in the wrong direction, or worse.

Therefore, it’s worth digging into the tactical process used to interview and assess a senior level hire. While there are many articles dedicated to great interview questions, sourcing, etc, I focused this one on the nitty-gritty steps through an interview funnel for a remote-first startup. Here’s the breakdown of how my team has done it at Crystal:

1. Have two screening calls (video not necessary)

When we have a potentially interesting candidate, whether from a cold email, warm intro, recruiter referral or resume submission, my first step is to do two screening calls, each 30-60 minutes. One is with me, and one with my co-founder (this can alternatively be with another colleague if you prefer). The benefit of two screening calls is a double check that whatever positive sense you got from an initial conversation is also shared by someone else on your team. These calls are designed to give you an indication of whether or not it is worth continuing investing time in getting to know the candidate. A few notes:

• Feel free to keep this call pretty flexible, casual and agenda-free
• To reduce “Zoom fatigue,” make it a phone call rather than video meeting at this stage

Consider concluding the call with transparency on whether or not you both want to continue the interview process. If yes, schedule the next round of video deep dives together during the call.

2. Conduct a series of video deep dives

If both you and the other interviewer (again co-founder, etc) left your screening calls with a positive inclination, it’s time to dig deeper and look under the hood of a potential candidate. In the remote world, this means a series of deep-dive video calls. I’ve found the optimal length to be 1-2 hours and you might do at least two sessions. I tend to make these more formal with a specific agenda of areas we want to dive into. This is a good opportunity for a candidate to demonstrate their expertise and illustrate how they are solving problems at their current or recent roles that are similar to yours. Some things I have found to be impactful:

• Screen share and walk through documentation the candidate has created. E.g. if sales, a sales process or pipeline. If marketing, a campaign outline. If product, a roadmap. Etc.
• Make plenty of time for the candidate to drive the conversation and ask questions. This is beneficial to both sides, as you can learn a lot about their thought process based on the questions they choose.

These sessions are a prime opportunity for both you and the candidate to open yourselves up with genuine candor. Share the core challenges your organization has and walk through how a candidate would approach solving them. Talk through how they specifically solved that challenge before, and what went right or wrong.

These deep dives may also include other members of the leadership team or other co-workers that this leader will be working with.

3. Request a 30/60/90 plan

After a few long video sessions, the candidate should have a pretty solid idea of your company, the role, and what is most important to you. The next step is to request that the candidate write a 30/60/90 day plan — essentially an outline of what precisely they would do during their first 3 months, and in what order, if they got the job. I have found this exercise to be particularly useful in several ways:

• It showcases whether or not we are aligned on how the leader should approach the role.
• It demonstrates how the leader writes and communicates (i.e. if the plan is sloppy and hard to follow, expect that their work-product when hired will be similar).
• It puts you ahead of the game if you actually hire them, because they already have the roadmap of what to do on day 1-90.

This plan doesn’t need to be 10 pages. To the contrary, it can be a relatively high-level outline (I’ve found most come out to a couple of pages). The key I am looking for is specificity and relevance to our specific role and organization. If it seems generic, it shows that the leader may not be willing to dig deep enough to understand the precise dynamics of our product/team/market and what is needed to be successful.

4. Follow up to review the plan

The next step is to meet again and walk through the 30/60/90 plan together. I typically ask for it to be sent in advance so I can read it, digest it, make comments and be prepared for a productive discussion. If there are items in it that are directionally correct but perhaps not as relevant for your organization, they are good jumping off points to dig into further together.

At this point, we’ve spent quite a bit of time together, we’ve talked through process, reviewed a written work-product, outlined the tactical plan for how it would work in the first 90 days if they actually got the job, and generally picked up on lots of verbal queues on how we might work together.

5. Gut check call on culture

If a candidate has made it this far, it’s time to do a final gut check to confirm this is someone you are eager to spend a lot of time with. Senior hires need to be great at the execution part of their jobs, but if you dread hanging out with them, it’s unlikely to work out well. If feasible, this would be an in-person dinner. If that isn’t feasible due to remote locations, I just make it a phone or video call. The agenda for this call includes:

• The candidate’s motivations and long-term goals
• The candidate’s values and what is most important to them
• How you interact when you’re not focused on work

6. Make the offer (verbal and written)

At this point, you’re at the offer stage. This step is fairly similar to how you’d make a job offer to anyone, regardless of seniority. I make sure to discuss it verbally, make sure we’re on the same page, and then promptly follow up with an offer letter.

7. Check references (don’t skip this!)

Ah the references… we all have the urge to skip this step and just seal the deal. However, it is an important item to checkoff to confirm you did your due diligence. I tend to ask for 2-3 references. In some cases the current employer isn’t appropriate, but mentors, former co-workers/managers and anyone who has had a close working relationship gives you an additional datapoint to help you get to know the candidate.

8. Keep them engaged until the start date

Often with a senior hire they will need to give more than 2 weeks notice at their current role. The time between an accepted offer and their official start date is a great opportunity to get them excited and up to speed so they can hit the ground running. Consider:

• Scheduling a weekly call to share any company news / momentum
• Preparing an onboarding checklist with reading material they can start on
• Giving them account access so they can get acclimated to your systems

Bottom line

This article outlines a high-level process for effectively interviewing a senior hire. There are a tremendous amount of additional variables to consider (e.g. which questions you choose, who you involve in the process, etc). Feel free to leverage elements of my process and intermix them with your own!

If you had told me in 2019 that in the following year I’d be hiring a VP Sales without ever meeting him in person, I would have burst out laughing.

Fast forward to 2020, and with the world in lockdown but business continuing, my team at Crystal doubled our headcount while operating completely remotely. Once the hires were made, we were left with the critical task of getting them up to speed and productive as fast as possible, all while working from home.

As I thought more about the task ahead, I recognized perhaps the most crucial difference between remote and in-person onboarding:

• In person, when your new employee has a complex question, it’s really easy and socially acceptable for them to walk over and ask you.
• Remotely, when your new employee has a complex question, they need to take the initiative to call you, or put the effort into wording it the right way in Slack.

The dilemma with remote onboarding is that when someone is confused, the barrier to getting clarity is much higher. When we’re in person, they can casually walk over to someone’s desk and get an answer. When we’re remote, suddenly those quick answers require more effort — either through calling or instant messaging, and the social friction required to do both. Especially for someone brand new, it is much harder to call a colleague (or even Slack a colleague) out of the blue vs. just walking over and talking to them.

As a result of this, we need to take a different approach to remote onboarding. From personally testing this strategy across several key hires, here is a breakdown of 6 best practices to take when onboarding a new employee remotely.

1. Create an onboarding checklist

The nightmare scenario of remote onboarding is your new employee is sitting at home, unsure of what to do and unsure of who to ask for help. At that moment they feel isolated, unproductive and unmotivated. To avoid this, the best tool in your toolbox is an onboarding checklist.

The onboarding checklist is a shared spreadsheet that outlines everything someone new should read, participate in, talk to etc during their first days/months of being at your company. Here’s an example of my checklist:

https://docs.google.com/spreadsheets/d/10ciSRqosfvjPjh0crav

Notice that the checklist includes everything from the very tactical payroll configuration to the very specific “explore X feature in the product.” The goal of this checklist is to act like a virtual guide for the new hire, which they can consult anytime, 24/7, to answer the question “what should I do next?”

Remote employees get the consistent dopamine hit of “checking off” each item and seeing the green “completed” label next to it. Managers get the benefit of transparency and clarity on a new employee’s onboarding status.

2. Create a first-day agenda hour by hour

Everyone remembers their first day at a new job. When that first day is entirely remote and we don’t have the option to create memories like taking a new hire out to lunch, we need to put even more focus into the structure and cadence of the day. To do this, create an agenda for that day that breaks down exactly what the new person should be focusing on. It should include:

• An intentional first meeting of the day with their manager to kick things off
• Invites to relevant training sessions or meetings to shadow
• Specific reading material (based on the onboarding checklist)
• An end of day recap with their manager to discuss and concerns, and plan day 2

While it might seem like excessive structure, creating an agenda that breaks down each hour of the day ensures that the new hire can be productive and operate without the pressure of essentially “cold calling” their colleagues in order to become productive.

3. Grant access to accounts in advance

Nobody should ever begin a new job without the tools they need to immediately start creating value. Especially when someone is remote, if they don’t have access to their computer and relevant app accounts, they are pretty much blocked from doing anything.

Consider adding a tab to the onboarding checklist for “accounts” and list out every app that this person should have access to, and who is responsible for configuring access. Ensure all of those are checked off prior to the start date, and credentials are emailed to the employee’s personal email so they can log in prior to their first day if they’d like.

The goal is avoiding any time where a new employee is twiddling their thumbs at home. Taking care of account access in advance demonstrates that you value their time.

4. Over-communicate prior to starting and during the first week

Most people have a mixture of anxiety and excitement leading up to starting a new job. Especially for startups, ambitious hires will want to hit the ground running and start preparing prior to their start date. Particularly for more senior hires, I prepare all of their onboarding materials (including the checklist and account access) well in advance of their start date. This way, they are free to start reading key documents, exploring their new accounts (e.g. our CRM) and formulating questions that we can tackle during their first week.

You may also consider doing a weekly call between the time they sign the offer letter and their start date. I use this time to keep them updated on important developments at the company (e.g. closed a new deal, made an additional hire) so they are in the loop when they start. Furthermore, finding opportunities to communicate starts to build that rapport and trust needed to make them comfortable and productive on day 1.

5. Split up heavy video call sessions into manageable chunks

Most remote onboarding sessions happen over long video calls. That is totally ok, and consider splitting up those calls throughout the day to avoid fatigue. As you outline the first day agenda, consider intermixing different activities such as team 1-1s, direct training sessions, solo reading and silent observing in other meetings. While some of these activities are similar to what you’d do in-person, the reality of remote is that it is easy to get “meeting fatigue” on video, so putting extra thought into how you split up onboarding activities makes a positive difference for the new employee.

6. Plan on daily check-ins and an end of week recap

In addition to over-communicating prior to start, remote work onboarding requires heavier communication during the first days and weeks. To overcome the “barrier to getting clarity” hurdle mentioned earlier, you should provide many opportunities for a remote employee to ask questions and get “unblocked.”

My approach is that typically in our first meeting, while reviewing the first day agenda and onboarding checklist, we create a running “Q&A” list at the bottom of the agenda. The employee can continuously add questions, and I periodically review the list, make comments with answers and discuss the complex ones at our daily check-ins. My aim is for the employee to never have to wait too long to get clarity and be left in the dark remotely.

We punctuate the week with a recap meeting that is similar to the one held at the end of the first day. We should enter the weekend by recapping the momentum made in the first week, and ensuring the new employee is making progress in accomplishing their 30/60/90 day plan.

Bottom Line

Remote onboarding requires extra consideration because of the challenges of quickly getting clarity when not in-person. By using a mixture of staying organized through an onboarding checklist and communicative through pre-start, first day and first week check-ins, you’ll be much more likely to set up remote employees for success.

The news hit me like a load of bricks:

Our VP of Sales and Customer Success were leaving the company.

At the time, my startup was going through the growing pains that many do, including turmoil amongst the leadership team. With this leadership transition, there was now an immediate gap that would need to be filled in order to keep the company operating smoothly.

I was serving as VP of Growth, overseeing marketing and operations. I had developed a reputation as someone who is willing to take on whatever is needed, and while I may not have been qualified to have the responsibility on Day 1, I was willing to quickly learn. So, it wasn’t a surprise that as the rest of the leadership team gathered, we decided that I should absorb those functions for the time being.

At first, the sheer volume of the responsibility was overwhelming. As I dug through the departments and learned about the current challenges and unique personalities on the team, it began to feel more attainable. I became a master at context-switching, jumping from a marketing strategy meeting to a sales pipeline review to speaking with an enterprise customer… sometimes within the same hour!

While I don’t generally advocate that you take on this level of responsibility permanently within your organization, as I did it, I noticed something interesting:

I was able to ensure the functions were working together like a well-oiled machine, because I was responsible for all of them.

In the past, when I only led marketing, my core focus was on driving marketing qualified leads to feed our sales team. While the other functional leaders and I strived to stay in alignment, meet regularly and keep an open line of communication, we’d often get lost in the weeds of our own department, and not have enough of an understanding of how our work may impact, positively or negatively, other functions of the business.

For example, our sales reps frequently asked for new collateral. As a small marketing team with a tremendous amount of competing projects, we constantly had to prioritize and make a best guess on what should be done first. I had some visibility into the other functions of the business, but it was far more limited. I relied on second hand insights to determine how important this collateral was, and if it needed to be prioritized.

Another example was the sales and customer success handoff. In some unfortunate cases, the sales team would bring on a new customer that was not a great fit for the company’s products, and the mess ended up in the laps of the customer success team. If someone was just focused on leading sales, it would be tough to have as much empathy for the customer success leader who actually has to deliver on the promises that the sales team made.

Suddenly, when I sat in all of those functional leadership seats, I got a huge shot of empathy, because there was nobody to pass the buck to. If my sales team sold a customer that wasn’t the right fit for our product, then my customer success team had to deal with it. I couldn’t escape!

This situation proved to be a blessing for myself and our company. My newfound empathy enabled me to make better decisions in each of the functional areas I was responsible for. It helped me better understand the struggles that my peers faced in their departments, and guided my way to make adjustments in how I led our marketing team to ensure I wasn’t just focused on meeting my own department’s goals, but instead was more aware of how our work impacted the broader business.

A simple way to describe this empathy and cross-functional awareness is “Multi-Functional Leadership.” It refers to leaders who consistently operate with the broader company’s goals in mind, and raise a red flag if they find that their department’s goals may be misaligned with the bigger picture. This is a characteristic that every successful leader should develop, and that great CEOs should instill in their executive teams. Consider these strategies to make Multi-Functional Leadership a part of your executive team’s culture:

1. Establish metrics that hold functional leaders responsible for company-wide goals

Good leaders will perform based on how they are measured. If leaders are held accountable to company-wide goals in addition to their department-level goals, they’ll have a clear incentive to help other functions flourish. Ensure that comp plans and KPIs are a healthy mix of department and global objectives.

2. Create service-level-agreements (SLAs) between functions

Establishing a written protocol on how departments should operate cross-functionally can be beneficial. This helps ensure that the marketing leader understand exactly what she is obligated to do to support the sales leader, and vice versa.

3. Expose leaders to other functions through immersion experiences

When leaders are exposed to the challenges of others, we naturally develop empathy. Having your engineering leader join the support team and answer tickets for a few hours, or having your marketing leader listen to sales calls can help foster a deeper understanding. For example, if the marketing leader hears first hand from prospects in a sales meeting that they’d like a certain piece of collateral, they will have far more conviction and urgency to get it created.

4. Insist on cross-functional transparency

As I’ve shared throughout this article, empathy comes from exposure and understanding. If there isn’t transparency on the challenges that each functional-area faces, it will be tough for leaders to make decisions in their own department that fully take into consideration the needs of other departments. That transparency can happen through your leadership meetings and weekly written updates.

There’s a common frustration with startup offices:

They are too loud.

Anyone who creates things — whether it be coding, designing, or writing — recognizes the benefit of deep work. The term was popularized in a book by Cal Newport, and the premise is straight-forward: in order to complete a cognitively demanding task, you need to focus without distraction. While this concept has been called many things, such as “hitting flow” or “being in the zone” it basically means that if you want to get shit done, you have to focus on it.

Your professional future usually depends on your ability to get shit done, and that’s a problem, because many startups are inflicted by a plague that has crept up among the ping pong tables, open floor layouts and endless chat conversations. That plague is noise and distraction, and it can kill productivity. When I say noise, I don’t just mean physical noise of people talking loudly in the office (though that is certainly part of the problem), but I also mean digital noise, from Slack channels and email threads that suck away our attention into conversations that we often have no need to participate in.

My team at Crystal experienced this problem first hand. Our office was loud, we involved the whole team in every conversation and we had more Slack channels than we knew what to do with. After some introspection and frustration with our progress as a company, we recognized that our culture had grown to accept distraction as part of our way of life, and our ability to be productive was taking a serious hit. We took a few concrete steps that made a world of difference. Here’s the playbook:

1. Delete your Slack channels

Slack has changed the way people communicate at work. It’s made it easier to quickly interact with colleagues, rather than wait a long time for email replies. It has also made remote work more accessible by enabling offsite team members to more easily participate in conversations. This is all the bright side of Slack.

The dark side; however, is that Slack has made it a bit too easy to communicate. Channels, or large group chats focused on a topic, can number in the dozens and for many companies, these are public. There is a #product channel, an #ideas channel, and a plethora of other custom channels, each hosting a conversation. The problem is that these conversations are often never ending, and to participate in them is a constant suck of time and attention. Employees fear if they don’t constantly check these channels, they may miss out on important information.

For example, if your Product Manager poses a question about a feature in the #product channel, soliciting feedback from the entire company, and suddenly a few people jump in with their suggestions, that original question may get buried high in the thread before a more focused employee dedicates the time to dig through the pile of messages. Those who don’t get to the messages quick may lose the opportunity to learn about that feature and give input.

At Crystal, we found this to be particularly problematic. On our small team of about a dozen, everyone was being included in every conversation about every product idea, because it was happening in the public #product channel. Every engineer that was supposed to be responsible for Project X was constantly bombarded with messages about Project Y in the #product channel, which was completely outside of their area of focus and responsibility.

While transparency is valuable and welcome in many parts of a company’s culture, allowing Slack channels to run wild with public, never-ending digital meetings is a perfect recipe for a distracted, unfocused and unproductive team. Once our team realized this, here’s what we did:

• We deleted every public Slack channel except #general for company-wide announcements, and #random for fun jokes
• We encouraged employees to start direct message threads with only the relevant stakeholders for a conversation
• We found other ways to gather feedback about product ideas, such as through a Trello board that doesn’t need to be checked constantly
• We added documentation to our culture deck about how we value direct conversation, and loath unnecessary, never-ending digital meetings

2. Create meeting space that isn’t people’s desks

Part of my role in leading product is to frequently interact with our designers, engineers and marketers to give feedback on features and guide the team in the right direction. As a small team with an open office, the fastest way to do this is to just wheel my chair over to someone’s desk. Easy enough, right?

The problem is that with our open, shared desks, I was basically starting a meeting with Person A, sitting just a few feet from Person B, who had nothing to do with the meeting and instead was focusing on their own project. We don’t typically have conference rooms without walls — so why would we turn every desk in our open office into a conference room? I realized that by doing this, I was a constant rolling distraction, creating chaos in every corner of the office.

To address this, we came up with a simple solution: when you want to meet with someone, step into the common area where we have couches, stand-up desks and some private meeting rooms. This designated meeting space is tucked away from where others are working. This enables us to still easily collaborate, but not turn it into an office-wide discussion. We do the same thing for video calls with remote team members: always in the common space or call booths, never at our desks.

The results of this have been impactful. Some visitors have noticed that our office is now particularly quiet. Call me crazy, but if we’re a company filled with “creators” (engineers, designers, writers, etc), giving them space to create seems pretty reasonable. For those that like the sound of coffee shop buzz, we have plenty of space to work in our office’s common area.

3. Skip the office-wide music

Especially in the early startup days with just a few people in a small office, it can be fun to play music and get the energy flowing. However, if your team is charged with creating, that music can be a painful distraction. Everyone likes to work differently and has their own preferences for type of music, or lack thereof. Having one person (either the CEO or a team member) decide what background music the entire office will listen to while working doesn’t make much sense. Instead, let everyone pick the type of background that works for them: their own music with headphones, silence, or light buzz of a common area.

4. Create rules on how to get people’s attention

If you’re “in the zone,” one of the worst things that could happen is for someone to tap you on the shoulder, rip you out of your focus only to ask an unimportant, non-urgent question. We avoid this by setting team rules on how to get someone’s attention. It’s an easy guide to follow:

• Do send them a message on Slack first.
• Do NOT walk over and tear them away from what they are working on.

If they have their Slack notifications off, it means they are trying to focus on their own project, and it’s best to let them do so unless it’s an emergency. This seems to me like common courtesy: why should I have the right to determine what you are focusing on? You should decide when to divert your attention to my question.

To be sure, we’re not perfect. If it’s an urgent matter that is turning into a blocker for multiple people, we’ll occasionally break the rule and burst into someone’s focus to get an important answer. But we recognize this can be problematic, and avoid it when possible.

5. Have quick calls rather than long chats

The convenience of text messages and chat is alluring: you can have a conversation without the full effort of stopping what you’re doing, talking to a person and making decisions in real life. You can take your time considering each response, a luxury unavailable on phone calls. The downside to this is that conversations on chat can be far more drawn out than conversations with voice. Chat lacks context. It lacks verbal queues and the ability to think through a concept out loud. As a result, while chat is exceptionally effective for getting quick answers, it is remarkably terrible for discussing complex issues.

Our team also stumbled here: we’d often find ourselves going back and forth with long, detailed messages in chat on Slack. Inevitably, one side wouldn’t fully understand the other, and confusion would ensue.

To avoid this, we now have a culture with a bias towards voice. If there is something complex to discuss (like clarifying how a new feature should be built by engineering), we should have that discussion verbally, either in person or through a call. Anytime we see a conversation on Slack start to get too complex, we’ve trained ourselves to respond with “let’s switch to a call.”

Importantly, when the group reaches a conclusion on a call, it’s important to document that in writing to ensure there wasn’t any miscommunication. For that phase of the discussion, Slack is perfectly effective.

Bottom line

Eliminating distractions and prioritizing your team’s ability to focus can be among the most impactful steps a leader can take to improve performance. Teams that “create” need deep work, and eliminating noise — both in real-life and digitally — is the best way to enable that to happen.