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
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!