The Benefits of Routine

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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!

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