Sometimes you have to meet in-person

For complex, high stakes decisions with uncertain outcomes, we haven’t found a replacement to a time-constrained, distraction-free, in-person working session.

👋 Hi, it’s Greg and Taylor. Welcome to our newsletter on everything you wish your CEO told you about how to get ahead.

Like many of you, we have a lot on our minds this week so we kept this post short, and published a day late. If you’ve got enough on your mind today, we’ll see you next week. 

Last week, Taylor and I spent two days together in-person in Chicago. Since 2020, Section has been fully remote – I’m in the Bay Area and Taylor is in Champaign, IL. However, Taylor and I still meet up in person, anywhere from once a month to once a quarter, to discuss the business.

We both left that session feeling much more clear and confident about our business strategy, and were reflecting on why that is. So this week, we decided to share what made that session so productive in the hopes it will help you when you face high stakes decisions.

– Greg

Our strategy planning process 

Building anything comes with a certain level of unknowns. There’s external forces – who wins the election, whether the Fed raises interest rates, capital availability, whether companies are cutting or investing, etc. And there’s internal forces – how our product will sell, turnover within our team, performance of our ad channels, etc. 

In moments when these unknowns feel particularly high, one of us has gotten on a plane and flown to the other. Then we’ve followed this process to build conviction and clarity about the business.

1. Make some assumptions

There’s no data we have that indicates next year will be much different than last year. So we start with that assumption – let’s assume that interest rates will remain high, companies will prioritize earnings (over growth), and the only area they’ll spend in will be AI. This helps us acknowledge those external factors, and set them aside.

2. Create a list of decisions to make

We do this before we meet, which sets the agenda for the time we have together. This is important since we often only have 48 hours – last week, we had a day and a half. We also usually tag the decisions by when we should discuss them – some can be discussed over a meal while others require a whiteboard or looking at data or a deck. 

3. Run a tight in-person working session

This is usually 1-2 days of uninterrupted working time. We’ve tried it once or twice via Zoom, but it’s much more effective in-person for a few reasons:

• Focus: It’s nearly impossible to focus, heads-down, on big meaty business discussions for more than an hour or two on Zoom. Being in-person all day is still exhausting, but it forces us to stay dialed in to the task at hand, and ignore incoming Slacks or other projects.

• Clear calendars: We clear our calendars for these sessions, with a few exceptions (board member call, client call). Therefore, we aren’t forced to cut important conversations short and can follow tangents and adjacent ideas that emerge.

• Moving high-low: Throughout the day, we move between big picture discussions about the future (what does the business look like 12 months from now?) and tactical decisions (how do we organize the team, who will own each project?) to move forward. It’s easier for us to follow these changes in altitude together in a conference room, with a whiteboard (again partly due to fewer distractions).

4. Summarize and pressure test

We usually leave these sessions with three things:

• A list of decisions we’ve made

• A list of projects that flow from those decisions

• A list of additional questions we need answered or data we need to get

So on the plane home or the next day, we summarize these items into a short slide deck. Then we discuss it with others including our leadership team and board members once we’re back home. The leadership team provides a great stress test from bottom up (feasibility, alignment with other projects, etc.) and the board provides another from top down (impact on enterprise value, etc.).

Our advice

We find ourselves hopping on a plane when we’re grappling with something that’s high stakes, high complexity, and high optionality – there are many potential paths forward, and it ultimately comes down to an informed judgment call. In these moments, we need quality time in-person with clear calendars and a set agenda. 

It comes with friction/cost but we haven’t figured out how to navigate these moments and build conviction over Zoom, or in another format. If you have, we’d love to hear about it.  

Have a great week,

Greg & Taylor