Published on Jul 12, 2023
Learning to work with your board is not a one-time lesson—it’s a constant, iterative process. Even if you follow best practices, they aren’t a one-size-fits-all solution. You have to experiment and accept that some of those experiments will probably fail.
Even for us, self-proclaimed experts in board management, working with our board has been an ongoing process of trial and error. So we did a little self reflection and thought we’d share some of the mistakes we’ve made and lessons we’ve learned along the way.
In the early days, we did board prep the way most companies do. Which is to say we spent a lot of time creating and formatting slide decks. We’d spend days making sure our slides looked great and included as much information as possible. During the meeting, we’d (quite literally) scroll through every bullet, line by line.
We thought this was good meeting prep. But what we were actually doing was setting the expectation that people didn’t need to show up to meetings prepared, because we’d run through everything during the meeting anyway. And we burned hours and hours of time in the process.
So we changed things up.
We ditched the slides and opted for a simpler memo format. We started prioritizing information—making sure our board had all of the context they needed—over aesthetics. And we added talking points for each agenda item, to help guide more productive discussion. While the talking points sometimes reference information from the pre-read materials, we no longer read through those materials during meetings.
By becoming less attached to slides, we’ve saved a ton of time on both board meeting prep and the meetings themselves. Plus, our meetings no longer feel long and frustrating—they’ve become a genuinely valuable time for problem solving and strategizing.
We always send meeting materials at least 3-5 days in advance. But even still, it can be challenging to know for certain if everyone is coming to the meeting prepared. So a few days after sending prep materials, we reach out to each board member to gather feedback and see if they have any questions.
This goal is twofold:
1. It sets the expectation that board members have to read through the prep materials before the meeting. Nobody wants to say they don’t have any questions, and they can’t come up with valuable questions if they haven’t prepped.
2. It helps the management team understand where to focus during the meeting. Knowing which topics your board has the most questions about can help you prioritize discussion items and create a more effective agenda.
Before we started practicing this, it wasn’t unusual for our meetings to get derailed because someone wanted to discuss something we hadn’t planned for. Now we start each meeting confident that everyone is prepared and ready to tackled the important issues at hand.
Whenever we put a meeting agenda together, we allot a set number of minutes for each topic. Not all topics are created equal—some should definitely occupy more meeting time than others—so we try to anticipate exactly how much time each topic will need.
It’s not a super official process. Our thinking looks something like this:
A quick personnel update? A few minutes should suffice.
Tackling a hairy issue? We should probably set aside more time.
It’s a practice we’d been following consistently. And somehow we were still consistently running out of time. Almost every meeting, we’d spend too much time on the earlier topics and have to fly through more important discussions later on.
We had essentially been using time to indicate weight (more time = more importance), but we weren’t actually using it to keep ourselves on task. Turns out, allocating time isn’t enough—you have to enforce it too.
So we started tracking our time during meetings (and even built that feature into our product). Now, if a discussion is running long, we have to make a conscious decision about whether we want to continue it at the cost of something else. If not, we’d better wrap it up and move on.
We talk a lot about how important post-meeting follow-up is. And we have a lot of internal processes that reflect that.
After every meeting, we summarize key takeaways and action items, and share it with our board for visibility. We’ve always been good about understanding what we, as a team, need to do. But we weren’t always communicating what our board members needed to do.
Early on, we sort of assumed our board would instinctively know what to follow up on. They were in the meeting, so they’ll know what needs to be done, right? Well, not necessarily.
Just because something was discussed, doesn’t mean it’s been clearly communicated as an action item for a specific person. And even if it was verbally communicated, it should be recorded and tracked in writing too.
Over time we’ve learned that officially assigning tasks to your board members increases clarity and accountability. By clearly communicating what we need from our board members, we’re actually empowering them to help us right now, not three months later when we awkwardly remind them at our next board meeting.
To be honest, it can feel pretty uncomfortable to assign tasks to your board. And we’ve had to remind ourselves that all of this work is a team effort. Our relationship with our board is not based on one-sided reporting—everyone has to be held accountable for the work they promised to do.
When we were first starting out, we only communicated with our board at quarterly meetings. At the time, it felt like that made sense. We didn’t want to annoy our board by reaching out to them all the time, and board meetings were specifically set aside as our time to meet.
As a result, board meetings were stressful. So, so stressful. We’d have a whole quarter’s worth of updates and issues piled up and honestly, not all of it was positive. Walking into a board meeting felt like walking into judgement day.
It took us a while to figure out how to fix this (we blame the myth that board meetings are inherently stressful for letting ourselves accept this as a given), but ultimately the solution was pretty simple: communicate with our board between meetings.
We started using asynchronous updates as an opportunity to keep our board in the loop, so there were zero surprises during meetings. And we didn’t just share good news. In fact, we found sharing bad news in real time was especially powerful.
One quarter, we were behind on our targets and knew we wouldn’t hit them before the board meeting. So we told our board. We sent an update with the details, outlined our original thinking behind the targets we’d set, and shared the lessons we learned.
The response was some of the most positive feedback we’ve received from our board. They not only appreciated the transparency and accountability, they came to the next meeting prepared to dive in and help.
Since then, asynchronous updates have become a fundamental part of how we work with our board and board meetings have become much less stressful and so much more useful.