February 24, 2026
Hi Everyone,
Board meetings put you in an uncomfortable position.
You need to surface problems to get useful input, but surfacing problems can feel like handing your board a reason to worry – or worse, intervene.
Jeff Bonforte, former CEO of Xobni, called board meetings "the height of insecurity for a CEO" – a group of people who can both judge you and fire you based on that judgment.
So many founders default to optimism. They present clean dashboards, highlight wins, and save the hard stuff for later.
Elizabeth Weil, formerly of Andreessen Horowitz, put it well when she observed that telling your board "we're killing it" is a great way to lose the leverage a board actually offers. If they don't know what's hard, they can't help with what's hard.
Today, we're sharing a formula for bringing problems to your board in a way that builds confidence rather than undermines it.
A formula for raising problems productively
The difference between "asking for help" and "sounding an alarm" is usually structure. When you bring a problem to your board with clear framing, you come across as someone who is on top of the situation and using every resource available – including them.
Before your next board meeting, try framing each problem you want to raise in four parts.
1. What's happening
State the situation in plain, specific terms. The more clearly you name the problem, the less room there is for the board to fill in the blanks with their own (usually worse) assumptions.
Vague updates like "things have been a bit soft" invite exactly the kind of follow-up questions that make the conversation feel like an interrogation.
2. What we've tried
Show your work. When board members can see you've already tested ideas and learned from what didn't work, they spend their energy helping you think forward instead of questioning whether you've done enough.
3. Where we're stuck
Name the specific constraint or open question. Many leaders avoid this part because it feels like admitting weakness, but it's actually what makes the board useful.
Without it, they'll either give you generic advice or poke around trying to figure out where the real issue is.
4. What I need from our directors
Make a concrete ask. This gives your board members a clear role and turns a problem update into a working session.
Without it, they default to judgment mode because they don't know what else to do with the information.
As Bonforte also observed, "Every single entrepreneur forgets that the board works for them."
When you come to a meeting with specific requests, you can properly tap into your board's network and experience. And you’re treating them as the resource they're supposed to be.
Pre-wire before you walk in
Mark Suster has a firm rule: never find out in real time how a group of individuals will vote on matters important to you.
A 30-minute call with each board member before the meeting lets you surface hard topics one-on-one, gauge reactions, and adjust your framing.
By the time you're in the room, nobody is hearing bad news for the first time. This also protects you from the group dynamic where one board member's visible concern triggers a pile-on – when concerns have been aired privately, the live discussion stays productive.
Before your next board meeting
Pick one real problem you've been holding back from your board. Write it up using the four-part formula: what's happening, what you've tried, where you're stuck, and what you need from them.
Then call your lead board member and walk them through it before the meeting. See how they respond when you frame it as a working problem rather than a crisis.
Go deeper
👉 First Round Review: Jeff Bonforte on how to run a board meeting – advice on sitting at the table as a peer and making specific asks
👉 Y Combinator: How to create and manage a board – YC's guide for founders setting up and running their first board
👉 Bain Capital Ventures: The 10 keys to a successful board meeting – covers pre-reads, closed sessions, deep dives, and the right meeting cadence
Coming up tomorrow
Tomorrow we'll cover three meeting rules backed by research that can save you hours this week.
That's it for today!
P.S. Have you ever held back a problem from your board and regretted it later? Or brought one up and been glad you did? Let us know.