Issue #57: The Board Meeting Playbook for Startups
A practical guide for founders and operators on turning your board meeting into a working session — not a performance.
The morning after one of our early board meetings at Cargado, I was having breakfast with Brad Svrluga, our lead investor and board member from Primary Venture Partners. He asked me how I thought the meeting went. I gave him my take — mostly positive, a few things we could tighten up.
Then he said something that stuck with me.
He told me a board meeting should feel like a really intense workout. Not necessarily fun, but rewarding. One of those grueling sessions where you walk away sore, but with more clarity, sharper focus, and better alignment than when you walked in.
He was right.
Because the truth is, most early-stage board meetings don’t feel like that. They feel like theater. Like a quarterly performance review dressed up with pretty charts and a few too many metrics that don’t really matter anymore.
I’ve been guilty of that myself. Especially during my first company, Forager. We reused deck structures for way too long. Glossed over red flags. Avoided the real conversation.
But the more experience I’ve had — as a founder, operator, and board member myself — the more I’ve come to realize how powerful a well-run board meeting can be. And how painful it is when you waste the opportunity.
This issue is a deep dive for founders and operators on what board meetings are really for, how to get the most out of them, and the lessons I’ve learned (sometimes the hard way) about how to run them right.
Why Board Meetings Exist
Most founders assume board meetings are a formality — a box to check every 6–8 weeks to keep investors in the loop. But if you’re only thinking about them as updates, you’re missing their actual purpose.
Board meetings exist for four core reasons:
1. Governance
The boring but essential part. You’re a Delaware C-Corp. The board is responsible for approving things like 409As, option pools, fundraising rounds, material contracts, and executive hires. This is what the board legally has to do — and a lot of the action items should be handled in the consent agenda or off the critical path of discussion.
2. Accountability
You raised money to do specific things. Did you do them? Why or why not? Board meetings are where you report on progress. That doesn’t mean spinning stories or shielding reality. It means being clear about where you are and how you’re doing.
3. Alignment
Your team, your investors, and your co-founders all bring different experiences and incentives. A good board meeting is where those perspectives get recalibrated around the current state of the business and where it’s going next.
4. Strategy & Feedback
The best board meetings are working sessions. Not pitch decks. Not TED talks. You’re in a room with smart people who’ve seen hundreds of companies — use them. Come prepared with real decisions to make or hard problems to solve.
The Forager Mistake
At Forager, I misunderstood what board meetings were for.
I thought the goal was to get through them. Impress people. Show momentum. Avoid too many questions. So we leaned heavily on presentation polish, slide templates, and safe framing.
We reused board deck structures quarter after quarter, even when those structures didn’t match the current reality of the business. We’d highlight the metrics that looked okay and skip past the ones that didn’t. We rarely paused to ask: are we even having the right conversation?
In hindsight, I wish we’d treated those meetings less like performance reviews and more like opportunities to challenge our assumptions and reset our priorities. We had good investors — but we didn’t use them enough.
That’s changed this time around.
How We Run Board Meetings at Cargado
The most important rule we follow is simple: no surprises.
I meet regularly with our investors — especially the ones who sit on our board or serve as observers. They already know where we’re headed, what’s working, and what we’re wrestling with. That way, when the board meeting happens, no one’s caught off guard. If a board meeting is the first time someone hears bad news or sees a major change in strategy, you’ve already lost the room.
We also treat board meetings as a team sport — not a solo performance by the CEO. The goal is to have real conversations about what matters most. Here’s how we build toward that.
🛠️ Our Board Deck Process: Step by Step
1. Define the purpose
Start by identifying the 2–3 main reasons for the meeting. What strategic issues, decisions, or challenges do you want the board to weigh in on? That’s the foundation for everything else. Write it down. Share it with your team. Make sure everyone knows what we’re really here to talk about.
2. Build the outline
Sketch out a rough outline of the deck. You don’t need slides yet — just sections and bullet points. Think about what needs to be communicated, in what order, and why. Include bullets for what you want to say on each slide so you don’t lose the narrative as you go.
3. Brain dump into a shell deck
Once the outline feels good, I create a shell of the deck with placeholder slides. Then I dump all of my notes, context, and raw data onto each one. It’s messy, but it gets everything on “paper” so you can step back and start shaping the story.
4. Build slides for clarity, not creativity
Every slide should have a clear takeaway — ideally called out in a dedicated “Key Takeaways” box on the slide itself. Limit yourself to three bullets max. Include supporting data, charts, or visuals only if they reinforce your point. Don’t over-design or over-share. This is not the place to debut new ideas or flashy slide transitions. It’s about clarity.
5. Build it with your team
Your leadership team should own their sections of the deck. Head of Sales owns sales. Head of Product owns product. But as CEO, your job is to coach, edit, and unify. The narrative needs to hold together — not feel like a patchwork of team updates. Review each section with your leaders and fine-tune the messaging together.
🎯 Choosing the Right Working Topics
Once you’ve built your shell deck and framed the story, you need to zoom in on the working topics — the parts of the meeting where you’re asking for input, not just giving a report.
Every good board meeting should include 2–3 of these. Here are some examples we’ve worked through at different stages:
Pricing changes: Should we move to usage-based pricing? What will the customer impact be? How do we measure success?
Org design and hiring: Who do we need in seats to get to the next stage? Are we over- or under-hiring in certain functions?
Fundraising strategy: When should we raise our next round? What does the story look like based on our current plan?
Customer or GTM challenges: Are we going after the right ICP? Is our messaging landing? Why did churn spike last quarter?
Product roadmap tradeoffs: What bets are we making in the next 6 months? Where are we cutting scope or shifting timelines?
Marketplace health: Are supply and demand in balance? Where are the liquidity gaps? Are we solving the right problems for each side?
The right working topics depend on the kind of company you’re building:
If you’re in SaaS, your GTM motion and retention strategy are likely top priorities.
If you’re early-stage, the focus may be team building — key hires, founder bandwidth, org debt.
If you’re building a marketplace, you’ll be talking about balancing growth between demand and supply — and how product or ops needs to shift.
If you’re heading into a raise, it’s probably time to talk runway, metrics, and storytelling.
I still remember our very first board meeting at Cargado — the board pushed me to hire a Chief of Staff. That ultimately led to us hiring both our Head of GTM and our Head of Operations, two of the most critical leaders on our team today. Sometimes the best conversations aren’t about what’s in the deck — they’re about the gaps you’re too close to see on your own.
💼 Advice for Founders
🧠 Prepare like it matters
Don’t slap together a deck the night before. Give yourself (and your team) time to organize your thinking. Put a draft together early. Write a CEO letter. Think through what’s changed, what’s stuck, and what’s unclear. Help the board see the business through your eyes.
💡 Pick your working topics
Every meeting should include at least two real conversations. Not fluff. Not “we’re thinking about maybe trying X.” Make the board part of the process. Bring strategic questions you want their input on — and actually listen.
📉 Own the hard stuff
Your board already knows where things aren’t going great. If you missed on net new ARR, churned customers, or pushed a product launch — say it. Explain why. Share what you’ve learned. Outline the fix. Your honesty builds credibility.
🔁 Evolve the structure
Your business changes every quarter. So should your board materials. Don’t be afraid to drop old KPIs, add new ones, or totally reframe how you talk about your funnel, org, or growth. Board decks should evolve — just like your product roadmap.
🗣 Coach your team
If your Head of Product or CRO is presenting, help them prep. Walk through the narrative together. Rehearse. Anticipate questions. Set them up to speak confidently, clearly, and concisely. You’re not just building a business — you’re building executives.
👥 Advice for Operators Presenting to the Board
🎯 Keep it tight
You don’t need to show everything your team did. This is not a status update. Pick the metrics that matter most and frame them with context and insight. Show up prepared to answer: So what? Why now? What next?
📊 Lead with insight
Don’t just show the pipeline — walk through the trends. Don’t just show NPS — explain what’s driving it. Don’t just report churn — highlight what you’re doing to address it. Data is just a starting point.
💬 Be real
You don’t need to spin. In fact, trying to “sell” your section often backfires. Be honest, concise, and direct. Share what’s going well and what you’re working to improve.
🤝 Coordinate with your CEO
Your section isn’t a standalone update. It’s a chapter in the story of the company. Sync with your CEO and co-presenters so the narrative flows. Make sure the messages are aligned and the metrics support the broader plan.
🧩 Closing Thought
Your board meeting is not a quarterly performance review. It’s not theater. It’s a workout.
The kind where you don’t necessarily enjoy every minute of it, but you show up, push through the hard parts, and walk away better for it — clearer, stronger, and more focused on what matters most.
Whether you’re the founder running the session or an operator presenting for the first time, the mindset is the same:
Prepare like it matters. Be honest about what’s working and what’s not. Ask for help. And then go execute.
Your company will be stronger for it. And so will you.