Why Have a Board

For founders, establishing a board can initially feel like relinquishing control. The early stages demand your full attention on product development, customer acquisition, and revenue generation. However, as your startup matures, the need for a board emerges – whether for fundraising or operational support. Beyond governance, a board offers a valuable opportunity to pause, reflect, and benefit from diverse perspectives.

Knowing when to embrace this transition and leverage it to your advantage is pivotal for growth and success.

Board Observers

As startup founders, early on, your focus is on building the product, finding customers, and validating your value proposition. And that’s exactly where it should be. But as your startups grows, the need for a board—and potentially a board observer—starts to take shape. Maybe it’s tied to raising capital or needing structure to help scale.

Here’s the thing about board observers: They might not have voting rights, but they’ll often have just as much to say as a full board member. They won’t hold back, nor should they. That’s why choosing a board observer is just as critical as choosing a full board director. Observers can bring valuable insight, challenge your thinking, and help guide your company.

The Board Made Me ...

Feeling like your board is a burden? That might be a sign that it's time to take a closer look at how you, as the CEO, are managing that relationship.

I've heard the complaints, and maybe you've said them too:
👉 “The board made me do this.”
👉 “They don’t understand my business, so I’m not going to listen.”
👉 “The board made that decision, and I didn’t agree.”

It's easy to fall into the trap of blaming the board. But here’s the truth: if your board isn't functioning well, that’s a CEO responsibility, not a board failure.

When to Start a Board

Startup Evolution: Understand how the need for a board evolves as your software startup progresses. Typically, in the first year or two, founders are focused on product-market fit, building product, finding customers, and generating revenue. A board's necessity usually emerges after this initial stage.

Timing is Key: Some founders try to avoid setting up a board, or are unsure when the right time is. You need to recognize the signs and make an informed decision.

CEO's Role: The CEO's role is critical. They must be proactive in setting up the board and selecting the right people.

It Shouldn't Be Easy

Founding CEOs: If your board meetings feel too easy, you have a problem.

I once sat in a board meeting where a portfolio company CEO presented a budget that just didn’t add up. I had to be the one to say it—this isn’t realistic, cuts need to happen. Not fun. But you know what? That tough call opened the floodgates. Other board members chimed in, concerns surfaced, and together we helped the CEO course-correct before reality did it for them. A year later, the company is healthy, capital efficient, growing, and managed to raise its Series B. On the other hand, if we had gone through the original budget, we would have likely run into a cash crunch and had to sell the company.

Here’s the takeaway: If your board just nods along, that’s a red flag. You need a board that challenges your thinking, pressures tests your strategy, and isn’t afraid to call out the tough stuff.

Unaligned Priorities

Have you run into a situation where different board member priorities don't align with the founders? Or different investor board members are not in-sync when it comes to exit size and timing?

Different Investor Priorities: Be aware that seed, expansion, and growth stage investors have different priorities. You need to understand each investor's fund horizon, liquidity priorities, and available follow-up investment dollars.

Some key questions to ask each VC:
1. Where are you in the lifecycle of the fund you used to invest in us?
2. Is it a new fund, or are you actively looking to exit?
3. Where do we rank among your other portfolio companies?
4. Are you actively looking to invest more in our company?
5. What is your personal priority? Are you looking to stay on the board much longer?

Board Preparation

The purpose of a board of directors is to have a set of experienced, value-adding board members who can help you figure out how to build your company. And for them to do that, they need to deeply understand your business and its health and prospects. It is your job to give them that knowledge. 

If preparing board packs feels like a huge effort, there are underlying issues that need to be addressed. Ideally, what you share with your board should be the same information you share with your executive team and employees. This includes:

• The health of the business (KPIs)
• Achievement against planned targets
• Detailed and accurate financial information
• Sales pipeline coverage and forecasts
• Any other analytics used to run the business day-to-day (product deliverables against timeline, customer churn analysis, etc.)

You should have all this information readily available because this is what you should be using to run your business day to day. At this point, you should not be running the business with your gut feel like you did when you first started. 

3 Board Approaches

The 3 Common CEO Board Approaches:

1️⃣ The Intimidated CEO – Nervous about tough conversations, sugarcoats bad news, and avoids pushback. This hurts the company because a board can’t help if they don’t have the full picture. Lead with the bad news. Seek honest feedback. That’s how you extract real value.
2️⃣ The Checkbox CEO – Views board meetings as a bureaucratic chore, something to endure rather than leverage. The result? A missed opportunity to get real strategic input. Your board isn’t a reporting obligation; it’s a tool for scaling your business.
3️⃣ The Pro CEO – Understands that a strong board makes them a better leader. Comes prepared, shares the same data they use to run the company (KPIs, financials, pipeline, execution against plan), and focuses the meeting on reflection, debate, and decisions.

At the end of the day, if your board isn’t valuable, it’s on you. You either:

✅ Haven’t structured it correctly
✅ Don’t have the right people in the room
✅ Don’t know how to run an effective board meeting

Founder in Denial

An unfortunately common challenge with startups: A founding CEO who is not delivering. I’ve seen this scenario play out more than once. It doesn’t happen overnight—it creeps in gradually until it becomes a full-blown crisis.

Let's be clear first. Early-stage founders are everything to a startup—vision, passion, execution. But as the company scales, the game changes. It’s no longer about sheer hustle; it’s about leadership, delegation, and execution at a higher level.

The best founders evolve. The worst? They stay in denial.

🛑 The single most damaging thing a founder can do is refuse to acknowledge there’s a problem.

The best thing? Own it. Ask for help.

A practical gut-check: Revisit your last fundraising deck and your last set of board meeting presentations. Look at the promises you made to your board and investors—growth targets, execution milestones, key hires. Now, compare those projections to reality. Are you where you said you’d be?

3 CEO Personas

There are three types of founding CEOs, and the difference between them isn’t just experience—it’s mindset.

➊ The Wise CEO – They’ve been through the startup grind before. They know what they don’t know and surround themselves with experienced operators, advisors, and a board that actively helps them execute their vision.

➋ The Coachable CEO – They may not have prior startup experience, but they recognize their own gaps. They listen, adapt quickly, and aren’t afraid to course-correct. This humility is a sign of true confidence—not weakness.

➌ The Lone Wolf CEO – They refuse to admit what they don’t know, fearing it’ll make them look weak. They resist hiring people who challenge them and avoid tough conversations with their board. Investors and board members see this as a major red flag.

The strongest founders aren’t the ones who have all the answers—they’re the ones who build a team (and a board) that helps them find the right ones.

Rosy Forecast Failures

🔥 Rosy Forecasts & Missed Numbers: What Your Board Is Really Thinking

 👉 You set an ambitious revenue target.
 👉 You miss it.
 👉 Now you’re in front of your board, trying to explain why.

Here’s the truth: The original revenue forecast? It probably started as a fundraising narrative but quietly morphed into your operating plan. And now it’s the number the board, your team, and maybe even you are holding yourself to.

So let’s be clear:
 👉 Missing a forecast isn’t the problem.
 👉 Failing to manage expectations—and not owning the miss—is.
 👉 Founding CEOs who get this wrong lose credibility fast.
 

Here’s what great CEOs do:
 ✅ They remind the board (and themselves) that startup plans are assumptions, not guarantees.
 ✅ They flag risk early and often.
 ✅ They shift the focus from blame to root cause—Why did we miss? What are we doing about it?

Are you building a culture that learns or performs for the pitch deck?

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