How to Communicate with Board Members and Drive Strategic Engagement

Great Board conversations don’t sell—they stretch your thinking. Having spent time both as a member of the management team working with the Boards and as a Board member myself, I’ve seen a few common pitfalls that even seasoned leaders fall into. Here are three that stand out: 1. Trying too hard to “sell” the strategy. Your job with the Board isn’t to pitch—it’s to inform. The goal is to create a regular rhythm of updates around the business, strategy, and execution. One of the fastest ways to lose credibility is to act like everything’s perfect. Every company—no matter how successful—has real challenges. Board members know this. Being candid about those challenges doesn’t make you look weak. It makes you trustworthy. Transparency matters. Your numbers already tell part of the truth. Bring the rest. 2. Keeping the strategic aperture too narrow. Executives often focus on operational detail and forget that Boards can be most helpful in widening the lens. Leverage their distance from the day-to-day as a feature, not a flaw. I cringe when I hear, “I need to dumb it down for the Board.” In reality, the best Boards raise the level of strategic thinking. Bring them into big questions: “What does our industry look like in five years? Where should we be positioned?” Boards are at their best when they help you challenge your assumptions and stretch your thinking. 3. Not asking for guidance. Some of the best advice I’ve ever received in my career has come from Board members. Don’t just report—ask. Tap into their experience. Invite their perspective. The Board appreciates humility, especially when you say, “I haven’t figured this out yet—I don’t have the answer. But what are the strategic issues you would consider if you were in my shoes?” Because here’s the truth: The smartest executives don’t try to impress the Board—they learn from it. And here are 3 things I’ve learned to always get from a great Board conversation: 1. Start with the commercial “why.” Boards aren’t there for a product roadmap walkthrough—they want to understand business impact. Always lead with the commercial dimension. Why does this matter for revenue, margin, competitive advantage, or long-term growth? When you start there, everything else has context. Your Board isn’t a stage—it’s your secret weapon. 2. Define what good looks like. One of the most helpful things you can do is to show what “great” would look like—clearly and with metrics. It gives the Board a benchmark to assess against, and it keeps the conversation focused on outcomes, not just activity. 3. Ask what you’re not seeing. The question I’ve found most consistently valuable: “What do you think we’re not thinking about as a management team?” You’ll be amazed at the insight that comes back. This invites perspective without defensiveness—and you’ll often uncover blind spots or strategic angles that weren’t even on your radar. Because Boards aren’t there to be dazzled—they’re there to help you see what you can’t.

CEOs, keep your board on your side by fighting the same enemy. I am a big believer in the power of a common enemy - the competition. Great CEOs understand how to convey this idea of togetherness to boards: “We have the same goal of winning market share in our category; let’s get after it together.” High-performing boards (just like high-performing teams) require investment in trust, alignment, and shared understanding. Great CEOs understand that keeping their boards aligned is not just about reporting performance but about instilling confidence that the team is executing the right strategy over the right timeframe. These CEOs also find ways to ensure the board feels connected and committed to the plan, not just approvers at a distance. How can CEOs achieve this level of effective communication and collaboration with boards? In my experience, it comes down to three key actions: 1️⃣ Inform the board of the broader landscape A board’s role is to guide and challenge, but it can only succeed here if it understands the external forces shaping the business. CEOs should ensure their boards have a clear view of market shifts, competitive pressures, and how the team is responding, both operationally and strategically. 2️⃣ Connect today’s actions to long-term success A CEO must help the board connect the dots on how today’s actions lead to long-term success. It is not enough to present updates and numbers; CEOs need to articulate how each decision and milestone is part of a larger strategic vision. This helps the board see (1) what is happening and (2) why it matters for the company’s ultimate success. By linking actions to results (and acknowledging when they don’t deliver as expected), CEOs help the board build confidence in a plan, not just the random walk of the market. 3️⃣ Reinforce a learning mindset Winning is the goal, but setbacks are inevitable. The best CEOs remind their boards that when the company is not winning, it is learning. By showing how the organization adapts and improves, CEOs instill confidence that challenges are being met with resilience and strategic thinking. The board and CEO are in this together: to grow, compete, and win. A well-aligned board is not a passive observer but an active partner in success.

My board members are some of the most valuable thinkers I’ve met. Here’s what I do to ensure the time we spent together is as thoughtful and strategic as possible: 1. Focus on collaboration & transparency I come prepared with questions and discussion points to get different perspectives and everyone involved. And use financial reports and performance metrics to tackle a strategic issue and company’s long-term direction. I’m honest about how I’m doing and how the market may or may not affect my goals. 2. Build a preparation plan I invest in heavy prepwork up to a month before every board meeting. I ask my department heads to put together a 3-6 page doc outlining where they’ve been & where they’re heading to get a better picture. We compile a single doc that we share ahead of the live meeting. This way, they have full context and background. Then in the live meeting, we can take advantage of the board’s expertise and focus on how to move the company forward. 3. Tap into your board’s superpowers What can each board member offer your department heads to help them move the needle? I like to learn the board inside-and-out and build the agenda around those key conversations. I intentionally facilitate conversations between my board members and my executive staff to ensure we’re fully taking advantage of these superpowers. I’ve been running Clari this way for 10 years, and it’s been essential to our growth.

THE BOARD STRATEGY THAT CHANGES EVERYTHING: WHAT GREAT CEOS DO DIFFERENTLY Do you live in perpetual dread of board meetings? You spend days preparing detailed progress reports, praying you’ve hit your numbers, hoping no one is going to ask the hard questions you don't have answers to. The error is in thinking your board is there to evaluate you when, in fact, they’re not. They’re there to AMPLIFY YOU. I think you’ll find that this reframe could change everything about how you experience your board relationships. YOUR THINKING BEFORE: The Report Card Approach 👎 Focus on proving you have everything under control 👎 Present problems only after you'd solved them 👎 Ask for money and approval 👎 Defensive when challenged 👎 Information flows one way: down to them AFTER THIS REFRAME: The Strategic Partnership Approach 👍 Focus on getting help with what you don't have under control 👍 Bring problems while you are still solving them 👍 Ask for insights and connections 👍 Curious when challenged 👍 Information flows both ways Here are some simple tactical changes that will help you transition from the first kind of relationship to the new and improved one: Send the board deck 48 hours early. Don't make them absorb information during the meeting. Use meeting time for discussion, not presentation. Lead with your biggest challenges first. Save the good news for the end. Board members want to earn their equity by helping you solve hard problems. Ask specific questions, not generic ones. Instead of "Any thoughts on our go-to-market strategy?" try "Sarah, given your experience scaling B2B companies, what would you prioritize: investing in outbound sales or product-led growth?" Hold post-meeting calls with individual board members. Some of the best advice comes in one-on-one conversations, not group settings. Share customer feedback, both positive and negative. Board members make better decisions when they understand your customers' real experience. Be vulnerable about what you don't know. The phrase "I don't know, but here's how I'm planning to figure it out" builds more confidence than pretending to have all the answers. Don’t forget: Your board members didn't invest in your company to sit in quarterly meetings and nod approvingly. They invested because they want to be part of building something significant. Stop treating them like parents who need to sign your report card and more like strategic partners. What's one challenge you're facing where your board's collective experience could actually help you move faster? *** I’m Jennifer Kamara, founder of Kamara Life Design. Enjoy this? Repost to share with your network, and follow me for actionable strategies to design businesses and lives with meaning. Want to go from good to world-class? Join our community of subscribers today: https://lnkd.in/d6TT6fX5