How to Address Board Challenges

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.

Most CEOs treat board meetings like show and tell. They trot out department heads to give status updates on every minor detail. I've been on both sides of the table, and the best CEOs I've seen take a very different approach. They focus on their top 1-2 most critical issues. These are issues that either: 1. Inhibit short-term success 2. Pose a risk to long-term success They know what business issues are critical to those two points, and they zero in. When you overload the board with random data points, they don’t know what’s important. If you bring them into the weeds on every issue, you’re inviting micromanagement. Personally, I’ve sat through way too many board meetings that feel like a departmental show and tell. But that’s not what the board is for. They’re a strategic resource, there to advise on the most important business problems. Want better board meetings? – Focus on the top 1-2 issues and go deep. – Get the senior leaders responsible to present the issues to the board. – Provide context (where we are today) using data and qualitative info. – Have responsible senior leaders present 1-2 strategies for solving the issue. Once you present the board with solutions to your big issues, THAT’S when things get interesting. Because you’ve given the board something specific they can actually respond to. When you provide them with a clearly defined problem and several potential solutions, they can drop in with insights and expertise—which is what they’re there for. Now you’re collaborating, problem-solving strategically. When you approach meetings this way, you demonstrate that you understand your major business problems and the data needed to quantify them. You show the board that your executive team is on the ball with solutions at the ready. Don’t waste your time with the board on low-level non-issues. Go deep on what matters and use their collective wisdom and broad perspective to take informed action.

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 

I talked about mastering board meetings at a recent webinar with Notion. Founders think these meetings are about delivering good news, but in reality, you need to be aggressively transparent, set clear expectations, and address tough questions directly. 1. Start with an executive summary that focuses on the largest drivers of revenue and distinguishes between fixed and variable costs. Keep it focused on what has the highest impact—this isn’t the place for deep dives into features. Give your board the information that actually matters. 2. Outline the top wins and the key challenges. Be transparent about setbacks. Board members want to know what didn’t go as planned and why. Always address those directly. This is how you build credibility and trust with the board. 3. When you’re talking about risks, don’t sugarcoat it. If there’s a major contract that fell through, unexpected costs that blew the budget, or an increase in attrition, bring it up. The board is looking for straightforward details to understand the current reality. 4. Use your financials as the core story. Share the P&L, balance sheet, ARR, CAC, and burn. These metrics let your board see exactly how the company is performing and can guide your conversation around strategy and risks. Puzzle helps with this. 5. Take the time to prepare for these meetings. Send materials at least a week in advance and follow up with each board member individually to address their questions. Use the template I made (link in the comments) to manage each of your board meetings and send out prior as a pre-read. 6. Use the board meeting to explore strategic decisions. Raise key questions like whether it’s time to launch a new product or if scaling hiring is an option. Leverage your board’s experience for big, directional conversations. 7. Keep the communication tight after the meeting. Send a follow-up email covering the minutes, unresolved questions, and clear next steps. This consistent communication keeps everyone aligned and avoids surprises down the road.

I have deep empathy for management as a board member. You have hard goals, and not enough resources to do everything. Having spent a lot of my time in board meetings, I wanted to give some guidance to managers/CEO’s who present to boards. 1. In general, your message to the board on the state of the business should be the same as to your employees. I have seen some managers who think that boards should have “the best case” presentation. This leads to the board getting a rosy picture of things, where perhaps there are actual challenges. The risk becomes that the first time the board will hear about the challenges is when something misses. Also, in this age, a lot of employees will communicate with board members and when the stories diverge it is always an issue. 2. When you identify your priorities, be consistent across meetings. Most board members are only getting information from attending meetings. Some managers will present the problem of the moment at each meeting. I think the best presenters are those who are consistent in saying here is what we said in the last meeting, and here is what we have done, and here is where we are going. What board members love is progress and a clear story of progress. 3. Give credit to others. Sometimes, the spotlight is seductive and managers will spend a lot of time on their accomplishments. I think it is super important to realize that leadership and management is a team sport. There is no reason to alienate other folks in the room with too much self focus.

A wise colleague told me once that boards do two things: 🔍They find problems; and 💡They help you solve them Faced with that reality, why would you ever let them find the problems? Don’t you have plenty of knotty problems you can bring to them? Wouldn’t you rather be the one asking the tough questions? Saying, “I need your help raising money” is not what I’m talking about. That’s tactical, not strategic. It’s real, but it’s not deep. That’s not the type of generative issue board members are hoping to solve. It’s the type of issue they will help you solve if they are fully engaged in the deeper issues of the organization – if it is just ONE of their responsibilities. Remember that Einstein once said, “If I had an hour to solve a problem I'd spend 55 minutes thinking about the problem and five minutes thinking about solutions.” Invite your board members to be part of the 55 minutes. ✅ Identify your biggest organizational challenges  ✅ Determine what counsel and advice you need to narrow the problem down ✅ Target board members who probably bring a viewpoint on the issue or whose understanding of the issue you want to deepen. Of course, all of this starts with your board president. Run the issue by her and suggest a few board conversations you would like to have. Now, helping you solve an issue is a full board activity.  Who knows? Maybe it will even lead to a strategic conversation at a Board meeting! I know it’s hard when you’re worried about the gala and end-of-year fundraising. Remember, if you want good end-of-year fundraising, you need your board to be highly engaged and passionate about the mission and helping you attract the resource you need to solve real problems YEAR ROUND. #executivedirector #nonprofit #boardofdirectors