Tips for Improving Strategic Thinking in Boardrooms

I’ve been both a CFO and a Board Director. This is where strong CFOs still lose the room. ↳ They speak finance. Boards speak trade-offs. Here’s an example: Early in my tenure, I told the board in a quarterly meeting: “The risk is too high.” A director smiled and asked: “Compared to what?” That question changed how I show up in boardrooms. 💡 Most CFOs learn to see risk in absolutes: - Can we afford it? - What’s the downside if it fails? - How does this hit the plan or forecast? Those are necessary questions, but they’re incomplete. Boards think in portfolios. They’re asking different things: - What does this unlock that staying safe won’t? - Is the upside meaningfully larger than the downside? - Which risks are reversible, and which ones lock us in? Here’s the bridge between CFO thinking and board thinking 👇 1) Frame risk relative to the whole business Not “this could fail.” But “this risk is small relative to our growth gap, capital base, or strategic exposure.” Context changes the conversation. 2) Separate visible risk from hidden risk What shows up in the forecast isn’t always the biggest risk. Inaction, delay, and missed learning compound quietly. Boards are very aware of that. ⏳ 3) Pair every risk with a lever for action If the risk starts to show up, what do you do? Slow it down, narrow the scope, cap the spend, or stop the initiative altogether. Boards aren’t risk-averse. They appear risk-averse when the risk isn’t framed in context. 🧭 When CFOs learn to speak in their language, they stop sounding like the brake. And start sounding like the guide.

I blew too many board decks early in my career. I’d walk in with 100 slides, every metric possible, proud of the grind. The board nodded… nothing moved. Waste of time. Now I sit on multiple boards. I see founders making the same mistakes. Here’s where it goes wrong, and how to fix it. - Data dump, no take You flood the room with numbers, then stop. No context, no call. Fix… for every chart add two lines: “What this means” and “What we’re doing next.” If you can’t write those, the slide doesn’t belong. - Activity theater You recap how busy the team was instead of how the business moved. Fix… tie updates to 3 company priorities. For each, show target, actual, delta, owner, next milestone. Busy is not progress. - Surprise agendas You spring topics in the meeting and hope for magic. It won’t happen. Fix… lock topics 5 days ahead. Send pre-reads 72 hours before with a clear “ask” for each topic. People do better work when they prep. - Jargon soup You assume investors know your world as well as you do. They don’t. Fix… plain language. Define acronyms once. If your mom wouldn’t follow it, your board won’t either. - No decision frame You ask for a decision without telling people how to think about it. Fix… give the lens. What tradeoffs matter, what factors carry weight, what risks you’ll accept. Guide the room to be useful. What the board actually needs from you: - The 3 metrics that matter Examples… ARR growth, net dollar retention, cash runway. Show target vs actual, trend, and the single root driver. One sentence each. - Why those metrics matter now Brief context… pricing change hit SMB churn, CAC rising in paid, enterprise sales cycle slipped 18 days. No fluff, just cause and effect. - The 1–2 decisions you want help with Example… EU launch Q4 or Q1, hire VP Sales now or post-Series A. Make the ask explicit. “I need a go, no-go, or guardrails.” - A simple decision framework Spell out how to weigh it… speed vs burn, growth vs dilution, risk vs upside. Give options A, B, C with pros, cons, and your recommendation. Show the tradeoffs like an adult. How to prep so the meeting produces decisions, not noise: - Topics agreed in advance Email the agenda and asks 5 days out. “We will discuss X. Please weigh in on Y using these factors.” - Context one-pagers For each decision, attach a single page: background, options, primary factors, risks, recommendation, the specific ask. No novels. - Plain English packet Kill the jargon. If you must use it, add a one-line definition. You’re aligning a room, not flexing. - Strategy over tasks Open with the 3 priorities, not the 30 tasks. Close each section with “impact on the mission.” - Traffic-light the plan For each initiative… status, owner, next milestone, blocker, help needed. Green, yellow, red. Ask for help on yellows and reds. My slide test is simple… Question, Fact, Meaning, Action. If a slide doesn’t pass that, it’s filler. You don’t get extra credit for volume. You get results for clarity.

Kiran had 8 years of experience. Sarah had 18 months. Guess who became his boss? • - - When Kiran first met me, he was frustrated and confused. "I don't understand it, Meera. I've been here longer. I know the business better. But somehow Sarah got the promotion I've been waiting for." Here's what I discovered during our first session: - Kiran treated every meeting like a surprise test. - Sarah lined up support before meetings even started. The difference? Sarah did the work before the room, not in it. • - - I taught Kiran four strategies that transformed how he operated: INFLUENCE HAPPENS BEFORE THE ROOM → Map the stakeholders who matter most → Understand their priorities and concerns   → Plant seeds in 1:1 conversations → Build alignment before you need the "yes" Example: Before asking the CFO for budget approval, Kiran grabbed coffee and asked about his month-end close concerns. He then repositioned his proposal around time savings during close periods. By meeting day, the CFO was already nodding. TURN OBJECTIONS INTO ALLIES → Ask "What would make this a win for you?" → Address concerns privately, not publicly → Give people ownership in the solution → Let them feel heard before you push forward Example: The Head of Sales always blocked ops changes. Kiran asked him privately: "What would make this easier for your team?" Sales wanted faster processing for urgent deals. Kiran built in an express lane. Sales became his biggest advocate. MAKE DECISIONS FEEL INEVITABLE → Share context that leads to your conclusion → Walk people through your reasoning → Create moments where they connect the dots → Let them arrive at your answer independently Example: Instead of saying "We need to hire," Kiran shared the numbers: "Volume is up 40%, and we're at 320 orders per week with two people who can each handle 200." His boss did the math and concluded they needed to hire. She thought it was her idea. POSITION YOURSELF AS THE STRATEGIC THINKER → Start conversations with "I've been thinking..." → Reference broader company goals in your proposals → Connect your ideas to leadership's priorities → Show you see around corners, not just straight ahead Example: Kiran connected his ops idea to the CEO's retention goal: "Adjusting our fulfillment by 2 days cuts late deliveries 30%, which hits the renewal rate target from the town hall." His SVP pulled him aside: "I need you thinking at this level more often." Two weeks later, he was invited to the quarterly C-suite planning sessions - a room he'd been trying to access for 8 years. • - - Three months later, Kiran got promoted to VP of Operations. "Before, I'd walk in hoping to persuade," he told me. "Now I walk in knowing I already have." That's influence done right. • - - If you're ready to go from "best-kept secret" to "next VP," let's talk. DM me. *Client details changed for privacy. References available for serious inquiries.

If every board meeting at your nonprofit organization leaves you feeling wrung out and wondering, “Why does this have to be so hard? You’re not alone. I spent my first six months as a new ED creating custom PowerPoints for each meeting. Staying up late to perfect slides that board members would glance at for thirty seconds. Here's what transformed our board meetings from heroic scrambles to strategic sessions: 𝟭. 𝗖𝗿𝗲𝗮𝘁𝗲 𝗮 𝗦𝘁𝗮𝗻𝗱𝗶𝗻𝗴 𝗘𝗗 𝗥𝗲𝗽𝗼𝗿𝘁 𝗧𝗲𝗺𝗽𝗹𝗮𝘁𝗲 Same structure every meeting: • Mission moment (a story that shows impact) • Key metrics dashboard (same 3-5 goals each time, like the photo) • Progress on strategic priorities • Challenges needing board input • Wins to celebrate The time lever? You're filling in a thought-out template, not reinventing the wheel. 𝟮. 𝗦𝗵𝗶𝗳𝘁 𝗙𝗿𝗼𝗺 𝗥𝗲𝗽𝗼𝗿𝘁𝗶𝗻𝗴 𝘁𝗼 𝗘𝗻𝗴𝗮𝗴𝗶𝗻𝗴 Instead of treating board meetings like show-and-tell: • Finance committee owns the financial dashboard • Program committee presents one strategic spotlight each quarter • Board members rotate leading a 5-minute reflection question • Every agenda item has a clear purpose: 𝗜𝗻𝗳𝗼𝗿𝗺 → 𝗔𝗰𝘁 → 𝗗𝗲𝗰𝗶𝗱𝗲.When everyone knows whether they’re hearing an update, moving something forward, or making a decision, the conversation stays focused and productive. When everyone is clear about whether they’re hearing an update, moving something forward, or making a decision, the conversation stays focused and productive. And now you're building engagement. 𝟯. 𝗕𝘂𝗶𝗹𝗱 𝗮 𝗥𝗵𝘆𝘁𝗵𝗺 𝗧𝗵𝗮𝘁 𝗥𝗲𝗶𝗻𝗳𝗼𝗿𝗰𝗲𝘀 𝗖𝗹𝗮𝗿𝗶𝘁𝘆 • Week -3: Committee chairs confirm and their pieces • Week -2: Compile materials using your template • Week -1: Send agenda and materials (yes, a full week early!) • Meeting day: Focus on decisions, not updates The predictability creates space for what matters: strategic thinking and real governance. 𝟰. 𝗠𝗮𝗸𝗲 𝗣𝗿𝗼𝗴𝗿𝗲𝘀𝘀 𝗩𝗶𝘀𝗶𝗯𝗹𝗲 Use the same dashboard every meeting. When board members see the same metrics improving (or struggling) over time, they understand the story. They can spot trends. They ask better questions. No more starting from scratch to explain context every single time. ----- Here's what happened when we made this shift: • Board meetings became energizing instead of exhausting, for everyone • Members showed up more prepared because they had the information and materials in advance • We made actual decisions instead of just sharing updates • My stress levels went waaaaay down Most importantly? The board stopped being an audience and became true partners in governance. That's what happens when you stop managing meetings and start building rhythms. When you make the process 𝗱𝗼𝗮𝗯𝗹𝗲, it becomes 𝗱𝘂𝗿𝗮𝗯𝗹𝗲. And board service becomes 𝗱𝗲𝘀𝗶𝗿𝗮𝗯𝗹𝗲. #DoableDurableDesirable #NonprofitLeadership #BoardGovernance

She spent WEEKS crafting the perfect slide deck. She never made it past slide 1. I watched an MD of Strategy walk into an ExCo presentation with 20 beautifully designed slides. By minute 5, the CFO had hijacked the entire conversation with one question about assumptions. The remaining 40 minutes? A masterclass in executive interrogation. Welcome to the reality nobody warns you about: Executive presentations aren't presentations. They're structured conversations where executives compete for influence, and your content is often just the playing field. After 25+ years watching brilliant leaders crash and burn in the boardroom, here's what actually works when the discussion off-ramps right on slide 1: 𝗧𝗵𝗲 𝗘𝘅𝗖𝗼 𝗦𝘂𝗿𝘃𝗶𝘃𝗮𝗹 𝗙𝗿𝗮𝗺𝗲𝘄𝗼𝗿𝗸 𝟭. 𝗕𝘂𝗶𝗹𝗱 𝗬𝗼𝘂𝗿 𝗗𝗲𝗰𝗸 𝗕𝗮𝗰𝗸𝘄𝗮𝗿𝗱𝘀 Your slide 1 isn't your opening. It's your entire presentation compressed into one visual. If they stop you there (they will), you've still delivered your core message. Think newspaper headline, not chapter one. 𝟮. 𝗧𝗵𝗲 𝟯-𝗣𝗼𝗶𝗻𝘁 𝗣𝗼𝗰𝗸𝗲𝘁 𝗦𝘁𝗿𝗮𝘁𝗲𝗴𝘆 Before you walk in, identify your three non-negotiables — the points that MUST land regardless of where the conversation goes. Weave them into every answer. Make them impossible to miss. 𝟯. 𝗠𝗮𝘀𝘁𝗲𝗿 𝘁𝗵𝗲 𝗥𝗲𝗱𝗶𝗿𝗲𝗰𝘁 𝗪𝗶𝘁𝗵𝗼𝘂𝘁 𝗥𝗲𝘀𝗶𝘀𝘁𝗮𝗻𝗰𝗲 "That's an important consideration. It actually connects to [insert your key point]." You're not fighting their agenda. You're incorporating it while staying on message. 𝟰. 𝗨𝘀𝗲 𝗤𝘂𝗲𝘀𝘁𝗶𝗼𝗻𝘀 𝗮𝘀 𝗜𝗻𝘁𝗲𝗹 𝗚𝗮𝘁𝗵𝗲𝗿𝗶𝗻𝗴 Their questions reveal what really matters. The CFO asking about assumptions? Cost is the hidden concern. Adjust your narrative in real-time to address their actual worry, not your planned story. 𝟱. 𝗧𝗵𝗲 𝗦𝘁𝗿𝗮𝘁𝗲𝗴𝗶𝗰 𝗣𝗮𝘂𝘀𝗲 When hit with a curveball: "Let me think about that for a moment." Those 3 seconds let you choose response over reaction. Executives respect thoughtfulness over haste. I once saw a Director of Product nail this perfectly. Her deck had 30 slides. She presented exactly zero of them. Instead, she read the room's energy, abandoned her script, and led a discussion that addressed every unspoken concern. She got full funding. And a promotion six months later. Because here's the truth: They're not evaluating your slides. They're evaluating your ability to think on your feet when the plan falls apart. Your preparation matters. But your agility matters more. The executives who thrive don't mourn their unused slides. They celebrate landing their message despite never getting past the title page. 🎯 𝗪𝗵𝗮𝘁'𝘀 𝘆𝗼𝘂𝗿 𝗯𝗲𝘀𝘁 𝗿𝗲𝗰𝗼𝘃𝗲𝗿𝘆 𝗺𝗼𝘃𝗲 𝘄𝗵𝗲𝗻 𝗮 𝗰-𝘀𝘂𝗶𝘁𝗲 𝗹𝗲𝗮𝗱𝗲𝗿 𝗱𝗲𝗿𝗮𝗶𝗹𝘀 𝘆𝗼𝘂𝗿 𝗲𝗻𝘁𝗶𝗿𝗲 𝗽𝗿𝗲𝘀𝗲𝗻𝘁𝗮𝘁𝗶𝗼𝗻 𝘄𝗶𝘁𝗵 𝗼𝗻𝗲 𝘂𝗻𝗲𝘅𝗽𝗲𝗰𝘁𝗲𝗱 𝗾𝘂𝗲𝘀𝘁𝗶𝗼𝗻? ------------ ♻️ Share with someone preparing for their next boardroom battle ➕ Follow Courtney Intersimone for unfiltered executive survival strategies

As a VC, here is exactly what I emailed every portfolio CEO before we joined their board: “Most BOD meetings create a huge burden on the CEO and are unproductive. You don’t have to make pretty slides (unless you’re visually inclined). A written memo format works too. Just make sure to send out any BOD materials at least 3 days ahead. Assume everyone has read it in advance so you can focus on the big picture. Think of the BOD meeting as a chance to get free advice on 1-3 strategic topics where you think other BOD members can help you. Aim for less than 20% of the time to be focused on metrics and at least 80% on the strategic topics of your choice. It all starts with how you structure the agenda. Don’t give too much time to the financials & metrics (as long as you sent them out in advance). Here’s an example of a format that can work well: 5m: CEO update 5m: Financial update 5m: Metrics update 5m: Industry updates 20m: Strategic Topic 1 20m: Strategic Topic 2 20m: Strategic Topic 3 10m: CEO & BOD members only discussion An example of some strategic topics to discuss might include: - We have 9 months of cash left, how should we manage burn - Our customer base is too concentrated. Let's chat about diversification. - Privacy policy changes in the industry and our reaction? - Can we get input on next year's proposed annual plan? - Should I promote this internal candidate or go external? - Our team and I are feeling burned out, what are we doing wrong? - I want to pivot the business, let's walk through my plans. Feel free to bring in other executives or fractional leaders if it helps sets context but make sure there’s enough time for just you & the BOD (e.g. the executive session).” No one gave me any of this advice and just expected me to know what to do. I wasted so much time putting together slides and then felt obliged to explain every single metric. It was also so boring for everyone involved. When you focus on strategic topics, you can put your BOD members to work for you and help you think through things that are important to you. It took years and years of making these mistakes until I finally figured out how to use this time wisely… so I truly hope this helps other Founders.

What I learned about #boardmeetings through two companies: Your board update shouldn't be a history lesson. Through #CoverWallet and now Functional Finance, I've learned that the best board conversations focus on variance analysis: What We Predicted: Our forecast What Actually Happened: Actual results Why There's a Difference: Analysis and our response This framework transforms backward-looking reviews into forward-looking strategy sessions. Your board members' experience becomes an asset in problem-solving, not just oversight. But here's what's made the biggest difference: pre-meeting engagement. I now send board materials early and specifically invite written comments and questions before we meet. Board members can digest the content, think through their perspectives, and share initial reactions. By the time we're in the room, we've already had multiple rounds of thinking. I can address their written feedback upfront, and we dive straight into the substantive discussions that matter. The result? Richer conversations, better decisions, and board members who feel genuinely engaged in helping solve problems rather than just receiving updates. This week has been all about analyzing what happened, planning for what's coming and changing what was not working. What's your approach to making board meetings actually valuable?

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.

Here’s why sharing strategic thinking “frameworks” without context is useless (and what actually works). I see posts like this infographic daily on social media—pretty boxes, buzzwords… and zero actionable insight. The brutal truth? Posting frameworks without explanation is career virtue signaling at its worst. Strategic Thinking Is actually critical right now: ✅ 57% of business leaders say strategic thinking is the #1 soft skill their workforce desperately needs (Springboard 2024) ✅ The World Economic Forum 2025 Future of Jobs Report confirms analytical thinking remains the TOP core skill demanded by 7 out of 10 companies globally. While everyone’s obsessing over AI and technical skills, the most successful professionals are the ones who can think strategically about those tools. Here are 5 ways I coach my clients to actually develop their strategic thinking which you can adopt right now: 1. Master the “So What?” Question After every data point, analysis, or meeting, → Ask, “So what does this mean for our goals?” Force yourself to connect dots, not just collect them. 2. Practice Scenario Planning Weekly Pick one business decision facing your team. Map out 3 potential outcomes and their implications. This builds your strategic foresight muscle. 3. Reverse-Engineer Successful Strategies Study companies that solved problems similar to yours. What assumptions did they challenge? What patterns can you extract? 4. Create a “Strategic Time Block” Block 2 hours weekly for big-picture thinking. No emails, no tactical work. Just strategic reflection and planning. Non-negotiable. 5. Teach Your Thinking Process Explain your strategic reasoning to others. If you can’t teach it clearly, you haven’t thought it through deeply enough. Strategic thinking isn’t about memorizing frameworks from infographics on Pinterest. It’s about developing the mental discipline to see patterns, challenge assumptions, and connect seemingly unrelated pieces. The professionals who master this will be irreplaceable. The ones who share pretty frameworks will be forgotten. Which one are you? Coaching can help; let's chat. | Joshua Miller #executivecoaching #professionaldevelopment #careeradvice #getahead

I sit on several boards across sectors, stages, and sizes. This is what separates an effective board that adds value from one that just ticks boxes 👇🏻 1️⃣ Clarity over theatre. A good board doesn’t perform. It sharpens. It brings clarity to strategy, risk, and execution, not just a quarterly review. 2️⃣ Diversity of perspective. Not just gender or background, though that matters too. I’m talking about cognitive diversity. Different ways of thinking. People unafraid to ask difficult questions. 3️⃣ Constructive tension. The best boards don’t always agree. They debate, challenge, and pressure test. But always with respect and alignment around the end goal. If your board feels too comfortable, it probably isn’t doing its job. Strong boards create stronger companies. Not through control, but through: ✅ Rigour ✅ Perspective ✅ Accountability When leveraged effectively, a board is a company’s most powerful asset.