👋 Hi, it's Greg and Taylor. Welcome to our newsletter on everything you wish your CEO told you about how to get ahead.
I spent last week in board meeting “training camp.”
Taylor is out on maternity leave, so I’m coaching a few team members on presenting to the board. These are sharp people with good instincts, but they’re new to this kind of work. And coaching them, I realized I’d never explicitly shared what works … even to myself.
Presenting to high-level stakeholders (the board, senior execs, your client’s boss) is more of a careful dance than a clear playbook. I’ve mostly mastered this dance, but it’s taken me 30+ years … and I’ve had plenty of blow-ups and awkward moments on the way there.
A friend who sits on a lot of boards said to me recently, “You’d be AMAZED how many board meetings are just updates – people are wasting this valuable time.”
I don’t want you to do the same. So here's how to nail your next high-stakes presentation to senior stakeholders.
- Greg
The 75/25 rule of board presentations
The #1 mistake people make is treating a board-level presentation as:
An update (100% presentation with a “sounds good” at the end)
A brainstorming session (75% discussion with a “we’ll circle back on what we go with” at the end)
Board-level stakeholders do not want to spitball with you. Nor do they want to hear you talk with no opportunity for input. They want to absorb your information and point of view, challenge where necessary, and give you a few hard-won insights. In a few cases, they might want to significantly change your recommendation or decision – but not often.
The 75/25 rule: 75% of the conversation should be presentation and talk track. 25% should be a carefully managed (NOT open ended) discussion.
Too structured (95% you talking), and they'll get frustrated at the lack of interaction. Too open (50% or less control), and they'll question why you're wasting their time without a clear perspective.
The presentation dance: Fast, then slow
The most effective presentations feel like conversations, even though they are mostly monologues. Here's the rhythm to master:
Go quickly through the slide content
Make your key points succinctly (and don’t read the slide)
Offer one insight not written on the slide (this shows deeper thinking)
Then shut up – and let them weigh in
Managing the 75% (the presentation)
The presentation should be the bulk of your time – a clear narrative that drives to an outcome. This isn’t a meandering update; it’s a carefully structured argument that helps shape the 25% discussion.
1. Know the outcome you’re looking for, and drive to it
Is it resources, a green light, alignment on a decision, etc.? Your narrative should get you almost all the way across the finish line to this decision. You’re not presenting two options for your audience to choose between – you’re giving an argument for the outcome you want.
2. Send a pre-read (even if it's just 60 minutes before)
Your most engaged stakeholders will read materials in advance. Make sure your deck can stand on its own – aka, it should tell your story without you there to narrate it.
3. Give the context they don’t have
These people aren't in your business every day. They've missed the hours or days of conversations that led to your recommendation. You don't want to replay all that, but you need to catch them up fast – plus give them context for why you’re making this recommendation (outside “I think it’ll work”).
Give a few clear and compelling data points on:
Competitive context: What are others in your industry doing? Board members care deeply about this.
Client anecdotes: Real stories that illuminate the market dynamics. "Three enterprise clients told us the same thing last quarter – they're consolidating vendors and need us to offer this additional capability."
Data-driven insights: Not just metrics, but what the metrics reveal. "Our three key performance indicators all point to the same conclusion: we're hitting a ceiling without this investment."
4. Choose your metrics carefully (and stick with them)
Metrics can make your argument for you – or they can make the board think, “What are we looking at here?” My principles for metrics:
The magic number is 3. Five data points is too many to process, one is not enough context. Three is just right.
Consistency is critical. The best executives or board members keep their notes from previous meetings (and just have good memories). Don't change your metrics between presentations. If you do need to evolve your measurement approach, explain why explicitly.
Show history. Pull in a slide from your previous presentation to demonstrate accountability and continuity.
5. Pre-empt the obvious questions
Senior leaders will immediately spot the gaps in your thinking. Don't wait for them to point these out – address them proactively. And if they ask questions early that you intend to answer later, have the courage to say, “I will get to that in a minute”.
If you’re struggling with the questions your stakeholder might ask, use AI. I use AI before every board meeting, and it’s able to predict the board’s responses with about 90% accuracy.
Ask AI: “Play the role of a critical and discerning board member. What questions would they ask about this strategy and what holes would they poke?”
6. Pre-test critical conversations
If you're proposing something risky or radical, never surprise the whole group at once. Have individual conversations with at least 1-2 board members (or your client, boss, etc.) before the meeting to test your thinking and get initial reactions.
If you get an "absolutely not" in the board meeting, you've usually skipped this step.
Managing the 25% (the discussion)
Not every moment is appropriate to get feedback on – you don’t want to stop after every slide and say, “Any thoughts?”
Instead, look for moments when:
You need their input about a strategic choice to move forward (“Given what we’ve shown you, do you agree with this recommendation?”)
They have specific expertise you lack (“How did you see this play out in telecomm 10 years ago?”)
External factors beyond your control could impact the business (“Are you seeing changes in the funding environment that could affect our timing?”)
Ask the question, then shut up. Give them time to mull it over and respond.
And when they do respond, resist the urge to jump in right away with an explanation or point of view. Tease out the “why” behind their feedback before weighing in.
"Say more about that. I hadn't considered that angle."
"That's an interesting perspective. How have you seen that play out elsewhere?"
"What makes you see it that way?"
When a stakeholder throws you off track
Usually, you’ll get feedback you’ve anticipated and can address. But occasionally, a board member or stakeholder will offer something truly unexpected — a piece of information you hadn’t considered — and disrupt your recommendation.
This is the most delicate part of the presentation, and where many aspiring leaders fail. The worst responses are either getting flustered (all the air comes out of your balloon) or steamrolling (hearing but ignoring as you drive to your conclusion).
You need the mental agility to:
Genuinely hear it
Reflect it back / acknowledge its value
Establish a clear plan to address it: "Let me take that away and come back to you by Friday with some thoughts"
My advice
At the end of the day, good conversations happen when the board (or your stakeholder) is aligned with your strategy. If there is no alignment to the core strategy, all the conversations become much more painful, and you end up arguing over smaller decisions.
At Section, our strategy is to bring 1 million students into “the AI class” via enterprise customers. We have plenty of debates over how to do that (consulting services, ProfAI, exec workshops, etc.) – but because we agree on the strategy, these conversations are productive.
If you’re following all the advice but the conversations aren’t working, consider having a strategy reset. Write down your strategy (best done with your leadership team) and the assumptions that drive it. Ask your board/client/etc. to read it and weigh in. Then go back to conversations about how to deliver on the strategy.
Greg
#2- The Pre-Read…needs to be able to stand on its own without you presenting it. I agree, but that would also make my team more inclined to put a lot more text on every slide to tell the story without them. We struggle with the line between “don’t just read everything on a slide” and how it’s read when it’s out of our hands
These are great instructions to presenting to any group who might shrug, look confused or give you the power to make your dreams come true.
Bonus (especially if this isn't a board and just people in your org) - send them this article as a primer - "This is how I plan on structuring how I'm presenting to you. We're jut as cricital as a board, right?"
Super Bonus - if you lead a team. Share this with them and suggest that you use this format moving forward. Excellent expectation setting exercise.