"You Don't Get Paid by the Note"
A CPO's field guide for communicating with CEOs
I’ve been leading a lot product interviews for clients recently, and I keep seeing the same thing: smart, seasoned operators…who can’t stop talking. As if volume and verbosity signals competence.
It doesn’t. It signals anxiety and lack of mental clarity.
Scratching my head to figure out what’s going on here. Maybe it’s the AI era of “workslop” starting to bleed into how people communicate? When it’s (too) easy to generate words, people forget the job is to reduce them.
Let me assure you: More ≠ competence. The job is clarity.
Back in my 20s and early 30s, I played bass alongside my friend Chuck Suong — a great drummer, and someone who could say more with a single groove than most people could in an entire verse.
Whenever I’d get fancy — young, overplaying, trying to prove something — he’d just look over, shake his head, and say: “You don’t get paid by the note.”
Product leaders: Neither do you.
Every extra sentence is a decision. Every explanation is cognitive load you hand to someone else. In high-stakes conversations — especially with CEOs — that load compounds fast.
But this isn’t new. Product has always been an editing discipline. If you can’t say it simply, you probably don’t understand it yet.
Your CEO doesn’t need more information. They need to trust that the product org has it handled — and that when you speak, it means something.
Let’s get into it.
Start with the CEO’s World
The CEO is context-switching between an investor call, board prep, a pricing conversation with the CFO, a recruiting decision — and then your update. Your whole world is a piece of theirs.
Each day starts with a stand-up meeting for the Fin leadership team, where we go over current customer issues, roadmap items, staffing, resourcing, and any key sales deals we need to be aware of or help push forward. A big part of my day is reviewing Fin product work..Outside of product work, as a founder, board member, and executive, I have a lot of other responsibilities: welcoming new hires, prepping for board meetings, and handling various high-level tasks across the business.
- Des Traynor at Intercom: The Open Source CEO on what the role demands
The product leader who gets this communicates differently. They stop writing updates that prove how much is happening and start writing relevant updates that show where things are headed. The CPO’s job is to hold the path — to give the CEO a clear, confident picture of how the product drives the business. That clarity, delivered consistently and concisely, is what trust is built on.
Part of holding that path is understanding the CEO the way a great PM understands their customers — with real curiosity about where their head is, what the board is focused on, what’s keeping them up at night. The better that picture, the sharper every update becomes.
Stay calibrated: The best CPOs treat the CEO the way a great PM treats a customer. You wouldn’t ship product without talking to users. Don’t manage up without doing the same work.
A few questions worth asking regularly — not about product, but about the business:
What's the narrative we're telling that you're least sure we can back up?
What have you changed your mind about recently?
What’s the thing you’re getting asked about most right now?
The answers change what you escalate. They change how you frame the roadmap. They make your communication relevant.
Follow their curiosity: When the CEO asks a question mid-conversation, answer it directly. Then:
“Can I ask — what’s on your mind there?”
That follow-up is almost always worth it. Their curiosity is rarely random. There’s a board conversation behind it, or an investor concern, or something they’ve been sitting with. When you follow it, you don’t just answer the question — you understand why it was asked. That makes you sharper.
The Operating System
Four simple tools to help avoid the mistake of verbosity in your communication with CEOs.
1. Frame it: Audience → Insight → Ask
This framework is a tiny slice of what Nancy Graves, an executive communication coach, taught me, and working with her genuinely transformed how I communicate. I've adapted the shorthand slightly here, but I want to be clear: this is her work, and it barely scratches the surface of what she does with executives and teams. If you have the opportunity to work with her, take it.
Audience (”As you know…”): Where did you leave off? Sum it up in one sentence so they don’t have to fake context.
Insight (”Since then…”): What’s changed? New data, a shift in direction, something you’ve learned.
Ask (”As a result…”): What do you need? A decision, alignment, a green light. Be specific.
Example:
[audience] As you know, we committed to launching the new analytics module this quarter to support expansion revenue.
[insight] Over the last month, we’ve uncovered consistent reliability issues in the core platform that are starting to impact renewals.
[ask] As a result, I recommend we pause the analytics launch and reallocate the team to stabilize the core experience. It puts near-term revenue at risk, but protects retention. I want to align before we make that call.
Can I walk you through the tradeoffs?
Anchor. Bridge. Ask. No preamble.
(Full post on framing here.)
2. Lead with the conclusion — and have an opinion
The Minto Principle: lead with the conclusion. Always. Let the details follow only if they’re asked for.
But here’s what most miss: you’re not a neutral information highway. The CEO doesn’t need a summary of competing options with a polite “thoughts?” at the end. They need your read. State the recommendation, name the tradeoff, and say why.
My mentor, friend, and two-time boss Steve Goldsmith used to say, “Give me something to say ‘Yes!’ to.”
Weak: “We’re losing enterprise deals. SSO, audit logs, and role-based permissions keep coming up. We could prioritize those or continue with the MCP v2. Wanted to get your thoughts.”
Strong: “We’ve lost five deals worth $200k in the last three months — all blocked on SSO, audit logs, and RBAC. My recommendation is we pause MCP v2 and clear these gaps first. Core retention is strong, so we have room. And this is squarely aligned with the Q2 company goals. I can have a scope in 48 hours if you’re aligned.”
Same situation. One is a status report. One is leadership.
The weekly update that earns trust is the one where the CEO reads the first line and already knows where you stand. One sentence summary. What’s changed. Three priorities, each with a why.
3. Pre-wire
Golden rule: No surprises. The meeting is the punctuation mark, not the sentence.
Don’t make the mistake of setting up an expensive meeting, and expecting your CEO to think through it and debate live.
Pre-wiring means every key stakeholder roughly knows what you’re going to say before you say it. A one-paragraph Slack drop on Monday. A 15-minute sync on Tuesday. A shared draft Wednesday with a comment asking for a reaction. By Thursday, no surprises. The meeting becomes a 15-minute alignment check instead of a 45-minute discovery session.
You shape the story, or someone else will. Drop context. No surprises.
4. The Micro-Yes
When you need to push back or challenge a decision, ask permission before you ask the real question. The moment someone feels ambushed, you’ve lost them.
Without it: “Why are we prioritizing monetization before we’ve validated retention?”
With it: “Can I ask a follow-up on the monetization timeline?” [yes] “I’m curious what’s driving the urgency — my instinct is we need to validate retention first, but I want to make sure I’m not missing context from the board.”
Same challenge. The first is a confrontation. The second is a conversation.
(Full post on the Micro-Yes here.)
Bonus: Tie It Together in a Prompt
Try this with Claude, with the ultimate goal of doing it yourself.
You are my executive communication editor. Rewrite what I give you using these rules:
— First line = where I stand. Lead with the conclusion.
— Have an opinion. Recommendation, tradeoff, why. Flag any hedging.
— Structure: Conclusion → As you know → Since then → As a result.
— Cut anything not earning its place. No throat-clearing.
Rewrite first, no commentary. Then a terse list of what you cut and why.
If I'm missing a recommendation, tradeoff, or ask — flag it and ask the one question that unlocks it.
Draft: [PASTE]
Audience + context + what I want: [PASTE]Remember: You don’t get paid by the note word.
CEOs need to trust that you’ve got it handled — and that when you speak, it means something. Every word you say either sharpens or dulls trust.
Product has always been an editing job. And in this AI era of abounding content slop, the clear, precise communication of a seasoned operator cuts through louder than ever. Do the work!