Years ago, I watched a head of product slowly lose their mind trying to execute what they knew was a terrible idea.

The CEO had suggested putting up physical signs around San Francisco to attract more users to their B2B software platform. Not billboards with our brand. Not transit ads with a clear value proposition. Just… signs. Like, go to Office Depot and buy poster board and markers and put up signs. Around San Francisco. To get enterprise software buyers.

The head of product came to me frustrated: “I know this won’t work, but he’s the CEO. He pays our salaries. We have to do what he says.”

Here’s what I told them: “Just don’t do it.”

Their eyes went wide. “I can’t just ignore the CEO.”

“You’re not ignoring him. You’re solving the actual problem he cares about.”

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The Power Imbalance No One Talks About

Here’s something I’ve observed in multiple companies, and it baffles me, but it’s true: CEOs often have no idea how much weight their words carry.

They’ll throw out a random thought, like “What if we tried putting up signs?” and move on with their day. Meanwhile, three product managers spend the next week researching sign vendors and calculating foot traffic patterns in SoMa.

The CEO wasn’t giving a directive. They were thinking out loud about how to get more users.

But because of the power imbalance inherent in organizational hierarchy, that casual thought becomes a mandate. The team treats it like Moses coming down from the mountain with stone tablets, when really it was just “Hey, here’s a random idea I had in the shower.”

What the CEO actually cares about is increasing users. Full stop.

They don’t care about signs. They care about results.

The Framework: Interests vs. Positions

This is straight from negotiation theory, and it applies perfectly to these situations.

Apositionis what someone says they want: “We need to put up signs around San Francisco.”

Aninterestis why they want it: “We need more enterprise users.”

Most people get stuck arguing about positions. “Signs won’t work because…” But that’s the wrong conversation. You’re defending against a solution instead of solving for the actual interest.

Here’s the better approach:

1. Assume Positive Intent and Good Judgment

Start by believing the CEO is smart and has good reasons for their thinking. They didn’t get to be CEO by consistently prioritizing bad ideas.

Ask: “Help me understand what you’re hoping to accomplish with this approach?”

Not “Why do you think this will work?” That’s defensive. You’re seeking to understand their goal, not challenging their solution yet.

2. Validate Their Interest (Not Their Position)

Once you understand the goal, validate it in a way that adds value to the conversation.

Don’t just repeat: “So you want more users.”

Instead: “You’re seeing that our current growth rate won’t hit the targets we need for the next funding round, and we need a way to accelerate user acquisition that doesn’t require a massive marketing budget increase. Is that right?”

This shows you understand both the immediate interest (more users) and the broader context (funding timeline, budget constraints).

3. Engage with the Solution Directly

Now you can address the proposed solution. But you have to actually engage, not just back down at the first sign of disagreement.

“I don’t think signs will achieve that goal effectively. Here’s why: our users are IT directors and CTOs at mid-sized companies. They’re not walking around San Francisco looking at signs when they’re evaluating enterprise software. They’re dealing with specific pain points in their current tools.”

Be prepared for pushback. If the CEO says “But it would create brand awareness,” you need to respond with data and alternatives, not just nod and leave the meeting defeated.

“Brand awareness is valuable, but we’re already losing users who try the product because of three specific friction points in onboarding. If we solve those, we retain 40% more of the users who already find us, which gets us to target faster than any awareness campaign.”

4. Offer a Better Path to the Same Interest

That’s where most people stop too early. They explain why the idea won’t work, but they don’t offer an alternative that achieves the actual goal.

In our case, we researched what our users’ biggest complaints were and addressed those issues. We improved retention, which increased active users faster than any sign campaign could have brought in new ones.

The CEO was happy. Because what he cared about was increasing users, not signs.

“But I Don’t Have Your Experience”

You may be thinking: “Matthew, you had 20 years of credibility when this happened. I’m three years into my career. I can’t just tell the CEO their idea won’t work.”

You’re right that the power dynamic is different. But here’s what I’ve observed: CEOs who are actually good at their jobs welcome input from anyone who can help them achieve their goals, regardless of title or tenure.

They don’t want yes-people. They want results.

The key is in how you approach the conversation. You’re not saying “You’re wrong.” You’re saying “I want to help us achieve this goal, and I think I see a faster path.”

That’s not insubordination. That’s exactly what they hired you to do.

What Actually Happens When You Speak Up

The risk isn’t as high as you think.

The worst realistic outcome isn’t that you get fired for respectfully disagreeing about strategy. It’s that the CEO says “I appreciate your input, but I want to try this approach first.”

And then you do it, because they’re the CEO and they get to make that call.

But most of the time? They appreciate someone who actually engages with ideas instead of just nodding and leaving meetings to complain in Slack.

You gain their respect by being willing to have a real conversation, not by agreeing with everything they say.

The Skill Behind the Skill

The broader lesson here is about organizational courage.

Most people treat disagreement with authority as inherently risky. But silence is riskier, both for your career and for the company’s success.

If everyone on the team knows something won’t work but no one says anything, you don’t just waste time and money on a failed initiative. You create a culture where people stop thinking critically and just wait to be told what to do.

That’s how smart teams ship terrible products.

Your job isn’t to do what you’re told. Your job is to achieve the outcomes the company needs, and sometimes that means finding a better path than the one initially suggested.

Even when that suggestion comes from the CEO.

Monday Morning Action

Next time you’re in a meeting and someone in authority proposes something you think won’t work:

1. Ask yourself: What’s the actual interest behind this position

2. Before you leave that meeting, ask: “Help me understand what you’re hoping to accomplish?”

3. Once you understand the goal, validate it in your own words

4. If you disagree with the approach, say so directly: “I don’t think that will achieve the goal because…”

5. Offer an alternative: “Here’s what I think would get us there faster…”

You don’t need permission to have these conversations. You just need to remember that the person behind the title cares more about results than about being right.

Try this approach once this week and reply to tell me how it goes. I’m genuinely curious whether this lands differently depending on your organizational context.

Best,

Matthew

P.S. This advice is based on negotiation theory and crucial conversations frameworks, but honestly, it’s just about remembering that CEOs are humans who want to succeed, not infallible authorities whose every utterance is sacred. Treat them accordingly.