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The conversation most managers get wrong

Week 3 of my 5-part series: how to say no without derailing the relationship (or the roadmap)

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Jul 29, 2025

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4 min read

In partnership with

There’s a specific kind of dread that comes from knowing you're about to say no.

  • No, we can’t take on that extra project.

  • No, we can’t squeeze it into this sprint.

  • No, that feature’s not going to make the launch.

You can already hear the sighs. See the Slack messages. Feel the tension rising.

And so instead of saying no, we hedge.

  • We say “maybe.”

  • We say “let me check with the team.”

  • We say yes—and figure we’ll work it out later.

And then everyone suffers.

The truth is: Saying no is a leadership skill.

It’s how you protect your team’s time. It’s how you defend priorities. And it’s how you build trust—by being clear, not by being agreeable.

But that only works when your “no” isn’t a dead end.

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Here’s a better way to frame it

If you’re struggling with how to say no without looking like the villain, try this structure:

  1. Acknowledge the ask

    ❝

    “I understand why this feels important.”

  2. Show the tradeoff

    ❝

    “To take this on, we’d need to push X or pause Y.”

  3. Offer an alternative

    ❝

    “What if we explored Z as a middle ground?”

This isn’t just softer language. It’s strategic clarity.

You’re not stonewalling. You’re showing how prioritization actually works—and inviting them into the decision.

What this does

It shifts the story from:

  • “They’re being difficult”
    to

  • “This is a complex call with real tradeoffs”

And that change matters - especially when you're working cross-functionally, juggling leadership asks, or trying to keep your team from burning out quietly while everyone else gets their pet project through the door.

One more note

Don’t make your “no” about your team being too busy. Make it about protecting the roadmap, the goals, the customer impact - whatever they care about.

That’s how you go from blocker to boundary-setter. And it’s okay if someone still isn’t happy with your decision. Part of leadership is accepting that you aren’t going to please anyone.

Next week: How to navigate the career expectations conversation (without crushing someone’s motivation).

P.S. My new course Tough Conversations breaks all of this down in way more detail. Preorder now for just $49 and get early access when it drops—plus frameworks, scripts, and a chatbot to practice with.

Preorder here →


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