You're not as clear as you think you are
The gap between what you said and what they heard.
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You’ve had this experience. You gave someone feedback. Clear, specific feedback. And then three weeks later, you watched them make the exact same mistake.
“But I told them” you think. “I was direct about it.”
Were you, though?
I’ve spent years watching leaders, including myself, convince themselves they’re straight shooters while their actual communication lands somewhere between “vaguely suggestive” and “completely unclear”. The gap between how direct we think we are and how direct we actually are is actually massive.
You soften the message
Here’s what happens in most conversations where someone needs to hear something hard:
You prepare what you want to say. You think about the relationship. You worry about how they’ll react. And then, in the moment, you soften the message. You wrap your point in so much context and caveats that the actual message gets lost.
You say: “I noticed the ADR had some areas where we might want to think about alternative approaches, and I was wondering if you’d had a chance to consider some of the patterns we discussed last quarter?”
You think you said: “This ADR needs more work before we can approve it.”
They heard: “Minor suggestions, probably optional, handle whenever.”
You need to make sure what you intended to convey is what the other person actually receives. And most of us are failing at that job while believing we’re succeeding.
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Why engineering leaders are especially bad at this
We’re trained to be precise with code. We obsess over naming, over edge cases, over making our intent explicit in the system. Then we walk into a conversation and suddenly become allergic to clarity.
Part of it is risk aversion. Saying something clearly means committing to it. If they push back, you can retreat: “Oh, I wasn’t saying it’s definitely wrong, just that it might be worth considering...”
Part of it is conflict avoidance dressed up as politeness. We tell ourselves we’re being kind when we’re actually being cowardly. There’s nothing kind about letting someone continue down a path that’s going to hurt them or the team. You’re just delaying the pain and making it worse.
And part of it is a fundamental misunderstanding of what directness means. Being direct doesn’t mean being harsh. It means being clear.
Bet on it
Next time you need to deliver feedback, try this: after the conversation, ask yourself what you’d bet money on. If someone offered you $100 to predict exactly what action that person will take based on your conversation, what would you bet on?
If you’re not confident they’ll take the specific action you wanted, your message didn’t land.
I like this test because it separates what you hoped you communicated from what you actually communicated. I’ve failed it dozens of times. I’ll leave a conversation feeling good about how I handled it, then realize I couldn’t confidently predict any behavior change. That’s a communication failure, regardless of how “direct” I felt in the moment.
Graduated clarity
The solution isn’t to start every conversation at maximum bluntness. That’s just trading one failure mode for another. You need to calibrate.
Start and see if it lands. If it doesn’t, get clearer. If it still doesn’t, get clearer again.
First attempt: “I think we should reconsider this architecture before we build more on top of it.”
If that doesn’t land, escalate: “To be specific, I don’t think we should continue building features on this foundation. I’d like us to pause and address the core issues first.”
If that still doesn’t land: “I need to be direct with you: I’m blocking this work until we fix the underlying problems. Here’s what needs to change.”
Most people never get past the first level because they mistake the initial gentle approach for directness. When it doesn’t work, they assume the other person is the problem. Sometimes they are. But often you just haven’t actually been clear yet.
Relationships
Being genuinely direct often strengthens relationships rather than damaging them.
When you’re clear with people, they learn they can trust what you say. They stop having to decode your real meaning. They know that when you say something is fine, it’s actually fine, because you’ve demonstrated that you’ll tell them when it’s not.
The leaders I trust most are the ones who’ve told me hard things clearly. Not cruelly, but clearly. I know where I stand with them. That’s incredibly valuable.
The people I trust least are the ones who I suspect are always softening things. Every interaction becomes an exercise in reading between the lines. Did they actually think my proposal was good, or are they just being polite? I have no idea, because they’ve never demonstrated they’ll tell me the uncomfortable truth.
Experiments to try
If you suspect you’re not as direct as you think you are, and statistically you probably aren’t, here are some suggestions for you:
Say the actual thing first. Most of us bury the point in context, qualifications, and backstory. Flip it. Lead with the conclusion, then provide context if needed. “This approach won’t scale” is clearer than five minutes of background followed by “so I have some concerns about scalability”.
Eliminate weasel phrases. Words like “maybe”, “might want to”, “could potentially”, and “I was wondering if” dilute your message. Sometimes they’re appropriate. Often they’re just padding that lets you avoid commitment.
Check for understanding explicitly. “What’s your takeaway from this conversation?” sounds awkward, but it surfaces misalignment immediately. If their summary doesn’t match your intent, you haven’t been clear enough.
Follow up in writing. After important conversations, send a brief summary of what you discussed and what you agreed on. This catches misunderstandings before they become problems.
A skill worth building
Most communication failures aren’t about the other person being difficult. They’re about you not being as clear as you thought you were.
That mindset puts the responsibility back on you. But it’s also empowering, because it means you can fix it. You don’t need to change anyone else. You just need to close the gap between the feedback you think you gave and the feedback they actually heard.
That’s a skill worth building. Not “being more direct” as some personality trait to cultivate, but getting genuinely good at making sure what you meant to say is what the other person actually understood.
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See you in the next one,
~ Stephane
Ouch, this is R E A L.
We all perceive the world from behind our eyes. We need a mirror to see ourselves. Feedback on how we deliver feedback.
If you're working remotely, see if you can record the feedback conversation (legally and ethically). If you can, watch yourself later, see how you delivered the message. Ask an AI to grade you on how clear it was.
If you can't record it live, then practice with a trusted mentor.
Just give yourself the opportunity to see yourself.