The 5 Conversations Every Great Tech Leader Must Learn to Have

Real leadership shows up in hard conversations. Here’s how to say what needs to be said, early, clearly, and with care.

People think the hardest part of leading in tech is handling priorities, people, and products all at the same time. But that’s not where things really get tough.

The real challenge shows up in a quiet meeting, when you need to say something uncomfortable.

Maybe someone isn’t performing well. Maybe two teammates are clashing. Maybe you made a bad call, and now it’s on you to speak up. Not just fix it behind the scenes, but actually say it out loud.

That’s the kind of moment that turns a manager into a leader.

And the truth is, no one really teaches you how to do it. You don’t learn this in school. It’s not part of onboarding. And when the moment finally comes, you already feel behind.

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I’ve seen brilliant engineers turn into average managers because they couldn’t talk through discomfort.

I’ve also seen humble, emotionally aware people lead with quiet strength, simply because they knew how to say what needed to be said, in the right way, at the right time.

So, in this article, I want to walk through five conversations that will probably come up in your journey, maybe sooner than you think. And I’ll share not just what they are, but how to start them. Because once you find your own words, it gets a little easier to lead with honesty and care.

Let’s start with something that happens more often than we like to admit: a team member is falling behind, and no one’s talking about it yet.

1. “This Isn’t Working”: The Underperformance Conversation

What is it

You have a team member who’s not delivering. Not failing entirely, just missing the mark more often than not. Tasks take too long. Reviews come with too many issues. Deadlines are hit with last-minute crunches. And maybe the most important part, nobody seems surprised anymore. You see the pattern, but it’s easier to justify it as “just a rough patch.”

Why it matters

When you stay quiet, you think you're being kind. But what you’re really doing is giving the problem more time to grow. Silent tolerance slowly turns into passive disappointment.

Others on the team notice you’re ignoring it, and their respect for you starts to shrink a little. And the person struggling? They feel it. Even without words, they know something is off. But without clear feedback, they can’t fix it.

And there’s a hidden trap here: the longer you wait, the harder the conversation becomes. Instead of giving feedback when the cost is small, you wait until it becomes a big deal. Then it feels harsh, even unfair. It’s like letting a plant die slowly and only deciding to water it once it's already brown.

How to do it better

Start early. You don’t need a formal meeting or a heavy script. Just be honest, specific, and human. Try something like:

“I’ve noticed a few things lately that I think we should talk about. You’ve been such an important part of the team, and I want to make sure we’re not letting small issues turn into bigger problems.”

Use facts, not feelings. Instead of “you’re not motivated,” say, “in the last three sprints, we’ve had three missed deadlines, and the QA feedback doubled.” That helps the person focus on what can change, not feel personally judged.

Then listen. This part matters. Maybe something's going on outside work. Maybe they’re stuck, confused, or just overwhelmed. Performance problems are rarely about laziness. Often, they’re about friction, either in process, skill, or confidence.

What to avoid

Don’t wait for a performance review. And don’t surprise someone with public criticism. No one improves from shame. Also, avoid vague feedback like “you just need to step up.” That feels like judgment without direction.

Instead, be the kind of manager who speaks early and kindly, like someone offering a map before the storm, not someone pointing out the wreckage after it hits.

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