On having tough conversations

The weight of saying it. The weight of staying with it.

There’s a particular silence that settles before a hard conversation. Not the loud, dramatic kind, but a shift in the air. A flicker of unease. A glance at the clock. The sudden urge to rearrange your tabs.

These days, I try to stay in that silence. Not fill it. Just sit with it, even when my chest tightens and my brain starts offering me an out: Maybe it can wait. Maybe it’ll pass. Maybe they already know.

In my early days of managing teams, I thought design leadership meant protecting the work, like pushing back on bad calls and defending the craft. But with time, I’ve learned that it has even more to do with people. Especially when things get uncomfortable.

Culture doesn’t take shape in all-hands or OKRs. It forms in quiet, uneasy, deeply human 1:1s, often the ones you most want to skip

Here are the things I’ve been learning (and relearning) along the way to make these conversations smoother:

1. Clarity is kinder than niceness

There’s a kind of feedback that sounds kind in the moment: polite, padded, easy to hear. But it leaves the other person unsure of what to do next. It also softens the actual impact of what needs to be said.

I’ve said things like, “You’re doing well overall, just a few small tweaks,” or “Maybe be mindful of tone, but it’s probably fine.” I thought I was being gentle. But I was being unclear.

Niceness makes you feel better in the moment. Clarity helps the other person grow.

Now I ask myself: if I were on the other side of this conversation, would I know what to do next?

✔️ Say:
“In the last two reviews, I noticed you moved quickly past tough feedback without engaging. That could signal defensiveness, even if that’s not your intent. Do you feel that way as well?”

✋🏼 Avoid:
“There were a couple of moments where the energy felt a little tense in the reviews. Maybe keep that in mind next time while presenting.”

Clarity doesn’t mean cold. It just means you’re giving them the respect of being direct and the support to meet you there.

2. Real conversations don’t follow scripts

I’m a fairly structured person. I used to prep for tough conversations very carefully. A thoughtful opening, sandwiching in the praise, a measured tone.

But people don’t follow scripts. And real conversations get messy.

There’s no template for what to do when someone goes quiet. Or looks away. Or says, “I don’t see it that way,” and you know they mean it.

And in that moment, what matters is not what you memorized. It’s whether you are fully present, listening, and able to adjust.

Some people need space before they can speak. Some want the context. Others just want the truth. One person hears feedback and feels energized. Another hears the exact same thing and shuts down.

The real work is knowing how to meet them where they are, not where your script says they should be.

A few shifts have helped me stay grounded in those moments:

🕰️ Check if they’re ready
“Do you want thoughts on this now, or would it help to sit with it first?”

This respects timing. Some people need a minute to breathe before they can hear you.

✍🏼 Narrate your intent
“I want to bring this up because I care about your growth, and I don’t want to let it slip.”

This reminds them you’re not trying to catch them off guard. You’re doing this because it matters.

️️️🗣️ Addressing your discomfort
“This is a little awkward to say, but I’d regret not bringing it up.”

This softens the moment. It tells them you’re being real, not performative.

They sound simple, but they shift the tone. They make room for honesty even when the topic is hard.

3. Avoided conversations also hold a cost

Some conversations are hard because of what needs to be said. Others are hard because they’ve gone unsaid for too long.

It usually starts small. A moment you notice but don’t name. A shift in tone. A deadline that slips. You tell yourself it’s not the right time.

But silence doesn’t stay small. It spreads.

People notice when someone speaks over others, and no one steps in. When deadlines slip and nothing shifts. When the energy changes and no one acknowledges it.

You tell yourself you’re being patient and giving space. But most of the time, it’s just discomfort you’re trying to avoid. The longer it sits, the more unclear everything becomes for you, for them, and for the team watching quietly from the sidelines.

4. The hangover post the conversation

Some conversations take more out of you than you expect.

You walk out of a tough 1:1, close the tab, and try to move on. But something lingers. A lump in your throat, but with a whiff of relief. The sense that, even if the words were right, the moment was heavy.

You replay what you said, again and again. Wonder if you were too direct. Or not direct enough. If they felt supported. Or blindsided.

It took me a while to realize this feeling isn’t a signal that something went wrong. It’s just part of the work. The quiet after something hard has been said.

I see this discomfort as a reminder that I’m showing up for the hard parts and that means showing up fully.

There’s no perfect way to have these conversations. Some days I still get it wrong. Some days I over-explain. Some days I underplay. But what I try not to do anymore is disappear from the moment.

I show up. I say the thing. I stay when it’s messy.

That’s the work. That’s the job.