The one question that breaks your team’s trust


Hey Reader,

Happy Tuesday, friends.

I’ve been thinking about how often the moments that count most aren’t the big ones.

It’s rarely the all-hands meeting, the formal review, or the moment when everyone is looking to you for direction. More often, it’s something smaller that happens in the middle of the day, when someone isn’t quite sure how to solve a problem and you’re already holding a lot in your head.

We’ve all been here: Someone on the team reaches out and says, “Do you have a minute?” and we can usually tell it’s not good news. A deadline’s missed or a client situation has gone sideways, and our problem-solving instincts kick in.

Immediately, we can focus on what happened, how it got missed, and how we can stop it from happening again. And sometimes, we ask a certain question:

“Why didn’t you catch this sooner?”

It’s not unreasonable, especially when we know that person is highly capable. And if we’re already in a busy period, that pressure has a way of narrowing down our focus to the problem in front of us. We forget, just for a moment, that there’s a person who’s also carrying pressure, and made a judgment call that coming to us was the right thing to do.

Our response feels natural. And fair. We help solve things as quickly as possible and everyone goes back to normal. (Right?)

Except, that person who came to you for help…might see it completely differently.

Think about what it took for them to knock on your door. They’ve probably been sitting with this for hours, maybe longer, replaying it, wondering if they should have caught it sooner themselves. Coming to you was the hardest part. They’d already decided to trust you with something they weren’t sure how you’d receive.

Instead of feeling supported, they leave feeling blamed. So they internalize a thought that has bigger consequences down the line:

“If a problem comes up again, it’s better to handle it on my own.”

Yikes.

Once that belief takes hold, it’s tough to let go of. The next time something starts to slip, they wait a little longer before saying anything. They try to predict how you respond, wait until they have more answers, and cover their bases thinking, “If I just get this right, I won’t have to bother anyone.”

This can work for a while, but sometimes there are problems that are just too big for one person to handle alone. And by the time they do reach out, the situation is much harder for everyone to navigate.

It all comes down to remembering how we can respond to our team, even when we’re all under a bit of pressure.

If you came from my LinkedIn Post, you’ve already seen some of the specific phrases that help when someone brings up a problem. (And if you haven’t seen it yet, you can find it right here) What I want to sit with here is how we can make it easier for us to notice what’s underneath the reaction.

Every so often, during a quiet moment, I think about a small interaction I’ve had with someone earlier that day or in the week. Then I ask myself two questions:

  1. Did I make it easier or harder for this person to come to me next time?
  2. If I could have that moment again, what would I do differently?

There isn’t always a clean answer, but noticing where our minds go first tells us something about what we were really paying attention to.

You don’t need to do anything with that this week. Just notice how you feel when someone brings you a problem. Notice what the other person might be walking in with. Notice how quickly the focus moves to fixing, and what else might be there alongside it.

What’s your experience with receiving (or delivering) difficult news?

Hit reply and let me know. I read every message.

From one human to another,

600 1st Ave, Ste 330 PMB 92768, Seattle, WA 98104-2246
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A Normal Tuesday by Clif Mathews

You built everything you were supposed to build. And you're questioning everything. Quietly. It's not burnout. It's not weakness. It's the slow realization that somewhere along the way, you stopped living your life and started managing it. You're not alone in this. I spent 25 years chasing achievement before I saw it clearly. Every Tuesday, I write about what I found. The patterns. The permission to want something different. The occasional uncomfortable truth. No optimization hacks. No hustle. Just honest exploration from someone a few steps ahead on the same path.

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