The question she asked herself at 2am

The sorting is the work most leaders skip.

I haven’t stopped thinking about a question Alyson Deutsch asked herself at 2am.

Alyson is SVP of Product at Lexia, a Cambium Learning Group company. Earlier that day, she’d shut down her Head of Product Management in a meeting, in a way she felt the moment it happened.

He’d raised something about the roadmap. Before he’d finished his sentence, she’d already cut him off with the historical context and the reasons his approach wouldn’t work. The meeting moved on. That night, the conversation didn’t.

She kept replaying it. And the question she finally arrived at was this:

Am I uncomfortable because I was direct, and direct isn’t my default? Or am I uncomfortable because I did something antithetical to my values?

Those questions have different answers, and they lead to different next conversations.

If you’re uncomfortable because you were direct in a moment that needed it, the work is to sit with the discomfort. Direct doesn’t always feel good, especially for leaders whose default is collaborative. The discomfort might just mean you were unfamiliar with what direct feels like to

you.

If you’re uncomfortable because you stepped off a line you actually care about, the work is repair.

Alyson was clear which one she was in. She’d been direct, yes. But that wasn’t what was bothering her. She’d shut down a person she respected in front of someone else, instead of being curious. That was a values violation.

By the time she’d sorted it, the next morning had arrived. And when she opened her calendar, the repair was already there.

A 15-minute meeting. He’d booked it. The subject line: “I want to talk about that conversation yesterday.”

“Thank you,” she said when they got on the call. “I do too. Thank you for putting this on the calendar. I’m going to start. I was out of line.”

The move he made, naming the conversation directly and bounding the time, is what I keep coming back to. Most people on the receiving end of being shut down send a vague “we need to talk” instead. That’s the heaviest message you can send, because it sits in someone’s head all day waiting to detonate. Or they say nothing, and let the resentment compound. He did neither.

That move isn’t reserved for direct reports talking up. It’s available in any direction. Name what happened, bound the time, send the invite.

And the response Alyson made, taking the first turn with “I was out of line,” is what most leaders can’t pull off in a repair conversation. They get defensive. They explain why they did what they did and make the case that they were right on the merits. Alyson didn’t, because by 2am she’d already done the harder work.

If she’d shown up still believing she’d been right to shut him down, the repair wouldn’t have landed. It would have been performance.

Most leaders feel the discomfort after a tough moment and either decide they did wrong, or rationalize it away as “I had to be tough.” Both moves let them skip the harder one.

The sorting is the work.

It’s harder than either collapse, because it requires sitting with the discomfort long enough to know what it actually is. That’s where the leadership happens.

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This an edition of the Full Picture Leadership series, where I talk with experienced leaders about the hidden dynamics behind high-stakes moments, so you can recognize them faster in your own work. You can connect with Alyson Deutch and me on LinkedIn.