Thirteen names on an email

I met Jesse Haines in a line at Kellogg over twenty years ago, and I think we connected before we'd even introduced ourselves. She's the friend who has a little extra dose of magic — the one who thinks about things from more facets than anyone I know, and who once gave me the push I needed to actually start this whole coaching chapter of my life during a walk at our last reunion. She said, "What's the worst that could happen? Just go out and say you're doing this." And I did.

Jesse spent 17 years at Google founding and scaling high-impact initiatives before becoming a partner at Shakti, an early-stage venture firm. When she sat down with me for Full Picture Leadership, Jesse described a morning that hasn't left me. It’s become a frequent touchstone in my coaching work because it gets to the heart of what leadership actually asks of us when no one is watching.

She woke up to an email with thirteen names on it. People she'd hired. Laid off. Some had already tried to badge into the office and been locked out. Jesse hadn't been consulted. Hadn't been briefed. Found out the same morning they did.

Listen to Jesse reflect, in her own words, on the impact of that morning.

Immediate reactions, even before a morning shower

Still in her pajamas, Jesse started calling the people who'd been let go. Not HR. Not her boss. The people. When I asked her about it, she said something I keep returning to: "I almost don't know if I was thinking about it. The human instinct just kicked in."

I love this line because it cuts through so much of what we think leadership preparation is supposed to look like. In my coaching work, I spend a lot of time with leaders rehearsing for hard conversations — anticipating objections, planning the message, getting the framing right. And that preparation matters, genuinely. But what Jesse's story revealed is something I think we all quietly know and rarely say out loud: the moments that tell you the most about who you are as a leader are the ones no one put on your calendar.

There's no rehearsal for the 6am email. It's just you and whatever instinct shows up first.

Jesse's instinct was to be human before she was a manager. I think that's worth sitting with.

The tension that is the job

Here's the part that stuck with me even more than that morning.

In the days after, Jesse described something I recognized immediately from the leaders I work with: in the morning, someone on her team is asking, "Does this company even care about me?" By the afternoon, she needs that same person ensuring key deliverables are completed on-time without a compromise in quality. There was no clean line between caring for her people and getting back to work. She couldn't do one and then the other. It was messy and overlapping and simultaneous. Her mantra through it: "I know this is hard. And I believe we can do this."

I hear a version of this tension in almost every engagement I'm part of — leaders who feel like they're failing because they can't separate the human part from the operational part. As if they're supposed to process the feelings, close that chapter, and then shift to execution. I've come to believe it doesn't work that way. Jesse's story confirmed it. The tension between care and execution isn't a sign you're doing it wrong. It is the job.

And maybe the most honest thing any of us can do in those moments is exactly what Jesse did: name both truths at the same time.

Something worth paying attention to

I want to leave you with something practical, because Jesse's story made me want to pay closer attention to my own patterns and I think you might find value in it too.

Next time something unexpected lands on your team, notice your first five minutes. Before the meeting. Before the email. Before you've figured out what to say. What do you reach for first — the plan or the people? Your laptop or your phone?

I'll be honest, my own instinct leans toward figuring out the plan before I've sat with the people. It's a pattern I'm trying to catch earlier, and Jesse's story is part of why.

That gap between the moment and the first thing you do — I think there's real self-knowledge in there. We invest so much energy preparing for the leadership moments we can see coming. It might be worth knowing who you are in the ones you can't.

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This is from my conversation with Jesse Haines on Full Picture Leadership interview series — where I talk with leaders I admire about the moments that actually shaped them. New episodes and reflections land here. If someone forwarded this to you, subscribe below.

I'm sharing more from my conversation with Jesse on LinkedIn this week and would love to hear what resonates.