Page 32 of The Hard Launch

She raises her marker to the - column and looks at me.

“I know who you’re going to put there,” I say.

“Do you disagree?” she asks me.

“Who are we talking about?” Kate whispers to Trevor.

“Keith. Our CTO is a dumbass,” Trevor whispers back.

I can’t deal with this right now. Give me a time machine dialed back half a year and sure, I’d hire someone better. At the time, Edmund was pressuring me to bring on a CTO, and what I liked about Keith—that no one else seems to appreciate—is that I knew he wouldn’t fight me on anything. The trouble is, he doesn’t fight the engineers on anything, either. Because he might be a dumbass.

“What if we don’t tell him there’s a dinner?” Lacey suggests.

“Or—hear me out,” Trevor says. “We bring Dave, but we gaslight Edmund by just insisting that he’s Keith.”

They all start laughing and I would too, except for the part where I start to see Edmund’s point about my leadership.

“I promise you two things,” I tell the team. “One, Keith will be fine. He’s at least clever enough to talk like a CTO. Remember, Glenn didn’t hate him at first. And two, if we survive the next month, I’ll bring in a proper CTO. I mean it.”

And I do. First I go check in with Rob, and discover he likes to talk about sports too much. Edmund only likes golf, and Rob’s entire personality outside of sales is college football. He’s not going to do us any favors. I mentally demote him from the ? list.

I spend an hour coaching Keith on the vision, the tech, and why he believes in this as the future of Lettercat. He might be a man out of his depth, but he’s a survivor. He certainly won’t wow anyone, but the bar for personality is basically on the floor when it comes to CTOs. After I decide he’s ready, I set a reminder for myself to check in with Keith after the next board meeting. Whether Lettercat survives or not, I owe the team something better.

I spend so much time on the business side of things that when Lacey pops into my office two hours before our dinner reservation, I don’t tell her we’ll be in beta next week. Because we won’t be. Instead I ask her if she thinks adding two contractors to the team would be at all worthwhile.

She sits down on my couch.

“We’ll figure that out tomorrow,” she says. “I want to hear your strategy for tonight.”

I confess that I don’t really have one outside of my usual, which is Try Not To Piss Off Edmund.

“I’m not claiming to be an expert in this—I’m not even done with the book Glenn recommended about it. But it’s called managing up; basically using empathy to improve your relationship with your boss. Just like when you talk about framing the Lettercat story for the board. Only it’s your story, and it’s for the person who manages you.”

I sit on the other end of the couch and listen while she tells me how I might adjust my communication style and method to suit the people in charge of me, how it’s especially helpful when they’re difficult. I need to be better at anticipating what Edmund wants from me and offering it to him before he even asks.

We go through all the things we think Edmund is looking to see from me tonight, and what I can do to reinforce that I have them. It requires a shift in my thinking, but I’m happy to do it. Whatever I’ve been doing hasn’t been working.

“Thank you,” I tell her. “I mean it. It makes a lot of sense.”

She nods and gets up, smooths her skirt. “You’re going to do great tonight. Don’t stress.”

She might say this last part because my head is in my hands.

“Lacey,” I say, looking up as she leaves. She turns around in the doorway.

“Did Glenn recommend that book to help you deal with me?”

She looks like she’s about to crack a joke until she sees how serious I am.

“Yes,” she admits. “But not because you’re a tyrant, Jude. I just never tried to see things from your point of view.”

I think about what I heard her saying on the elevator that day, but decide to let it be.

“Before I go, one more bit of unsolicited advice,” she says.

“Anything. I’ll take all of it,” I tell her.

“This one’s more of a question: do you have any shirts that don’t say ‘Lettercat’ on them?”