I saw a Threads post the other day from Dave Minnigerode that made me laugh and then immediately feel called out. He was responding to something and wrote: "Sorry that is. definitely tl;dr. But also kinda ai;dr. Some of those sentences...yeesh."

ai;dr

As in, AI-generated, didn't read. Hilarious.

I'm feeling the ai;dr, folks. It's creeping into our companies. Into our Slack channels. Into our strategy docs, planning decks, and meetings. Who are the people generating it? Sometimes it's the executive. Sometimes it's me.

So yeah... this week's edition is about two things I'm wrestling with. First, what happens when you get genuinely good at AI and accidentally drown your team in output they never asked for? (Hi. I'm the problem, it's me.) Second, a coaching conversation that held up a mirror on something I've been doing for years... asking for permission to do the job I was already hired to do.

Two pieces. One about the ugly side of AI speed. One about the ugly side of our own heads.

♥️kyle

You Got 10x Better at AI. It's Killing Your Team.

We recently acquired a company called 365Talents. During the planning of the announcement, I was using Claude to pull together messaging and positioning... key narratives, stakeholder considerations, internal and external angles, competitive framing. Everything. All the considerations we needed.

And it took twenty minutes. Maybe less.

And I just sat there because guess what? It was good. Really good. Why? Because I'd set Claude up the right way... the projects, the skills, the markdown files, all of it tuned and layered with context. This is what happens when you invest the time to build the system. It works.

My second thought was, "FUCK!" haha.

I produced in twenty minutes what would have taken me days a year ago. Maybe longer. And my team was about to receive a DELUGE of information. Like, way too much information.

Someone who doesn't have that setup. Who doesn't have twenty years of context baked into every prompt. Who's going to open this doc, read it, process it, react to it, and build a launch plan from it?

I made it in twenty minutes. It might take them days to do anything meaningful with it.

Oh shit, it's me. Hi. I'm the problem, it's me.

Here's what I've noticed over the last few months. When you set up AI the right way… and I mean really set it up, with the right projects, the right context, the right Skills… you do become genuinely 10x more productive.

I'm not f'in with you.

I can research, produce, and deliver a strategic brief, a competitive analysis, a campaign framework, a quarterly review doc, and feedback on three different initiatives in a single afternoon. That used to take me a week.

And most of the time, it feels incredible. You feel unstoppable. You feel like you've unlocked a cheat code, because honestly, you probably have.

And then you start to realize your team may not have been given the same cheat code. Maybe they haven't had time to fully set something up. They're still operating at human speed. They're still processing your last doc when you've already moved three ideas ahead.

Yep. You created a firehose, whether you knew it or not.

And here's what is crazy, the bottleneck USED TO BE ME. I was the slow one. I was the leader who couldn't get to everything, who owed people feedback, who was behind because my calendar was literally eating me alive.

Now? I'm still the bottleneck sometimes, but nowhere NEAR where I was before. The bottleneck is the team's capacity to absorb what we are all producing.

That's weird as hell. Because the instinct is to think, "Great, I'm more effective." But effective for WHO? If I'm producing at 10x and my team can only absorb at 1x, I haven't actually created value. I've created noise. I've created ai;dr... except it's landing in my team's inbox, not on the internet.

(And nobody wants to be the leader whose team quietly groans when they see "Kyle shared a doc with you" in their notifications. Hellllll no.)

The expectation creep is the sneaky part. I never said "I expect you to match my pace." I never sent a Slack message that said, "Why haven't you responded to the three documents I sent this week?" I'm realizing that the volume itself becomes pressure. When your boss is shipping that much strategic output, the implicit message is: keep up. Even if you never said those words. Even if you didn't mean it.

I'm trying to think about this differently as we evolve with this massive technological shift in the way we work. The skill should never be "how do I produce more?" The skill is how to produce at AI speed but RELEASE at human speed. How do I batch my thinking?

How do I create space for my team to think, react, push back, and actually engage?

What I don't want to kill is the healthy debate. Because the "I think you are wrong" conversations are what make the work better and more enjoyable in the long run.

Speed without absorption is just noise. And I refuse to be noise.

On Building an AI-Ready Team Without Breaking Them

So if the speed gap is real (and it is), what do you actually do about it?

I've been wrestling with this because there are two truths that exist at the same time and they pull in opposite directions.

Truth one: You cannot keep people around who refuse to adapt to technological change. I've written about this before. AI is not optional anymore. If someone on your team is still doing everything manually and dismissing these tools as hype... that's a performance issue that needs to be figured out.

Truth two: You cannot burn out the people who ARE adapting just because you, the executive with a fully customized AI setup, can move faster than them. And confusing the two will cost you your best people.

And that distinction matters a fucking lot.

Someone who refuses to learn AI? That's a conversation about expectations and fit. Someone who's learning AI but can't match the output velocity of a CMO with Claude Projects, Cowork, and fifteen years of strategic context baked into every prompt? Performance gap? Hell no. It's a gap in your self-awareness.

So, here's where I'm taking it because I don't have a clue what I'm doing but I do have some principles that fit pretty well:

Set the expectation on adoption, not on speed. I expect every member of my team to use AI in their work. Experimenting. Building workflows. Finding the tools that make them better. What I don't expect is for them to match my output volume. My job is different than theirs. Measure adoption, not output.

Create the space to absorb before you ship the next thing. When I finish a doc, my instinct is to send it immediately. It's done. It's good. Why wait? But I'm learning to ask: does this need to go out today, or can it wait until the team has processed what I sent Monday? The worst thing you can do is make your team feel like they're perpetually behind on a reading list they didn't sign up for.

Protect the debate. When you're moving fast and producing a lot, there's always the desire to "just execute this." Why would anyone push back? But that's exactly when you need pushback the most. If your AI-assisted output is so polished that nobody feels like they can question it, you've built a machine that optimizes for speed and kills judgment. And judgment is the whole game.

Look, the speed gap isn't going away. If anything, it's going to get wider. The leaders who adopt AI early and deeply will continue to accelerate. And the question isn't whether you should slow down your own learning... you absolutely should not. The question is whether you can accelerate yourself without accidentally leaving your team in a pile of docs they never asked for.

I'm still figuring it out. But at least I know what's happening.

Stop Asking for Permission to Do Your Job

Have you ever felt this way?

You're sitting in a leadership meeting. You've done the work. You know what needs to happen. You have a point of view that is better than half of what your colleagues are muttering. And instead of saying it... you wait. You reframe your opinion as a question. "What do you think about..." when what you really mean is, "Here's what I'm going to do." You look around the room and defer to the loudest voice.

We know they are probably not right, but they are damn loud. 

I’ve done it. More times than I’d care to admit. 

Early in my career as a marketing leader, I would walk into meetings with a fully formed strategy and still present it like a suggestion. I'd soften everything. "I was thinking maybe we could..." instead of "Here's what we're doing and why." I'd send my boss a Slack message before making a budget call I had full authority to make.

It wasn’t humility. GOD KNOWS it wasn’t humility. It was asking for permission to do the job you were already hired to do. 

Hindsight, ofc. I thought I was being thoughtful, being a team player, reading the room. But what I was really doing was outsourcing my confidence to other people. Waiting for someone to say, "Yes, Kyle, you're right" before I'd let myself believe it.

I was in a coaching conversation recently and heard the exact same pattern being thrown at me. And this was an extremely capable and sharp leader. They also struggle to speak up in rooms full of loud, dominant personalities because they've convinced themselves that their voice doesn't carry the same weight.

And I thought... yep. I know that feeling. I've lived in that feeling.

I wrote about the Shadow Tool a while back (shoutout to Phil Stutz and Barry Michels), and one of the scenarios I shared was sitting in a board meeting, replaying past mistakes in your head while a voice whispers, "What if you get this wrong, too?" That voice doesn't care how many wins are on your resume. It just keeps whispering.

And here’s the thing, it’s not a confidence problem. It’s a permission problem. This person was asking for confirmation on decisions they already had the authority to make. Budget calls, team structure, strategic direction... they had trust and they were still checking in like they needed my thumbs-up.

Same thing I used to do. Same thing I still catch myself doing.

Why the hell do we do this?

Part of it is the room you're in. If you're surrounded by people who are louder, faster, more assertive... it's easy to shrink. You start measuring yourself against their operating style instead of your own. And that’s poison, my friend.

Part of it is how you got to the seat. There's a real difference between building a team from scratch and inheriting one. When you build, every hire is yours, every win (and failure) is clearly yours. When you inherit, there's this question: Am I leading this, or am I just managing what someone else built? That question breeds doubt, even when the answer is obvious to everyone else.

And part of it... honestly, the biggest part... is just head trash. Max Yoder wrote in Do Better Work that great leaders aren't the ones who always have the answer. They're the ones who say, "I don't know, but let's find out together." Owning your mistakes and asking for help doesn't weaken your leadership, it strengthens it. I believe that. I've written about it. And I still catch myself doing the opposite.

So here's what came out of that conversation, and what I keep reminding myself:

Stop asking for permission to do the job you were hired to do. Move from "What do you think?" to "Here's what I'm doing, and here's why." The shift from seeking confirmation to sharing decisions is small in practice and massive in impact. 

The presence of doubt doesn't mean you lack ability. It means you care. That's what the Shadow Tool taught me. You don't fight the doubt. You acknowledge it, you say, "I see you, but I'm in charge now," and you make the call.

And if anyone has told you their imposter syndrome went away, they were LYING TO YOU. It’s always there, it just shifts a little bit. At the director level, it's "Am I strategic enough?" At the VP level, it's "Do I belong in this room?" At the C-suite, it's "Am I going to be the one who breaks this?"

Same voice. Different whisper. Same answer: make the call anyway.