What My AI Reminded Me About Leadership

Back before Slack. Before smartphones. Before "BRB" was a status option, I was working from home, and I was paranoid.

Not in a dramatic way. It was the kind of paranoid where you convince yourself that the moment you stand up, someone important will call and you will somehow miss your entire career. Or you’ll get fired because they don’t believe you’re really working.

This was way back when, remember? Nobody knew how to work from home.

So, I stayed put. Hour after hour afraid to move away from my desk.

Eventually I got a dog. Not because I'd always wanted one, though I had. I got a dog because I needed an excuse. An actual living creature that would look at me with those pleading eyes and force me out of my chair a few times a day. She became my permission slip to be human.

I've been thinking about that dog a lot lately.

Because this week, I've been chained to my desk again, except this time it's not anxiety driving it. It's excitement. The kind that hijacks your brain at 11pm and makes sleep a negotiation. AI, and specifically Claude, has been producing ideas, suggestions, analytics, graphics, and strategic to-do lists faster than I can process them. Some days I don't want to stop. I lose track of time. I forget to move away from my desk. Just like before I adopted that dog.

Other days? Frankly, I get up and take a loop around the house just to cool down.

Because Claude also drives me absolutely crazy!

The New Employee Problem

Here's what I didn’t initially realize about working with AI: it's a lot like onboarding a new hire.

You get ready. You create the training docs. You set the expectations. You hand over the processes, the org charts, the prior work samples. You assign them a few simple tasks with a set of instructions and that good natured, “feel free to grab me if you have any questions.”

 And then you look at the first output and think, what the heck is this?!

So, you ask questions. Kindly. Patiently. You try to figure out where things went sideways. And more often than not, the answer comes back: the instructions were a little vague.

And you want to be offended, because you wrote those instructions. You know exactly what you meant.

But then you go back and reread them, and you see it. The gap. The assumption you made without realizing it. The context you forgot to include because it lived so clearly in your own head that it never occurred to you to say it out loud.

Oh. Right. I never told you about Sue. And you'd need to talk to Sue to get the data to do the thing I asked.

That's been my week with Claude. Every time I start a conversation outside of the dedicated project I set up, Claude starts fresh. No memory of the style guides. No context from our previous sessions. It's like handing someone a blank Word document and expecting them to execute flawless copy in your brand.

Maddening. And mostly my fault. Yet, completely fixable. Just like our leadership approach.

The Leadership Lesson I Didn't Plan to Write

Here's what I keep coming back to: this is exactly what we do to our people.

We hire someone. We give them the agenda, the videos, the org chart and an office tour. We introduce them to six people in forty minutes and expect them to remember every name. We hand them the onboarding doc we wrote eighteen months ago and haven't updated since. And then we wonder why their output doesn't match what we envisioned.

We assume they absorbed what we said. We assume they know the unwritten rules. We assume they understand the why behind the what, because to us, it's obvious.

It is rarely obvious.

To shift from frustration and considering this another “issue” all comes down to how self-aware you’re willing to be.

Do you see the part you play?  You can get frustrated that the expectations weren't met. Or you can ask yourself: did I actually set those expectations clearly? Did I communicate them in a way the other person could receive? Did I check in before I checked on the output?

Taking a step back to discern the root issues, to clarify expectations, to minimize assumptions, ask questions, and explore perspective compassionately, those are not soft skills. They are the hard work of good leadership. They are also the skills that no AI, no matter how sophisticated, can replicate on your behalf.

On Watches and Compassion

I expect Claude to go check our existing files and conversation history before answering me. It doesn't, unless I explicitly tell it to check them.

It’s a bit like how I expect my team to hold the details of our strategy in their heads at all times. They don't. Neither do I, honestly.  And your new employee surely won’t grasp and recall it all.

I lost my watch once for an entire year. An entire year. It was in my house. If I can’t remember where I put my own watch, it’s reasonable to expect we all need repeatable process, diverse and frequent communication, and a chance to clarify before assuming misalignment.

The answer isn't lower standards. It's more intention. Clearer communication. And a generous, ongoing supply of compassion, the kind you extend to your new hire, to your AI, to your team, and to yourself.

Aim. Act. Adjust. That's the Helm Method. And the Adjust part? It always comes with a side of grace and a huge helping of compassion.

The Unmachined Skill Set

Here's the thing about working alongside AI every day: it makes the human skills more obvious, not less.

Claude can write fast. Claude can generate frameworks and pull patterns and synthesize information in ways that would take me hours. What Claude cannot do is read the room.

It didn’t know I was annoyed at repeating myself. Claude cannot feel the frustration rising in a team nor decide, in the moment, to pause and just ask how someone is actually doing.

Judgment. Presence. Compassion. The ability to hold a mirror up to your own assumptions and adjust before any damage is done.

Those are the Unmachined skills. The ones that make you indispensable when you hone and harness them with intentional leadership. The deliberate development of those capabilities, in yourself and in your leaders, is what Boss at the Helm is built around.

Being Unmachined doesn't mean resisting technology. It means harnessing it while staying relentlessly, deliberately human.

Your Move

If any of this sounds familiar, whether you're the leader who forgot to tell someone about Sue, or the one who keeps wondering why everyone else is the problem, then start here:

• Watch our weekly Mini but Mighty℠ Leadership Lessons on YouTube at youtube.com/@BossattheHelm. Short, practical, and free. New every Friday.
• Ready to go deeper? Our Boss at the Helm online courses will give you and your managers a practical, no-fluff framework for leading with intention. Available to individuals and teams.

And if your organization is navigating transformation and your managers are winging it, let's talk. Reach out at [email protected].

Lead yourself. Then lead others. Be a Boss.