Leading With Meaning

If you manage people, here’s something uncomfortable.

Whatever you model around rest, your team is copying.

Not because you told them to. Because that’s how culture actually works.

My team watched me answer emails from the airport. Watched me come back from every trip spending the first week on every call apologizing for being slow, as though I’d done something wrong instead of using time the company formally gave me.

Nobody had to write any of that into a policy.

When your best person takes a week off and answers Slack the entire time, that isn’t a character flaw they showed up with. That’s your training program, working exactly as designed.

I eventually took four years off. Not a sabbatical with a return date. Four years, out of corporate work entirely, to deal with everything I’d been pushing aside. It cost me money. It cost me momentum. I have never regretted it for a second.

What I regret is the arithmetic that made it necessary.

After the reset, my final score was two email checks per vacation. That was my improvement after thirty years in the business.

Progress. Technically.

But to everyone still in it: two weeks costs a lot less than four years.

Take them. And don’t apologize on the way back in.

I missed a border crossing in Thailand because I was answering an email nobody needed.

On the trip of a lifetime.

We were doing a train trip across Southeast Asia. A night on a houseboat on the River Kwai. Best food I’ve ever eaten.

And I spent part of it in my inbox.

Lost track of time zones. Ended up on the wrong side of a border watching my train leave. What followed was a taxi, a gap in a fence, and a sprint my wife won by a comfortable margin.

I’m pretty sure I heard her laughing.

Thirty years of telling my team to actually disconnect on vacation. Knowing better and doing better - not always the same skill.

That gap is what this week is about.

Part 1 of 3.

You only need 4 stories to ace your interviews.

I talk to a lot of folks who are in the middle of their next job search these days, and I always hear people express: “Interviews are scary.”

Why?

“I hate feeling like I'm on the hot seat.”

“I'm never certain what they're going to ask me. I try to prepare for thousands of different potential questions.”

But by over-preparing, you actually put yourself in a position to come across as less confident.

One of the biggest tips that I give my coaching clients is this: Have three or four stories that you know cold.

Stories that demonstrate your skill, your strengths, your experience, that demonstrate how you work, how you collaborate with others, how you think, how you solve problems.

Have four stories like that that are adaptable to a wide variety of different types of questions.

You want stories that don't necessarily paint you in the best light, but that you learned from to show your ability to learn and grow.

You also want a story that talks about one of your greatest successes and ties it to specific business results.

But the main thing is to make sure that as you're telling your stories, you have intentional places where you can pause and ask a question back to the interviewer.

That's how you turn that interview from an interrogation into a conversation, and a conversation is where you're going to win.

For more tips like this or to have a conversation ahead of your next interview and see where your stories stand, go ahead and click the link in my bio and set up a time to call or just drop me a note.

I look forward to working with you on the next phase of your career.

I’ve started calling it the prison of “one day, maybe.”

The irritating part is that the door isn’t actually locked.

People wait to feel like leaders before they lead. Wait to feel ready before asking for the promotion, changing careers, having the conversation.

And the wait doesn’t resolve.

Because the feeling you’re waiting for is manufactured by doing the thing.

You have the hard conversation badly. Then the next one slightly less badly. You delegate something and it comes back wrong — congratulations, you just learned something about delegation. You make a decision with incomplete information, own what happens next, and discover that despite all available evidence to the contrary, you survive.

That’s the curriculum. There isn’t another one.

I should probably admit that it took me fifty years and a layoff to apply this to myself. I had savings, a network, options. I already wanted to do something different.

And I still waited until somebody else picked the timing for me.

I don’t particularly recommend that part.

So if there’s something you’ve been sitting on — don’t make it dramatic. Pick the smallest real version of the move. Ask for the meeting. Send the email you’ve rewritten eleven times. Register the domain. Have the conversation.

Not because you’re ready.

Because readiness is on the other side.

Part 3 of 3.

I told a client to take two weeks off.

She was a talented journalist, mid job search, completely fried. The scattered, high-speed version of her wasn’t helping anyone, least of all her.

So I said: stop. Rest. Two weeks.

When she came back, she apologized for taking the time off.

I had assigned it. She apologized for doing it.

That’s when I started thinking about what I now call the inner scorekeeper.

It’s the part of you that doesn’t care what your manager said, what your coach said, or what your out-of-office message says. It has its own standard of what’s acceptable, and it runs quietly in the background keeping score.

That’s why you send the “I’ll be back Monday” note from the beach. Why you do the apology tour when you return from holiday. Why you feel the need to perform busyness even when someone has explicitly told you to stop.

External permission can’t quiet it. It doesn’t accept that currency.

The note from your boss saying “enjoy the break” doesn’t reach it.

The thing worth asking is whether your inner scorekeeper is actually serving you — or just keeping you tired.

Confidence is not the fuel.

It’s the exhaust.

I’ve had a few hundred coaching conversations at this point, and this pattern is remarkably consistent.

Someone wants the promotion. The raise. The career change. They’ve apparently owned the domain for their future business since around 2012.

I ask why they haven’t done it.

The answer is usually some version of: “I’m not ready yet.”

Then they show me the person they’re comparing themselves to. Someone with the title. Someone who made the jump two years ago. Someone on LinkedIn who apparently wakes up every morning radiating executive certainty.

Here’s the thing.

I’ve coached those people too. They’re improvising. They just started improvising sooner.

And somewhere between the things that worked, the things that didn’t, and the things they somehow survived — confidence showed up.

That’s the whole stupid thing.

You don’t need it to start the trip. It’s what you bring home from taking it.

And then everybody looking at you assumes you had it before you left.

Part 2 of 3.

Tomorrow: what actually happens when you keep waiting.

Confidence is not the fuel.

It’s the exhaust.

I’ve had a few hundred coaching conversations at this point, and this pattern is remarkably consistent.

Someone wants the promotion. The raise. The career change. They’ve apparently owned the domain for their future business since around 2012.

I ask why they haven’t done it.

The answer is usually some version of: “I’m not ready yet.”

Then they show me the person they’re comparing themselves to. Someone with the title. Someone who made the jump two years ago. Someone on LinkedIn who apparently wakes up every morning radiating executive certainty.

Here’s the thing.

I’ve coached those people too. They’re improvising. They just started improvising sooner.

And somewhere between the things that worked, the things that didn’t, and the things they somehow survived — confidence showed up.

That’s the whole stupid thing.

You don’t need it to start the trip. It’s what you bring home from taking it.

And then everybody looking at you assumes you had it before you left.

Part 2 of 3.

Next up: what actually happens when you keep waiting.

Gen Z has got it all figured out - see why 👆

There’s an interview mistake I’ve seen really, really smart people make.

Mid-interview, they find themselves rambling for minutes in response to a question that should have taken 30 seconds to answer.

Smart people especially fall into this trap because they know they have the experience and knowledge to impress the interviewer, and want to be sure it shows up in their answer. They want to be sure they come across as the most qualified candidate.

But the truth is that interviewer is typically not looking for proof of your experience.

They got that from your resume. It's how you got the interview in the first place.

What they want to see is how you answer questions under pressure and how you think on the clock.

That means it matters how succinctly you can answer the question and then move on to the next part of the interview.

You want to answer that question in the first 15 to 20 seconds.

Only add color if they ask a follow-up or ask for more detail.

It lets you take control back over the interview instead of just suddenly finding yourself in the midst of a long explanation that you probably didn't need to give in the first place.

For more tips like this, or to have a conversation ahead of your next interview and see where your stories stand, go ahead and click the link in my bio and set up a time to call, or just drop me a note.

I look forward to working with you on the next phase of your career.