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Who Is The Better Executive Coach? Dave or dAvId (My AI Clone)

Three scenarios. Two different takes. You decide the one winner.

Read Time: 4 minutes.

My Biggest Management Regret

I thought my job as a new manager was to have all the answers. To always show confidence. To fake it until I make it.

But all that did was slow down my growth and alienate my team.

I was fortunate. I had a boss early in my career who a) called me on my bad habits and b) showed me a better way to lead.

Most new managers aren’t as lucky.

Which is why we created MGMT Fundamentals. Leading a team is hard. But the right skills supported by the right systems make it easier.

Our last cohort until the Q3 kicks off on Tuesday April 8th.

Join the 41 leaders are already enrolled.

A couple recent stats caught my attention:

  • 91% of employees are using AI (McKinsey)

  • 15% of managers use AI consistently (HBR)

This is a bad look for managers.

While I’m not a doomsayer who thinks AI will take our jobs, I am confident that someone using AI will.

AI is just familiar enough to think you get it (“It’s just a really good search!”)
And it’s just different enough that you can’t learn it without being “hands on keys.”

And since I never write about things I don’t do myself, I’ve been leaning into using AI more and more in our business. And incorporating it into our training programs.

Today. I wanted to explore the question:

Could an LLM (in this case Claude from Anthropic, trained on editions of our MGMT Playbook, we’ll call dAvId), offer better coaching on real management problems than me?

I wrote my answers first. Then I asked dAvId and included the answers unedited.

You be the judge.

At the bottom, I’ll ask you to vote on a winner.

Scenario 1: The High-Effort Underperformer

"I have an employee who has been underperforming. He's putting in tons of effort and extra hours but not getting the same results as his peers. I've given regular feedback, and there are moments where I see glimmers of progress. What's the right move?"

Dave's Advice:

You know the move but lack the confidence.

If you've set clear, realistic expectations and provide regular, helpful feedback, and they can't seem to hit the mark, they probably need to go.

But you already knew that.

So what you really need is more confidence in your decision. Here's how I'd build it:

  1. Would you rehire this person today based on what you know? It sounds like No.

  2. The Netflix Keeper Test: If this person told you they were leaving for a competitor, would you fight to keep them? Again, it sounds like this might be a gift.

  3. If you hired a "typical" candidate from the outside, how long before they overtook this person in terms of output? If this number is less than 6 months, it's make your decision easy. If it's more than a year, perhaps you have unrealistic expectations.

If all three questions point you the same direction, it’s probably the correct one.

dAvId's Advice:

"Let's run an energy audit here. Have them track for one week:

  • What tasks consume the most time

  • Which activities produce actual results

  • Where they feel most confident

  • What drains their energy

My hypothesis?

There's a mismatch between effort and impact. Extra hours often mask inefficient processes or unclear priorities.

Three immediate moves:

  1. Shadow your top performer for a day - what do they do differently?

  2. Identify what tasks could be automated or eliminated

  3. Create clear success metrics for each key activity

The goal isn't to work more. It's to make impact easier.

If after optimizing the system, they're still struggling, we have better data for that harder conversation."

Scenario 2: The Overworked Team

"I have an overworked team that's been under capacity for the last couple of months. They seem to be burning out. I tell them they should go home or take a vacation, but no one seems to listen. And it looks like my boss is about to add another critical project next week. Help!"

Dave's Advice:

You won't want to hear this, but this one is on you.

The hard truth that nobody tells us when they make us a manager is a big part of our job is to say No. We can't always say it directly, but we need to embrace that reality.

For example, you can't take that new critical project on unless something else drops.

How are you going to tee that tradeoff up to your boss?

And your team has been overcapacity for months? How are you dealing with that?

From the outside, not very well.

Just like a patient on the edge, you need to triage the situation:

  • What administrative work can we defer?

  • What low-value work can we delete?

  • What meetings can we shorten?

  • Who can you borrow capacity from?

  • Can you hire temp capacity?

  • Can you change service terms?

Use your constraints to drive your creativity.

Once you pull some of these levers, you need to use what little capacity you free up to make real improvements to make your operations more sustainable. Otherwise, you'll be back in the same sport shortly.

Only worse, because you'll probably lose your best people.

dAvId's Advice:

Let's do some capacity mapping:

Current State:

  • List every project and its true time cost

  • Map dependencies between team members

  • Calculate your real capacity (not theoretical)

  • Document where work breaks when someone's out

System Fixes:

  • Create explicit coverage protocols

  • Build rest into project timelines

  • Set up vacation rotation schedules

  • Document key processes so knowledge isn't person-dependent

Before Your Boss Meeting:

  • Show real capacity numbers

  • Present impact analysis of new project

  • Offer clear tradeoff choices

  • Propose phased implementation

Your team needs to see rest built into the system, not offered as an optional suggestion they have to risk-taking.

Scenario 3: The Persistent Promotion Seeker

"I have someone on my team who constantly asks me when they will get promoted even though I don't believe they're ready. I've shared my view on the gaps they'd need to close before moving to the next level, but they think I'm being overly critical. I see a dip in their performance every time it comes up, and I'm fatigued from repeating myself. What should I do differently?"

Dave's Advice:

My guess is there are 1 of 3 things at play:

  1. You're not being as clear as you think you are. I'd invest 15-20 minutes to write down the capabilities needed at the next level, ask them to self-assess against those capabilities (with examples), and assess them myself (also with examples). Then, we could compare notes and uncover where the discrepancies are.

  2. You're not being firm enough about cutting off the complaints. At some point, we need to move forward as a team. And debating promotions is not improving our output. Set a timeline to revisit it (end of year), but be clear you're not interested in revisiting the topic before then. You should know you run the risk that they find someone at another company to bet on them, but if they're not ready, they're not ready.

  3. You're not helping them see the demand side of the problem. If they entered the workforce between 2012 and 2022, chances are the past couple of years are the first slowdown they've seen. So they could be a decade into their career, and the only factor was readiness. However, not all companies are slowing down or even shrinking, so there are few necessary promotions. They may be close to ready; there's nowhere to go.

dAvId's Advice:

Let's build a promotion clarity system:

Create a Performance Position Map:

  • Current level expectations (must-haves)

  • Next level expectations (measurable outcomes)

  • Gap analysis (specific metrics)

  • Progress tracking mechanism

Design the Growth Dashboard:

  • Monthly self-assessment

  • Peer feedback metrics

  • Project impact scores

  • Leadership behavior indicators

Implement Regular Checkpoints:

  • Monthly: Progress review

  • Quarterly: Gap reassessment

  • Annually: Career trajectory planning

This turns 'not ready' from a judgment into data, and transforms promotion from a question into a project they can manage.

Now it’s time to vote. Let’s see where we stand in the Age on AI.

Who gave the better coaching?

Login or Subscribe to participate in polls.

And if you liked this, check out the recordings of our free workshops on Using AI to Optimize Your Management and Using AI to 10x Your 1:1 meetings.

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Dave & Mar

Ways To Work With Me

1:1 Executive Coaching - If you’re the CEO of a growing company with 50-250 employees who need help scaling your systems and upgrading your talent, we should talk. Drop me a note to set up time to see if we’re a good match.

MGMT Fundamentals - Join our next sprint. April 8 - 18, 12:00 pm -1:00 pm ET. Perfect for managers with 0-3 years of experience who want to quickly build the skills and systems to lead their team effectively from Day 1. Enroll today!

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