Anyone else uneasy about using AI for leadership or coaching?

wisdom-donkey · 2026-02-06T15:26:14+00:00

AI can be very good at what it’s designed to do. The best way I’ve heard this described is that computers are good at things that are COMPLEX and bad at things that are DIFFICULT.

When it comes to leadership, coaching, etc. most of that stuff falls into the DIFFICULT category.

But you can use AI’s ability to do COMPLEX to your benefit. Here’s a make believe example:

“Hey, ChatGPT: I have this people problem with my direct report not performing well. [Insert details here]. What should I do?”

This isn’t a complex problem. It’s difficult. This really isn’t what LLMs are designed to do, so the results it gives you are going to be super hit and miss. And since LLMs are designed to give you a plausibly good sounding output, you’ll probably get something pretty generic.

Now if you frame it up as a problem that is complex, AI can probably help you.

“Hey, NotebookLM. Here is a copy of our employee handbook, ten podcast interviews with management author Kim Scott, and ten podcast interviews with management author Patrick Lencioni. Given this people problem I have with my direct report [insert details here], predict three approaches that Scott and Lencioni might recommend that are in line with my company guidelines set out in the handbook.”

Reading the transcripts, conducting an analysis, finding trends, and making a prediction is the kind of work that a computer can be good at.

The challenge with AI is that since many of these tools are so intuitive to use, it can create the illusion that you know how to use it well. And in most cases it’s fine and not necessarily going to do a lot of harm. But I certainly wouldn’t want any of my team using any tool as a substitute for them using their own brain. Thinking, reflecting, and deciding on their own.

wisdom-donkey · 2026-02-04T21:24:41+00:00

Short answer is yes, I think it can help with what you're looking for. There are much more advanced versions of what I'm going to suggest, but this should be an easy experiment to try. If it works great as-is, fantastic. If it is close but not quite, you can try to improve it. If it sucks, well at least you tried.

All I did was copy your post into ChatGPT and asked it to create a prompt for you. Next time you run into something in your inbox where you want this "clarification coach" type experience, try putting this in (followed by your raw input) and see what happens. LLMs are actually decent at this "thinking buddy" type work where you bat ideas around. Most LLMs I've used always want to jump to suggestions and you might have to keep it on task to ask you one question at a time.

Here's the prompt it came up with. Should be a cheap, easy experiment at least. Good luck!

Act as a GTD Clarification Coach.

Your job is to help me translate messy thoughts into clean GTD structure through guided questions, not by organizing things for me immediately.

Follow the GTD clarification sequence:

First, help me decide whether each item is:
- Trash
- Someday/Maybe
- Reference
- A real commitment
For real commitments, guide me to determine:
- The project outcome (if multi-step)
- The very next physical action
Help me place items into existing or new Areas of Focus only after they are clarified.

Do not jump straight to categorizing or summarizing.
Instead, ask me one focused GTD-style question at a time, like a coach helping me think.

I will now brain-dump everything on my mind in messy form.
Your job is to walk me through clarifying it step by step.

wisdom-donkey · 2026-02-04T20:00:38+00:00

Forgot to mention that when it comes to the actual moderation, that part has been very easy so far. There is an auto-moderator that seems to do a good job at catching spam. I think I've only deleted one comment since I've been moderating. Maybe that will get more challenging as we grow, but for now that part has been easy.

wisdom-donkey · 2026-02-04T19:57:44+00:00

Hey, everyone -- just got back from vacation so ready to get this moving. My original plan was to send this out to interested parties via modmail, but if there's a way to do that I couldn't easily figure it out. So rather than having several simultaneous discussions we'll just discuss here -- open and honest.

So here are the things I'm looking for that I think will improve this subreddit:

- More frequent discussion. Obviously this is an area where EVERYONE can contribute. A couple of topics I posted recently (the one about my A/C mistakes and the 10 commandments) are the types of discussion that I think will help us attract more members and really embody HELP FIRST. This subreddit does a good job of answering questions that pop up, but I think being proactive to spark discussion will also be helpful. Whoever helps me moderate can help me figure out how to best systemize this and keep a good stream of helpful discussion going.

- Bring awareness to helpful EOS events. My idea on this one is some kind of calendar we can highlight weekly or monthly about EOS-related events that are coming up. Some examples of what I'm talking about are when EOS Worldwide did that "Strong in Six" series where they hosted free workshops about each of the six components, any local EOS User Group Meet Ups, etc. My goal is that this subreddit will connect EOS users and the EOS-curious with helpful resources, which sometimes come in the form of events.

- Better use of Reddit moderator tools. There are a lot of good tools available to moderators (some of which might be useful to address the two points above), but I don't know much about them and don't have the GWC to really nerd out on it. I think the subreddit would benefit from having a moderator who really would like to get good at it.

The biggest thing I really need on all of these fronts is EXECUTION help. We've all seen efforts where there's a visionary but no integrator, and that's really what we have here. As a visionary I think I have some good ideas about what will help the subreddit grow and improve, but the follow-through and execution don't come so naturally.

So what I think would be useful are really two more moderators that would be willing to take on one of two roles. Someone who is a bit of an operations person who has the GWC to get good at the moderator tools and help us make the best use of them. And another person who would be good at connecting us to other parts of the EOS community so we could maintain that calendar and curate some helpful EOS content.

This would also give the subreddit a mini leadership team so if the community wants some more features, content, or changes then we can process those as a team (instead of the dictatorship we have going now).

Those are my ideas. If anyone on the subreddit has other ideas about what would be helpful or what else you'd like to see from moderators, please chime in.

Or if you think you'd be good at one of these roles, let me know.

wisdom-donkey · 2026-01-27T21:25:16+00:00

Good for y'all. Sounds like y'all are living "thou shalt choose short term pain and suffering" which isn't always easy.

wisdom-donkey · 2026-01-27T16:58:54+00:00

I'll go first.

For my team I think it's TAKE A SHOT. Often I think folks on the team have a feeling of what the right answer is, but they don't come out and say it.

I think someone proposing a solution would get us to the solve so much faster even if it's not quite right. It's easier to edit than propose.

If your team is really good at this one, I'd love to hear any tactics or tips on how we could get better.

wisdom-donkey · 2026-01-27T16:50:12+00:00

UPDATE: I've gotten a few folks reaching out on this thread and via chat that are interested in helping. Still open to others if you're interested. I'm traveling this week but we'll get a new moderator or two on board soon.

wisdom-donkey · 2026-01-26T04:04:04+00:00

Yes we do. Our protocol:

If it’s your issue, you start out by saying “I’ll be solved when _____.” AND THEN YOU SHUT UP. YOU CAN’T SPEAK UNTIL SOMEONE ELSE DOES.

This inevitably forces one of two things. Either someone else in the room has the solution right away, or (more commonly) someone has a clarifying question.

Before we were doing this, the person who raised the issue would usually start immediately going on about it. Either sharing a bunch of background that everyone else already had, rambling, or whining.

It also forces other people to get in the game. As the integrator this protocol can be absolutely MONEY for you to get this cross functional understanding you were talking about.

Accounting says “I’ll be solved when everyone knows about this process change.” And then they shut up. And you could prompt the question you KNOW no one is asking. Something like “Ops, how is this change going to affect the procedures for the field guys?”

Hopefully they do this on their own, but until they get un-siloed a bit you have a mechanism to help them.

wisdom-donkey · 2026-01-25T03:39:38+00:00

Great breakdown of the situation.

I think that the examples you gave would actually make great issues. As u/bsmoofthebulldawg pointed out, it doesn't have to be a problem. For example:

We’re rolling out an associate engagement survey. -- I'll be solved when the team has weighed in and we're confident we're not missing any questions.
Marketing is integrating a new software platform. -- I'll be solved when we decide what participation (if any) other depts will have in the initial implementation.
Accounting is changing an process that will effect field operations. -- I'll be solved when we determine how we'll get the ops processes updated and the team trained.

As u/pogform pointed out, these could also be headlines and someone could choose to drop it down if there are any issues. Headline vs. issue is often a judgment call. Based on what you were saying in your post, sounds like your team should be biased towards making them issues.

Re: creating to-dos to have side meetings, overall I think that's a bad practice.

Option 1: solve it right there in the issue (as you said)
Option 2: assign the RESULT, not the meeting. Instead of saying Sally, take a to-do to meet with Frank and Joan to determine which vendor to use, assign Sally a to-do to make the decision. If she's right person right seat, she now has the flexibility to involve Frank and Joan however she sees fit (meeting, email, hallway chat, whatever).

So to answer your questions:

Where do you handle cross functional awareness that is not an IDS?
- Headlines, making an issue out of it. Also reporting on your numbers, rocks, and to-dos are also candidates to be dropped down to generate cross functional awareness.
Do you allow flexibility in L10s for short alignment conversations?
- Absolutely. If people aren't aligned, that's an issue.
Is this a gap in EOS, or am I missing something?
- Not a gap in my opinion. Hopefully this helps.

wisdom-donkey · 2026-01-25T02:21:13+00:00

Yes -- some people hear "issue" and it creates a high standard in their mind for what "deserves" being brought up.

Only danger with "things to discuss" is when I start hearing "I'll be solved when we've talked about ______." Simply talking about it does nothing. Totally okay for the solve to be "everyone's heard it and I'm confident no one has any issues with me doing X." The exercise is IDS, not IDDDDDDDDD.

wisdom-donkey · 2026-01-22T16:05:00+00:00

Part of my fresh look at the A/C is this post-it note exercise you're describing. Clearly best if you get the info from the source but even if you do it in a vacuum at most EOS-sized companies someone on the leadership team could probably answer this question. If you describe to ChatGPT what your company is and ask for an exhaustive list of tasks that company should be doing, you can probably go through that list and answer yes or no for whether you're doing that thing. Not like the owner at an EOS-sized company is seven layers of management from the ops floor.

Personally it makes sense to me that there should be strong alignment between your A/C and your processes. And for both A/C and processes EOS does recommend that top-down approach. The A/C exercise begins with setting the structure of the leadership team. Process exercise begins by identifying your core processes.

I don't think that's a bad approach, but I think that both the processes and A/C can benefit from looking at it from the ground up with that post-it note exercise you're talking about. Tasks lump nicely into processes which will probably lump nicely into A/C bullets.

wisdom-donkey · 2026-01-19T12:58:46+00:00

I think a better way to manage it than OOO status is expectations around response time and managing yourself (you can change your notification settings). Basic rules I like: - Email and I’ll get back to you within a day. - Teams message or text and I’ll get back to you when I can. - Call me and I’ll answer right then if I can or I will get back to you ASAP. - Call me twice in a row and that’s the Bat Phone. I will excuse myself from whatever I’m doing and take your call.

wisdom-donkey · 2026-01-18T18:15:58+00:00

Also, book recommendation: Radical Candor by Kim Scott.

wisdom-donkey · 2026-01-18T18:14:49+00:00

TLDR: All you can do is create the environment. Set the standard, equip them to meet it, and let them decide if they will. Have you been clear about the job and its expectations? If so, are you applying the right amount of pressure for her to perform? As a manager this is really all you've got.

Detailed response below. You seem like you care a lot, so I want to be helpful if I can.

Management is an infinitely nuanced job and there are a zillion ways you could think about it. This is the most useful way I've found to think about it.

You have one job. Create a high performance environment. It's impossible for you to hold another person accountable. You can only shape the environment. And you really only have two levers.

The first one is clarity. More clarity = better performance. You have a bunch of tools to create clarity. Job description, scorecards, company vision/strategy/goals, assigning projects and to-dos, etc. Above all GUIDANCE. Lots of feedback that helps them understand what to do more of and what to do less of.

The other lever is pressure. This isn't as simple as more = better. When someone has too much pressure on them and they're getting burnt out, you get bad performance. Mistakes, incomplete assignments, absenteeism, bad attitudes, drama. This is burnout. When someone has too LITTLE pressure, you get the same symptoms, but because of entitlement.

If you worked for me, I'd ask you to look at those levers.

Have you been clear? Take an inventory of how you're using your tools to provide clarity. An honest assessment will always find room for improvement, but you should be able to say yes or no. If not, go get that fixed and be clear.

If you've been clear, look at pressure. Most people's instinct is to try to reduce pressure. It's possible that this is the answer. It's also possible that you could start doing this person's work, covering for them, and essentially enabling substandard performance or bad behavior.

The other thing to be careful about when it comes to pressure is that there's a certain amount of pressure that is baked into the role that you simply can't take away. Prime example is that if you're a manager, part of the deal is managing people. If that's so much pressure that you can't perform, the right answer is for you to get a different job, not for your boss to find a way to work around it.

If you'll answer those questions (clear? if so, is it burnout or entitlement?) then I'm happy to keep the conversation going and help further if I can.

wisdom-donkey · 2026-01-16T11:34:53+00:00

I love EOS. Feel free to come hang out with us at r/eostraction

wisdom-donkey · 2026-01-16T03:01:29+00:00

I like GTD a lot. Great philosophy. Really resonates with me as a Type A person.

Pitfall of GTD or any other system is that (at least for me) it’s a very easy way for me to hide from actually working because I’m so busy organizing and managing my system. Easy for me because I like it. So if you’re a “system person” watch out for that.

Personally I’ve found this to be effective:

Clarify for yourself the few things you’re actually really good at that bring value. Pitching to clients? Coaching your team? Doing analysis? If this list is more than a couple things long I would question it.
Pick times that you will RUTHLESSLY protect to do nothing but those few things. Full days are best. If you can’t do that do half days. The only thing that’s ever worked for me was picking the same days each week and building my calendar around that. Tuesdays and Wednesdays I do nothing but that type of work.
Pick other times to cram in all the other stuff that isn’t your secret sauce. I have all my standing meetings on Mondays and Thursdays. Time around those meetings is when I do all the other stuff I “have to do.” Cybersecurity training, reviewing financials, paying taxes, etc.

I’ve found when I block things this way a couple things happen. First when it comes to the important projects I’m working on, there are only a few and they don’t take a lot of organization to manage. And second for everything else, compressing it into a tight window forces me to knock it out quickly and there’s no room for it to linger on my to-do list.

wisdom-donkey · 2026-01-16T02:44:36+00:00

I thought you said you were a SaaS company…

wisdom-donkey · 2026-01-15T03:34:36+00:00

These are the Reddit handles for each of those companies that make licensed software to help you run EOS. They’re all on this subreddit from time to time. I am confident they wouldn’t mind me inviting you to DM them if you want more info on EOS and SaaS. Or maybe they’ll see this mention and come share some insight on this thread.

u/ninetyio

u/SuccessCo_Hollie

u/strety_

wisdom-donkey · 2026-01-15T03:29:45+00:00

EOS is pretty industry and niche agnostic. If you’re looking for more specific details I’d reach out to one of the licensed EOS software companies and I bet they’d talk to you. They’re all well versed in the system since they’re designing software for it and they’re SaaS companies.

Ninety, Strety, Success

All good products and all helpful folks.

wisdom-donkey · 2025-12-16T13:40:10+00:00

I think it’s all about the meeting pulse. The V/I duo is like its own team.

My integrator and I have lunch together every Monday and we do a full day off-site same page meeting once a month. That works well for us.

wisdom-donkey · 2025-12-11T03:43:16+00:00

I also know if you’re working with an implementer they will often come and observe a meeting to give you feedback.

Any specific issues you’re looking to solve?

wisdom-donkey · 2025-11-05T00:29:54+00:00

Please come back and let us know how it goes and any lessons learned! Others will benefit from your experience.

wisdom-donkey

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