The B2B Podcast Index
Index
All categories
MarketingSalesSaaSFinanceHROpsLeadershipCustomer SuccessAI & DataProductStartups & FoundersRevOpsEngineering & DevTools
MethodologySubmit
Best of:MarketingSalesSaaSFinanceHROpsLeadershipCustomer SuccessAI & DataProductStartups & FoundersRevOpsEngineering & DevTools
An independent project byFame
SearchBest episodesGuestsInsightsMethodologySubmit a podcast
Index/Leadership/Leadership Unlocked
Leadership Unlocked artwork

Most People Use AI Like Software. That's the Problem - E66

Leadership Unlocked · 2026-06-24 · 21 min

0:00--:--

Key moments - from our scoring

Substance score

26 / 100

Five dimensions, 20 points each

Insight Density8 / 20
Originality7 / 20
Guest Caliber3 / 20
Specificity & Evidence4 / 20
Conversational Craft4 / 20

Most leaders approach AI like software - issuing one-shot commands and expecting perfect results. Speaker A challenges this posture, arguing that the real problem isn't technical but rather a fundamental shift in how leaders must engage with AI systems. Drawing on examples from leaders like Jamie and Tricia who run construction and finance operations, the episode reframes AI management as people management. Instead of treating AI as a tool you command, the speaker advocates managing it like a developing employee: setting clear charters, defining what great looks like, coaching across iterations, and building accountability through gates before output ships. The core insight is that leaders already possess the skills needed - they've spent careers developing people - but leave those leadership capabilities at the door when sitting down with AI. By replacing commands with questions ("What would you propose?" instead of "Do this"), asking what questions the tool has before proceeding, and treating multi-turn interactions like coaching sessions rather than transactions, leaders unlock dramatically better outputs while building lasting capability in their organization. For operators struggling with flat, disappointing AI results despite trying different tools or taking prompt engineering courses, this episode offers a completely different diagnostic: the gap isn't technical prowess but leadership posture.

Key takeaways

  • →Stop commanding AI tools with one-dimensional prompts and instead treat them as team members by establishing clear charters, expectations, and definitions of success upfront.
  • →Replace directive prompts like 'do this for me' with collaborative questions like 'here is my problem, what would you propose?' to unlock better outputs and possibilities.
  • →Apply the same five leadership practices you use with people - clear expectations, systems of measure, definition of done, coaching across reps, and accountability gates - to AI tools for compounding results.
  • →The teaching tax of investing time to properly guide and train AI tools pays dividends by Friday as first-pass results improve and team members begin adopting the same leadership approach.
  • →Your existing leadership skills are more valuable than learning new technical prompt engineering - the gap is posture, not technique, and requires shifting from command-and-control to collaborative direction-setting.

In this episode

  1. 1The Software vs. People Mode Problem with AI
  2. 2How Leaders Misuse AI: The Command vs. Direction Gap
  3. 3Real Examples from Jamie and Tricia: Recognition Over Teaching
  4. 4Five Leadership Practices for Managing AI as a Team
  5. 5The Power of Asking Instead of Telling
  6. 6Practical Framework: What Questions to Ask Your AI Tools

Mentioned

Leadership UnlockedJamieTricia

Topics in this episode

Prompt engineeringDelegation and coachingAI leadership postureaccountability systemscharter creationdefinition of donepeople managementthe teaching taxexpectation-settingleadership principles in AI ageLeadership UnlockedLeadership InsightsDusty HolcombServant Leadership PrinciplesSelf-Leadership Strategies

Questions this episode answers

Why does AI produce disappointing results even when you try different tools or prompt engineering techniques?

The problem isn't technical - it's a posture problem. Most leaders treat AI like software by giving one-shot commands rather than managing it like a person. You're not leading the tool; you're just commanding it. The gap closes when you apply the same people-management skills you've already mastered: setting clear expectations, defining done, coaching across iterations, and asking questions instead of issuing orders.

What are the five core differences between managing AI in software mode versus people mode?

Software mode: one-line commands, no measure, no definition of done, single attempt then blame, unsupervised output. People mode: write a charter with context and priorities, set clear measures of success upfront, define what great looks like before starting, coach and train across multiple iterations, and build accountability through gates before shipping. The shift from telling to asking is the lever that pulls all five together.

What specific prompt change creates better AI outputs and reveals better thinking?

Replace command-style prompts ("Do this for me, build X") with question-style prompts ("Here's the problem I'm trying to solve. What would you propose?"). Follow with a second question: "What questions do you have for me before you proceed?" This forces the tool to think before acting, surfaces assumptions you didn't know you were making, and surfaces options you wouldn't have considered alone.

How do you know when you're truly managing AI like a person rather than software?

You'll know it's working when you forget the name of one of your AI agents the way you'd forget a new hire's name three weeks in. Speaker A experienced this when he couldn't recall which assistant he was handing a task to - at that moment, he realized he wasn't operating software but running a team. Once leadership becomes instinctive, you stop forgetting names because you're genuinely leading.

Why does teaching AI to do work feel slower initially but compounds into better results?

The first two days feel slower because you're explaining yourself and coaching rather than just doing the task - this is the 'teaching tax' every leader pays. By Friday, first-pass results are sharper. By month's end, the work you used to carry yourself is being done by the tool. Additionally, your team begins adopting the same leadership approach with AI, amplifying the impact across the organization.

What our scoring noted

Our reviewer’s read on each dimension, with quotes from the episode.

Insight Density

8 / 20

The episode has one defensible core idea - manage AI like a new hire rather than a search query - but stretches it across 21 minutes with heavy repetition, motivational padding, and a five-point framework that is simply standard people-management advice relabelled. The actionable density is low; a smart operator could extract the episode's substance in under three minutes.

The move was never to command it. The move was to lead it, to manage it like a person. You are responsible for developing.
What would you propose? For example, here is my problem. What would you propose to solve it? That one change pulls expectations, definition of done, and accountability into the same breath.

Originality

7 / 20

The 'software mode vs. people mode' framing and the anecdote about forgetting an AI agent's name are genuinely memorable rhetorical moments, but the underlying thesis - prompt AI like a manager, not a search engine - has been widely circulated. The five-point framework is textbook delegation repackaged with no first-principles argument.

I had just forgotten the name of one of my workers, the way a CEO forgets the name of an account executive who started three weeks ago.
Most leaders are running A.I. uh, in what I call software mode. The discipline I want you to adopt is to run it in people mode.

Guest Caliber

3 / 20

This is a solo monologue episode; there are no guests. The only named practitioners - Jamie and Tricia - are unnamed-company clients referenced as brief anecdotes rather than participants who speak for themselves, so their seniority and credentials cannot be evaluated from the transcript.

Jamie runs a construction and engineering firm, and she sits on multiple boards, and Tricia runs the finance side of that same business.
They are not my students in this story. They are you two senior operators, excellent at leading people who sat down at the tool and hit the same wall.

Specificity & Evidence

4 / 20

The episode contains almost no verifiable specifics: no company names, no tools named, no metrics, no dollar figures, and no before-and-after data. Even the timeline claims are vague assertions rather than evidence drawn from real deployments.

By Friday, your prompts look a little different. Your first pass results are a little sharper. By the end of the month, the work that is being done is the work that you use to carry yourself.
Jamie runs a construction and engineering firm

Conversational Craft

4 / 20

There is no interview and therefore no conversational craft to evaluate; the episode is an uninterrupted monologue. The host's only substitute for dialogue is rhetorical listener-address and self-answered questions, which are competently structured but produce no genuine challenge, follow-up, or productive friction.

You tell me if this is you.
What should I be asking the tool to do? And how should I be asking it? And that's the real question.

Conversation analysis

Computed from the transcript - who did the talking, and the words that came up most.

Most-used words

tool22software17mode15lead11team11already10back10leadership10first9leader9command9problem9build8instead8whole7second7

Episode notes

Dusty goes solo to challenge one of the biggest misconceptions leaders have about AI: that it should be managed like software rather than led like a person. Building on the themes of recent episodes about identifying opportunities and revealing hidden insights, he argues that the disappointing results many leaders experience with AI have less to do with the technology and more to do with the leadership posture they bring into the interaction. Drawing from conversations with experienced executives and his own evolution from “prompting” to effectively managing a team of AI assistants, Dusty introduces the distinction between “software mode” and “people mode.” He explains how the same leadership practices used to develop high-performing employees - setting expectations, defining success, coaching through iterations, creating accountability, and asking thoughtful questions - are precisely the skills required to unlock better outcomes from AI. Through practical examples and a simple shift from issuing commands to asking “What would you propose?” he demonstrates how leaders can move beyond treating AI like a vending machine and start leveraging it as a capable collaborator.

Full transcript

21 min

Transcribed and scored by The B2B Podcast Index.

Speaker A: In episode 65, you turned on the black light and you saw it. The opportunity that was already on your page. The work that could not be done before at any price, sitting right there in your own business. We spent the whole episode inside that first room. And so you did the brave thing. You walked into the second room, you opened up the tool, you pointed it at the opportunity you finally saw, and you hit a wall that nobody warned you about. Because seeing the opportunity is not the same as leading the thing that chases it. You typed out what you wanted and the output came back fine. Not great. So you tried a different tool, same result. And a quiet thought crept into your mind. Maybe this stuff is just not ready. No, here is what actually happened. You walked into that second room holding the most powerful tool any leader has ever held, and you ran it like software. You gave it a command and you hit go. The move was never to command it. The move was to lead it, to manage it like a person. You are responsible for developing. This is leadership unlocked. Let me describe what this looks like at your desk on a Monday. You tell me if this is you. You sit down with the tool open. You type a sentence. Do this for M. Me. Build this, clean this up. You hit go. A few seconds later, it hands you something. It's fine. It is not wrong. It's just not what you would have done. So you judge the output. You feel a flicker of disappointment, and you close the window. Maybe the tool is overhyped. Maybe you need a better one. Now, let's be clear. This is not a tool problem. This is a posture problem. You talk to it the way you would type into a search bar. One shot, exact words, fire and forget. You did not lead it the way that you would lead. A new hire, an incredible leader I work with named this without meaning to. She runs the finance side of a growing company, and she put her whole struggle into one sentence. What should I be asking the tool to do? And how should I be asking it? And that's the real question. Not which model, not which subscription, not which prompt engineering thing should I be using. Exactly what do I say and how do I say it? And here's the answer almost nobody gives you. You were trained to treat this like a Google search, where you tell it exactly what to do. Not anymore. The most capable thing you will ever delegate to does not want a command. It wants direction. The cost of getting that wrong shows up in three places. It shows up in your team who get the same flat output that you got. Decide that AI is not ready for the real work. And they go back to the old way. It shows up on your plate because the work AI could have carried stays where it was. And the headcount math keeps tightening while you keep doing it yourself. And it shows up in your future because you build no muscle for this. No muscle memory, no expansion of capability. And so when the next tool lands and it will, you start over from zero. Now, uh, here's the part that should make you angry in a useful way. The standard fix is wrong. Everyone treats the gap as technical. Take a prompt engineering course. Learn how the model works up under the hood. And none of that touches the actual gap. The actual gap is that you already know how to lead a person to a great outcome. You have done it for years and used almost none of that skill. The moment you sit down in front of the machine, you give it orders. You never give it a charter. You never tell it what great looks like. You never ask what it would propose or what questions it has before it starts. Everything you know about getting the best out of a human, you leave at the door. So here is the permission that I want to give to you, and it's the same kind that I gave you over the last two episodes. That disappointment that you felt staring at that flat output is not proof that you're behind. It's your judgment telling you that there's something off here, that there's not quite right about what we're doing. And you're right. You've been pointing one of the most powerful instruments that any leader has ever held at the problem in this second room, the one that you walked into from that first space. And you're running it like software. Let me tell you about the morning I watched two incredibly sharp leaders catch themselves doing exactly the same thing. A few weeks back, I got on a call with two amazing leaders that I work with. Uh, Jamie runs a construction and engineering firm, and she sits on multiple boards, and Tricia runs the finance side of that same business. Both of them manage people for a living. Both of them are good at it. And both of them sat down to use AI Uh, and felt exactly what you have felt. Tricia said it very plainly. Her struggle was not the software. It was knowing what to ask it to do and how to ask. She kept defaulting to things that she already knew how to automate another way, because that was the only language she had for talking to the tool Jamie named the deeper version. She said the honest reason that work piles up is that it is just easier to do it myself than to teach somebody else how to do it. And then she said the thing that turned that around. You have to spend the time teaching it, but once you do, the outcome is better. And sit with that for just a minute, because she was talking about people. And it is the most precise description of managing AI I, uh, have heard from anyone. It feels slower to teach than to do. And so you do it yourself and you stay buried. Let's think about this for a minute. That has been the number one challenge for delegation for decades. It's easier for me to do it, so I'm not going to delegate. And when we think about it, that's exactly the problem we're facing with AI. Now, let me be honest about my own side of this, because the honesty is the whole point. I did not arrive at this in a clean moment of inspiration or with a clean track record. For a long stretch, I was the leader giving the machine orders, go, do this, build that. And it would come back with a flat response. I was blaming the tool in. And then I would reach for a different one. I was managing the most capable thing, just like I was managing a vending machine. Put in a command, get out a snack for me. The turn came in a strange moment. I was showing Jamie and Trisha how I actually work now live. And on that call, I had built a set of assistants. And each one is set up for a very different job. I went to hand one of them a task, and I couldn't remember its name. And I said out loud, I can't remember the name of this one. I need to rename that thing. And the second it left my mouth, it hit me. I had just forgotten the name of one of my workers, the way a CEO forgets the name of an account executive who started three weeks ago. My head exploded a little right there on the call because I was not using software. I was running a team. I was giving a team of employees clear direction, making sure they knew what great looked like, coaching them when they missed. And it wasn't prompting. That's people management. I've been doing the most ordinary thing a leader does and doing it with workers made of software. And here is why I'm telling you about Jamie and Tricia instead of just telling you about me. They are not my students in this story. They are you two senior operators, excellent at leading people who sat down at the tool and hit the same wall that I see everyone hitting the same wall that you might be hitting. The shift that happened on that call when this analog moment happened when. When you could see them realize, wait, I already know how to do this. That's the shift I want for you. Not because I taught them a new skill. I didn't. Because they recognized one they already had and they saw where to point it. This is the frame I lead with now, and it's the one that I want to hand to you. Because I've recognized that over the last year, year and a half, even two years, I have been treating the machine like a team. I've just been leading the way I lead people. And it creates different and better results when I do that. It's been an evolution. I've been learning this and getting better at this. And it's in contradiction to what I'm seeing right now. Most leaders are running A.I. uh, in what I call software mode. The discipline I want you to adopt is to run it in people mode. It's the same tool. It's a completely different posture. The difference is not technical. It's the difference between giving a command and giving direction. Last week we talked about how the right question helps a person see the dots on the page that our job as leaders is to shine the black light that lets them see. This is that same instinct turned towards a tool. You're not operating it, you're developing it. Let me walk you through the five things that you already do well with a great employee and what you each one looks like in software mode versus people mode. And you're about to recognize every single one of these because you already do them. Number one, expectations. In software mode, you type in a one dimensional line and you hit go build a forecast. That's the whole brief. In people mode, you write the charter first. You would never hand a new hire a task with no context and no sense of the priorities and no alignment to where we're going. And you should do it with a tool either. I say it to myself like this. I am creating the job description for an employee. Here's the context, here's who you are. Here are your core responsibilities. If you write it once every command after it lands on a foundation instead of just a new command prompt. So start with clear expectations. Start with the Charter 2, a system of measure. In software mode, there is no measure. You eyeball whatever comes back and decide if you like it. In people mode, you tell it how the work will be judged before it starts. You would tell a person, hey, here is what good looks like and here is how you will know you're hitting the mark. So you should tell the tool the same thing. Here is What I will be checking here is what I will be expecting back from you from a measure perspective. If you set the standard up front instead of reacting to whatever it shows you, you get a better result. 3. A definition of done. In software mode, you say go clean this with no picture of what clean means. And then you're surprised if it doesn't give you exactly what you want, if it doesn't give you the picture that you have in your mind. In people mode, you define what great looks like first. This is the oldest move in your leadership toolkit. What is the goal? What is the desired outcome? What is it we're trying to achieve? What does done look like? If you get that wrong with a person, you get busy work, you get a second, uh, iteration, you get a missed target. If you get that wrong with the tool, you just get the same thing but much, much faster. Number four, coach and train. In software mode, you take one shot, judge it, blame the tool when it misses, give it another response, and eventually maybe you get on target. And here's the truth every leader knows and keeps forgetting. It is slower the first time to teach than to do. I watched a CEO I work with live out this exact lesson with his human successor. He was very intentional about how he stepped back back from the work. He would give feedback and then let the other person figure it out because he knew that if he stepped in to solve the problem, he would never actually build up someone who could. And it's the same move with the tools that we leave. If you show it how you think, if you correct it, if you build it up over a few reps, it then carries the work. The leader who refuses to spend the time teaching, training, evolving, enhancing. The tool never builds the capability, not in a person, in a tool. Number five, a culture of accountability. In software mode, you turn it loose, let it run unsupervised, and blame it when the output is off. In people mode, you build the gate. Nothing ships without a check. I don't let my go do things before it confirms what it is going to do or ask me its questions or proposes the approach first. That's not micromanagement. That is the same accountability that you build into any team. Clear authority, a checkpoint before action, a review before it ships. Now here is the move that ties all five of these together and it lives in a single set of keystrokes. In software mode, you give the command. In people mode, you ask the question the next time you go to type something into your AI, uh, tool set. Whichever one that you use do this for me. Stop and type four words instead. What would you propose? For example, here is my problem. What would you propose to solve it? That one change pulls expectations, definition of done, and accountability into the same breath. Because now the tool has time to think, so to speak, before it acts and you react to a plan instead of cleaning up a result. I have learned that if I tell it what to do, it will do it, but it will never bring to bear the possibility it could have created. Ask instead of tell, and you get that possibility again. Think about this through the lens of leading people. If you tell people what to do, you are limiting them. You are giving them a ceiling. But if you ask them what they think, if you ask them how they may solve the problem, you're raising their floor. We want to do the same thing with the tools that we lead. This simple mindset shift allows you to ask better questions. And then just one more question that goes right behind that. What would you propose? What questions do you have for me before you proceed? That's the question you would ask any sharp new hire before they run with something. It surfaces the assumptions that you did not know you were making. It is people management in the prompt window, and you will know that the analog is real the day it happens to you the way it happened to me. The day you reach to hand off a task and you cannot remember the name of the worker you're handing it to, that's not a glitch. That's the tell. You forget an agent's name the way you forget that new hire's name. Because at that point, you were not operating software. You're running a team. And then the real magic happens is you no longer forget the names because you really lead like a team. A few episodes ago, I made the case that your leadership matters more in this era, not less, and that the principles do not expire when the tools change. This is what I meant. Clarity, alignment, execution. The whole value creation chain, the whole leadership execution chain still holds up. Uh, you're just running it on a worker made of software now. So here's what I want you to do this week. It costs you nothing but to avoid the impulse to give an order, and you can run it in your very next AI session, take the next prompt you are about to type, and before you type it, do two things. One, write it as a question. Replace. Do this for me with. Here is the problem I'm trying to solve. What would you propose? You are not handing it a command, you are handing it a problem and asking it to give you perspective, input, what it thinks. 2. Before you turn it loose to start doing the work, ask the second question. What questions do you have for me before you proceed? And then read what comes back. It will ask you for any context that you did not give it. It will surface an assumption that you didn't know that you were making. It will offer an option you would not have considered on your own. Now, I'm going to be honest with you about the catch here. The first two days, this will feel slower. It will feel like you're explaining yourself to a machine. We could have just done the task. And that feeling is real and is the same tax you pay when you're coaching a new hire instead of doing the work yourself. It's the teaching tax and it pays back the same way that it always has. By Friday, your prompts look a little different. Your first pass results are a little sharper. By the end of the month, the work that is being done is the work that you use to carry yourself. And here's the part that really compounds by then, your team's prompts are starting to look different too, because they've watched how you lead the tool, you've shown them what your getting that's better and you're sharing these ideas with them and they begin to lead the same way. Do this for a week. Every meaningful AI interaction. Stop telling. Start asking. Let the worker think before it acts. You already know how to do this. You do it with people every day. You were just doing it in a new room, now with new team members. So let me leave you with the whole thing in one breath. You do not need a new leadership skill. You need to use the one you have already spent an entire career building. Stop typing commands into software. Start giving direction to a team you cannot see. Write the charter, define what great looks like. Coach it across reps, hold it accountable. Uh, and when you go to tell it what to do, ask it what it would propose instead. And here's the one line that I want you to carry out of this. Do not manage AI uh like software that you fire commands at. Manage it like a person. You are developing. You already know how. You just haven't pointed that skill at the machine yet. Everything that we've been talking about over these last few episodes, the lever, the black light, managing the machine like a person, it's all based on one idea. Our ability to lead others is a based on our ability to ask the right questions, to cast the right vision, to ensure that people understand where we're going and where they fit in. These concepts aren't new, they are ancient principles. Those principles are what will create the difference for the leader in the age of AI uh. There's much more to come on this topic because it is something that I'm hearing so much about and the more noise we have in our system about tools and technology, the more important leadership is. AI uh will either amplify the impacts of great leaders or it will expose the flaws of those who are not leading. Hey, before you go, if this episode helped you see leadership differently and I have three personal requests. First, and this is the most important one, share this with one leader who needs it. Think of someone in your network who's frustrated with their team's execution or is trying to scale their own impact. Copy this episode link right now and text them, hey, I just listened to this episode and I think you'll get real value from it. That simple act of sharing that is servant leadership in action. Second, subscribe to Leadership Unlocked. Whether you're on Apple Podcasts, Spotify, YouTube, or your favorite podcast player, just hit subscribe or the Follow button. That way you won't miss the next episode and it helps us reach more leaders like you. And third, if you're willing, this will be a huge help for us. Leave a five star rating and write a quick review. I know it takes 60 seconds of your time, but here's what it does. It helps other leaders discover the show. Every rating, every review. It's how we expand our impact together. So those three things Share with a friend. Subscribe, Leave a review. I'm deeply appreciative and that would give us so much help. Thanks for being part of the Leadership Dunlop community. Now, um, go create some clarity for others.

Related episodes across the Index

Other episodes covering the same guests and topics, from across The B2B Podcast Index.

  • Why B2B Brands Are Using AI to Write Sales ProposalsThe Growth Operator with Fexingo · on Prompt engineering85 / 100
  • Episode 018: Season 2, the $75 Consult and the Frankenstein StackAI Tools for Practicing Lawyers · on Prompt engineering84 / 100
  • Episode 111: Building Your Defences Against AI MisinformationValue Driven Data Science · on Prompt engineering83 / 100
  • Episode 7: AI & the Power of a "Thin Core"Architecting the AI Enterprise · on Prompt engineering82 / 100
  • How B2B Marketers Use AI to Personalize at Scale for EnterpriseB2B Marketing with Fexingo · on Prompt engineering82 / 100
  • 477. The Nitty Gritty of AI From an Attorney and AI Expert with Mike BrownThe Game Changing Attorney Podcast with Michael Mogill · on Prompt engineering81 / 100

More from Leadership Unlocked

All episodes →
  • The Fastest Way to Kill Buy-In Is Your Own Good Idea | Dave Garrison - E7166 / 100
  • Escaping the Prison of Prior Conditioning | George Bryant - E6775 / 100
  • Stop Being the Leader with All the Answers - E6546 / 100
  • The Problem Isn't AI - It's What You're Using It For - E6441 / 100
  • The Leadership Skill AI Can’t Replace | Kurt Luidhardt - E70
Explore the best B2B Leadership podcasts →
All Leadership Unlocked episodes →