The Difference Between Asking AI a Question and Thinking with It 

 Most leaders are using AI like a search engine. The best ones use it both as a thinking partner. 

by Janet Ply, PhD · The Practical Leadership Newsletter · June 9, 2026

AI as a Leadership Thinking Partner 

Picture two leaders, both at the same level with similar team sizes. Both their teams have started missing deadlines.

The first leader opens his AI tools and types: “My team is consistently missing deadlines. How can I hold them more accountable?” Ten seconds later, he gets a list of tips to use in his next team meeting, confidently generated by AI.

The second leader opens the same AI tool and starts differently, asking the AI tool to challenge her thinking:

Leader:
“Act as my leadership thinking partner. Challenge my assumptions, pressure test my reasoning, and help me identify blind spots instead of simply agreeing with me. My team keeps missing deadlines. I think I have an accountability problem.”

AI:
“Maybe. But before concluding that, are expectations, priorities, ownership, and consequences consistently clear to everyone?”

Leader:
“Probably not. Priorities change a lot.”

AI:
“Then the first issue may not be accountability. It may be leadership ambiguity. If priorities constantly shift, people stop fully committing because they assume direction will change again.”

Leader:
“I hadn’t thought about it that way.”

AI:
“That’s the value of strategic thinking partner. Strong leaders don’t just solve visible problems. They challenge the assumptions underneath them.”

Both leaders used the same AI tool on the same problem. And got completely different results, because the second leader came in looking to think, not looking for an answer.

The Search Engine Problem 

Most of us were trained to use technology as a search tool. You have a question, you get an answer. Google taught us that. And it works great for a lot of things - trivia, for recipes, for directions and other information.

It’s a terrible model for leadership.

Leadership decisions are almost never information problems. You already know you need to have the hard conversation. You already know the project is behind. You know you need to deal with a situation but often don’t know how. When you use AI like a search engine, you get answers to the questions you already know how to ask. You miss the questions you don't know to ask. And those are almost always the ones that matter most.

What a Thinking Partner Actually Does for You 

A good thinking partner doesn’t tell you what to do or just give you the answer. They push back, ask questions, and ask you to defend your reasoning. Fact vs. belief. They surface the thing you’re avoiding. They make you better by making you work hard, not by doing the work for you..

That is exactly what AI can do for a leader - if you set it up that way.

MIT researchers studying AI-augmented reasoning put it this way: the goal isn’t AI that provides accurate information. It’s AI that actively engages users in reflective thinking, so they arrive at better decisions through their own reasoning process. The AI output isn’t the output. The output is sharper thinker to stretch the leader.

Notice what the second leader in the example earlier did. She didn’t ask AI to solve the problem. She asked AI to question her and then they answered honestly. Her assumptions became known through the dialogue, not because AI guessed them but through good questions that drew them out. That’s the shift you want to make. It’s not about a smarter prompt - it’s a different mindset entirely.

The Thinking Partner Prompt Structure 

Instead of: “How do I handle a difficult team member?”

Try: “Here’s the situation: [ describe specifically]. I’ve already tried [X]. Here’s where I need help: [Y]”

2.  Instruct AI to ask you clarifying questions, one at a time. This is the move many leaders skip. Instead of asking AI for advice, ask it to draw out your thinking first. One question at a time forces you to think about each response before moving forward. Many times the clarifying questions have given me insights I wouldn’t have thought of otherwise.

“[Provide context on the situation or question] Before you give me advice or recommendations, ask me up to [X] clarifying questions, one at a time. Wait for my answer before asking the next one.” I usually default to five clarifying questions so the AI tool doesn’t put itself in a loop and keeps asking questions. I also want the questions to be one at a time because how I answer one question may cause AI to ask something different. It also gives me an opportunity to course correct if I see it’s going off track.

3.  Ask AI to challenge what you’ve shared. Now that you’re thinking is out on the table, ask AI to challenge it.

“Based on what I’ve shared, what am I assuming that could be wrong? What are risks that I haven’t listed? What is the strongest argument against my current plan?”

4.  You apply judgment and make the call - not AI. After you’ve pressure-tested your thinking, it’s time for you to make the decision. Consider the information that you’ve been working with. Your AI thinking partner sharpened your thinking but the judgment and outcome belong to you. Ask yourself, “If a team member brought this deliverable to me, where would I push back? Where would I want more convincing? What questions would I ask?”

The More You Bring to It, the Better It Gets

What separates a good AI thinking partner from a great one? Context. The framework above world with any AI tool right out of the box. But what it gives you is only as good as what you bring to the conversation.

Think about the difference between calling a trusted advisor who has history with you, your team, and your company versus calling someone who’s hearing about your situation for the first time. Both might ask good questions but only one knows the nuances, what you’re feeling and experiencing, and what’s going on with the company.

Over time, you can close that gap. Before you start the next AI conversation, think about what you can bring to your thinking partner that would be useful to know.

Here are a few ideas:

• Frameworks - Leadership, decision-making, processes.
• Context files - for you and your team
• Organizational information - team structure, current priorities, work underway, systems in use
• Reference materials - project documentation, standard operating procedures, guidelines

You don’t need this every time you use AI but it’s good idea to create the context files, continue to update them, and use the relevant ones when needed. If you want to use AI to help you decide how and what to delegate to team members, it’s helpful to have a context file that describes your team members, their strengths, and career aspirations and another context file that has information about the work and outcomes the team is responsible for. Otherwise, you’ll get generic pattern-matching that may or may not be useful.

 A general purpose AI tool can ask you good questions. An AI thinking partner that knows your frameworks, your team, your patterns, and your goals is much better equipped to ask you the right questions. That’s the difference between a tool and a partner.

The next time you’d like to have a thinking partner (think decision-making, executive presentations, difficult conversations, or any time you wonder, “How should I handle this?”), use the framework above for AI to enhance your thinking.

The Leadarity AI Thinking Partner

The hardest part of leadership development has never been learning the framework. It's applying it, in real time, under pressure, when the stakes are high and no one is watching.

That's exactly why I created Leadarity (short for leadership clarity) AI thinking partner built on the same system behind my book, Practical Leadership. Every concept in the book, from building trust and developing awareness to goal setting, leading projects, and building high-performing teams, is embedded in how Leadarity questions you, challenges you, and helps you think.

Dr. Marshall Goldsmith, Thinkers50 #1 executive coach and bestselling author of What Got You Here Won't Get You There, called Practical Leadership "a practical and actionable guide, grounded in real-world experience - not just theory, but a road map for real transformation."

Leadarity is what makes that road map available to you at 9pm on a Tuesday, when a real leadership challenge lands in your lap and you need to think it through before tomorrow morning.

If you're curious about bringing Leadarity into your organization or your own leadership practice, let's have a conversation. Schedule a call with me at janetply.me

And if you don't yet have the road map itself, pick up a copy of Practical Leadership on Amazon or your favorite local book store.

Janet Ply, PhD
Author, Practical Leadership ~ Creator, Leadarity AI Thinking Partner and the Practical Leadership System