Great Leaders Lead with Questions, Not Just Answers

In this episode of Value-First Leadership, Chris and Tony break down why curiosity -- not control -- is the true measure of leadership. 

Together, they explore the fourth Value-First Leadership commitment:

“We will ask powerful questions rather than provide answers.”

They discuss why great leaders don’t position themselves as the smartest person in the room—but as the one who creates space for others to think, question, and grow. From psychological safety and autonomy to AI’s impact on empowerment, this episode challenges leaders to trade certainty for curiosity.

What You’ll Learn

1. Why great leadership starts with questions — and how to replace control with curiosity.

2. How to build psychological safety so your team feels safe to think, speak, and fail.

3. How to prevent “learned helplessness” in your organization by distributing authority where knowledge lives.

4. Why AI is forcing leaders to evolve beyond command-and-control management.

5. How to cultivate creativity as a discipline, not a buzzword.

6. Practical ways to rehumanize work, from sales playbooks to leadership conversations.

7. How to flip the modern workflow — letting humans lead with empathy and AI handle structure.

Transcript

Good morning and good afternoon, LinkedIn friends, Value-First Nation. Welcome to another episode of Value-First Leadership with Tony Dowling.

How you doing, Tony? It’s been a little bit.

Tony

Yeah, it’s been a while. You know, we drift apart and come back together. We always come back together, but it’s great to be back—and good afternoon.

Chris

Yeah. We’ve got a couple of changes to the clock coming up. I’m not sure where we are, other than you’re on one end of the day and I’m on the other.

Tony

Yeah, six or seven hours between us. I look forward to AI just handling that.

Chris

I think we’re getting close. I feel like Claude is—I’m not having to remind him of the date, and whatever recent update they’ve done where it’s checking chats all the time, it’s checking context.

So I think we’re almost there. Just focus on being present and let the time and logistics take care of themselves.

Tony

Yeah, absolutely.

Chris

All right, good to get back to this series with you.

Where we had left it—and maybe I didn’t realize this before—it helps to read through whatever principle we’re talking about for the day, and then dive in.

As a refresher, since we stopped doing this in August, we had already gone through the first three principles or commitments of Value-First Leadership:

1. We will create conditions for value rather than controlling outcomes.

2. We will distribute authority to where knowledge naturally exists.

3. We will illuminate paths rather than dictate routes.

And as I say this last one—and I’m going to read through number four here—it sounds very similar. But the thing I love about the breakdown of Value-First is that we’re trying to address all the nuance that gets in the way.

So, number four today is:

We will ask powerful questions rather than provide answers.
We believe leadership’s wisdom emerges through inquiry more than instruction.
We commit to using questions that activate collective intelligence and enable discoveries that no single perspective could achieve alone.
This means we will lead through curiosity rather than certainty and positioning ourselves as having all the answers.
We will create space for exploration before rushing to solutions.
We will use questions that expand thinking rather than narrow options.
We will develop organizational capacity for critical thinking at all levels rather than concentrating analysis at the top.
And we will value diverse perspectives over conformity of thought.

Tony

Easier said than done—very much so.

To kick it off, there are two aspects, which may be why this is one of the more difficult things to achieve from a leadership perspective.

You might want to practice this; you may have a natural tendency, although it’s unlikely—but unless you get both elements right… The first element is psychological safety.

This is extremely difficult in a typical industrial dynamic—to create a team who feels safe and able to fail. Without that, they don’t take responsibility. If they’re punished in some way—even a throwaway remark or a bit of office banter—it quickly ends the development of the autonomous mind in the team.

That’s one. The second is that you’ve got to teach people to be autonomous. You’ve got to teach them to make decisions. That’s where the questions come in.

We’re not trying to patronize people. We’re not asking questions that trick them into doing what we wanted all along. This is a big deal.

Now that I’ve taught you, empowered you, enabled you—whatever you want to call it—because you can’t just say “Go on, take the risk,” right? Now that I’ve ensured psychological safety, if you mess up, it’s fine. We’re all learning together.

Then you’ve got to stand back and let it happen.

So, there are maybe even three parts:

1. Create psychological safety.

2. Teach people how to make decisions through questions.

3. Put up with their mistakes—or create a mechanism to intervene only when necessary.

You can agree this with your team: “If you’re going to spectacularly explode, I’ll step in. Is that okay with everyone?” You’re not going to get blamed.

Or maybe not—maybe not.

Chris

Well, this is why it’s hard for leaders: you’re still accountable for the results. That’s why it’s easier to step in and make sure it gets done.

When I was coming up with this framework, after the AI Summit, the theme of learned helplessness kept coming up. It’s one of the most damaging results of the industrial complex—especially when you hire talented people and then teach them they’re not empowered, that it’s not in their best interest to think critically because everything must be run up the chain.

Even when people know something will get approved, the fact that they have to go up the chain adds mental drain.

If you’ve been operating without psychological safety, you can’t suddenly say, “Okay, guys, it’s on you. Figure it out.” You can’t make people feel free to ask questions in a culture that says that’s a bad idea.

Tony

Exactly.

You’ll end up nurturing the same patterns. It’s like pruning a rosebush—it grows a certain way. When you create an environment where people always have to run things up the chain, you’re reinforcing that culture.

It’s one reason companies go through lifecycles: introduction, growth, maturity, decline. Nothing lasts forever. Eventually, the organization pollutes itself and starts to fall.

And look how fast that happens today—decades compressed into weeks. Digital companies like Amazon and Facebook, and now OpenAI and Anthropic, evolve at breakneck speed.

But I digress.

Chris

That’s a good point, and it’s why this part is so important.

AI is adding an intelligent layer of infrastructure to civilization—its goal is to empower humans. If you’ve got people locked away in command-and-control structures, that’s not sustainable.

We can’t stop being exposed to empowerment. Every new phone asks, “Do you want to try this thing you’ve never done before?” That exposure changes expectations.

For instance, people talk about cleaning up CRM data. Once it’s cleaned, it’s going to get messy again unless you fix the process.

Often someone says, “That field doesn’t make sense.” If leadership ignores it, they check out. The best salespeople don’t have time for bureaucracy—they keep doing their jobs. Adoption drops off.

Tony

Great real-world example.

Our friend Clement says we should view data as an ongoing project. People do a massive cleanse, think they’re done, and six months later it’s dirty again. If you keep reinforcing the same pathways, that’s all you’ll ever get.

Organizations seem pre-programmed to move from innovation to stagnation. They start agile and fast; then, as they grow, they build processes, culture changes, objectives change.

Startups like Zappos become something else over time. The organization loses what it was.

You could argue HubSpot has changed, too—still strong, but different from before.

Sorry—go on.

Chris

This might be a new talk track.

Planned obsolescence is built into industrial capitalism. I’ve always said: think of your product as the experience.

Your people and process are part of that. If you plan obsolescence, you must reskill or replace people. It’s literally built into the roadmap.

Tony

Exactly.

The only way to kick back up the maturity curve—the cash-cow phase—is to innovate again. But organizations that prize process and consistency find innovation extraordinarily difficult.

A friend told me about Krulak’s Law from the military: you have to empower your front-line employees. Generals are too far removed from the action to make good decisions.

Big business, though, was built on conformity—machines repeating motions for efficiency. That’s the legacy we inherited.

Today the answer is creativity, but we’ve spent decades drumming it out of our kids and organizations.

Look at the downside of LLMs—the hallucination problem shows how little critical thinking remains. Lawyers cite fake cases; journalists quote nonexistent sources. We’re so dumb in some ways.

Chris

Right, and that’s the mindset shift.

We expect AI to be perfect when humans misremember and misinterpret constantly. It’s a mirror.

There’s a book—maybe Think Like a Freak—that describes growth as continuous S-curves: one after another.

And yet, we still idolize The Art of War, which is built on scarcity and competition, while we’re moving into a world of abundance.

Most people already have access to incredible intelligence on their phones.

As leaders, step one is realizing: I have this in my hand. You can’t keep me from all-knowing, all-checking everything you say.

Tony

Exactly!

How much of business and commerce relied on a mismatch between seller and buyer—where the seller knew more?

Digital leveled that. HubSpot and inbound marketing helped reclaim consumer power.

Now everyone knows everything. You can’t hide behind information asymmetry. The only differentiator left is creativity and innovation.

Like a four-man squad behind enemy lines—you can’t call the general for orders. You must teach people to think on the fly.

Otherwise, you create a process-bound dinosaur. The only way forward is creativity: teams solving problems on the ground, free from learned helplessness, educated, safe to take risks, and connected.

Chris

Exactly. And if “creativity” feels uncomfortable, think of it as creative application of what you already know.

Tony

Yes. It’s not about drawing or singing—it’s problem-solving. Though you might have those talents too!

Chris

Right.

We’ve all had fun on whiteboards. The goal is to explain problems clearly.

Every buyer wants the same thing—to be seen, heard, understood, and have expectations met.

All you need to do as a human is say, “Oh, I was just talking to Tony yesterday, and he’s dealing with something similar.” Then apply whatever insight you have to get people thinking differently.

We all want answers badly, but without critical thinking we rely on scripts. Everyone wants a playbook—but unless you adapt it, it doesn’t work.

Those four soldiers in the minefield must operate differently from the firing squad at the front line.

That’s the human side of creativity—using what you know and sharing experiences to facilitate thinking.

When leadership is all playbooks and rigid discovery questions, everyone hates it—both sides.

If you can’t get someone off script, there’s no value. I’ve been on HubSpot calls like that: “I’m not answering that question—it’s irrelevant.” If they can’t deviate, we might as well end the call.

Tony

Exactly.

We were discussing this in Christopher’s group about how pointless sales-school scripts are. Everyone agreed.

Think about it: we willingly play roles we’d hate to face ourselves. The organization taught us that—the playbook you can’t advance past until you fill in every field. It’s insane.

Value-First means: I have a thing, you want that thing. It behooves me to give you value and get what I want in return as easily as possible.

It’s not a battle anymore. The language of sales—close the deal—is outdated. Maybe that’s why hand-offs fail: “It’s closed, I’m gone.”

So much of Value-First is about replacing language. Humans aren’t naturally dehumanizing; we do it because systems force us not to see people as people.

Calling them leads and MQLs dehumanizes. When I care more about the playbook fields than the person’s answers, it’s because I’ve got metrics to hit.

And that’s not the reps’ fault—it’s the system’s.

Chris

Yes.

That’s where Value-First tries to intervene.

If we can’t root out the dehumanization of process, it persists. The thousand-to-hundred-to-ten funnel already dehumanizes by design.

When I have a call list, the only way I do things I’d hate done to me is if I don’t feel the person on the other side. There’s no connection.

Tony

Exactly—and that’s my biggest problem with RevOps as a concept.

We’ve been sold the idea that manipulating numbers generates results.

Even when we talk about “alignment,” we ignore people. I rarely hear RevOps experts talk about salespeople as humans.

Velocity, ratios—all those metrics should inspire people, not replace them.

You can’t raise close rates by 5 percent without teaching salespeople to be more human, creative, free to go off script.

Like Krulak’s Law says: “You’re a salesperson in the wild. You’re with a human. Make a decision. Is it right for them and for us? Then do business.”

When I started in sales, we weren’t taught playbooks. We were taught mutual benefit and negotiation.

The sales process is a consequence of the salesperson, not the other way around.

Culture drives behavior. Behavior drives process. You can’t shape a salesperson with a process built in reverse.

There’s so much nonsense—play your cards, win-win, lose-win—all scarcity thinking.

Even Trump talks about “who has the cards.” If that’s how we think, we’ll never progress.

Chris

Exactly.

And for RevOps folks—this is the challenge you signed up for: design internal processes without making them about the process itself.

One of the worst examples is forcing workflows that push deals through every stage even when those stages never happened.

Top salespeople don’t follow that—they get verbal approvals and move.

When systems are designed just to make reports work, you lose reality.

Deals aren’t linear. “Closed Won” should really mean “Activated.”

If you treat someone as deeply educated when they’re actually just discovering the topic, you’ll kill the deal.

The best salespeople know how to adapt—stop, bring the CTO in, change course on the fly.

That’s the kind of contextual agility AI can now support—if we give it guardrails.

Tony

Exactly.

What you’re describing shows that our models have overtaken reality.

We build frameworks based on what we think happens, not on observation.

If we could measure what really goes on at a macro level, we’d build better systems. But instead, we force people through stages so the math works.

If we genuinely observed human behavior and built from that, it would be revolutionary.

Right now, we take one salesperson’s results and think we understand the whole market. It’s madness.

AI can flip that—empower the salesperson and the customer. Both come to the table informed; they can have a real conversation.

And it empowers the organization too: we might discover our salespeople aren’t “good closers”—they’re good helpers.

So let’s double down on helping, not pressuring.

“Can you sign by the 28th?”—who does that help? Only you.

Chris

Exactly.

I look forward to that shift—where humans are at the beginning of the process and AI is at the end.

That’s completely opposite from how people think about it now.

It’s been fun to get back together, man. I’m glad we picked this back up.

So much of what we’re talking about starts and ends with leadership.

AI is making it impossible to ignore your process problems, your data problems, your human problems—and you don’t get to solve them any way you feel like.

That’s the fun part: software let you be opinionated; AI enforces reality.

Behavioral analysis and unstructured-data insights are going to be huge.

That’s why we’ll be here each week moving forward—finishing these seven principles.

Next week we’ll be talking about removing barriers rather than adding pressure.

The end-of-month stuff—we’ve got to cut that out. Artificial barriers.

Tony

Exactly.

We make them up. We create our own problems and then spend the rest of our lives dealing with them.

Chris

So until next time, next Monday at the same time, we hope everybody has a great week.

Thanks so much, Tony.

Tony

Yep. I’ll see you then. Thanks, Chris.