A Counterintuitive Way to Solve Problems: How One Simple Exercise Expands Your Awareness

In one of our early IGE (Inner Game of Entrepreneurship) community calls we did a counterintuitive exercise to help founders solve their problems…

And by counterintuitive, I mean, we didn’t give any solutions.
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Here’s what happened…

One of the founders shared his current challenge—an underperforming team member with potential but low follow-through. He had ideas, but none felt right. He wanted support.

Now, here's where most groups would jump into advice-giving mode. You know how it goes: "Have you tried setting clearer expectations?" "Maybe switch to weekly check-ins?" "Just fire him."

But we did something completely different.

We asked him questions... and didn't let him answer a single one.

But what happened next shows why most of our conversations actually miss the mark entirely.

Why Most "Helpful" Conversations Aren't

Here's what I've noticed after fifteen years of coaching founders: We think we're being helpful when we jump in with solutions, but most of the time… we're just recycling thoughts they've already had.

Think about it. When someone shares a challenge with you, what's your first instinct? To fix it, right? To solve the problem, offer advice, make it better.

The thing is, that approach assumes they need more information. But most of the time, what we actually need is more awareness.

Moreover, trying to fix reinforces the idea that there’s something wrong with them or their life; that they are a victim and need your help.

Real transformation happens from the inside-out. You can give someone the perfect advice, but if they don't see and feel it for themselves—if it doesn't click internally—nothing changes.

Many times, we already know what we want to do deep down. But what we lack is the clarity or courage to act on it.

So what if there was a way to expand someone's awareness without giving them a single piece of advice?

What Happened On Our IGE Call

I've been working on what I call CORE conversations in our community. It's a framework built around four principles:

Curiosity instead of being right
​Openness instead of withholding
​Responsibility instead of victimhood
​Empathy instead of judgment

Here's how it works:

Someone shares a real challenge. Then everyone takes turns following their curiosity by asking open-ended (not yes or no) questions .The person with the challenge? They don't answer. They just listen.

That's it.

When we did this with the founder I mentioned, people asked questions like:

• "What are you avoiding feeling?"
• “Who might have a useful perspective on this?
• "How do you know none of your ideas will work?"
• "What's in the way of you already knowing the answer?"

No solutions. No advice. Just curiosity in question form.

And something shifted. You could see it in his posture, his energy. Not because anyone told him what to do, but because the questions illuminated something he couldn't see before.

The Deeper Question This Raises

This makes me curious about something bigger. What if the goal isn't to actually try to solve our challenges within our startup at all…

But instead to expand our awareness in order to transform how we see them in the first place?

I mean, think about your own leadership. How often are you trying to solve problems versus stepping back and asking what you might not be seeing?

Most founders I work with—myself included—think our job is to have all the answers. But what if our greatest leadership superpower was asking better questions?

Not just of our teams, but of ourselves?

Practice Expanding Your Awareness

What challenge are you facing right now where you might be stuck in your own thinking?

Instead of brainstorming solutions this week, what if you wrote down ten questions about it? Don't answer them. Just let them sit there and see what shifts in your awareness.

Or better yet, try this with someone on your team. Ask them to share something they're grappling with. For five minutes, take turns asking only questions. They don't answer. You don't advise. You just stay curious.

Then switch.

You might be surprised what surfaces—not just for them, but for you.

Because here's what I keep seeing: The quality of your leadership is directly tied to the depth of your awareness.

And sometimes the fastest way to expand that awareness is to stop trying to be right and start getting curious.

What would become possible if you brought this level of curiosity to your next challenging conversation?

With love,

- Dave Kashen

P.S. On Wednesday the 25th, I’m hosting a free workshop on The Inner Keys of Becoming a World-Class Leader. If you want to join us to expand your awareness and improve the quality of your leadership, you can sign up here.