What Problem Are We Solving? The Question Most Strategy Sessions Skip

Created

Oct 28, 2025 2:18 PM

Tags

BlogStrategy

Author

Chris Kobylecki

"What problem are we solving?"

Such a simple question, yet so often overlooked in conversations about strategy.

One of the fathers of strategy, Richard Rumelt, writes that strategy is an organization's response to its gnarliest challenge. Not its goals. Not its ambitions. Its challenge.

But here's what I see in most strategy sessions: teams jump straight to solutions. New products, new markets, new org structures. And if you can't name the problem clearly, your strategy is just a wishlist.

The Discomfort of Sitting with the Problem

Finding your way through complexity takes time. Sitting with the pain isn't comfortable. But understanding the cause rather than just treating symptoms makes all the difference.

The first step to solving a problem is admitting that we have one.

There's a saying that a well-defined problem is already more than half the battle toward a solution. Some versions put it at 80%. Let's not exaggerate, but the point stands: diagnosis matters more than most leaders think.

From Frustration to Strategy: A Simple Tool

To transform complexity, grievances, and complaints into a defined problem, I use a tool I learned from Mike Murray. It involves four simple questions:

The 4-Question Framework

1. Write down the frustration in one sentence → My frustration is that…
2. Identify the real concern beneath it → My real concern is…
3. Express your concern as a wish → What I really wish is that…
4. Transform the wish into a goal starting with HOW → Therefore my goal is HOW…

Real Example from Our Work

An real case example form our work:

Founder said to us: 'Nobody knows our priorities.' We walked through the four questions:

1. My frustration is that: the team is scattered across 12 initiatives
2. My real concern is: we're making no real progress on what matters
3. What I really wish: the team could focus energy on the one important thing
4. My goal is: HOW do I communicate one clear priority to the leadership team?"

In less than 15 minutes, we moved from vague frustration to a specific, addressable challenge.

Finding Your Gnarly Challenge

When I sit with a team for a strategy sprint, we typically generate 10-20 frustrations in the first few hours. Over the course of our work together, one main challenge crystallizes.

Is it uncertainty after an acquisition?

A business model that's shifting?

Silos blocking execution?

This is what Rumelt calls a gnarly challenge - complex, interconnected, resisting easy resolution. The kind that requires real strategic thinking, not just better planning.

What Problem Are You Solving?

Strategy isn't about having all the answers. It's about asking the right question first.

Not "What should we do?"

But "What problem are we actually trying to solve?"

Once you can answer that clearly, the path forward becomes visible.

Ready to tackle your gnarly challenge?

Get in Touch if you want to talk about the problem your organization is facing and how strategy can address it.

Chris Kobylecki

Cofounder of Leave a Mark

Chris builds magical experiences that help people to excel.

He focuses on strategy and team development. Applying his decade long experience of Venture Capital & Private Equity Firms