Lunch & Learn: Why Some Problems Feel “Insurmountable” (and What That Actually Signals)

What this is

This is a leader-focused session that looks at a different question:

Not: “How do we solve this problem?”

But: “Why does this problem feel impossible in the first place?”

The core idea: “Insurmountable” is not a property of the problem.

It is a cognitive and systemic signal that the current way of thinking is failing


Who this is for

  • Senior leaders
  • Heads of function / programme
  • Anyone dealing with problems that:
    • don’t respond to effort
    • keep reappearing
    • feel stuck despite multiple attempts

What happens in the session

Over ~90 minutes:

  • Leaders bring a real “stuck” problem
  • We don’t try to solve it directly
  • We examine how it is being framed, interpreted, and reinforced

The session moves through a structured set of shifts:

From:

  • “The problem is too big”
    To:
  • “We may be using the wrong logic”

What the session explores

1. The Size Illusion

“Too big” is often a perceptual distortion
(Prospect theory, availability bias)


2. Solving the Wrong Kind of Problem

Leaders often apply the wrong logic to complex problems
(Cynefin, second-order change)

Trying harder within the same frame often guarantees failure


3. The Trap of the Single Frame

Experience creates blind spots

  • Einstellung effect
  • Confirmation bias

Result:

“We tried everything”
…within the same mental model


4. What Actually Drives the Problem

The issue is rarely where it appears

  • Systems thinking (Meadows)
  • Reinforcing loops
  • Hidden constraints

You don’t fix the problem where it shows up
You fix what keeps recreating it


7. How it’s designed to work

  • Less about steps, more about shifts in understanding
  • Uses theory as a lens, not as an academic exercise
  • Focuses on real problems leaders are already dealing with

The progression is deliberate:

Psychology → Problem type → Cognitive traps → System structure


8. What leaders leave with

Not a checklist.

Instead:

  • A reframed view of their problem
  • One key assumption challenged
  • A clearer sense of what not to do next

And three diagnostic questions:

  • Am I treating a complex problem as complicated?
  • What evidence am I filtering out?
  • What reinforcing loop am I inside?

Download the leader session (PDF) here

 

If you’re looking for a more practical, team-level session that focuses on immediate action, there’s a simpler 4-step version here:

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