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Dear Reader

Somewhere right now, a senior leadership team is in a conference room with a whiteboard, four marker pens (one of which is dead, but nobody’s thrown it away because that would require a decision), and a problem statement they’ve been optimising against for nine months.

They’re very good at solving it. They’re also likely solving the wrong thing.

I want to tell you about a man named Takeru Kobayashi.

In 2001, he entered the Nathan’s Famous Hot Dog Eating Contest on Coney Island and absolutely obliterated the competition. And not by a little bit. He nearly doubled the existing world record.

The previous record was 25 and 1 eighth hotdogs eaten in 12 minutes.

Kobayashi ate 50 (!!!) in the same time.

And now that you have this seemingly entertaining piece of trivia, you’re asking: what does this have to do with me and my impact?

Here you go...

Everyone else in that competition was asking the same question: "How do I eat more hot dogs?"

But Kobayashi asked a different one: "Why are hot dogs so hard to eat?"

When he answered that, he realised the problem wasn’t effort. It was friction.

So he separated the bun from the meat, snapped the hotdogs in half, dunked the bread in water… and suddenly the entire system moved faster.

No extra effort or stronger jaw muscle exercises required.

Just a better question.

And here is shortcut summary you'll want to remember: Instead of asking “how”, he asked “why”.

The “why” revealed the real constraint.

And once you see the real constraint, everything else starts to look… a lot easier.

Most leadership teams are like Kobayashi’s competitors.

Asking questions...

…around the wrong problem.

You see it everywhere:

→ “How do we get more output?” (when the real issue is unclear ownership)

→ “How do we speed this up?” (when the real issue is decision paralysis)

→ “How do we improve performance?” (when the real issue is emotional avoidance in the team)

You can pour intelligence, time, and budget into the wrong question and still get nowhere.

Which is why asking better questions is not a soft skill. It is leverage.

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The process (the one I use with my exec clients)

If you want to stop solving the wrong problems and start creating disproportionate results, this is the structure:

1) Get to the real problem

Most teams start with goals. That’s already too late.

Instead of:

• What is the goal?

Ask:

• “Why is that a problem?”
• "What’s not working about that, specifically?”
• “And if we solved that… what would actually be different?”
• “What are you really trying to achieve here?”

You’re gently peeling away the polite version of the problem until something real shows up.

This is where people usually pause and say, “Oh… that’s not actually the issue.”

Yes. Yes. Exactly.

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2) Challenge assumed constraints

Cue the discomfort. It's good, I promise.

Instead of:

• Identify constraints

Ask:

• “What’s making this hard right now?”
• “What are you assuming has to stay the same?”
• “Who says that’s the way it has to be done?”
• “If that constraint disappeared, what would change?”

Most constraints are inherited. Not real.

They’ve just been around long enough to feel official.

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3) Break it down

Now we get practical.

Instead of:

• Trying to speed through to solve it with the usual solutions.

Ask:

• “Walk me through how this actually happens, step by step.”
• “Where does it start to slow down or get messy?”
• “At what point do things tend to go off track?”
• “What part of this feels heavier than it should?”

This is where friction lives.

And most teams have normalised it so deeply they can’t see it anymore. These questions help.

⸻

4) Reimagine the system

This is where leaders either come alive… or look mildly alarmed.

Instead of:

• Keep doing things the same way because it seems easier

Ask:

• “If you could start this from zero, how would you design it?”
• “What would you stop doing completely?”
• “What would you do in a completely different order?”
• “What feels unnecessary when you say it out loud?”

This is like Kobayashi separating the bun from the sausage.

⸻

5) Push experimentation

Now we stop thinking like philosophers and start behaving like leaders with deadlines.

Instead of:

• Run tests

Ask:

• “What’s one small thing you could try this week?”
• “What would happen if you did the opposite of what you usually do?”
• "How could we test this without overthinking it?”
• “What’s the quickest way to learn something new about this?”

Small bets get faster better results.

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6) Surface new constraints

Because solving one problem tends to reveal the next.

Instead of:

• Identify new bottlenecks

Ask:

• "If this worked, what might become the next challenge?”
• “What would this require from you that you’re not doing yet?”
• “Where might this stretch you?”
• “What would need to change for you to sustain this?”

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The real takeaway: It's not hotdogs

Most leaders are not underperforming.

They are over-solving the wrong thing. Over and over again.

Which is far more exhausting.

Because effort without clarity feels like progress. Until nine months later when someone asks, “Why are we still here?”

And you realise…

You’ve been eating hot dogs the hard way.

The FREE "Help me find the real problem fast" AI Prompt

​Click this link for a a free AI prompt you can use to take yourself through this process properly. Paste it into ChatGPT or Claude and let it guide you, question by question, until you’re actually solving the right problem. Which, as it turns out, is rather helpful.

Your executive coach,

Terez

PS: The prompt above is essentially a portable version of me asking, “Yes, but what’s the actual problem?” with slightly less eye contact. You're welcome. :)

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