Why Smart Teams Get Stuck on SimpleProblems

You’re not dealing with complexity — you’re dealing with perspective

I was in a strategy session recently with a management team trying to build a forecast.

Good business. Smart people. Plenty of data.

And completely stuck - not “this is tricky” stuck, but “we’ve been talking in circles for an hour” stuck.

They were trying to answer a simple question: What does next year’s revenue look like?

Here’s how it went:

• “Let’s build it from customers.”
• “No, contracts are more reliable.”
• “But what about new logos?”
• “Wait — renewals will drive most of it.”

Back and forth - around and around.   At some point, I stopped the discussion and asked: “How are we choosing to look at this?”

Silence.

Because the honest answer was… they hadn’t chosen.

Two ways to be right (and still go nowhere)

There are usually multiple valid ways to look at any business problem. Take revenue forecasting:

• You can model it based on customers (how many, what they buy, how often) 
• Or based on contracts (pipeline, timing, conversion rates) 

Both are valid. Both can get you to a solid answer. But trying to use both at the same time? T

hat’s where things break. You double count. You miss things. You debate assumptions instead of making decisions.I

t’s like trying to follow two GPS routes at once. You don’t get there faster — you just get confused.

The real issue isn’t complexity

We tell ourselves these are complex problems, but sometimes they are.

But more often, the issue is simpler: We haven’t committed to a single lens.

• We want the “complete” answer.
• The one that captures everything.
• The one that keeps all options open.

So we hedge. We blend models. We mix perspectives. We try to keep both doors open.

And in doing so, we make the problem impossible to solve.

Why the customer lens changes everything

Back in that meeting, we made a call: “Let’s build this from the customer.”

• How many customers do we actually have?
• Which segments matter most?
• What do they buy — and when?
• What’s likely to change?

Within 20 minutes, the fog lifted. Because now we were grounded in something real: customer behaviour.

• Not pipeline guesses.
• Not optimistic close rates.
• Not theoretical scenarios.
• Actual people. Actual buying patterns.

And here’s the interesting part: once we had that view, we could see things we couldn’t before.

• Which segments were actually driving growth 
• Where expansion would come from 
• Where we were overestimating demand 

That’s the power of a good lens — it doesn’t just simplify the problem, it reveals insight.

I’ve seen this movie before

This shows up everywhere:

• Companies that try to be everything to everyone struggle to explain what they do, and end up resonating with no one.
• Sales teams that target “anyone with a pulse and money” burn cycles instead of closing deals.
• Businesses that drift during scale-up often try to serve multiple customer types with one offering — and it creates friction across the whole model .

Different problems. Same root cause: No clear point of view.

A simple way to get unstuck

The next time you’re stuck — on forecasting, pricing, expansion, hiring — try asking: “What lens am I using?”

If the answer is “a bit of everything,” that’s your problem.  Instead:

• Choose one perspective (customer, product, contract, geography — doesn’t matter) 
• Build your model from that lens 
• Solve the problem 
• Then sanity-check it from another angle 

Clarity first. Completeness second.

Final thought

You don’t need the perfect model. You need a usable one.

And that usually starts with a simple decision: How am I going to look at this?

Because once you choose the lens — especially one grounded in your customer — the problem often solves itself.

If you’re stuck on something right now, it might not be because it’s too complex. It might just be because you’re trying to solve it from two directions at once.  

See you next time, 

Andrew