Are You Solving the Problem - or Finding Problems With Every Solution?

There’s a particular kind of stuckness that can look a lot like good decision-making.

You identify a problem in your business. You consider a possible solution. And almost immediately, you can see everything that’s wrong with it.

It will be too expensive.
You don’t have enough time.
Your team won’t agree.
Your clients might not like it.
You’ve tried something similar before.
The timing isn’t right.

These might all be perfectly reasonable concerns.

But there comes a point when identifying problems with every possible solution stops being useful analysis and starts becoming the reason nothing changes.

And for capable, thoughtful business owners, that distinction can be surprisingly difficult to see.

When every solution creates another problem

One of my kids came to me with a problem recently.

He was trying to organise an upcoming holiday with friends, and they were running into all the predictable complications: getting leave at the same time, agreeing on where to go and working around everyone’s schedules.

Naturally, I started offering solutions.

Every single one was met with another problem.

That won’t work because…
We can’t do that because…
Yeah, but…

After a few rounds, I realised what was happening.

He didn’t actually want to solve the problem at that moment. He wanted to talk about it. Maybe vent a little.

And the clue was that every possible solution simply generated a new reason it wouldn’t work.

There was nothing particularly significant about the conversation. But I recognised the pattern because I see versions of it in business all the time.

Sometimes in teams.

And very often in our own thinking.

The hidden problem with how we make business decisions

Imagine a team discussing something that clearly isn’t working.  Someone suggests a change.
We’ve tried that before.

Someone offers another approach.  That won’t work because of X.

Someone suggests doing something differently. There’s no way they’ll agree to that.

Every objection may contain something worth considering. The problem isn’t that people are identifying obstacles.

The problem is what happens next.

Instead of using the obstacle to improve the solution, the obstacle becomes evidence that the solution should be abandoned.

So the team moves to another idea.
Finds the problem with that one.

Moves to another.
Finds the problem with that.

Eventually, a meeting that was supposed to solve a problem has produced an extremely convincing explanation for why the problem cannot be solved.

Nothing changes.

This happens inside our businesses too.

We spend enormous amounts of time asking what is wrong with a possible solution, and surprisingly little asking what would need to happen to make the solution work.

That difference matters.

Identifying an obstacle is not the same as reaching a conclusion

Let’s say you know you need more support in your business.

You consider hiring someone.
Immediately, you think about the cost.
That’s useful information.
But what happens after that thought?

One version of the conversation is:
I can’t afford to hire someone.
End of discussion.

Another is:
I can’t currently afford this role at the salary I had in mind. So what would need to change for additional support to become viable?

Perhaps you hire for fewer hours. Perhaps you delegate different work. Perhaps the role needs to generate or protect a certain amount of revenue. Perhaps hiring isn’t the right solution after all.
But now you’re investigating the solution rather than simply collecting evidence against it.

The same thing happens with difficult conversations.

You know you need to address an issue with a team member, but you can immediately think of all the ways the conversation could go badly.

Or you know an offer in your business needs to change, but you can list all the reasons changing it might upset existing clients.

Or you want to pursue a new opportunity, but there are enough unknowns that waiting feels more sensible.

The concerns themselves aren’t the problem.

It’s whether they become inputs into the decision or the end of the decision.

Why smart people can be especially good at this

Thoughtful people are often very good at anticipating problems.  That is usually an asset.

If you run a business or lead a team, part of your job is to think ahead. You need to notice risks, understand consequences and avoid making every decision based on enthusiasm alone.

But that same ability can work against you.

Because if you’re good at analysing situations, you can usually construct a very compelling argument for why something won’t work.

You can find evidence.
You can anticipate other people’s reactions.
You can remember the last time something similar failed.
You can explain why now isn’t quite the right time.

And because the argument is logical, it can feel like you’ve made a considered business decision.

Sometimes you have.

But sometimes you’ve simply devoted far more thinking to disproving the solution than developing it.

What looks like discernment can occasionally be discomfort wearing a very sensible outfit.

Sometimes problem-finding is a way to avoid making the decision

There’s another reason we do this.

Finding another problem can feel safer than making a decision.  As long as you are still evaluating, you haven’t committed yourself to anything.

You don’t have to have the uncomfortable conversation.
You don’t have to spend the money.
You don’t have to ask for something and risk hearing no.
You don’t have to try the new strategy and discover that it doesn’t work.
You don’t have to make a choice that other people might disagree with.

Most importantly, you don’t yet have to become responsible for what happens next.

So your brain keeps doing something it is very good at: finding legitimate reasons to stay where you are.

This is one reason decision paralysis in business isn’t always solved by getting more information.
Sometimes you already have enough information.

What you don’t yet have is certainty. And those are very different things.

Why more productivity advice doesn’t solve this

When business owners feel stuck, the problem is often framed as one of productivity.
You need to prioritise better.  Block out time to think.  Get clearer on your goals.  Make a better plan.

There are situations where those things help.

But no time-management system can solve a problem that is actually happening in the way you respond to uncertainty.

You can have a beautifully organised week and still spend three months considering a decision you probably had enough information to make in week one.

You can have a clear priority and still avoid acting on it by continually finding reasons your proposed solution won’t work.

You can create more thinking time and simply use that extra time to think of more objections.

The issue isn’t necessarily that you need more clarity.

It may be that you need to notice what you are doing with the clarity you already have.

A better question: What would need to be true?

The alternative isn’t relentless positivity.

You don’t need to convince yourself that every idea is brilliant or ignore genuine constraints.  Good leadership requires questioning.  It requires you to notice what might go wrong.

But it also requires you to stay in the conversation long enough to find out whether an obstacle is a genuine dead end or simply something that needs to be solved.

So when you notice yourself thinking: That won’t work because…

Try not to make that the end of the conversation.  Ask instead: 
What would need to be true for this to work?
If hiring feels too expensive, what would make it financially viable?
If your team might resist a change, what would help them understand or participate in it?
If you don’t have enough time, what would have to stop, change or be handed over?
If you don’t know whether something will work, is there a smaller way to test it?

You may still conclude that the answer is no.  That matters too.

The aim isn’t to force every solution to work. It’s to make sure you are genuinely evaluating your options rather than automatically building the case against them.

This is part of the work of being a CEO

I think this is where the role of CEO becomes particularly interesting.

Imagine the part of you saying, That won’t work because… as the difficult person in a leadership meeting.

Your job isn’t to kick them out.Their concerns may be valid. Their perspective deserves consideration.

But you don’t let them run the meeting either.  You listen. You investigate the objection. And then you keep the conversation moving.

What if it could work?
What would need to change?
What haven’t we considered?
What could we try?

There is a difference between considering an obstacle and treating it as a verdict.

One helps you make better business decisions.  The other can leave you circling the same problems for months while believing you are still working on them.

Calm leadership isn’t the absence of doubt. It’s being able to hear doubt without automatically handing it the chair.

And sometimes the most useful thing you can notice is not another problem with the solution, but how much energy you’ve been putting into explaining why something can’t work instead of discovering how it might.