Why Leaders Waffle (And How to Stop)

You make a decision. Maybe feel good about it.
Two weeks later, you are questioning everything.
A month in, you reverse course.
Three months later, you are back where you started, ready to commit again.

That is waffling.
Not thoughtful reconsideration.
Not pivoting based on new information.

It is the exhausting cycle of yes–no–maybe–yes that leaves everyone confused and opportunities dead.

My client had dozens of PE firms reaching out to buy his business.

Revenue had plateaued. Couldn't get to the next big milestone, 8-figures. Thought maybe he wasn’t the person to get it there. So they started the exit process.

Narrowed it to six offers. Picked one. Two-thirds through due diligence, they came to me and said:

“Now we think we can get the business past the plateau. Seeing what PE plans to do with the business, we can do it ourselves.”

They backed out of the deal.

They spent six months implementing things they heard the PE firm would do.

And couldn’t do it.

“There’s a lot of money out there. Let’s just go back to selling it.”

We went to the next firm. Got a deal. Two-thirds through diligence, they backed out again.

“We don’t like them as much as when we started talking. WE don’t want them to have us or the business.”

Three months later, they continued to notice more peers were selling. FOMO kicked in.

“Let’s sell.”

This third time, they sold. Never looked back. It was a good deal.

It took a year and a half of waffling to get there.

When I Waffled

I get it. I’ve done it.

The first time I was offered a CEO job, I didn’t feel ready. I’d spent my career as a tech guy. What did I know about running a whole business?

My predecessor was miserable. I was the one who led the cavalry while the general was sweating bullets. Why would I want his job?

A colleague told me that once you become a CEO, you can only apply for CEO jobs in the future. What if I wasn’t good at it? What if I hated it?

I waffled for weeks. Restless nights spent reworking the story I'd imagined for my own career. I never wanted to be a CEO. I wanted to build things, not manage corporate performance or board meetings.

I was too afraid to say no. And too afraid to say yes.

A friend finally pushed me.

“What do you have to lose? They’re offering you a CEO job. Why aren’t you taking it?”

He was right. I was overthinking it.

I took the job.
The risk to my career was low. More good would come from it than bad. 

That title opened doors I never expected.

Why Now

I see this more than ever. Leaders stuck between decisions for months.

Sell or grow. Hire or hold. Commit or wait.

Here's why:

1. You're not gathering data anymore. You're shopping for permission.

Your spouse says one thing. Your coach says another. Your advisory board disagrees with both. Your board of directors disagrees with them. You ask twelve people and get twelve answers.

Then there's AI. Ask ChatGPT, get one answer. Ask Perplexity, get another. Keep asking, and eventually you get the answer you wanted in the first place.

You're swayed by your most recent conversation. 

The facts don't change. Your emotions do.

2. Everything is changing too fast

This is a period where the only certainty is uncertainty.

Post-pandemic and current world political and economic factors have made today’s business climate more uncertain than ever.

My clients should already be planning for 2026. Many can’t even forecast how 2025 will end. They'll come to me in January asking for planning sessions. By the time we finish, Q1 is two-thirds over.

3. Leaders freeze in the face of risk

Monday your CFO shows you how to afford a new hire. You're ready.

You post the job. Start talking to candidates. Six weeks in, your sales pipeline dips.

You freeze. The job sits open. Candidates wait.

Six weeks later, you either close the position or change it. By then, the best candidates are gone.

This is how "ghost jobs" happen. Not necessarily malice. Indecision.

Waffling often comes down to one thing: you're treating uncertainty like a problem to solve. 
It's not. Uncertainty is permanent.

The question isn't whether you have enough information. 
It's whether you're willing to move without it.

The Cost

Indecision isn’t neutral. It’s corrosive.

Post a job, then waffle? Candidates waste weeks. Your reputation suffers.

Your team watches you commit to something, then walk it back. They lose confidence in your leadership.

Waffle on selling your business? Deals expire. Buyers move on. Market conditions shift. The window closes.

Waffle on annual planning? You start the year without direction. Q1 ends before you have Q1 goals.

he more you waffle, the harder it becomes to make any decision. The pattern reinforces itself.

How to Stop

After coaching hundreds of leaders through big decisions, here’s what actually works:

1. Take one step at a time

Forecasting the next three years isn’t required. Focus on month one.

Can you afford it? Is the plan clear? What’s your fallback?

Big decisions are usually small steps in disguise.

2. Walk through the worst-case scenario

Hire someone who doesn't work out? You've handled that before.

Take a job you don't love? You'll find another.

Sell your company and regret it? You still have the success of a sale, and can also build again.

Walk the worst case all the way through. It's usually survivable. More good will come from it than bad.

3. Write down your boundaries

What's your floor? What's non-negotiable?

One client wrote: “I will not take less than $12M. I will not stay past two years. I will not report to anyone but the CEO.”

He taped it to his monitor. 
Every time a buyer pushed, he looked at that paper. 

When one tried to negotiate to $11.5M, he walked. 
No waffling. The next buyer exceeded his number.

When you start to waffle, ask yourself:

Have the facts changed, or just my emotions?

4. Do an old-fashioned pro/con list

On paper. Not in a file you can minimize or close.

Paper makes it real. It also makes it harder to change.

When you revisit it weeks later, you'll know instantly whether your facts have changed or your fear has.

5. Seek fewer opinions, more sounding boards

You don't need more advice. You need better questions.

A good sounding board doesn't tell you what to do. They listen. They ask questions. As you answer them, you process. You decide.

I can't reconcile twelve different opinions. I can answer twelve questions.

Indecision Is a Decision

When you waffle, you're not avoiding a choice. You're making one.

You're choosing to stay stuck.
You're choosing to slow your team.
You're choosing to let opportunities expire.

My client who sold his business on the third attempt? The business hadn’t changed. The market hadn’t shifted.

He did.

Most of the time, the facts that informed your original decision haven't changed.
Only your emotions have.

Make the decision or don't. 
Stop pretending indecision is neutral.

It's not. 
And it has consequences.