The real risk isn't wrong decisions

The other week, someone reached out after one of his team heard me speak at an event.

He couldn't make it on the day, so we jumped on a call instead.

Great operator. Solid brand. Good team.

And like most people in the messy middle… way too many things he could work on.

New offers. Price changes. Team structure. Store layout. Marketing ideas.

All half-circling his brain. None of them moving efficiently.

Not because he was lazy.

Because every decision felt large. And permanent.

"If I pick the wrong thing, it'll cost me." "What if the team hate it? What if customers hate it?"

So he did what most of us do Dian: nothing.

We don't know where to start, so we don't. We don't know which one will give us the biggest bang for buck, so we do none of them. 

We sit with it and hope clarity arrives.

Meanwhile, the business keeps chugging along with all the same problems.

Here's what was obvious from the outside:

He had incredible opportunities sitting right under his nose.

A great team who cared. A solid customer base. A database of email subscribers he wasn't talking to.

All of those people held answers to his questions.

He just wasn't engaging them. He wasn't testing anything.

In that moment, the wrong decision isn't your biggest risk. The real risk is treating everything like a forever decision, when it could've been a cheap 30-day experiment.

Most decisions in a small business are reversible.

You can change your hours back. You can pull a product off the shelf. You can roll back a price rise. You can revert a script or a process.

But in our heads, we frame them as irreversible, identity-level moves.

No wonder we freeze.

The first thing we started looking at was: shrinking the problem. 

I asked:

"When was the last time you asked your best customers why they choose you?"

"When was the last time you asked that new group of people what would make them come in more often?"

"Have you asked them what nearly made them choose someone else or what other places under-deliver on?"

Crickets.

He had this loyal crew of people quietly buying from him. A list of subscribers just sitting there. All the raw data he needed to de-risk decisions was locked in their heads.

If that’s you too, step one is: Talk to your customers. Talk to your team. Hit it with deep curiosity.

Ask them:

• What do you love about us?
• What do you wish we'd fix?
• When do you go somewhere else instead, and why?

You'll get a list of ideas and irritations fast.

Then, instead of carrying that weight alone, you turn it into experiments.

A Dead-Simple 30-Day Experiment

Here's a simple lens I use:

1. Is this reversible or irreversible?
   Don’t bullshit yourself here. Most things are reversible. Treat them that way. It immediately lowers the stakes.
2. What's the smallest version we can test in 30 days?
   It’s not about changing the whole business model or rolling out top-to-bottom pricing changes next week. Think more along the lines of: "This weekend, or for the next 30 days, we're trialling X at one site / on one product / with one team so we can get feedback."
3. What does good look like as an outcome?
   Define it before you start. More sales? Higher margin? Better feedback? Less chaos? Our outcome was about increasing cash into the business with no extra money spent.

If it's reversible, small, and time-boxed, it's an experiment, not a life sentence.

How This Has Shown Up In My Business:

New hours: Instead of "We're changing our trading hours," try: "For the next 30 days we're opening an hour earlier on weekdays at one location. If it doesn't move the needle, we revert."

New product: Launch it as a limited edition special. Track sales, feedback, and ops pain. Kill it or scale it after that.

Pricing tweak: Test a price rise on one product, or on one customer set for 30 days with a clear margin target. Don't rebuild your whole price list until you have proof.

Script or process: Let one team trial a new script, greeting, or service flow for 30 days. Debrief: What changed? What broke? What felt better?

Roles and responsibilities: "For the next 30 days, you own X. Here's what success looks like. Then we'll sit down and review as a team.”

Suddenly, people feel part of the process instead of victims of random change. And you stop feeling like you're gambling the whole business every time you try something.

Your Real Job

Your job isn't to sit in a room and conjure perfect answers.

It’s to:

1. Remove the weight of making permanent, irreversible calls
2. Design low-risk experiments anyone on the team can run
3. Pull customers and staff into those experiments
4. Celebrate and scale things that work
5. Kill what doesn't without drama

Running low-risk micro tests rapidly gives you something most founders are starved of: clarity.

Real data, from real customers, in your real business. Not in your head.

Once you have it, you can confidently invest in the bigger, longer-term fixes without the usual "shit, I hope this works" anxiety.

Here’s a rapid thing you could test this week.

Take one decision you've been overthinking for more than a month.

Write it down.

Then answer:

• Is this actually irreversible? (It probably isn't.)
• What's the smallest 7-30 day version of this you can run?
• How will you know if it worked?

Give it a start date and a review date. Tell your team (or your customers) you're running a trial.

Then go.

I hope this helps.