Transforming caution into critical thinking

How I unlock better decision-making with my favourite coaching prompt

When coaching, I have a prompt I fall back on time and time again, I picked it up when the kids were young through a parenting book or newspaper column.

It was based on the idea that if you constantly remind your kids to ‘be careful’ you don’t set them up to take risks in the proper way. The theory is that responding to risky behaviour with words of caution means your kids don’t learn how to take risks—or rather, how to think through risk-taking in a constructive way, and calculate when risks are worth taking.

So, as the theory goes, when you see your kid up a tree or treating a high wall like a balance beam, instead of ‘be careful! You might fall!’ you say, ‘have you thought about how you’re going to get down?’ It encourages them to think their actions through and make decisions based on the situation.

I use this all the time with the kids and over time I’ve found it creeping into my 1:1 meetings and coaching sessions.

Just the other day, someone was walking me through a delivery plan that felt overly ambitious. I caught my words of caution before they came out, and instead of saying ‘that’s a really aggressive timeline that depends on a lot going right,’ I rephrased it: ‘Have you thought about what you’ll do if there’s sickness in the team, or if the first round of user testing goes badly?’

I think this transfers to coaching because the same concept applies. When I’m coaching I’m not trying to tell people what to do; I’m teaching them how to think. So rather than giving words of caution, I want to guide them through their decision-making, having them check their own thought process.

Good coaching should always be time-limited and planned so that one day you’re not needed any more. Focusing on prompts and techniques that teach good thinking applicable in multiple situations will eventually work you out of a job, and that should always be the main goal.