What keeps you awake at night?

It’s one of the most interesting questions to ask, and it cuts right to the heart of what makes us tick. It’s really hard to swerve or dismiss, and unless you are one of the luckiest, happiest people on the planet, it’s generally hard to say nothing.

So, if you’re really interested in how someone is, or how their business is doing, asking them what keeps them awake at night will certainly elicit a response. Either a very worried look that reminds them of how they felt at 2am that morning, or a sense of surprise that there’s something very interesting in the question that has made them think.

Having heard Keith Coats of TomorrowToday talk at a recent Academy for Chief Executives event about why we all need to be ambassadors of hope, if we are to be future fit leaders, I posed the question at a recent round table of CEOs. The answers tend to fall into these categories – money, health or people, and usually it’s about fear or guilt. The starkest answer I got back from that same group of business leaders was that what kept them awake at night was the number of people living on the street without the safety and warmth of a home. People, fear, guilt . . . . and maybe a bit of frustration and helplessness thrown in too.

That made me think (although not at 2am I might add). As service providers, whether we’re commercial or social businesses, we know we should be checking that what we do every moment of every day is really going to make a difference. And to do that we need to know what keeps our customers, our staff and our businesses, awake at night.

We then need to work out how we make the difference and what we can do to help. Generally that requires some right-brain thinking – often a challenge for the analytical business leaders amongst us! I’ve picked up three top tips for addressing this challenge:

To begin, think of the ridiculous – yes, the most ridiculous ways of addressing the issue that’s bothering you, or someone you care about – and then pick at those ideas until you find something novel and useful to try out.

Secondly, be constantly curious – ask more questions than you answer, go to unlikely sources to learn about new things, turn left five times to explore a new location, and so on.

And finally, get a blank piece of paper and draw on it, no words mind, just pictures. Think about what’s keeping you awake at night, and then visualise what calmness, happiness and success might look like – not only will you be amazed at what comes out in the mix, but you’ll imprint some pictures in your mind that you can refer back to at 2am.

So, if you want to make a difference to someone’s life or business, seek a quiet moment and ask the question – anything might happen but one certainty is that both of you will learn something from the answer.

Nicola Winn

About Nicola Winn

Company founder and co-owner. Nicola is a motivational leader with substantial experience of business and marketing. She is an active member of the Academy for Chief Executives, and is chair of PM Training, part of the Aspire Group.
Nicola’s passion: stylish interiors.