Why you need to stop asking what keeps you awake at night

Recently I asked a group of people I was working with in an engineering firm what they think is one of the most overused sales questions of all time.

We were having a conversation about questions you can ask to unearth the other persons ‘challenges’, hopefully getting them to paint a picture of what is going on in their world, and where they might need some help.

They threw a few ideas at me, and eventually I put them all out of their misery and said that “One of the most overused questions in sales meetings is ‘what keeps you awake at night?” I then asked them “How many of you have used it recently?”. Amidst a bit of laughter, at least half the room put up their hands.

HALF the room are asking the exact same question of their clients. And you can be guaranteed that if they are asking it, at least 50% of all other sales people meeting with that same person are asking it too. Now, I don’t have any actual stats around whether this actually is one of the most overused sales questions, but I have simply determined this from personal observation over the last 30 years, and the fact other people have been writing for years about how this is one of the most overused questions in business.

Not only is it boring for the other person to get asked the same question by multiple people, but because it’s so overused it has become a trite buzz question, a question that the client immediately now recognises as a sales question, which will put them on the back foot and potentially make them want to shut down.

And yet people continue to ask it – why?

Why people ask it

For me, the answer to this is fairly simple.

It’s easy. People don’t need to think too much before they ask it. Most people who find themselves in sales meetings, particularly in the professional services, have never actually received any proper sales training. So they have to rely on doing what they think is ‘right’. And if so many other people are asking this question, it must be good…..mustn’t it?

Maybe it was good 30 years ago, if asked of the right person. But today there are a lot better, more engaging, and more impactful questions to ask.

There is another major reason why that question, and similar ones, might actually not be effective.

Be mindful of asking questions about challenges to opportunistic people

Before I share with you some alternative questions, I first want to caution you about asking questions to unearth challenges.

Not all people are wired to want to talk about their challenges – because they don’t see things as challenges, they see them as opportunities. These people are high in what we call ‘Opportunity’ on the ‘Opportunity/Fear’ behavioural preference scale as part of our Octagon Behavioural Tool. If you are more wired towards ‘Fear’ you are more likely to ask questions about challenges and risks – but if you’re meeting with someone who is highly opportunistic, this will immediately disengage them and they will want to do nothing but leave the room. I am high in Opportunity, and when someone asks me about my challenges, I can actually feel the hairs on the back of my neck stand up – and not in a good way.

So, keep attuned to how people respond to questions about challenges – if they turn them into a positive, make your language more positive. If they are happy to delve into all their challenges – go ahead and ask questions about challenges to your hearts content. And if you’re not sure either way, always just err on the side of caution and hedge your bets either way.

What should you ask instead?

Instead of asking ‘what keeps you awake at night?’ think about reframing the question.

Fear/risk oriented person who is happy to talk about challenges:

  • What are your three biggest concerns right now?
  • What do you see as the most significant risk to you not achieving your strategy?
  • What plans do you have for managing your most critical risks?

Opportunistic person who doesn’t like to talk about challenges:

  • If everything went perfectly, what growth would you like the business to achieve?
  • 5 years from now, what would perfection look like?
  • Of all the things that are going well in the business, which ones are going the best?

Not sure and want to ‘hedge your bets’ either way:

  • What are your biggest hopes and biggest fears for the project?
  • What are the most critical issues you are facing regarding your strategy?
  • How would you describe your outlook for the next 12 months?

Ultimately, this is all about what you are doing to build trust in the moment, engage the other person, and differentiate yourself from every other seller in the market. Asking a question that is asked by 50% of sale people is not only going to do nothing to differentiate you, but it could do more harm than good.

This article was first published on LinkedIn. Head over to that post to join the conversation.