Digital marketing

Please don’t ask what keeps me awake at night

- March 14, 2018 3 MIN READ

I got asked this “classic” sales question just a couple of weeks ago by a very well-intentioned business person. However, it didn’t really produce the response that he was looking for.

Instead, rather than let my mind go to that dark place of worry and waking up in a cold sweat late at night, I brushed it off with a simple joke, “My kids!” This is, in fact, true, and it also perhaps gives an insight into my personality. Firstly, I try to use humour (admittedly the comedy greats aren’t quaking in their boots) to defuse an uncomfortable situation and deflect from something I’d rather not answer. Secondly, like many other people you’ll meet, I don’t really see the world as a series of challenges, instead I see challenges more as opportunities. Is this relevant? Absolutely, because people who see opportunities, not risks, want to be asked questions around just that, exciting prospects – not dwelling on their current challenges.

Surely you should always ask someone what their challenges are?

And my answer to this is absolutely not. No one question works with every person, every time. Put simply, we are all vastly different. Some people are glass half full and others are glass half empty. Personally, I’m already eyeing up the next drink! Now that’s seeing the real opportunity, or maybe just my Pommie heritage coming through!

At the most extreme, some people you meet won’t believe that they have any challenges. Obviously, they do, but they either see them as opportunities or deny their actual existence. Therefore, when you ask them “What keeps you awake at night?” they are taken to a dark and scary place that they have no desire to ever visit. They’ll have an urge to leave the meeting, which isn’t really the response that you are looking for!

Of course, for those people who see risk, this can be a great question. They are comfortable and actually happy talking about what their challenges are.

So how do I know what type of person I’m dealing with?

My first question would be, do you know what type of person you are? Do you see opportunity or risk – what we call ‘fear’? An effective way to find out which side of the spectrum you fit on is by using our free Online Octagon profiling tool.

It is important to have an awareness of your own behavioural preference to help you be conscious of the types of conversations you like, and the types of questions you will naturally ask. You can then start to think more about the person you’re meeting, and what type of person they are. If they say the word “but” a lot, this is a clear sign that these people are likely to be risk driven. They come up with great ideas and then say statements like “But have you considered….” to highlight the risks. On the other hand, if someone talks more about the future and how well things are going, it is likely they are a more opportunity focused person.

Next, think about the organisational role of the people you are meeting with as this can give you an idea as to where they sit on the opportunity/risk spectrum. I have many professional services clients including lawyers, accountants and engineers who do sit towards the risk side, so I will ask them about their challenges. When you think about it, considering what we typically appoint them for, it is comforting that they do!

CEOs, entrepreneurs and solopreneurs tend to sit more towards opportunity. They are looking at where the next gap in the market is, or what future innovations they can capitalise on to help progress the business. So if you meet a CEO please don’t ask them what keeps them awake at night.

If I can’t ask you what keeps you awake at night, what can I ask?

There are clues but no definites in recognising someone’s behavioural preferences, so if it is a first meeting why not just ask: “What do you see as the challenges and opportunities ahead of you?”

This gives them the choice straight away whether to talk about opportunity or risk. It is a simple and effective way of giving them control of what they talk about and share, which they’ll appreciate.

I often ask people “How‘s business going”?  If they respond with something like “Awesome, couldn’t be better”, I’ll assume they’re positive by nature, so I’ll avoid risk questions and focus on the future and how things can get even better. However, if they something like “Okay, some things are pretty tough at present” then I’ll most likely ask more about their challenges. Of course, this could be dependant on how the business is going, but their tone and language really does give an insight into which side of the spectrum a person sits.

In conclusion, if you should ever meet me…

I’d really appreciate it if you don’t ask me what keeps me awake at night. At worst, it takes me to that dark place I don’t want to think about. Alternatively, it may remind me of how at 4 or 5 in the morning either one or both of my sons chose to wake me up to tell me that they need to watch some YouTube on my phone! Now I’ll just be wishing I can leave the room to catch-up on some much-needed sleep!