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Why you should never ask a CEO what their challenges are

By Keith Dugdale

People love asking about challenges in sales meetings.

In my many years of observing sales people, ‘What are your biggest challenges?’ would only be surpassed in popularity by an equally doomsday style question ‘What keeps you up at night?’.

Don’t get me wrong – asking about their challenges can be a very good question, and is certainly a better question than ‘what keeps you up at night?’ which has become as frequently used in sales meetings as Big Macs are seen in McDonalds. If you’ve built a level of trust with the other person before you ask it, it can definitely unearth a whole host of interesting information, and hopefully gives you an opportunity to give the other person lots of ideas about how they can tackle these challenges (and not just with your own product or service, of course).

But this doesn’t mean it’s a good question to ask everyone….and particularly to ask CEO’s.

If it can be such a great question, why shouldn’t you ask it of a CEO?

CEO’s, and most people who have C-suite roles, are not going to respond well to your question ‘What is your biggest challenge?’. This is because by the nature of their roles, their preferred behaviours are usually more opportunistic than risk oriented. These are often learned behaviours over time, and the higher up in the organisation someone gets, the more opportunistic their behaviours will need to be in order to get those roles.

Their jobs require them to see the opportunity in things and make these opportunities come to life. Sure, there will be challenges along the way, but they’re focused on making things happen, not on all the reasons why something can’t or won’t happen.

In short, the CEO is not the person in the room saying ‘But…’ to every idea.

Challenges are the buts…they are the reason things are not going to happen, or all the things that can go wrong. When you ask a highly opportunistic person what their challenges are, it’s like handing them a lead balloon. Their interest and enthusiasm for the conversation will immediately drop because it’s just not a topic they want to talk about.

And in that moment, you are significantly reducing your chances of getting a second meeting.

If I do want to find out about their challenges, what should I ask instead?

The first thing you need to do is work out what your own orientation is – are you opportunistic or risk oriented? You can do this by using my free Online Octagon profiling tool.

If you are risk-oriented in nature, you need to become hyper-aware of this tendency when you’re dealing with people ‘higher up the food chain’, and be prepared to ask questions that are more opportunistic even though it might feel quite uncomfortable and you just really, really want to talk about challenges.

When I meet with a CEO, instead of asking them about their challenges, I make the question a more positive one. So, I’ll say something like:

  • ‘Of all the things that are going well right now, is there anything at all that could be going better?’ or
  • ‘For this to be the huge success that you want it to be, what do you think are the 2 or 3 things that you absolutely must get right?’

These questions will unearth what the challenges are, but in a way that is not negative and won’t take the other person into the dreaded black hole of doom that could well spell the end of getting them engaged in your meeting.

Of course, not all CEO’s are the same

This is not to say that you won’t come across risk-oriented CEO’s – in my work with engineers, accountants, and lawyers, I have certainly come across quite a few in my time. But what it does mean is that you should veer on the side of caution and start out with your questioning being much more opportunistic to begin with – then if you notice that they revert to talking about challenges, you can confidently talk about challenges to your hearts content.

If you’re interested in hearing my interview with Andy Paul for his podcast ‘Accelerate’ where I talk more about this and other sales tips, you can listen to it here.

If you’d like to join the conversation about this post, head over to the LinkedIn Post here.

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