How to Stop Asking What’s Keeping You Up at Night

One of the ways salespeople were taught to uncover a compelling reason for their dream client to change or the source of their dissatisfaction, was by asking the single question, “‘What’s keeping you up at night?” I am not certain where this question originated or who provided this as a choice for salespeople, but ‘it’s been around for as long as anyone can remember, and lately has fallen out of favor. Instead, you are supposed to know what should be keeping your dream client awake at night, a better strategy if you want to be a consultative salesperson.

However, if you are meeting with an executive level stakeholder in one of your dream clients, there is no doubt that something is keeping them up at night, even if you might ask a better question than “‘What’s keeping you up at night.”

The Sources of Insomnia

If you meet with and sell to executive level stakeholders, you can make some assumptions about what might have their attention and what might be of concern.

  • Growth: There are very few executive-level stakeholders who are not concerned about the growth of the business. The CEO is responsible for leading the organization into the future, a future that will need to be better than the present as measured, in part, by revenue or profit or market share or some other financial growth. The work the marketing executives do is to drive growth, and even the IT director needs to ensure the infrastructure supports growth, with the proper tools, technologies, and support in place.
  • Strategy: An executive leader will always be concerned about their strategy. If they are confident in their approach, ‘they’ll be concerned about the execution. If the plan is right, and the implementation is good, they’ll be concerned about what comes next, how they might find a more significant competitive advantage. Many will be interested in hearing about what happens next and how they get their first.
  • People: Great companies are built on great people. Executive leaders work very hard to surround themselves with the most competent people they can find, knowing that better players make for better results. There are not many executives who aren’t concerned any acquiring and retaining the best talent available to them. ‘They’re often concerned about improving the caliber of their team and their workforce.
  • Gaps in their thinking: Effective executives don’t like surprises (even good ones). What keeps them up at night is sometimes their concern that there is a gap in their thinking, that they have a blind spot that will become a problem for them later. They worry about not knowing what they don’t know.

Systemic (Wicked) Problems

There is another category of concerns, one with more power to compel change.

  • Systemic Problems: Even though all of the categories above might rise to the level of being a systemic challenge, there are challenges in some verticals that are inherently difficult to overcome. In the medical field, for instance, it is tough to compel patients to follow the doctor’s orders, an example being stats showing that 50% of people prescribed insulin for diabetes miss necessary injections. At the time of this writing, there is a shortage of truck drivers, making it more difficult and more expensive to move goods.

The areas where systemic problems and challenges don’t often get the attention they deserve, making these areas especially effective in helping to compel change. It is difficult for someone in an executive leadership role to ignore the systemic challenges—or potential solutions. Nor is it easy for leaders to ignore the problems of growth, strategy, people, or the unknown.

Asking Better Questions

Some questions are better than others. What is problematic about asking “‘What’s keeping you up at night,” is that it doesn’t indicate you have any idea about what should be keeping them up at night and that you lack a theory as to what your dream client might be doing better.

In Eat Their Lunch: Winning Customers Away from Your Competition, I outlined a process for capturing mindshare, developing an executive briefing that outlines the systemic challenges that provide context for a conversation about why your dream client should change now. In that chapter, I shared ideas about how you can develop views and values that allow you to address the challenges your dream client’s struggle with, opening up the conversation and creating an opportunity to help them improve (the core of what we do as salespeople).

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Sticking with the diabetes example above, instead of asking “What’s keeping you up at night?” you might ask: “What initiatives are you currently pursuing to increase compliance with the doctor’s prescription and plans for their patients, and how much improvement have you seen over the last 12 months?”

There is a lot in that question, so let’s unpack it. First, it presumes that there is a compliance issue, which may or may not be accurate, but because it is a systemic challenge based on human behaviors, it’s a pretty safe bet. Second, it presupposes the person you are asking has initiatives around the improvement in an outcome. While it could be true that they have other, more critical initiatives, the systemic challenges tend to be worth a conversation, if there are ideas that would help improve results. Finally, the statement about improvement over 12 months is a request for an objective measure of success in an area where improvement is difficult at best.

I am not sure asking, “‘What’s keeping you up at night?” accomplishes as much as another question might. It tends to miss one of the primary goals of discovery now: Helping the client discover something about themselves (or for themselves).

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