Stop Asking What Keeps Them Up at Night

By Mitchell Schuckman, PCC | Founder, The Schuckman Group

A senior partner, let's call her Samantha, opened her client meeting the way she always did. She leaned in, made eye contact, and asked: what keeps you up at night?

The client answered. New SEC disclosure requirements were creating reporting headaches across his division, the team was stretched thin, and the timeline was short.

Samantha nodded, wrote it down, and spent the next twenty minutes presenting her firm's capabilities around the new requirements. Everyone left happy.

Three months later the client put the work out to bid. Samantha found herself one of six firms responding to an RFP on a project she thought she already owned.

The Answer You Get Is the One the Client Rehearsed

I debriefed with Samantha afterward, and she was sure the meeting had gone well. On the surface it had. The client was engaged, the presentation was relevant, the follow-up was prompt.

What she missed was that the client's answer was factual, but it was not personal. When you walk in and ask what keeps someone up at night, you are signaling that you have come hunting for a problem to sell against. So the client hands you the safe, defensible version of his concern and keeps the real one in his pocket.

And there was a real one. His CFO was pushing hard, had no patience for surprises, and wanted everything concise and never late. Worse, the disclosure work would expose a gap in how his division tracked certain data, and he was afraid it would surface before he had a chance to fix it. He did not need a firm that could manage a reporting timeline. He needed one that could help him get out in front of a problem his own leadership did not know about yet.

None of that came up. Samantha heard a basic answer and moved to her deck.

The People Who Do This Well Walk In Already Knowing Something

I will admit that when someone asks me what keeps me up at night, the honest answer is spicy food and bad dreams. Neither has ever started a useful business conversation.

The partners I have admired most over the years never opened with that question, or any question like it. They did not ask the client to do their homework for them. They had already done it themselves. They came in with one specific observation about that client's situation, offered it early, and asked whether it connected to anything the client was actually wrestling with.

Sometimes it lands and sometimes it doesn't. Whether or not it lands isn't the most important thing. When it lands, the client opens up in a way no direct question ever produces, because the observation proves you saw him before you walked in the door. When it does not land, you simply ask where his attention really is, and you follow that instead.

I used to think the point was to show the client what you knew. It is not. The point is to earn the right to hear what he has not yet said out loud.

The Conversation Most People End Too Soon

Once the door is open, the instinct is to rush toward your solution, and I have made that mistake myself more times than I would like to count.

What I learned to do instead was stay in the question a little longer. If you had a magic wand, what would you wish for here? What would you want to be able to tell your own leadership six months from now? What would have to be true for this to feel like a great year?

Those questions ask a client to think rather than recite, and they produce something a faster conversation never reaches. You get an honest picture of what success means to this particular person, under this particular pressure, at this point in his career. That is what the relationship, and a valuable solution, are built on.

What One Observation Was Worth

When the RFP came in, Samantha called me, and we pivoted her strategy. Rather than jumping into a proposal document that led with her firm's qualifications and project plans, Samantha asked the client for a short conversation. She started by sharing an observation. Disclosure processes like this one often expose gaps in how data gets tracked, and she wanted to know whether the client was navigating that.

The client talked for forty minutes. We wrote a proposal that centered on what he was actually worried about. Samantha won the work.

Afterward, the client told her she had been the only one who asked the right question. That for the first time, he felt someone had actually seen him, and understood what he was up against.

That is the whole thing. Clients do not open up because the question was clever. They open up because you proved you did the work before you arrived.

What keeps you up at night gets you a rehearsed answer. Proving you saw them gets you the truth.

Mitchell Schuckman is the Founder and CEO of The Schuckman Group LLC. He is a Professional Certified Coach credentialed by the International Coaching Federation and the author of I'll Tell You a Great Story. He coaches senior executives, partners, and BD professionals across professional services firms worldwide. theschuckmangroup.com

Note on privacy: Some examples are composites. All identifying details have been changed.