A Meeting In Which Nothing Went Like You Planned

When the client shows up to a different meeting than the one you prepared for

I remember the meeting more clearly than most from that year of my career.

I had prepared for it the way I prepared for every meeting in my second year. Notes on the client’s holdings. A prepared narrative about the market. Three planning ideas I thought would be useful. A folder with everything printed and tabbed. I had rehearsed the opening in the car.

The client’s name was Frank (no, not his real name). He was seventy-one (and no, not his real age). A retired mechanical engineer who had built and sold a small parts company. He had come to me through a referral from his neighbor, another client. This was our second meeting. The first had been introductions and paperwork. This was supposed to be the substance.

Frank sat down in my office and put a small notebook on the desk between us. He said, before we start, can I ask you a question.

I said of course.

He said, “do you like your job?”

I did not have a prepared answer for that.

I sat there for what felt like a long time, though it was probably less than five seconds. My rehearsed opening was still queued up in my head. My tabbed folder was on the desk. My three planning ideas were sitting there waiting to be delivered. And Frank was looking at me across the desk, not unfriendly, just waiting.

I told him yes. And then I told him I was not entirely sure how to answer beyond that, because I had only been doing the job for a relatively short while, and I did not yet trust my own answer.

He nodded and said, that is what I was hoping you would say.

Then he opened his notebook and started asking me about my life. Not about my credentials, or the firm I worked at, or my investment philosophy. About what I had studied in college. Whether I had siblings. What my parents had done. Whether I had ever built anything with my own hands.

I answered his questions for about forty-five minutes. Somewhere around the twenty-minute mark I stopped feeling like the meeting was going wrong. Somewhere around the thirty-minute mark I realized he was interviewing me in a way that had nothing to do with the questions in my folder.

At the end of the forty-five minutes, he closed his notebook and said, thank you. That was useful. Now, tell me what you think I should do with my money.

I gave him the three planning ideas. He listened carefully. He asked two questions. He said one of the ideas made sense to him, one made no sense, and one he wanted to think about. Then he left.

Two weeks later he called and told me he wanted to move his assets over. He had chosen me over two other advisors he had also met with. When I asked why, he said, because you did not pretend to know things you did not know. And because you let me ask you weird questions without trying to steer the conversation back to your agenda.

I thanked him and hung up the phone and sat at my desk for a long time.

I had not planned any of what happened in that meeting. I had done almost none of what I had prepared. Almost every piece of the meeting had gone in a direction I had not anticipated. And it had been, by any measure I understood at the time, the best meeting of my young career.

That meeting taught me something that no training program had. And it took me a long time to name it.

The thing was this. My prepared meeting had been about me. It had been about proving I knew what I was doing. It had been about establishing my competence. It had been about hitting the marks in the sequence I had rehearsed.

Frank had shown up to a completely different meeting. He had come to find out if I was somebody he could work with for the next twenty years. Everything he asked me was aimed at that question. My credentials were irrelevant to him. My market narrative was irrelevant to him. My three planning ideas were, at most, a small piece of what he needed to know before he could decide.

He had come to interview me as a person.

I had come prepared to perform as an advisor.

The gap between those two things is where most young advisors lose the meeting. Not by making a mistake. By preparing for the wrong meeting.

I have watched other young advisors go through this same recognition, in different forms. Sometimes it is a Frank asking an unexpected question. Sometimes it is a client who cries in the meeting. Sometimes it is a client who tells you, gently or not gently, that they do not want to hear about the market. What they all have in common is that the client is trying to have a different meeting than the advisor prepared for, and the advisor’s success depends on being able to notice, in real time, and switch.

You cannot prepare for those meetings. Not the way you prepare for the ones that go according to script. What you can do is show up ready to be redirected. To let the client run the meeting when the meeting is not going the way you rehearsed. To be more curious about what they came in with than about what you brought.

The advisors who learn this early build meaningfully better practices. The advisors who never learn it spend a career trying to force clients through the meetings the advisor prepared, and wondering why the same clients slip away two years later.

Frank stayed with me for almost twenty years. He passed away in 2019. When his family called me to tell me, they said he had asked, in his last week, that I be the one to help them settle things out. That felt like the fullest possible confirmation of the meeting we had had thirty-four years earlier.

If you are early in your career, and you are still preparing for meetings the way I prepared for that meeting with Frank, I would offer you only this. Prepare thoroughly. Then be ready to throw all of it out. The best meetings will not look like the ones you rehearsed for. And the clients who will stay with you for decades will be the ones you were willing to listen to before you were willing to perform for.