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Photo by Dominik Scythe on Unsplash

Why they say goodbye

And how to stop them

In life, most people leave us. Customers, Advisees, , Employees, Volunteers, and Romantic Partners. At my age, many of them die or retire.

It’s lot of work to bring someone into your life who adds a lot of value to it. It is often a pity when they leave.

A lot is said, despite little being done about employee and customer retention. Much less is said and even less is done about the others.

For romantic partners leaving, we have a lot of data about their feeling unappreciated, unsupported and/or ineffective at making their partner’s life better. For employees and volunteers, we also a lot of data about their feeling unappreciated and/or not being given clear instructions or the tools to make a contribution. Somewhat similar.

I have reviewed several decades of our history about  consulting and advisee leaving. When we remove entities that stopped existing, it is too small a data set to draw broad conclusions, but am unfamiliar with a published literature, so I will make do with what I have.

For our consulting clients, it has almost always been the case that our primary point of contact had left the company. (Often they retain us at their next company.) When a project completes, there is generally a next project, so it’s not that. So perhaps we should be broadening our contact base or else helping those companies to retain those particular staff members who like us.

For advisees, I see four failures modes.

First, and most rarely, some outside force wants to “clean up the cap table”  by getting rid of the perhaps even the angel investors. I don’t think I’m going to fix this one.

Second, the advisee doesn’t want to cope with the “bad news” that I (perhaps too bluntly) deliver. Things like “These projections assume our user base will exceed the region’s population … even if I count dogs, cats, goats and sheep,”  “We aren’t investor ready yet,” or “Google is showing dozens of established companies in the field where we claim to be the first and only.”

Perhaps I can learn to say things in gentler ways; perhaps not. I have always presumed that people would not be surprised about my “style” if they have survived our first 15-minute session.

Third, mismatched expectations. Again pretty rare. “No, as an advisor, I am not going to build your entire product in a month that would require a team of ten experts in fields that I am untrained in, to dedicate five years,” “No, I am not going personally invest or solicit investment for you,” or “No, I am not going meet with you for two hours each day, seven days each week.”

Here I should be clearer than I am and explicitly explain to them exactly how the boiler plate advisor agreements that I won’t sign are unrealistic.

We fall of each other’s radar

Fourth, we fall of each other’s radar. This one is the largest of them, though still small. We either have no explicit plan for regular meetings or else we had a plan and they stopped scheduling them. Perhaps they got busy. Perhaps one meeting was on their anniversary. Perhaps their calendar failed.

Suddenly a year has gone by. They haven’t asked anything. We haven’t answered anything. They rightly feel  that value hasn’t been recently delivered.

If people were as attentive and considerate once they were together.

This one seems solvable and worth solving. It seems to be occur in other context as well. Even people with strong CRM systems to track leads, often don’t effectively continuing tracking once the contract has been signed.

Let’s jump back to romance for a moment. How many relationships would continue into “happily ever after” if people were as attentive and considerate once they were together as they had been while they were just dating? They seem to be willing to put that effort into finding their next relationship, but not into sustaining what they have.

I need to do better tracking in general, but most of all I need to have faith in no calendar other than my own. Specifically for each monthly or quarterly meeting, before the meeting ends, I need to either have the next meeting coordinates or at least a personal reminder so that I will notice if that next meeting fails to be scheduled.


Advisees. Clients. Friends. Customers. Employees. Mentors. Volunteers. Partners. If they were worth getting, they are worth keeping.


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      Written by Russell Brand

      Entrepreneur in residence at Founder Institute, he has mentored, performed due diligence on and invested in numerous early stage companies. Hundreds of these early stage companies have described Russell’s insights and advice as the most useful thing in the history of their companies. He has always had an inborn ability to find more valuable uses of new ideas and faster ways to achieve results.

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