“Difficult to Work With”


I wanted to share a bizarre and hilarious email that one of my husband’s friends received from a prospective job applicant.  It’s timely given this week’s topic (names have been changed):

Dear Jimmy,

My interest is weening
And my mind is not set.
I hate to just do this
But I gotta accept:
I’m not passionate about this position
I’ve found something else.
It’s not you, it’s me
Sweet Jimmy.
Besides not feeling well at all
I won’t be available to take that call
11am CST, it’s just you, no me

– Bob

And with that, let’s dive into today’s newsletter…

Difficult to Work With

Every once in a while I come across a company that meets all of my investment criteria, with one exception. I cannot imagine spending the next few years working with the person across the table.

In the dating world, this is called a “lack of chemistry.” In the employee recruiting world, this is called “failing the airplane test.” In my world, it’s typically the direct result of actions or words that indicate the person across the table is a giant “difficult to work with” person.

First of all, the irony of a private equity professional evaluating whether someone is “difficult to work with,” is not lost on me. However, I believe that this is one of the most important criteria when making any major business decision. Do I really want to work with this person?  Said another way, do the benefits of working with this person outweigh the potential headache I’m going to endure working with this person?

Each person has different tolerance levels when answering this question. For example, the investors in Uber clearly have a very high tolerance. I tend to have a low/moderate tolerance and have no problem passing up what are otherwise good opportunities if the management team is “difficult to work with.”

The purpose of this newsletter isn’t to call someone out for being “difficult to work with.” It’s quite the opposite. Sometimes we all need to remind ourselves that the person sitting on the other side of the table is coming to their own conclusions about how “difficult to work with” we are.

That is all.  Have a nice weekend!

About the author

Danielle O'Rourke

Recovering Investor. Mom. Wife.

By Danielle O'Rourke

Danielle O'Rourke

Recovering Investor. Mom. Wife.

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