How to Handle Difficult People

For all the attention paid to Product Management on the strategies to build a product, I wish more people wrote and shared about working with "difficult people."

I imagine part of the reason is it's personal and often traceable.

But learning how to manage difficult people should be a certification in and of itself.

Here are some examples, how I tried to deal with it, and how I wish I did things differently.

Controlling

I think there's a persona which isn't at every company, but I've definitely seen it often enough.

I worked with someone who had her own lane, but was very specific about her way and her timeline and pulled in entire teams to work on these projects.

If during her presentation your chair creeked, she'd glower.

However, if you were doing your own presentation, she'd pull out her snacks, wrappers and all, and start unwrapping and munching.

So one day I thought I'd ask her to stop politely. I hesitated on whether to make the connection with how she is for lesser infraction.

My thought: model grace, and it will come back.

Nope.

Next meeting, when I pulled out my iPad and it wasn't able to pull up her slides, she glowered and demanded to know why I needed to use an iPad.

Was this just interpersonal friction?

Unfortunately, it wasn't.

During a team meeting, another PM was presenting on his roadmap for a networking product and the design was totally non-standard, in fact, it was the opposite in almost every way from a topology recommended by a Gartner analyst we were going to meet with. She seemed to get along with that PM.

The problem was when I raised the point that his presentation was presenting a topology that a) didn't exist in the industry; b) explicitly was not how the analyst describes the solution space, rather than listening objectively, what did she do instead?

She glowered and asked why do I have to oppose my teammate?

Up to then, I had done a number of things to try to smooth things out (long before these incidents):

Nothing seemed to really work.

So...I tried the approach I usually take: went direct.

I scheduled a meeting and outlined some of the actual incidents as I described above.

She actually was quite accepting and said something like, "I have a temper, I'm Italian."

I said that I don't think that's a good way for us to work, what can we do to change it?

I don't remember what she said, and perhaps that's where I should have addressed things. At the end, she just left and said, cheerfully, "Thanks, that was a good talk."

What would I do differently?

I looked at other people, and the sentiment was just to avoid her. Which I couldn't because we did have intertwined workstreams.

In retrospect, I used to be a bit closer to her manager, but as the company got bigger, I never talked to her. I think one of the benefits of working in a smaller start-up before it gets big is getting to know people in more contexts.

The only other thing would have been to double-down on meeting regularly for lunch.

I probably met twice during the year or two, and that might not have been enough. I think those who are working super close and, ironically, might be difficult deserve more attention. Frequency of in-person meetings can, in general, resolve these tensions and, hopefully, increase capacity to hold safe conversations.

I observed this overall temperament of a) controlling; b) prone to irritation or anger; c) doing things 'her' way and I decided that, perhaps, those environments aren't really for me.

As an alternative, I've been thinking that being more upfront "ReadMe" (README cultures) style with all people I work with is probasbly best: how I work, how do we address conflicts or issues, and just have the conversation early might work better.