Working with strong-willed people

I used to be dogmatic. I used to think that there was a “right” way and a “wrong” way of doing things. I also used to think that for the sake of the “truth” I had to shut people down when they were doing something “wrong”. It was the “right” thing to do.

Retrospectively, I was probably not an easy person to work with. Now, I think it’s fairly difficult to be positively collaborative with someone who will jump at me at the hint of something unclear or inaccurate. But, there’s other types of difficult relationships. One dynamic I find quite interesting is the dynamic of a consultant and client. Clients have pain points that they find painful enough to warrant hiring a consultant.

Especially after having made a big investments, it’s difficult to change a client’s mind about their goals and objectives. Why? Because different people value different things. It’s a fine art of speaking to a person’s values, moving the needle, showing them a better path forward, without insulting them, and while keeping or gaining their trust. Tough.

My old self certainly wanted to poke holes at ideas. If the idea survived the barrage, it was solid. This annoyed many people.

I have experienced technical conversations where no matter how solid it was, it did not resonate. On other occasions, I have witnessed technical discussions where the idea had little sustenance but the delivery had emotion and it resonated. And of course, in other occasions, emotions and quality mattered little to a person and instead it was all about the timeline.

So when working with someone difficult or strong-willed, understand what they value. It’s useful to see how they see the world and why something is important to them. From there, you can make choices to start gaining their trust. You can speak their language. You can propose ideas that resonate with their values.

As Seth Godin says, “other people don’t believe what you see, and they don’t see what you see”.