Dealing with prickly stakeholders

Sean K. Gabriel
Developing Samurai
Published in
3 min readMay 26, 2020
Photo by Dan Gold on Unsplash

We’ve all had them — the stakeholders who don’t want to get along. Who seem to have a hidden agenda. Who, no matter how much you try, are never satisfied. Much of the standard advice focuses on “managing” such stakeholders through proactive engagement, understanding their needs, and delivering clear and effective feedback so you can get on with your work.

However… the reason they’re prickly is because this probably isn’t your first encounter with them. You wound up back here even after spending all that energy “managing” them. The problem often stems from a zero-sum mentality — and a sneaking suspicion that you’re right and they’re wrong. That you’re doing everything you can and they’re just being difficult.

Things are rarely so black and white when working together. You may well be right about this particular issue. But what if you could stop hitting an impasse every time? A first step is to stop viewing them as your adversary — you might have better luck playing a different game.

Staying in the game

When engaged in a contest of wills, what exactly are we trying to win? Why does the other side have to lose? If we were to instead frame the contest as an infinite game, the goal becomes not to win but simply to stay in the game:

Infinite players look to the future. Because their goal is to keep the game going, they focus less on what happened, and put more effort into figuring out what’s possible. They are more concerned with positioning themselves to deal effectively with whatever challenges come up.

This isn’t to say we should drop the point of argument — rather, we need to be open to the possibility that their reality is different from yours. And you won’t be able to argue against someone’s reality any more than I could convince you that the sky is green.

This stems from the mysterious power of beliefs. Beliefs color our outlook on the world, influencing our behavior and ultimately our perception of what’s happening — which can in turn reinforce those beliefs. This is where we need to think beyond classic “win-win” stakeholder management, the kind where we seek to identify someone’s needs and align them with our own. Consider instead: what does your counterpart believe?

The fundamental tool for eliciting this information is a question.

Listening without an agenda

Too often, we bring a zero-sum mentality straight into our stakeholder conversations, listening only enough to play offense against their point, or play defense when ours is challenged. It’s much easier said than done — but if you can resist the urge to prepare your counterpoint in your head while the other person’s talking, you’ll be able to listen purely to understand.

This is where empathy becomes your sword. You’re suddenly engaged in their reality, and you might be surprised to hear yourself saying: “you’re right about that.” This concession doesn’t make you weak when you’re playing an infinite game. Follow it up with: “and have you considered this?” Through gentle questioning, you can get at the core of their beliefs.

Of course, you may find those beliefs still back you into a corner. But once their reality starts to edge up against your boundaries, a questions-based negotiation can be powerful: “how am I supposed to do that?” This invites your stakeholder back to your reality, to help solve problems from your perspective, without arguing against their reality.

Accepting what you can’t change

When we find ourselves misaligned with our stakeholders, we’re usually navigating something much more fundamental: our innate desire for control. Any approach that attempts to take control away from another party rarely ends in a positive outcome.

If we accept that we ultimately can’t force anyone to think a certain way, we can stop trying to win purely on the strength of delivering our well-reasoned argument. (We also happen to believe in honor over winning.) Usually, the best we can do is to prompt others to question the situation themselves, and perhaps expand their understanding of it along the way.

Hopefully, you’re willing to expand your understanding along the way, too.



Sean K. Gabriel
Developing Samurai

Aloha (🤙。◕‿‿◕。)🤙 big on team building & lean product dev. Author @ Thinking aloud with #weeknotes. Works best when caffeinated ☕️