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How to Think About Helping a Stubborn Coworker Switch to Your Side

In many of my most difficult client assignments, my job is to facilitate and resolve situations in which people are dug in on opposite sides of an issue. Somehow, their history of disagreement — or the way they’ve behaved in their disagreements — has caused one or both sides to disrespect the other.

The participants rarely see that their disdain for their colleagues makes it almost impossible for them to bring their colleagues around to their point of view. Often they’re so fed up with what feels like a lack of progress that they don’t even want to dignify their opponent’s humanity and good intentions. Unfortunately, when colleagues lose their sense of curiosity about their opponents, they stop  trying to motivate or persuade them. They settle more firmly into their conflicting views, hoping to wait out their opponents or pressure them until they finally give in.

No More Standing Aside with Arms Crossed

This is poor strategy and ineffective tactics. In the first place, even people who say they’re hoping for their opposite number to see the light don’t often mean it. For instance, in a recent coaching conversation, an up-and-coming middle manager expressed her frustration with the positions and behavior of one of her colleagues, and her tone was scornful. So I asked her if she felt capable of respecting her colleague.

She replied that she’d have to “wait and see,” which really meant that she wants to see what he does and if he changes to her liking. I suggested that when most people say they’re going to wait and see, they’re really waiting to find out if/when person will mess up again, or if another shoe will drop. 

“So,” I said, “your saying ‘wait and see’ was a polite way of saying, ‘There’s not much he could do that would change my mind — but I’m not saying that because I don’t want to sound negative.’ Is that right?”

“Yeah, it’s probably true,” she agreed. “Unless he completely changes his behavior. It would be great if he did, but I don’t have a lot of faith that he would.”

If Only Opponents Could Ask ‘What If?’ 

Sometimes the only way to get someone out of this frame of mind, in which they’re waiting for their opponent to confirm that there will never be agreement, is to have them imagine a better outcome. That may mean believing in a version of their opponent that they don’t think could exist today, but speculating, “Wouldn’t it be great if…?”

Fantasizing like this can stop you from waiting for the other person to change just because you want them to, and instead, start conceiving a future in which there is reason that matters enough for them to want to change. If that new reason or condition were in place, they might naturally shift their behavior, rather than being forced to shift. When conditions change, people’s mental energy may accommodate that shift, and they could start behaving in new ways.

For example, the manager might be able to have her boss create some new opportunity for her colleague: a chance to discuss new approaches to the work, reassign talent or resources to various tasks, or even work together on some new initiative in which they might learn to perceive each other differently.

 Build Higher Regard on Both Sides

One of the most important factors, though, would have to come from the manager herself. Why should someone give you what you want if they can tell that you don’t respect them? When I asked the manager that question, she couldn’t answer. She didn’t know how to think of her colleague with respect, having been disappointed by him so many times in the past.

The manager and her opponent remind me of something many children experience — remember not wanting to play with another kid who you believed didn’t like you? And that’s the direction in which my work with this manager will continue. We’ll try to find points of commonality or shared concerns between her and her opponent to help create new impressions on both sides. In a case like this, whatever we can do to help both parties have higher regard for each other creates an opening to highlight mutuality of interest. And that can lead to the possibility of opponents being on the same side, at least in some things.

Onward and upward —


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