Does Your Boss Avoid Controversy? See If These Approaches Work 

Recently, several people have asked me for help with the following situation: They aren’t the appropriate decision-maker on a tough issue, but they can’t convince the relevant leader (whether it’s their boss or a colleague with power) to do anything about it. Because the leader is hesitating or deferring, the team is unable to take any necessary next steps, so project deadlines are being missed, progress is stalled, and the team is wasting time or going in circles.

Reluctance to make decisions often happens with good people who actually care about the issue, but also worry that their decision will create risk or cause blowback, particularly if there’s any internal conflict involved. They may cope with their concern by ignoring the issue, making it a low priority, waving you away, or conveniently forgetting the details you’ve already told them. 

In the end, you may give up so as not to damage your relationship. But in the meantime, you want to be able to give direction to your team or convey a resolution to colleagues who are resisting you. Here are a couple of options for managing up and trying to move the situation forward.

Show Your Boss You Can Help Them Solve the Problem

Think about it this way: If your boss felt comfortable dealing with the problem, they’d have done it by now. You may have to come back to this uncomfortable issue several times—even a great number of times. The stance you choose to take should demonstrate your desire to alleviate their tension as well as resolve the problem. If you can, try to find several different ways to bring up the subject—pleasantly, of course, because although it’s perfectly reasonable for you to bring it up, you don’t want to wear out your welcome. And you certainly don’t want to sound repetitive or overly insistent.

Here are a few examples of language you can use to open the conversation:

  • How would you like me to tee this up for you?
  • When would be a good time for me to show you the data?
  • What do you need to know to be able to make a decision about this situation?
  • Boss, I’m just bringing you up to date on the XYZ situation.
  • How can I fit the needs of the XYZ plan into the rest of the projects for this month?

Of course, your boss can continue to put you off, but if you pleasantly and persistently keep returning to the table, using a variety of ways to present the request, it’s more likely that the exec will actually focus on some of them. If they hear the same request over and over in the same language, though, they may perceive that you’re being argumentative—especially if they’re feeling defensive either about the issue itself or about putting you off so many times.

In effect, what you’re doing is creating a few seconds of preamble during which your boss can get reoriented to the situation you’re raising. The fact that you’ve made multiple approaches from different angles will help them focus, allowing all the pins in the tumbler to line up when the key piece of information or situational shift finally slips into place for them. 

This way, you’re accomplishing several helpful things. You’re  demonstrating that you want to take action in a way that works for them. This approach also shows you in a better light: You’re not being defensive or argumentative or trying to make things difficult for them, and you’re potentially reducing the heat and helping them ground themselves in the issue you need them to be thinking about.

Let Your Boss Know They’re Not Alone

The second technique is to build your boss’s confidence in the direction you want to go in or in the conclusion you want them to reach. It involves a particular bit of phraseology that says they’re not on their own or going out on a limb. It’s structured like this:

“We need to talk about/ head in the direction of X because we all recognize that [provide a description of the problem or decision].”

I helped one client set up the conversation for her boss this way:

“Boss, we need to figure out what temporary workarounds we’re going to need in terms of extra staff or outside expertise because we all recognize that Finance has not been able to keep its reporting commitments.”

The crucial language here is “because,” which links the necessary action to the problem, and “we all recognize,” which declares that agreement already exists. (Of course, you have to be sure that it does.) With this approach, you’re stipulating the fact that the executive you’re trying to persuade will not stand alone—they have a community of agreement to draw from and rely on. You’re essentially saying, “We’re all on the same team, dealing with the problem that we all acknowledge.”

Some people are so risk-averse that you’ll never convince them to act (and they’re usually not the best people to work for). But if there’s a possibility that someone can be nudged, these two techniques may help. 

Onward and upward—

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