Why Is It So Hard to Bring Up a Difficult Issue With Your Boss?

During a coaching session, Whitney, a mid-level manager, told me that she wished her boss Liam had handled the situation differently.

The “situation” was Liam not addressing Whitney’s counterproductive management style until Whitney did something that almost got her fired.

Whitney said that even though she was finding coaching very helpful, she wished it hadn’t taken the near job-ending incident for Liam to suggest it.

Why didn’t you say something to me?

She said “You know, it would have been nice if Liam had said ‘Hey Whitney, you need to work on how you’re coming across,’ and not wait until I did something that almost got me fired before he pointed out I needed coaching.”

As Whitney talked more, it was clear she felt betrayed. Even though she respected Liam, because he didn’t give her a heads up before things blew up, she questioned Liam’s ability as a manager.

When I asked Whitney if she would be willing to tell Liam that she would have appreciated getting the heads up earlier, she couldn’t imagine doing so. She envisioned Liam getting angry and defensive if she brought it up.

Who wouldn’t get defensive?

“Like what am I going to say ‘Hey…you dropped the ball here…you should have brought this up a long time ago if you saw it as an issue’?

Obviously, if Whitney were to bring up the issue in that way, Liam would likely get defensive and angry.

Whitney’s fear of bringing up the issue, and her fantasy of how she would go about it, are perfect examples of why people are so reluctant to address difficult issues, especially with their boss.

When they think about bringing up an issue, the method they imagine is the way they typically experience other people bringing up difficult issues. Since most people do so in clumsy, often antagonistic, ways, they rightfully fear addressing it will trigger defensiveness and antagonism.

So they decide instead to remain silent.

When people don’t talk it out, they often act it out

Just because nothing is spoken, obviously doesn’t mean the issue — and their feelings about it — go away.

Rather than express their displeasure with words, they express it through actions.

They act out their anger, frustration or resentment.  When employees don’t like how they’re treated, but are unwilling to talk about it, they end up expressing their anger or hurt by:

  • Not caring as much about their boss’s or employer’s goals.
  • Not being as interested in pleasing their boss.
  • Not looking for, or offering, ways to provide more value.
  • Withholding that extra 10 percent of effort.
  •  And so much more

How DO you bring up a touchy subject?

So how should someone in Whitney’s situation bring up such an issue?

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When bringing up a potentially touchy issue, one of the most important factors influencing whether the conversation goes well is where you “come from.” For the conversation to go well, it’s critical to come from a position of curiosity, rather than accusation and judgment.

We want to open up the conversation in a way that communicates our sincere desire to understand where the other person is — or was — coming from.

I will give you four examples of how Whitney might bring up the issue. Notice how the following openings — what I call the Declaration/Invitation — vary in terms of how accusatory and confrontational they come across. I did this on purpose to give you a chance to compare and contrast various approaches. My intention is to show a variety ways of bringing up a touchy issue, and how important even a small change in wording can be in creating a very different impact.

Imagine you are Whitney’s manager Liam and each Declaration/Invitation is being addressed to you.

Notice how the different approaches affect you, and what words and phrases make you feel judged and accused and what make you feel like you’re being invited into a real dialogue.

I would love for you to comment below on your observations, and perhaps offer your own suggestion of how Whitney could bring up the issue.

“Hey Liam…I was thinking about how the whole blow-up thing with Napoleon triggered the coaching I’m getting. Even though I’m finding it helpful, I wish it hadn’t taken things coming to such a head for me to get coaching… (followed by each of the four different endings).

  1. … why didn’t you say something earlier?”
  2. … I wish you had said something earlier about what you saw me needing to work on, so it didn’t  have to come to this…you know what I mean?”
  3. … I was thinking I wish I had been told ‘Whitney…you’ve got some rough edges that need to be smoothed over’ or something like that earlier on…and then I started wondering if you have been trying to give me that message and I wasn’t hearing it?”
  4. … and I started wondering if you had been trying to give me that message and I wasn’t hearing it?”

What did you notice — and what do you suggest?

So, what did you notice about the tone and approach of each Declaration/Invitation and which do you think would trigger the most productive response from Whitney’s boss Liam?

What other ways would you suggest bringing up the issue?

Please share your observations and suggestions in the comment section below.

David Lee is the founder and principal of HumanNature@work and the creator of Stories That Change. He's an internationally recognized authority on organizational and managerial practices that optimize employee performance, morale, and engagement. He is also the author of "Managing Employee Stress and Safety," as well over 100 articles and book chapters. You can download more of his articles at HumanNature@work, contact him at david@humannatureatwork.com, or follow him on Twitter at http://twitter.com/humannaturework.

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