Is It Safe to Be Candid with Your Boss? First Learn What They Want

Liz Kislik February 17, 2021

A few months ago, I did a Dear HBR podcast on how hard it can be to confront your boss. One of the difficulties is that we can’t anticipate the true needs of someone whose experience we haven’t had.

I’m reminded of a story my son’s fourth grade teacher once told me. My son loved this teacher, and when his work was finished, he would go to her and ask, “Is there anything I can do for you, Ms. Tobias?” Sometimes she gave him a little chore, but she told me what she really wanted to say was, “Oh, it would be help me so much if you could just go get me a cup of coffee while I struggle with the rest of the class!” My son never would have guessed that — and of course she couldn’t say it.

In the Dear HBR podcast, two editors and I discussed three scenarios which were quite different but led me to the same set of conclusions. When a boss is demonstrating squirrely or annoying behavior — assuming it’s not inherently unethical or immoral — it’s likely that:

• They have goals that they don’t always communicate them to the team, so it’s hard to understand why you might be working at cross purposes,
  
• They’re probably trying to keep themselves safe, so it will help you be successful if you keep them safe too, and
  
• There is no ESP or mind meld, and you may not actually understand each other, so it helps to find out more of what they actually care about before you assert yourself.

Don’t Criticize So Much

In one example, we talked about a boss who was noticeably caring and adaptive, but also excessively critical of the team’s work. One of the editors suggested documenting examples of when the boss’s feedback seemed out of line. But I see this as an absolutely last resort (again, barring immoral or unethical behavior). If your boss’s actions don’t make sense to you or upset you, beginning documentation, as if you’re making a case, probably won’t be helpful to either of you. If you treat them like the enemy, they’re likely to feel like the enemy, and that’s not a good construct for resolving anything.

Instead, think about how you would treat your boss if they were a beloved relative, and check and confirm along the way with prompts like: “Here’s what we think you said you wanted. Is this what you wanted? We’d like to do it the way you asked for it. Look, we did the thing you wanted!”

Try to get closer rather than pushing them away. The goal should be to ask the boss how he wants things, and to show him that the employees are trying to deliver that. After all, the boss’s critiques could be his way of trying to improve the work product and demonstrate his commitment to excellence. He might not have remembered his earlier directions, but giving him reminders could reduce his need to correct so much every time.

Stop Taking on Extra Work

In another example, we discussed an executive who joined a company right after a merger and kept accepting extra projects for her team. It wasn’t clear whether she was trying to ingratiate herself with the leadership, protect her team by showing how invaluable their work was, or if she had other goals.

One team member was especially distressed by the extra responsibilities and the new boss’s lack of contextual communication. I suggested that the upset team member could help herself and her colleagues more effectively if she would act as the boss’s ally rather than as her adversary. Curious conversations about what the new boss felt was important might create more opportunity to negotiate how the extra work would be done, what the timing would be, or how many more new projects could be attempted, and might even create new motivation for the team.

Stop Accosting and Accusing

It’s hard to be honest with your boss if you’re afraid your candor will be taken as a challenge and your boss won’t react well. It’s awkward and uncomfortable to know that another person might be aggravated with you, and it can be dangerous to put your day-to-day relationships and comfort at risk, not to mention your employment and income.

And yet, at the same time, employees can take steps to strengthen their relationships with their bosses. As much as it is a leader’s responsibility to communicate with and understand their people, employees may need to go out of their way to make their bosses feel understood and comfortable. Then, by relying more on curiosity and concern, employees may be able to convince their bosses that they’re all on the same team.

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