Q&A – How to Have a Crucial Conversation with Your Boss

ANSWER

Dear Nervous,

The sentiment that stood out to me the most about your question is your concern that approaching your supervisor with a Crucial Conversation is disrespectful to them or their role as a leader. You’re not alone in thinking or feeling this way.

Too often people make the tradeoff between saying something to their supervisor and simply stuffing their concerns for fear of being disrespectful or even out of line. But what you need to realize is that silence isn’t noble, it’s destructive. One of the most important principles taught in Crucial Conversations is that what you don’t talk out, you’ll act out.

Over time, your resentment about your supervisor’s micromanagement, oversharing, and overstepping of boundaries will grow unmanageable. Inevitably, your frustration will manifest itself in ugly vent sessions, backbiting, and gossiping to teammates, friends, family, and anyone who will listen. I also find unresolved and unspoken concerns are at the root of most passive-aggressive behavior. And, if, by some miracle, this toxic behavior stays hidden from your manager, ultimately it will cause you to disengage from your role.

So, the way I see it, the only way forward is to speak with your supervisor about your concerns. And it is possible to be both candid and respectful with anyone—regardless of power, position, or authority—another tenet of Crucial Conversations. Here are a few ideas for having a Crucial Conversation with your supervisor.

WORK ON YOURSELF FIRST, THE SUPERVISOR SECOND
Before you have a Crucial Conversation, get your emotions in check by looking for ways in which you add to the problem. It isn’t that your supervisor doesn’t have faults; it’s that we tend to exaggerate the role others play when problems affect us. Honestly examine your own behavior to see whether and how you might be contributing. For example, you admit to withholding information from your supervisor. I believe this behavior is contributing to a vicious cycle: your supervisor doesn’t receive the communication they need so they micromanage or overstep boundaries, which bothers you, so you withhold information. And so on.

START WITH YOUR GOOD INTENTIONS
Ask for permission to talk about a concern in private. Once you sit down, thank your supervisor for taking the time. The first thirty seconds set the tone for the rest of the conversation. Explain your desire to work through a problem in a way that meets both of your needs. This win-win tactic may seem obvious, but many people enter conversations with the goal to improve only their own situation—not a good starting point.

FOCUS ON THE ONE ISSUE YOU CARE ABOUT MOST
It appears that you’ve waited far too long to address your concerns, which is why you have a whole list of gripes like micromanagement, oversharing, and disregarding communication boundaries. While it’ll be hard, avoid airing all these gripes in your first conversation. Instead, work on one issue at a time. Give them time to digest, respond to, and work on your concerns before starting with another issue. This will require careful analysis of what issue is most urgent or problematic. To narrow the field, consider what you really want for yourself, for your supervisor, and for the relationship. For example, if what you want most is a relationship of trust, address the pattern of micromanagement and wait till that’s resolved before tackling communication boundaries.

STICK TO THE FACTS
Describe the problem you’re experiencing by starting with the facts. For example, perhaps they asked you to complete an assignment and proceeded to ask for updates several times a day. This is a fact. You may feel they think you’re incompetent or don’t trust you, but these are conclusions. Conclusions are often inflammatory, can be wrong, and frequently create defensiveness. So, start with the facts. What specific actions led you to your conclusions?

SUGGEST REPLACEMENT BEHAVIORS
After you’ve explained the problem, suggest what you’d prefer. “It would work better for me if we could check in on the project every other day instead of several times a day. At the current rate, I’m not able to stay focused or create quality work for fear you’ll be interrupting me at any moment.” Often, people behave poorly because they don’t see alternatives. Give them alternatives. If necessary, jointly brainstorm until you come up with a strategy you can both support. One idea: commit to sending a project report every 48 hours detailing what’s been done, what’s in progress, and what is on deck. This may be enough to stop the micromanagement altogether.

DEFINE “WHO DOES WHAT BY WHEN” AND EXPRESS YOUR THANKS
Wind down by describing exactly what each of you will do to help improve your working relationship. And finish by expressing your appreciation for their willingness to listen to your concerns.

See how this approach is both candid and respectful? You respect your supervisor’s schedule by asking for time to talk when it’s convenient. You respect their reputation and privacy by sharing your concern discreetly rather than in front of the team. You assume the best of them by checking your emotions and story to find where you are contributing to the problem. And you thank them for taking the time to consider how you can work better together. Nothing about this approach should come off as disrespectful. It can also be used with anyone, not just your supervisor.

With the right skills, it’s possible to approach anyone with any title. If they refuse to accept your skillful and thoughtful conversation, that’s their choice, and you may end up where you would have had you remained silent—disengaged and looking elsewhere.

However, if you follow the steps I’ve outlined above, at least you’ll know it’s not for lack of trying to improve the situation. And really, that’s all you can do.

Best of luck,
Brittney