Dear Crucial Skills,

At our company, management has the option of being flexible with certain time-off guidelines. Other bosses are quite flexible, while my boss is very restrictive. I also think she is not compassionate regarding work-life issues.

For example, when a coworker’s in-law died, my boss called her at home, asking her to come into work on the day between the visitation and funeral in order to limit her paid time off.

How do we have a conversation with our boss about the impact she has on employee morale and engagement without causing her to become defensive and to potentially punish us later (e.g., salary performance reviews)? Also, should I bring this up with her individually or publicly during a team meeting?

Unengaged and Frustrated

Dear Unengaged and Frustrated,

There are a few points I can offer on this concern. I’ll start by answering your last question first.

Make your first conversation safe and private. Talk to your boss privately; at least the first time. Why start with a private talk? The main reason is that when there are other people in the room (even one other person), the dynamics can change. If you don’t talk to your boss privately, she may feel the need to defend her position of authority or save face. Safety is a key component of any crucial conversation. We need to make sure we go into the conversation in a way that makes it safe for the other person. That means that our nonverbal signals (our face, our tone of voice, and our body language) all illustrate that we are in inquiry mode—that we have noticed something and have some questions. We should also try to find a convenient time for the other person to meet. Trying to talk to your boss when she’s stressed or trying to meet a deadline is not the best approach.

Rapidly and respectfully resolve problems as a team. Our crucial conversations research shows that the best companies and teams achieve strong results and relationships because they rapidly and respectfully resolve problems. A safe, private conversation is usually the best starting point, but it is also healthy for teams to work on their skills so they can bring up issues and resolve them rapidly. Rather than walk on egg shells or play games, the most effective teams put issues on the table, maximize input, explore options, diagnose causes, brainstorm ideas, and decide how to proceed. The reason they can do this is that they have worked on developing mutual purpose and mutual respect. Getting to this point is, of course, best done with the help and leadership of a boss. So perhaps this is a conversation you could have with your boss. Ask how the team could work together to more effectively bring up and resolve problems in team meetings. If you create this condition, the problems that concern you will be brought up and resolved.

To answer your other question—How do we have a conversation with our boss without causing her to become defensive and potentially punish us later?—I would like to address two concerns.

What you don’t talk out, you act out. Ask yourself why a reasonable, rationale, decent person would be acting this way and what you can do to help. Then use the skills above and go for it. Be tentative, but ready to share the reasons for bringing up the issue (e.g., “I’m concerned that strict adherence to time-off guidelines is having a negative effect on employee morale and engagement.”) If you make progress, that’s great. If she gets defensive, reaffirm your purpose. If she is quiet and agreeable then later acts in ways that seem revengeful, address these concerns, and if the problem persists, talk to HR.

I know it is tough to contemplate negative consequences, but I also know that if you don’t talk to her, or if you talk to others about your concerns, the issue will not be resolved, productivity and effectiveness will decrease, and relationships may be damaged.

Without preparation you won’t solve problems. Find a friend and practice before you hold the conversation. First ask the other person to be agreeable while you practice, then ask him or her to be defensive and difficult. Practice, practice, practice, then set an appointment to hold a crucial conversation with your boss.

Best wishes,
Al