Dear Madeleine,

I manage the creative design department for my company and have for years. We have a reputation for offering inspired and visually arresting products—because of me, basically. My boss is a great guy; I actually followed him here from another company. In fact, that may be the problem—my boss is just too nice.

I have the kind of job that requires my team and me to deliver on tight, time-sensitive deadlines. Everyone who works with me knows that sometimes we will have to work late or come in early, and that we can’t take undue time off during crunch periods. I am also extremely rigorous about the work we produce—after all, our reputation depends on it! I often give direct reports hard feedback to help them bring their work up to standard.

Sometimes when one of my people wants to take time off and I have told them no, they go running to my boss. The next thing I know, he calls me on the carpet for being too tough. What’s worse is when he tells a person they can take the time off they want, even when they are working on a big fat deadline. Of course, he doesn’t talk to me about how I am supposed to meet the deadline! I recently was admonished by HR when a direct report exceeded their PTO and it was because my boss told the person they could!

It is impossible to get things done when my boss doesn’t support my decisions. He wants everyone to love him, but it is at my expense.

Overridden

Dear Overridden,

So many middle managers are busy protecting their people from the slings and arrows of the folks upstairs—but you seem to have the opposite problem. This is definitely a tough one. Your boss wouldn’t be the first leader to be undone by their own need to be liked.

I hear the anger and resentment you are feeling and it is probably getting in the way of what really needs to happen—you need to sit down with your boss and hash out some boundaries.

Here is something I have tested with both myself and clients. It is a 7-step process for a conversation, taken from the book Fierce Conversations by Susan Scott. This approach is a good way to call out natural, forgivable human behaviors that everybody engages in at one time or another.

1. Name the issue (g., your people go running to your boss when they don’t like what you’ve said).
2. Select 2 or 3 specific examples of the behavior or situation you want to change.
3. Describe your emotion about this issue (e.g., it makes you feel unsupported by him).
4. Clarify what is at stake—and be very clear about this. Is this a problem because you can’t get your job done or because you are losing credibility?
5. Identify your contribution to the problem. Is it possible that you are too tough on your people? Be honest.
6. Indicate your wish to resolve the issue, being specific about what resolved looks like to you. This is critical and will provide you both with a measure so that you will know if the fix is successful.
7. Invite your partner/boss to respond.

The thing I like most about this process is that it forces you to prepare for a conversation about one problem and one only. You can’t pile on with everything your boss does that drives you crazy—but maybe you can get him to change one thing he does that is hindering your success.

Good luck to you.

Love Madeleine

About the author

Madeleine Homan-Blanchard is a master certified coach, author, speaker, and cofounder of Blanchard Coaching Services. Madeleine’s Advice for the Well Intentioned Manager is a regular Saturday feature for a very select group: well intentioned managers. Leadership is hard—and the more you care, the harder it gets. Join us here each week for insight, resources, and conversation.

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