Leadership Advice

You, your boss and your staff: Who’s talking to whom?

Advice from Jill Geisler, Bill Plante Chair in Leadership & Media Integrity, Loyola University Chicago and Freedom Forum Fellow in Women’s Leadership

Here’s a quick quiz for managers:

You see one of your team members having a conversation with YOUR boss. Is your response:

  1. I’m uncomfortable because I fear that staffer is doing an end run around me
  2. I’m curious about what they’re discussing, but not concerned about it
  3. I’m glad to see people getting time and attention from my boss

I hope you landed on numbers two or three, either of which is a sign of a healthy team — one that includes you, the person you report to, and those who report directly to you.

It means that both you and your supervisor encourage people to reach out whenever they have something on their minds. It also means you and your supervisor communicate regularly and have strong trust between you. If one of your team members brings something to your boss’s attention, your boss will automatically ask if the person’s already discussed it with you. If not, the next step will be to make sure that happens. Your boss makes sure that you’re in the loop.

If you’re a good manager, you don’t fear people having routine conversations with your manager. You’re not so hung up on “chain of command” that you feel people need your permission before they’d even dream of talking to someone higher than you on the food chain. You know your people — and your boss — well enough that there’s no downside. No backstabbing. No game playing. It’s just open, creative, friendly communication — and a great way to work.

Now, things don’t always work out that neatly. You may work for a supervisor who doesn’t loop you in about conversations with your staff, cuts side deals with them or arbitrarily reverses your plans or decisions. In that case, you need a conversation with your boss about the problems such actions cause you as a manager. If the problem persists despite your best good-faith efforts, you need to explore your options — which range from going over THAT boss’s head, to finding a new job. 

You may have an employee who routinely bypasses you to get time with your boss to promote themselves, dump on others, or sow dissension. In that case, both you and your boss need to get on the same page with that employee, setting boundaries and expectations about behavior.

And, sad to say, if people go over your head, you might be the problem. The way you lead — or fail to lead — may leave your staff with no alternative but to talk with someone above you. It may be their only way to get solutions to problems you’ve caused or neglected to solve. Here’s a reality check: If you forbid your people to talk to your boss without your express permission, I suggest you give some deep thought to your level of insecurity, your need for control, and the trust that’s missing in your work relationships.

But let’s not end on a downer like that. Let’s go back to the quiz. If you’re not quite sure you’re at answer number three: “I’m glad to see people getting time and attention from my boss,” now’s the time to work on it. It’s especially important as people return from remote work to the new normal, when people will be under the same roof. Make certain yours includes open doors, open minds, and open communication.


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