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Advice / Succeeding at Work / Work Relationships

The Trick to Working With a First-Time Manager (Who's Struggling)

boss and employee
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I have a secret for you. Are you ready?

No matter where you work or what you do, working with other people will always be a challenging part of the job.

I’m sure you can relate—how many times have you had to deal with a co-worker who was difficult, unreliable, or overly involved?

But what’s even more challenging than learning how to work with others is learning how to manage up.

Many first-time bosses are trying to compensate for their lack of experience and avoid looking vulnerable, which causes them to sometimes come across as egotistical, power-driven, micromanaging, or unproductive.

But believe me when I tell you there is anguish on the other side of the desk, even if your new manager appears unfazed. They constantly question if they’re doing it right, if they’re liked or respected, if they’re trusted, and if they can trust you.

The upside of your role as their first direct report is that you’re in the position to strategically anticipate and meet their needs, which eases their stress of being responsible for you in the first place. And removing that stress makes it more likely that they can focus on what you need them to do (you know, leading your team, setting goals, and all the other stuff good bosses do).

Of course, in order to do this, you need to understand what’s currently making their job hard.

I know, hearing this may have you thinking, “But why do I have to be the one to do all the grunt work?” And I get it, it stinks to have to be the resourceful one when your boss isn’t.

But like I said, your manager’s most likely acting like this because they don’t have a good handle on their responsibilities. By offering to take work off their plate, you not only put them in a better mood, but get rid of some of that bottlenecking you might be dealing with. And that, as you know, will only make it easier for you to work more effectively and productively. As you can guess, that will make you look pretty good to anyone who’s working closely with you.

Doing this starts with asking your boss the right questions in your next one-on-one (or, setting up regular check-ins to begin with):

  • What can I do to make your job easier?
  • How can I keep you informed in a way that doesn’t require more of your time?
  • What can I easily take off your plate?
  • What can I do for you that I’m not already doing?
  • What questions should I ask that I haven’t already asked?

These might seem a bit too obvious or nebulous, but the purpose is to ask them in a way that elicits usable information, so that you might then design your priorities in a way that alleviates some of the burden.

For example, years ago, I could tell one of my first-time managers was flailing. He was a new parent—a stressful change for anyone—and struggled to juggle the additional responsibilities of his new role.

So, I looked for ways to make myself invaluable. I took it upon myself to volunteer to do the parts of his job he didn’t like doing, the parts that ultimately kept him from managing clients, a critical part of his new role. It was a win-win scenario. I grew my skill set by taking on more work, I built a stronger relationship between the two of us, and I helped position him for success. He still thanks me for it to this day.

When first-time managers are flailing, doing some of the work for them makes everyone’s life easier—especially yours.

And, just think: being empathetic, proactive, and collaborative might even get you promoted to a—wait for it—first-time manager yourself.