Old Job, New Boss? How to Impress the Hell Out of Them


After five years of working together, Sheldon’s boss has moved on to greener pastures. His new boss hasn’t even been selected yet, but he’s seriously freaked. “What if I don’t like them?” he complains to anyone who will listen. “What if they don’t like me? What if they’re some kind of control freak who wants to tell me how to do my job? What if they have totally different expectations than my old boss had? What if they want to bring in their own team and we all get fired?”

Few things are more stressful in a career than the prospect of a new boss. But if managed correctly, the experience can be positive for both you and them.

Before they start:

Look forward to working with a new boss.

I mean, actually look forward to it. Assume that your company won’t hire an idiot. In fact, consider the possibility that maybe, just maybe, a new boss with a fresh perspective is exactly what you need to enhance your skills and take your career to the next level.

Do your research.

Connect to them on LinkedIn with a nice note about how much you’re looking forward to working with them. While you’re there, take a look at their career progression, any interests or associations they have listed, where they went to school. Take a look at their endorsements and recommendations. Then have a peek at their other social media accounts. Search to see if they’ve made any media appearances – interviews, guest posts, podcast appearances or op-eds.

Use this information to get an idea of who they are, and what’s important to them.

In their first week:

Be welcoming, but not fawning. Any boss worth their salt can smell bullshit a mile away. Instead, be warm. Keep it light. Ask them if they have any questions. In other words, just be kind and decent.

In your initial meeting, follow their agenda, but be sure to get these three key points across:

  • This is what I’m good at.

  • This is what I’m working on.

  • This is what I’m excited about.

That’s it. In the first meeting, they don’t need to know your thoughts on which projects are bogus and which of your colleagues needs to be fired. Keep office politics out of the discussion. Make it clear that you are there to support them and help them get up to speed as soon as possible.

Over the next few weeks:

Make time for them.

New bosses often have a ton of questions. Take time to answer them as clearly and honestly as you can. If appropriate, prepare a short deck outlining your key metrics, strategies and challenges and take them through it.

Clarify expectations.

Are they expecting you to be super-fast in your work? Or super accurate? Or both? Do they want weekly check-ins, or are they cool only hearing from you when there’s a problem? Would they like you to regularly pop into their office for a chit-chat or are they more formal?


There’s a good chance your new boss’s expectations will be different than those of your previous boss. It’s best to get clear on that ASAP.

Set boundaries.

Sometimes, even the best-intentioned bosses can accidentally step on toes. If your new boss accidentally meanders into your area of responsibility, simply say, “I can take care of that”. If you have to leave work every day at 5:30 to pick your kid up from daycare, let them know as soon as possible.

Watch their back.

If you see your new boss about to step into a hornet’s nest, let them know. If they’re in danger of unknowingly missing a deadline, let them know. This is how you build trust. And it’s how you become a valued employee.

Let go of the past.

This is perhaps the most important step. Things will change. This new person may have a different style, different ideas and different priorities than your last boss. Clinging to what was is a sure-fire way to become more of a hinderance in their eyes than a help.

What if the new boss actually turns out to be a bit of a jerk?

Okay, I admit that can happen. But if it does, it doesn’t have to be the end of the world. Remember: no matter what, you’re in charge of your career.

You can read more about that here.


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