How to Work with Your Boss’s Boss and Boost Your Career

 

In many organizations, it’s tough to see where career growth will come from. Maybe your boss isn’t going anywhere soon, and there don’t seem to be any useful lateral opportunities at the moment. It isn’t always easy finding ways to “develop in place” in the meantime. Even if your boss thinks highly of you and wants you to succeed, they may not have thought about sharing with you one of the few resources they have: access to their leadership, whether it’s their own boss or their boss’s boss.

It’s pretty typical for a senior leader two or three levels up not to know much about you or your quality of work, or even to have any interest in you at all. They may not recognize you, know you by name, or have any idea what your strengths are — which can’t be great for your career, right? And yet, for all you know, the senior leader may be crying every night, “Isn’t there someone who can step up to handle more work?”

Will Your Boss Put in a Good Word for You?

It can be tough to get in front of a senior leader who is not thinking about how to strengthen the talent bench, plan for succession, or even get to know the people on the team, no matter how well your own boss speaks of you.

Here’s something to try: Encourage your boss to say that they’re bringing you to the next significant meeting. Your boss can explain, “Jane is actually running point on this. Of course, I’ll be there to answer any questions, but Jane and I have discussed everything, she’s doing the right work, and I want her to be able to tell you about it herself.”

If the senior leader is relatively new to the team, your boss could set up the situation this way: “Senior Leader, you’ve been here for X months and you’ve already accomplished Y and Z. We’ve done all this great work, and we see the results of A, B, C, and D. Now that we’re [stable/on an upward trajectory/finding our footing], what do you think about experimenting to see how we could run things better by involving some other members of the team?”

Get Your Pitch Ready

But say your boss doesn’t want to expend their scanty political capital by putting you in front of their own boss. In that case, you may have to find other allies, whether they’re other senior leaders you already know, your HR business partner, or even a supplier you work well with — anyone who has a positive relationship with the senior leader.

Or you may have to find the opportunity to make a pitch for yourself, whether you do that by email or perhaps at the beginning or end of a meeting. Before Covid-19, I even encouraged mid-level leaders to learn their senior leaders’ schedules and “run into them” in the breakroom or restroom!

But first you need to figure out your pitch: Why are you the right person at the right time, and what would you like to accomplish, both for the organization and for yourself? For example: “I’ve been thinking that, based on [our recent organizational change/the experience I’ve had on the ad hoc task force, etc.], I could take on more responsibility for execution. My team is in good working order and I have strong interdepartmental working relationships, so I could take on some of these new projects directly, which would let me learn more about the business.”

Managing the Interaction

Many senior leaders are wary of building relationships two and three levels down with people who are unfamiliar with how they like to work or are unused to the amount of pressure they’re under. So you’ll want to show that you can take the heat — and that you’re eager to learn from any feedback the senior leader has to offer.

If you’re overt about your desire for feedback and specify that you’re comfortable absorbing it, there’s a greater chance that the senior leader will actually share their views with you. The more concrete you are about your willingness and ability to absorb their comments and adapt, the better chance you’ll have that they’ll be willing to be direct.

You could begin: “Senior Leader, I have a lot of views on this subject, but just cut me off if you don’t like the direction I take.” In effect, you’re declaring, “I’m on your team — here to work with you the way you want to work. And I can take criticism.” If the senior leader does cut you off, acknowledge it: “Okay, I see you stopped me there. You don’t like this approach.” Not only are you showing that you understand, you won’t come across as resistant or defensive. When you have the opportunity, you can ask explicitly, “I’m trying to learn how to present things to you better. Could you tell me what I said or how I said it that set off alarm bells for you?”

It’s not always easy to gain access to your senior leadership, and it can be challenging to know how to interact with them. But if you can get that opportunity, it’s a good way to start to raise your profile, develop more political savvy, and possibly advance your career.

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Author: Liz Kislik

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