How To Have Career Conversations With The Leadership Team Without Stepping On Your Boss’s Toes

When it comes to scaling your career, clearly articulating your goals up the ladder to people who are at a higher level than your boss is absolutely critical. But…there’s a right way and a wrong way to do it.

Here’s what I mean:

You may be tempted to go around your boss to have these higher level conversations.

And I get it.

Perhaps you and your boss don’t have a great relationship.

Or maybe your boss simply doesn’t support your professional development goals.

This is an obstacle, I agree. But if you’ve been tempted to by-pass having a direct conversation with your boss about the future of your career, you need to do this before you take one more step:


Stacy Mayer here. I coach corporate managers to get promoted into higher level executive positions, and in this edition of Your Promotability Factor, I’m going to show you how to have career conversations with the leadership team without stepping on your boss’s toes.

Here goes.

Step #1: Have a very direct, open, and honest conversation with your boss FIRST.

Before you speak to anyone at a higher level, you first need to have a conversation with your boss.

And to be clear, this conversation is about your own professional development.

Not your job performance.

Not how to be a better manager.

It’s about your long-term career expectations.

And one of the benefits of talking about your long-term career goals is that it is a lot less threatening to your boss. 

I would approach it like this:

Tell your boss how you hope to have X role in the future (for example: maybe you want to be vice president, CRO, or CFO). Then, explain exactly why you believe you are uniquely qualified to occupy that position someday.

Then ask your boss this question:

What would you need to see from me in order to make this happen?

This will help you get clear on what leadership attributes you would need to demonstrate in order to set yourself up for promotion.

Now, you might be thinking: ‘Stacy, my boss doesn’t support me. They don’t want to talk to me about my career.’

I get that.

But I don’t care.

Even if your boss isn’t invested in your career, you are still allowed to schedule a 15 minute, 1:1 talk with them to discuss your professional development.

Now, fair warning, your boss may annoy you.

She may say you need to wait it out.

But none of that matters.

By having a career conversation with your boss first, you’re showing that you expect to move into a senior level leadership position over the next five to 10 years.

And you need to put these long term career goals on the table with your boss before you can move onto step #2.

Step #2: Have that conversation with your boss’s boss (or above)

So you’ve talked to your boss about your career goals.


NOW is the time to start reaching out to other members of the leadership team.

Because, by laying it on the table for your boss, you’ve established that you are gathering information from people about what it will take for you to become a c-suite executive.

NOW, when you approach other people in your organization, you won’t be stepping on your boss’s toes. Because if you’re gathering information about your professional development, it’s natural that you would talk to everyone you could, right?

So have more meetings, gather that information, and reveal those big plans you have for the future.

If you want to take this work deeper and learn how to think and communicate like a c-suite executive so you can move into your next role with ease, I welcome you to check out my upcoming executive group coaching program: Executive Ahead of Time.

Join the waitlist here.

PS: If you have a question you’d like me to answer on one of my upcoming Your Promotability Factor Weekly Q&A, direct message me the answer to this question: “If you and I were to have 30-minutes together and you could get my input on anything, what specific questions would you have for me today, this week, this month?”

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