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How to Talk to Your Boss About Your Career Path

Whether you’re just starting out at a new company or you’re a longtime stalwart, that conversation about where you are versus where you want to be is always a stressful one. And of course it is! It carries with it a necessary tenor of dissatisfaction that’s just pretty hard to shake, and nobody wants to be the one complaining to their boss or demanding a raise.

It’s awkward, is what I’m saying.

But it’s time to stop having this conversation in the bathroom mirror (ideally, pointing determinedly at your reflection and demanding what you’ve earned) and start having it with people who can do something for you. That’s right: it’s time to start making constructive life decisions.

A good, healthy career path discussion can help you keep your career from being too jumpy and inconsistent and ensure you develop the right skills to help you advance. The problem, though, is that nobody wants to have a conversation that implies an intent to leave; it looks like you already have one foot out the door and are asking for their help in training you up – just so you can go somewhere else!

So if you’re gonna do this, buddy, ya gotta do it right.

  1. Who You’re Talking To

These are hard conversations to have no matter what, but they’re even harder if you and your boss don’t have a solid, or at least friendly, relationship. Time and experience working productively with someone means that you’ve probably already sorted out how to talk to one another, and trust one another to have the other’s back.

That means that these conversations, at their best, can be extremely frank and forthright; it’s a fraught, complex topic, but it’s vital that you communicate where you are versus where you want to be in a way that doesn’t cause your boss to panic or decide that you’re more trouble than you’re worth. You need to be able to understand who your boss is, how they’ll react, and how to ease their fears; if you don’t have these assets, the conversation is going to be much harder.

But it won’t be any less necessary.

  1. When You Have the Conversation

“Timing,” as they say in comedy, “is everything.”

This is true.

A badly-timed career conversation is going to be unproductive at best – and career-damaging at worst.

You want to make sure both parties are prepared for the conversation; approach your boss beforehand and say that you’d love to have a conversation about your career goals and how you and your company can work together to further them – and then schedule a meeting. That ensures that, when it finally happens, everyone is ready instead of distracted, and it prevents you from springing the topic on people out of the blue, before they can digest what it means. A spur-of-the-moment reaction is much more likely to go badly for you.

  1. Think Ahead

You need to know what you’re going to say before you walk in there.

This feels obvious, but it’s a big question, and that means it’s hard to think about. Where do you want to be in five years? Do you want to still be at this job? Do you want to be married with kids? Do you want your spouse to not have to work to help support the family? Do you want to move? Do you want to throw it all away and go be an artist in Tahiti?

You need to be able to answer these questions. If you don’t want a job that’s going to consume your life, you need to communicate that. If you’re a workaholic who thrives under pressure, you need to communicate that. If you want ample vacation time, or the ability to work from home, or a shorter commute, or the flexibility to see your kid’s soccer games, or the opportunity to travel more – you need to communicate that.

Because career development isn’t just about what your title or your paycheck is. Your company is thinking of it in terms of resource allocation – and that means increasing your value by increasing your skill level. So start thinking ahead; what does the company need, and where does that align with your goals? You don’t go in demanding a company car or more time off; you go in and offer constructive ways to ensure that your goals mesh with the company’s in a way that’s mutually beneficial.

Think about where your team is now, and where it’ll be in a year. Are positions expected to open up? New departments? New opportunities? Are there places you can go to get the experience and skillset that will help you move forward? Businesses love volunteers. Put yourself out there for these opportunities, explain why they’re important to you and why you’d rock them, and you’ll be able to have a conversation about your future that isn’t about why you’re probably going to have to quit, and is instead about how much more you want to offer.