How to Ask for a Promotion (and Have Other Tough Conversations With Your Boss)

Last year, my colleagues launched a tool called The Next Five to help people navigate through those times in their career where they’re feeling kind of stuck. You know — when you’re just not sure what the next step is on your career path.

And while many of us think about this stuff from time to time — and maybe even practice the speeches to go with them in the shower or in the car — I don’t think we often verbalize our thoughts on where we want our career paths to go, if we even know ourselves.

So, we did a little research to see how often people are actually asking for promotions, or talking with their managers about the next steps in their career paths. It’s pretty hard to find a ton of hard data on it — if you know of any, please send it our way — but we did find this: The Bureau of Labor Statistics reports that the average tenure for today’s worker is 4.4 years. If you focus on just younger employees, that number halves.

What’s more, 91% of workers born between 1977 and 1997 report going into new jobs with the intent of staying less than three years.

While it sure seems like a jumpy career path is normal, there’s more to be said about the importance of these career discussions. After all, if your manager or employer yourself, which would you prefer: helping your team progress internally, or having them leave for what seems like a better opportunity elsewhere?

And if you’re looking to have this conversation with your boss, keep that question in mind. To help you get the conversation started, let’s take a closer look at why they matter and how you can get the most out of them.

Why Ask for a Promotion? Do Career Path Conversations Even Matter?

Some workplaces look at job-hopping as a phenomenon we just need to accept in this day and age. And they’re probably right … to an extent. I don’t think many industries should expect to return to a time when people stayed at companies for decades. But we might be able to find more longevity out of our roles than we do right now.

Quite frankly, job-hopping sucks for more than just the organization that has to rehire and retrain someone every couple years — it sucks for the employee, too. Yes, maybe they get promotions and raises — in fact, it’s not an uncommon way to make your way up the career ladder. But it also means taking a risk, adjusting to a new team and a new manager — possibly finding out one or both of those are a poor fit — and figuring out the nuances of a workplace and job that you could end up hating.

Worst case scenario? You end up out of work at the end of all that, and you’re back on the interview circuit.

So I think it behooves of all of us to have these conversations about what we want our career paths to look like with ourselves, and our managers. It helps us get closer to the work and life we want, and it helps clue our managers in on how to give it to us.

A Few Helpful Guidelines

Before we jump into the nitty-gritty of these conversations, let’s set some ground rules for how these conversations go. Keep these in mind before you launch a large-scale discussion about your career path.

Think about your relationship with your boss. If you’re on good terms, great — chances are, the door is open and you can be candid about what you see for your career trajectory, or your confusion around it. The best managers are the ones who know how to create or find opportunities that combine your skills, interests, and challenges, so these are some things to outline before the conversation. However, if your relationship with your boss isn’t so splendid, or she’s just not in a decision-making position like this one, look higher. Figure out who the best person is to speak with, even if she works in a different department.
Chat with colleagues who are changing roles. When someone on your team is leaving her role, knowing why can help you determine what you see for your own career path, and perhaps give considerations to possible changes that you didn’t otherwise think of. Plus, if she’s leaving a vacancy as a result, that might be an opportunity for you — find out what the true nature of the role is; then, determine the next steps for applying for it internally, if it’s a good fit.
Be your own hiring manager. Many managers crave a sense of proactivity and the ability to solve problems independently from their teams. Remember what we said earlier about what makes a good manager? By figuring out some of these things yourself — like the types of opportunities that are a truly a strong combination of your skills and interests, as well as the team’s unmet needs — you might be able to create your own promotion and subsequent role. Explain why your idea checks off those boxes and meet with your team or boss to discuss it. But be sure to come prepared with a clear idea of what’s next, and how to plan to execute this development should it be approved.

What Elements Make Up an Effective Career Path Conversation?

I’m gonna put my money where my mouth is and talk about my own experiences with these conversations.

I’ve had career path conversations with many bosses — the last formal one was around March — but I’ve also held them with people on my team. Both have been awkward … sometimes. But both have been totally normal and non-cringe-inducing just as often.

When I look back at all those conversations at a macro-level, the good ones (whether they were about my career or my teammates’) all came down to three elements:

Relationship
Timing
Forethought

1) Relationship

Technically, this shouldn’t matter. You should be able to have productive career path conversations no matter the manager-employee relationship. But it would be naive to think the relationship you have with your boss doesn’t play into how well these conversations go. That’s not to say the closer you two are, the better the conversations go — sometimes the closer you are, the harder it is to have frank conversations.

But the better you know each other, and the more ease you have talking with one another, the more likely you’ll have already sorted out communication styles that work. You’ll just know how to get from point A to point B with less pain and awkwardness, because you’ve done it before.

It also gives you the ability to “read the room,” so to speak. You can tell if something you said is being poorly received or misunderstood. Those soft skills matter when you’re talking about career paths because they can accidentally veer into uncomfortable territory and leave people feeling insecure if the communication is off.

If you don’t already have a strong working relationship, it doesn’t preclude you from pulling off a successful conversation. It just makes the next two items — timing and forethought — all the more important.

It also might help to run a few practice rounds with someone so you can make sure you’re clearly verbalizing what you intend. Former HubSpotter Katherine Boyarsky does this and can’t recommend it enough: “Have a mantra that you can repeat in your head during the conversation that helps center you if you go off on a tangent,” she explains.

Aim to be very clear, direct, and forthright with what you’re looking to do without putting the other party on the defensive.

2) Timing

There have been a few career conversations I’ve had in the past that were ill-timed. It didn’t turn them into an utter disaster, but they just didn’t seem to stick. The most common instances where the timing has been off in my experience have been:

My boss didn’t know I wanted to have the conversation/I sprung the conversation on a team member in our 1:1. When it comes to talking about your career path, you can’t expect great results from a conversation in which half the people in the room are unprepared. Give everyone some time to think about this. After all, it’s a massive topic that has a lot of moving parts to consider.
We tacked it on to the end of a meeting but didn’t have enough time to finish the conversation. Because your career path is such a massive topic, allot enough time to do it justice. I think career discussions are best when they take place over a series of conversations, so it’s alright if you just have a quick thought once in a while. But if you haven’t had this talk with your boss or employee yet (or it’s been a while), make a separate meeting dedicated to this, and only this.
I could tell my boss was distracted due to other sources of stress. This is where that “reading the room” I mentioned earlier comes into play. Even if you’ve pre-planned a career path meeting, sometimes things come up that distract one or both of the participants. If you’re picking up on some body language — or spoken language — that indicates distraction, reschedule the meeting.

3) Forethought

A lot of this post so far has been a 50/50 thing — managers and employees should both be held accountable for this career path stuff. But when it comes to forethought, this lies largely on the employees’ shoulders. We need to think about what we want to do in our career. No one can tell us the answer to: “What do you want to do in five years?“

Sure, your manager, a mentor, or your family and friends can all talk you through that stuff, but it does come down to you to take ownership over the direction in which you want your career to go.

So, put some forethought into the ways your career path could take shape before broaching the subject with your manager. Some people tend to have really clear career goals, while others are a little more … floaty. That’s fine. If you find yourself in the “floaty” camp, here’s are a couple things to think about to get your brain going:

First, it’s okay to not know what you want from your career at all times. I tend to bucket my life in quadrants:

Relationships (friends, family, love)
Career (skill development, promotions, satisfaction from the work I’m doing)
Hobbies (beach bumming, ghost stuff)
Health (exercise, cooking, happiness, clean home)

Typically, not all of those areas of my life are banging on all cylinders at once. When life is going great, usually three — maybe only two — are rocking and rolling while the rest are in stasis for a bit. Sometimes, that thing that’s in stasis is your career. And that’s fine. You don’t need to be thinking about your career path all the time. But if you feel a general ennui, it might be that too many of those areas of your life are lagging — and one could very possibly be your career.

If that’s the case, ask yourself this …

What does the team look like today, versus a year from now?

First, think about this question hypothetically — assessing gaps that will need to be filled down the line, and aligning them with company goals. Then, talk to other leaders in the company and on your team about where they see the team going in a year, and what kinds of goals people might focus on in the future.

This is where your manager can help you, and where I have seen really successful (and non-awkward) career path conversations begin. If you can get a sense of what the organization’s needs will be over the next 12 months, you can start to see which of those needs you’re interested in helping fulfill — because even if your dream job is X, there’s not much anyone can do for you if the company’s investments are in Y.

Finally, remember that career progress comes from a lot of different places, and that progress is indicated by a lot of different things. It comes from skill development, networking, and aligning with projects that advance both personal and company goals. And all of that takes time.

If we want to benchmark our progress, we need to look at more than just promotions. Instead, we need to focus on whether we’re developing new skills, being given more responsibility and autonomy, putting ourselves in mildly uncomfortable situations that help us get better at stuff (hello, public speaking), working with new people in the organization, being asked for our opinion more often, or being pulled into meetings with people we respect and admire.

These are all really good signs of progress that are hard to formalize, but indicate you’re taking the right steps to get your career on the path you’re aiming for.

What Would an Expert Say About All of This?

I’m glad you asked.

That was all based on my experience — holding career path conversations with team members, and with my own manager. But let’s ask an actual HR professional who has spent a lot of time thinking about this stuff.

I talked to our Senior HR Business Partner Brianna Manning, and asked her for the advice she would give someone who was struggling to hold productive conversations about career advancement. She echoed two of the sentiments we’ve already talked about — preparation, and giving a heads up that you want to have this conversation. One point in particular Manning shared regarding preparation is the importance of establishing career trajectory dialogue from the beginning of your relationship together:

“If your manager is well aware of what direction you want to take your career, they can purposefully plan on assignments and projects that help set you in the right direction. In fact, if you want to follow your manager’s path, specifically, you should be direct and let them know that. Ask them to lunch to talk through their challenges, and learn what kinds of projects they took on to help get the skills they needed for the role.”

If you feel unsure of how to start that conversation because you don’t have that solid relationship yet, she provided some sample language that helps make it less intimidating:

“Try opening with something like ‘I learned about this really great resource to help us make the most of our 1:1s and layer in some career development focus — would you be open to trying it?’ or ‘I want to make sure we bake in time for communication around career development in our 1:1s, can we set aside five minutes for that on the agenda on a weekly basis?'”

But Pierce hit on one other important point in initiating these conversations I would be remiss to gloss over: You have to build trust and credibility to have productive career conversations.

It’s really difficult for your manager to focus on your career path if you aren’t succeeding in your current role. Make sure you’ve got a handle on your responsibilities before setting your sights on the next thing. In some cases, it might be wiser to focus on the “now” of your career path rather than the next turn down the road. As Pierce put it:

“If you demonstrate that you always deliver on current responsibilities, and always try to go the extra mile, you’ll build credibility and trust around your own personal brand. This will open doors for you. Just remember that it all takes time. It can’t happen overnight.”

She emphasized that credibility also comes from owning the follow-through on those career conversations. If your manager has opened up some doors for you, make sure you own your progression by nailing those stretch assignments, introductions, or whatever it is you’ve been given an opportunity to shine doing.

What Should You Expect to Get From These Career Path Conversations?

If you’re expecting a specific result out of one conversation, you’re setting yourself up for failure. You wouldn’t expect your manager to come in and dump a promotion on your lap, so you shouldn’t expect to solve your career destiny in one swoop.

In order for those doors to open, all relevant parties must be envisioning you in a certain role for a few months, at least.

I would say the best results typically come from people that think about their career path often, and have frequent — whether formal or informal — conversations about it.

Most of all, those with the most interesting paths tend to just keep an open mind about the different, jagged, very weird ways we all make our way through our careers.

Need help doing a little soul-searching? Take a few minutes to check out The Next Five.