3 Questions to Guide a Successful Career Discussion


3 Questions to Guide a Successful Career Discussion


All too often, we set career goals without sharing them with the person who can most easily unlock opportunities for us: our manager. Maintaining a close relationship with your direct supervisor provides them with absolute clarity about your interests, strengths, and potential, all of which play in your favor when opportunities are on the table.

One-to-ones and team check-ins are great places to start, but to truly maximize on your manager relationship, you need to begin scheduling formal career discussions.

Sure, it might be uncomfortable at first. Maybe you don’t have a proper update, need more clarity on a goal, or feel nervous about feedback. Regardless, you can’t wait around for your performance review to connect with your manager and align on expectations.

Why? Because decisions are made on your career trajectory long before you ever step into a review. You don’t want to be skipped over for a promotion or project simply because your manager didn’t know how to advocate for you.

Hit these three points at least quarterly (if not monthly) with your manager to stay on track year-round toward reaching (and excelling beyond) your career goals.

1. What work have you done (and what excited you about it)?

1. What work have you done (and what excited you about it)? 

Much of your work goes unnoticed by your manager. It’s not personal. It’s just a fact of the matter that she is busy and sometimes only has the bandwidth to assess the big picture.

That said, this doesn’t mean that she doesn’t care and doesn’t wish she could know about your accomplishments… Yet another reason why scheduling time to go over your work is so important.

Get out of the mindstate that claiming your “wins” (whether personal or org-related) is “bragging.” Sharing work you are proud of and feel passionate about leaves a lasting, positive impression on those around you. It’s also one of the simplest ways to build your personal brand.

Managers use this information to match projects with the right team member(s) and consider who might be the best fit for leadership responsibilities. In other words, when your manager is aware of your talents and what keeps you energized, she will connect the dots to ensure you get more of that work.

After all, the last thing she wants is for you to burn out from work that doesn’t interest you, and coming to her directly with this insight instead of waiting around for your performance review will save you both from the pitfalls of fizzling out.

2. What do you want to do?

2. What do you want to do?

This is the big question that most of us assume should be on the agenda, yet we often approach it from too broad of an angle. Instead of talking about the “dream”, take some of the stigma out of your career discussion and share a goal that feels doable in the next six months to a year.

Is it a learning experience? More exposure? More work that you love? Do you want to learn a specific skill? Build relationships in a certain department? It doesn’t matter. It just needs to be true to you.

The “where do you see yourself in five years” prompt is overrated, and frankly, not helpful. So much can happen in a five year span, and if we set our sights too far down the line, we forget to actually pave the road directly in front of us to get to that far-off place.

Odds are, there’s nothing your manager will be able to do today to help you become Chief Financial Officer of your org in five years. She could, however, introduce you to the current CFO, or make sure you’re getting more financial planning projects.

Sharing your immediate career goals rather than your dreams tells your manager that you are thinking critically about your growth, and leaves room for practical involvement on her part to assist you.

By bringing them to her more frequently than just your performance review, you’re also fostering a relationship of accountability.

3. Where do you stand?

3. Where do you stand?

Watch the clock and ensure you have time to ask for feedback from your manager. If you set aside 30 minutes to an hour, it’s going to fly by, and you don’t want to miss this key part of the discussion. Still, it’s important that you save it for the end.

Lead with your accomplishments to set the tone for the meeting and then share your career goals as a guidepost for your manager to tailor her feedback in a way that feels meaningful to you.

Don’t overthink it: just ask your manager how she thinks you are doing. Are there areas she feels you can strengthen, or skills you can work on? Is the perception positive?

Remember: always come from a place of curiosity and ask how you can support your manager. What does she need to be successful, and what does she want to do next? How can you help her get there?

Ultimately, you want to be well-informed so you can adjust. Even if you don’t feel your manager has the right perspective of your work, make an effort to understand the perception gap and create a plan to make amends over the next few months.

The Bottom Line

The Bottom Line

If you’re not aligned with your #1 stakeholder, your mobility within your org (and your career) will be limited.

Scheduling career discussions signals the kind of initiative and attention to detail that managers want to uplift. If you can get it on her calendar early (a month out, ideally) and show you’re respectful of her time, she’ll be all the more grateful to sit down and connect about where you are, where you want to go, and how she can help you thrive.

Use what you’re loving (or not loving) about your work right now to brainstorm where you want to go with your career, and check in with your manager monthly to align on your progress. It’s that simple… and it works!