Last night, I sat down to dinner with my husband in a busy restaurant in Manhattan after a long day of work. It was Korean restaurant in the heart of midtown down the street from my office, and at 7 pm, crowded full of young professionals. As I was telling my husband about my upcoming annual performance review, I overheard the couple sitting next to us discussing the very same thing. “How do you think I should talk to my boss about my career development?”, the boyfriend/husband asked his girlfriend/wife. “I think you should start with asking for their feedback,” she replied.

This quick exchange suddenly got me thinking. At my current organization, I spent some time surveying leaders and employees on the biggest challenges that they face. Time after time, having career development conversations come up. It seems like we often get mixed messages – do we appear too forward if we ask for a promotion? Should we wait for our manager to approach us first? What if my plan isn’t to stay with the organization for the next 5 years? Should I be honest? Will that prevent me from getting that raise?

“Career development, like dating, is messy. But just like dating, the best policy is to not play games; but to be honest, authentic, and assertive about what you want.”

— Nikki

According to Gallup, 87% of millennials rate “professional or career growth and opportunities” as important to them in a job, and 59% of millennials report that opportunities to learn and grow are extremely important to them when applying for a job. Knowing just how much we prioritize career development, why do we oftentimes leave this important task in the hands of others?

If you have regular one-on-ones with your people leader, you should be having career development conversations. And if your people leader doesn’t bring it up, you most definitely can! After all, it’s your career we’re talking about here.

Here are my top suggestions for having a positive career development conversation with your boss:


Plan for the conversation and start with a positive atmosphere. The last thing you want to do is to catch your boss off-guard. If you have regularly scheduled one-on-ones, let your leader know that you’ll want to spend some time during your next meeting to discuss your career development. If you don’t, ask to schedule a meeting. Before the meeting, find a quiet place, an office, or even a casual coffee shop to have the conversation. Limit distractions by putting away your cell phone or closing your laptop to demonstrate a commitment to the conversation.

Be honest about both your short-term and long-term goals. You don’t necessarily have to put time stamps on each of those, but giving your boss the bigger picture of where you want to go in life helps set the foundation for how he or she can best help you to develop. Be open about wanting something different from your current position in the future. If you have a supportive leader, chances are, they will be able to help you get to your next step in many ways. Down the line, they can give you stretch assignments or challenges to help you meet your goals, and potentially introduce you to your next role, whether it is in a different department or even outside of your organization.

Be clear about what you want to learn and how it will help the business. Spend some time thinking about areas in which you could either improve on or new skills you can build to get better at your job. Identify one or two concrete plans – whether it is a course offered internally or externally, a conference that pertains to your profession, or a book that you want to read. Make a strong connection of how the learning plan ties into your role and how it will enhance the business. Don’t be afraid of rejection. You don’t get what you don’t ask for, and the worst he/she can say is “no”.

Ask for actionable positive and constructive feedback. Once you have clued your leader in on what your short-term and long-term goals are, show that you are ready to take initiative to learn and grow. Ask for open and honest feedback about your performance. If the feedback seems vague, dive deeper and ask your leader to provide you with specific examples and ideas on how you can improve. Remember that feedback is truly a gift. Take on a positive growth mindset and see constructive feedback as a reflection of your performance at the time, not a reflection of you as a person or your character.


Having a career development conversation with your leader can be daunting, but it doesn’t have to be hard. The most important thing to remember is this: be honest and authentic with yourself and your leader. Take the time to really imagine the life that you want for yourself and make bold steps towards those goals. You are in control of your career development, so don’t dream your life, live your dream.

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