“Are you someone who has a clear, long-term career goal in mind, or do you tend to be more opportunistic about the jobs that come your way?’
This is a big, intimidating question! But it’s been such a useful way to learn more about the people on my team that I try to ask it the very first time I sit down with them 1:1. (I changed jobs recently, so I’m asking this question a lot these days!)
Why is this such a useful question? I’ve found that it works on multiple levels, to:
Build a foundation of trust. By starting with these questions, I can make it clear that my job is to partner on someone’s overall career goals, not just their current role on my team. That automatically starts our relationship on stronger footing, and we can be more open with each other when it comes to feedback, goals, and expectations.
Channel specific projects or skill-building activities their way. While I’m not the main person determining which projects they work on (their direct manager is), it’s helpful for me to have an idea of what each person gets excited by. As I have more conversations, this can also help me see where there are overlapping or complementary goals around the team, so we can match projects to people who would be most excited by them.
Show that it’s okay to not have a clear path outlined. I used to feel that not having a clear career goal would hold me back. After all, it seems like so many of the successful people I know had their career mapped out before they finished kindergarten!
But I’ve found that what’s worked for me is to look for interesting opportunities and keep an open mind about what I take on. It took me a long time to get comfortable with the fact that I was probably never going to have a crisp 5-year plan — but that didn’t have to hold back my career. So no matter how someone thinks about their career direction — or lack of one! — I try to validate that they have the tools to be successful.Start building a growth plan. By talking about what the person wants next, whether it’s a specific long-term career goal or just the next job that looks exciting to them, we can identify skills together that make them better at their current job and set them up for the longer-term career they want.
I ask them to work with their direct manager to choose one specific skill, write it down as part of their goals, and carve out time to get better at it every week. That gives them a portable skill that makes them better at their job today and which they can take with them for future roles. As a bonus, working on growth skills is usually really energizing! When everyone feels themselves getting better at something every week, it usually means there’s more energy on the team.
The first time my manager asked me about my long-term career goals, I was surprised. I wasn’t expecting them to spend time thinking about how they could support me beyond keeping me productive on their team. But by opening up this conversation, my manager turned our relationship into a strong, long-term partnership that I still appreciate today — and that experience inspired me to ask this same question to the folks on my team.
In my next post, I’ll talk about the other big question I ask in that first 1:1: “How do you know you’re being successful in your role?”
I think this is a great question, but not for the first 1:1. For most people to respond genuinely, the foundation of trust needs to already be there, which requires time. Otherwise there is a risk for them to tell you what you want to hear. I would ask this question after ~1 month of managing someone.
Huge +1 on #3. Thanks for calling that out - sometimes it can be nerve wracking to see most people around you have specific goals and plans and you start doubting yourself- should I be making plans too? What should they be? Am I too late? It is always heartening to have senior leaders validate that it is OK to not have that kind of clarity and be opem to explore and learn. What we need to adopt and hone is a curiosity mindset, and define what our values are, or what truly makes us happy/fulfilled and then be open to opportunities that align with those and help us learn and grow.
Thank you for your really insightful writing!