Committing To Your Team With Career Conversations
My experiment with career conversations & why you need to do these with your team
One of my favorite things about my team is how open they are to trying new things. So in December when I read about career conversations in Radical Candor, and suggested three structured conversations, they were game to be my guinea pigs.
Why You Need To Do These
We live in a reality where, in tech, the average career tenure at most companies is around 3 years, or less. Having these conversations is a way of acknowledging this reality, of letting people know that it’s ok to think about what they want to be doing 10 years down the road, and trying to find the right path for them during their time at your company.
I benefited enormously from these conversations. First, I got to know everyone on my team better. I found surprising things that I had in common with my reports: childhood events and activities and interests outside of work. As a manager it’s important to establish trust and show that you care about your team, as people, and this is where I felt like we really started to connect.
Second, I learned more about what drives each person on my team, and learned where they want to be. I learned that I have a team of people with complementary strengths, and this opened doors for Quill that we didn’t know we had. For example, two people wanted to learn to write grants. We needed help writing grants. Our Executive Director was so used to doing them himself, though, that he didn’t know people wanted to help. Once I told him, we rebalanced workloads a bit so that one person could start helping out immediately, and she awesomely got us two opportunities that we probably wouldn’t have pursued otherwise. We’re hoping to get the second person involved this week.
But Everyone Is Already Busy…
When I told people about this, some responded with “but X is so busy…” This misses the point for two reasons. First, when people are clear about their dreams and the skills they want to pick up, they’ll work harder. In my experience, “I’m too busy” is usually only a problem when the work isn’t interesting. Obviously there are extremes — when I was working law firm hours I wouldn’t have taken on anything else, no matter how great. But we’re talking about normal, 9–5 hours here, where even the busy people have some time to give to a passion project. You may be busy, but if you’re given the chance to work on something that’s personally exciting, you’ll probably take it and still manage to get everything done.
Second, people need time to work on what they care about. If someone is too busy to work on anything that aligns with their long-term interests, you should probably be worrying that that person is looking for other jobs on the weekend. So giving people the time to help your organization — in ways that align with your long-term goals — is a win-win; your organization benefits both from their work and from people having time to do work that makes them happy.
Getting Started: Structure Is Everything
A career conversation is what it sounds like: a discussion (or series of discussions) with your manager about where you want to go in your career. In theory, this sounds great. In practice, it’s easy to do wrong. At Facebook, I remember that in manager training they told us it’s important to have career conversations, but not how to structure them. So they turned into rote 10 minute conversations, which I first had with my managers and then, when I became one, started having with my reports. These were surface conversations. We never got to 10 years down the road. We didn’t make plans. Box checked, everyone kept doing what they were already doing.
This time I wanted to try something different because career conversations are hard. It’s scary to talk about your hopes and dreams. It’s vulnerable. You may not even know where you want to be 10–15 years from now, let alone be ready to discuss this with your manager. And as a manager trying these for the first time, it feels incredibly awkward to ask someone to tell you their life story. That’s ok, keep going.
The Three Conversations
To get past the awkwardness and have meaningful conversations, Russ Laraway suggests three conversations, spaced two weeks apart. The first conversation focuses on the person’s past. The second looks at the future, at their hopes and dreams. The last one ties them together with a “Career Action Plan.”
I was skeptical going in because, like I said, it feels awkward. Beyond trying to ask coaching questions, I’m not usually very scripted with my team. So going in with a script was new for me. And also, I was skeptical because it seems like this is asking a lot — there’s homework and soul-searching, not always your ideal way to spend the holidays.
Despite my skepticism, it worked. I think my team liked doing these conversations and gained clarity by asking themselves where they wanted to be, and, as mentioned above, the exercise was enormously valuable for me.
Here I’ll interject and say that from this point forward it gets subjective; this is what the experience was like for me, but team if you are reading this and feel like I got anything wrong, please let me know.
Conversation 1: Tell Me Your Life Story
In his article, Laraway suggests being the person’s “Barbara Walters” and starting with a relatively simple prompt: “Starting with kindergarten, tell me about your life,” and following up with questions about inflection points, times when the person started or stopped something, what they took away from significant events, basically anything that gets to what the person values and what motivates them.
When I did the first one, I acknowledged the awkwardness and said “Ok this feels awkward and I kind of feel like a therapist, but this article says to say I’m your Barbara Walters and ask you to tell me your life story” (I forgot the kindergarten part). There was some awkward laughter, but I think the conversation worked. Thankfully, the person I spoke to very graciously told me her life story and went along with my shaky first attempt.
After this conversation, I sent the article to my team so that they knew what we were going to do. Since this was an experiment, I felt like it was only fair to share the parameters with everyone.
Also, I added two things that, to me, made the conversations feel more fair. Outside of a therapist/life coach’s office, people usually expect that if they share something, the other person will reciprocate. So I tried to create opportunities for connection in two ways. First, although this wasn’t in the article, I offered to everyone that if they wanted we could switch roles in the future and I’d tell them my life story.
Second, I didn’t do these as a pure Barbara Walters. I decided to be human and inject some of my own stories while talking to my team. While I made sure to focus on them in the conversation, when it made sense I’d say something like “that happened to me too,” or “I had a similar experience.” I’d spend a few minutes on that, and then get back to the other person. To me, this felt like a way of making the conversation feel more human and less robotic.
It turns out most people like talking about their life stories; so once we got past the initial awkwardness these were actually relatively easy and enjoyable conversations to have.
Conversation 2: Hopes and Dreams
For the second conversation, Laraway suggests asking the person what they envision themselves doing at the pinnacle of their career. In Radical Candor, I think Kim Scott phrases it as something like “tell me your dreams.” After asking these questions, Scott suggests having the person make a chart with their dreams, the skills they’ll need to get to them, and having the person rate where they are with each sill now. So I tried asking these questions with my team. A few things stood out.
First, this was a much more stilted conversation than the first one. While some people had one or two very clear goals, most of these involved someone at least starting with “I don’t know” or “what I’m doing now.” It took some digging to get to the person’s actual goals. I get it — it’s a hard question to answer on the spot, I have a young team, and even if I was asked this I’m not sure I’d have had a clear answer.
Relatedly, my second takeaway is that this one takes work outside of the conversation. Most of these conversations ended in “I need to think about this more.” That’s where the 2 weeks in between conversations really helped. Everyone was surprisingly game for spending the holidays thinking about where they want to be, and by the time we met for the third conversation, people had much clearer goals to focus on.
Third, there were upsides and downsides to having the person make a chart and list their dreams. By making people list 3–5, it usually became apparent which one they were most passionate about. That part was great, and especially with time to reflect I hope my team came away with greater clarity on their goals.
But once it became clear that a person wanted to do one thing, having them list skills for the others felt like a rote exercise. For example, someone would say something like “I want to be a musician,” and the skill would be “Learn an instrument.” Writing this down, and then trying to rank where the person was, felt like a waste of time.
Similarly, my team looked a bit underwhelmed when I asked them to rate their skills. So I think a better method would be to focus more on the most resonant dream, and ask the person the skills they need to pick up. Asking how they feel about where they’re at now can be good, e.g. if someone already feels like they have everything they need and want to focus on another area. But trying to assign a formal rating was probably overkill.
In the future, I think I’ll try to focus more of the three questions in Laraway’s article, rather than the chart approach recommended in the book.
Conversation 3: A Career Action Plan
My team really impressed me with this one. I came into these meetings expecting another somewhat stilted conversation. But not only had my team put in the hard reflection work after conversation 2, they had mostly already put together action plans.
Probably because I’d sent them the article, most people came into the conversation with a plan already started. To me this was very useful. I think everything Laraway suggests is spot on: make sure you identify action items and answer “who will do what by when,” look at how you can develop the person’s role and who you can connect them to, think about whether there are conferences or resources for them to help learn skills, and identify immediate next steps.
So I recommend Laraway’s approach, with the modification that people should put together a draft plan before this conversation. That way you can reflect on it together, and focus on strengthening it and on using your knowledge to help the person (e.g. connecting them to someone you know in a field they are interested in). They can modify it and send you a final draft or go over it with you again in a future 1:1, but this way you aren’t wasting time watching someone list things, and they aren’t rushing to get through everything they want to do in 45–60 minutes.
Since we’ve started doing OKRs, I asked everyone to make sure that at least one of their OKRs related to their personal development. Because Q1 just ended I’m still in the learning phase as to how well this worked, and anticipate a future post reflecting on whether my team succeeded in following their action plans, not just over the quarter but over the year. Still, I was very pleasantly surprised by how detailed everyone’s action plan was and how much thought went into these. It makes sense — if you ask someone to think about where they want to be, they’ll probably be excited to start going there.
Overall I really enjoyed the opportunity to do these, and I’m excited to keep doing them with new team members in the future. Thank you, team, for being my guinea pigs and letting me try this out with you.
If you end up trying career conversations, I’d love to hear from you (you can comment or email me at tltcoaches@gmail.com). And if you’re interested in coaching, you can find me at The Leadership Team.
