How to hold effective Career Conversations - Their life story 📙 (part 1 of 4)
Deeply get to know your people's past to support them on their path.
💡 This post is part of a series about holding Career Conversations with your team based on the book “Radical Candor”, but evolved and adjusted for practical (re)use.
Part 1: Their life story 📙 (this post)
🔗 Supporting material:
Why you should hold Career Conversations with your direct reports
Going through this process is immensely valuable for both your direct reports and yourself and can cause various benefits, for example:
Increased trust between your direct reports and yourself
Deepened understanding of their strengths, weaknesses and how those came to be
A deeper, more personal care for them and their aspirations (a boost in your motivation)
Increased retention due to the tangible career action plan that they own (a boost in their motivation)
A new, massive source of feedback for them and for you
To me, there are few things in managerial life that excite me more than actively supporting my folks in reaching the pinnacle of their professional careers. This is essentially the goal and approach outlined in Kim Scott’s leadership hallmark book “Radical Candor”. A core concept of the book is Radical Candor, caring about the people in your team and challenging them directly. With Career Conversations, the ambition isn’t to retain 100% of your people forever but to actively spend time with and support them on their path in a way that is meaningful to them.
These are the three conversations you will be facilitating:
Listening to their life story (past)
Learning about possible career dreams (future)
Collaborating on a career action plan (present)
Interestingly, we start with the past, jump into the future and return to the present to connect the two. By completing this process you should have a significantly deeper understanding of who your people truly are, where they want to go in their professional lives and how you can help them bridge that gap.
Finally, I’d argue that the most important part of the process is the ongoing guiding, coaching and mentorship you ought to provide which is not the book’s focus. After experimenting with this approach over a dozen times, I hope to share some meaningful key learnings with you in the hopes that they are useful.
Before your first conversation
Do not attempt this with someone you’ve just started managing! Without a good level of trust, they will not feel comfortable sharing.
Make sure to share the concept, its purpose and its source with the person you plan to do this with. Briefly cover each conversation and step in the process.
Consider reading a few of the prompts and interesting bits of the book out loud to prepare your directs for these deep conversations in your 1:1.
Tell them explicitly that they don’t have to share anything they’re not ready to share. You are there to listen, learn and help them in their career.
For your first few rounds of conversations, mention that this is also new for you, how you are invested in them and want to support them even further in their professional life.
Set up calendar invites including each conversation’s main goal.
🔥 Feel free to use/adapt my Career Conversations - Meeting Invite Briefing template.
The first conversation: Their life story
For the first conversation, you should focus on listening and taking extensive notes. You want to learn about their life story, their motivations and values. Whenever they were at a crossroads you want to make sure that you understand what options were available and why they went for a certain path. As long as you stay curious and attentive, you’ll be able to reap the first benefit of this process: a deeper level of understanding of your direct report.
Here is the prompt you use to start the first conversation:
Starting with kindergarden, or whatever point in your life you feel comfortable starting at, tell me about your life.
I’ve added the “feel comfortable” bit to honor the privacy and personal history of the person you’re listening to. Whatever moment they choose is the right one. For some, it will be their first actual memory and for others, their first job.
I follow up with a disclaimer that I’ll be taking detailed notes while listening attentively. I might even ask them to slow down or interrupt them softly by raising my hand to ask a clarifying question. If the conversation is going smoothly, I prefer adding little symbols and circling words or bits to dig deeper later as opposed to breaking the flow. Here are some examples:
❤ for things they adore or love
❗ for key events or general emphasis
❓ for questions
⚡ for struggles or challenges
:D :O :´( and other simple emojis to capture emotions
Good things take time: 80 to 90 minutes per conversation to be precise
The authors recommend holding these chats as part of your weekly 1:1s, but I disagree. 1:1s are typically 30 minutes, so even extending them to an hour would give you at best 30-40 minutes to talk about their life story on top of what’s on their mind that week. In my experience, you can easily fill 60+ minutes per conversation, so I typically schedule each for 90 minutes (80 if you do speedy meetings). I believe giving your folks enough time and space shows that these conversations are not your typical “tell me about yourself” interview prompts, but deeper, more meaningful exchanges.
On average, people took 60-70 minutes to share their stories. I recommend reserving the remaining time (20-30 minutes) for follow-up questions, probing deeper, wrapping up and giving an outlook on the next conversation. I always close down in the same way with
How are you feeling right now?
Do you have any questions?
Thank you so much for sharing your story with me and answering all my questions!
I usually feel absolutely drained after just one of these, so leaving space before my next meeting or scheduling them at the end of a day has been serving me well to manage my energy.
🎉 That’s it! You’ve completed the first part of your Career Conversations!
What’s next?
You’re not done! Check out the other posts of this series and the supporting material to get the full picture when it comes to Career Conversations:
Part 1: Their life story 📙 (this post)
🔗 Supporting material:
Where I learned this approach
Kim Scott’s popular book Radical Candor.
I recommend this to any leader, yet Career Conversations fill only a handful of pages in the book. I tried looking for more information online, but the only meaningful resource I could find was this article on the Radical Candor website. So, I set out to try it out myself, ran into some issues, refined my approach and am now ready to share it with you all.
Let me know your thoughts or how it went in the comments! 💬