How to hold effective Career Conversations - Their dreams 💖 (part 2 of 4)
Look into the future and figure out how the pinnacle of their career might look like.
💡 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 2: Their dreams 💖 (this post)
🔗 Supporting material:
The second conversation: Their dreams
You finished the first conversation armed with tons of new insights regarding their story, how they ended up where they are, what decisions shaped their life and what they value. Now it’s time to look into the future and figure out what your folks want from their professional lives. We’re not trying to chart a path to a potential peak in their career just yet. That will come with the third conversation.
It’s crucial to share the context, desired output and outcomes for each conversation upfront. This is especially true for a fluffy and aspirational topic like “career dreams”. If you don’t know what to say or put in the meeting invite, I’ve got you covered with my Meeting Invite Briefings. Like with every one of the three conversations, plan up to 90 minutes for this one too!
Before the Dreams conversation, ask your direct report to create an empty spreadsheet to capture their dreams and career action plan moving forward. This makes it clear that they are the owner and that you are the supporter of their career. This detail matters because they might not be with you or your organization forever, and it enables them to take this document with them wherever they go.
Here is the prompt you use to start the second conversation:
How do you imagine the pinnacle of your career to look like? Imagine being in that moment or looking back at it with a sense of “I’ve made it”. Which scenarios come to mind and why?
Before jumping into a spreadsheet, it’s time to listen carefully and take detailed notes. Can you spot contradictions when comparing the way they have lived their life versus their aspirations? Maybe they want to be present in their children’s lives every single day until their early school years, but they also desire a top leadership role in one of the most prestigious organizations. You might have learned that they would love to work for a nonprofit organization, but at the same time aim to retire early or become a millionaire. These seeming contradictions shouldn’t be challenged outright, but serve as points for further inquiry and discussion.
At this point, you might be wondering where this is all going. Well, this entire Career Conversations framework relies on breaking down ambiguity and eventually charting a concrete path that your direct reports can take to move gradually and confidently toward one (or more) of their dreams. For the Dreams conversation, you want to arrive at a specific job or role so you can break it down into skills and start working on the action plan. In my experience, the challenge is that it’s rare to find a person who has three to five dreams and knows them by heart already. This brings me to the two types of dreamers I’ve met so far.
Two types of dreamers
Type 1: Considers concrete jobs or roles
Some professionals actually do imagine specific jobs or roles. When you ask them about how a potential peak in their career might look or feel, they will say things that are very easy to translate into concrete jobs, if they aren’t just specific roles already. For example:
I want to be a VP of X!
I’ve had this one product idea for a while and I want to become a founder
I want to be a super senior professional in my role
After being successful in my role I’d love to teach about the subject
Looking at the bold parts should give you a strong sense of what job they are looking to pursue.
Type 2: Considers circumstances and results of a job
These folks imagine specific circumstances or what their job has resulted in when looking back at their lives. This might sound a bit vague, and it can be. They might say things like:
I want to be financially independent!
My dream job definitely has a great work-life balance
I’ll be highly respected in the field
It has to be something I enjoy
I don’t want to be stressed out at work, but I still want to grow over time
As you might realize, it’s very difficult to continue this Career Conversation process with this ambiguity. You simply can’t start charting a concrete path from the present to these circumstances. What skills would you need to “enjoy your work” or “have a great work-life balance”? You need to look for concrete jobs before you can think about what skills are required to succeed in them.
Forcing yourself into these constraints might seem challenging at first, so here are some tips:
If the conversation starts off as described above, don’t try to move to concrete jobs immediately. Stay curious and spend a few minutes listing factors, feelings or circumstances that they think of first when imagining a successful career.
First, try nudging them with a more concrete prompt toward specific jobs or roles. “When thinking about being at the peak of your career, does a specific job or role come to mind?”. Sometimes that’s all it takes to focus their mind.
If they can’t come up with anything, look at the factors and circumstances they described to suggest a few possible jobs. Practically every expert career track has a level for the highest seniority, so that’s a common path. Are they curious about leadership roles? Suggest one. Do they value work-life balance and their family life? What about a well-paid part-time role? Their reaction is more important than how proud you are of your personal suggestion. If it doesn’t resonate with them, drop it.
If you’re not getting much progress, but you have a trusting relationship with them, consider this prompt:
Is there something on your mind that’s almost too embarrassing to share, but it’s still a dream for you?
The number of personal Etsy stores, aspirational travel bloggers and startup ideas this question has surfaced to me is staggering. Give it a try! 🤞
For Type 1s you can skip all of the above and move straight to the next step: adding their dreams to a table to start figuring out the required skills.
A table filled with dreams
At this point, I like to move from paper to digital tools like Google Sheets. It’s much easier to collaborate on this digital sheet than on paper, considering that this is a current snapshot but might change over the years. The shelf life of their dreams and action plan is their life span after all.
For each column, collaboratively brainstorm what skills they might need to live that dream successfully. In their vision, they obviously don’t want to underperform or even fail at living that dream, so consider both the required skill and the minimum bar. If you don’t know what skills would be required for a job you’re not familiar with, I have some suggestions and tips in a moment for you.
For now, keep in mind that this isn’t a scientific process. After you are happy with the skills, start coloring and bolding them as such:
Here’s what the colors and bolding mean:
Red: The person doesn’t have this skill or has a severe lack of experience in comparison with the desired job.
Yellow: The person has some understanding and experience in this skill, but there are significant gaps. Maybe they simply aren’t confident to succeed in the desired role.
Green: The person can perform the skill successfully in the role - they are “good enough”.
Bold: You might brainstorm 15+ skills for each dream, but for every job, some skills are critical. For example, you can’t be a successful Software Engineer if you can’t actually code. You can’t be a successful VP of a medium or larger organization if you struggle to build relationships or communicate in front of groups.
How to go about coloring and bolding each skill
I prefer to do the bolding part before the coloring. This way you should be able to transition smoothly from the creative brainstorming mindset to the evaluative thinking required for the next step of the process. Either I ask the person to do a quick self-review with my support, or we split the list of skills and start assessing simultaneously.
💡 If you keep getting stuck in discussions about the right color or font style, remind yourselves that good is better than perfect and that this document will evolve anyway. If you forget about an important skill now, you can always add it later. If a skill turns out to be unnecessary after all, remove it.
If you’re like me, you might wonder if the same skill should have the same color in different columns. Going back to the “minimum bar for each dream” topic, the answer is that they can actually have a different color. Imagine a person who would be happy to be a super senior individual contributor or a vice president at some point in their professional life. Both roles require communication and decision-making skills, but the bar and nature are quite different. So, yes, it is possible that you have significant gaps at the same skill for one column, but less or no gaps in another.
Figuring out the right skills for each dream
There is no such thing as “the right skills” if you consider the evolving nature of your direct reports’ lives, your knowledge in general and every practice or craft on this planet. There is only “good enough”. Maybe a software engineer is happy with the label “UX Skills” and can actively work with it, but this is certainly not specific enough for a digital product designer. The awesome and scary thing about Career Conversations is that you can never predict what your folks aspire to, which also means you can never predict all the potential skills that they might need to live these dreams successfully.
That said, here’s part of a list of skills I keep coming back to:
If you can’t find enough relevant skills in my template, consider googling your practice or a specific job and attaching “skills” or “competencies”. For example “accounting skills”, “social media skills” or “chief of staff skills”. Another trick is to look for specific job ads on LinkedIn and look for required skills there.
What’s important is that you and your direct report have a shared understanding of the skill, so a definition or short description is useful. You don’t want to throw out a bunch of random competencies and then fold on the first “what is the difference between these two skills?” question.
As a user experience leader, I rely on resources like “8 competencies of user experience” or “research skills framework” a lot. I would recommend doing your own research in your field of expertise too. I’m confident that you have something similar that you can leverage.
The result is clarity for them and you
Maybe you didn’t know where this was going in the beginning, but by now you should start to see some emerging benefits, for example:
You might spot multiple dreams that have the same skill colored in red. This is a great way to prioritize the upcoming learning efforts and items on the action plan, especially if you also consider which skills are bolded.
It’s possible that your direct reports have deeply considered or discussed their career aspirations for the very first time. Simply giving them the space to think beyond a single career path and documenting this journey is likely to trigger various positive emotions and a burst of motivation.
A deeper understanding of their past and what career success truly means for them. You have a major opportunity to use this knowledge to make your feedback more personal and effective to power their growth. If you know where they might want to take their career, new opportunities will become apparent that you didn’t even notice or consider before.
Congratulations on completing your second conversation! 🎉
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 2: Their dreams 💖 (this post)
🔗 Supporting material:
Where I learned this
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! 💬