When I think back through the various stages of my adulthood I see very little in the way of active career management. Even studying graphic design at university was because one art teacher made a casual comment that I might enjoy it. Even from the very start, I’ve never had a solid plan.
Casually swanning from one thing to the next throughout my career has been fun but it feels like I've led the path of an opportunist, not that there is anything particularly wrong with that, it's just an observation at this stage. Once I finished uni and moved to Melbourne, I had lots of trouble getting my first job (being schooled in freehand rather than Indesign set me back) so my first job was whatever I could get - which was luckily in publishing. That led to being a book designer for 5 years till I went rogue and became a freelancer.
Before you can settle down into your niche, if you ever find one that is, you’ll probably try ten’s of different things and being a solopreneur exaggerates the amount of roles you will dabble in. Some days I’m a designer, others a book keeper or a sales manager. On the odd occasion I’m a guest speaker and a content creator but I still feel like I'm an opportunist underneath it all who just happens to strike gold every now and then.
I’m a pretty firm believer in just showing up and bringing your whole self but imagine if I actually had a plan! A real life map of where I am today and where I'd like to be 18 months from now or even 3, 5 or 10 years from now! I think this calls for a “Career Conversation”.
In Radical Candor by Kim Scott, my new favorite book, about being a kick-ass boss there is a whole section on how to talk to your direct reports about their career aspirations and why it’s so important. If you’re a manager of people, it’s vital to be aware of where people are in their career journey and where they want to be in the near and far future. As we all know I don’t actually manage a team but going through the exercise I’m about to walk through is something that anyone can do. In every job I’ve had with a manager - no one gave a shit about what I wanted to be when I grew up - to be honest I didn’t know, but in my situation at least, and many others I assume, career goals have become this taboo topic.
There are two many reasons for this - the first is that the traditional promotional model means that the next job in line for you is probably your manager's job. Not too many people would feel comfortable telling their managers that the next role they see themselves in is their one. The second reason is that often a different job at a different company or business is where someone wants to be and not many people would admit that to their manager without feeling disloyal to their current team and company.
‘Career conversations’ are part of the ‘radical candor’ framework but in summary it's a once yearly meeting that you should be having with each of your direct reports or in this case with yourself. The objective is to..
“Understand people's motivations and ambitions to help them take a step in the direction of their dreams”
Everyone is on their own growth journey. In BB#99 I wrote about Rockstars (gradual growth trajectory) and Superstars (steep growth trajectory). Throughout one's career there will be times when they want and need to be challenged and other times when they just need to be awesome at what they are doing today.
There are three parts to a successful ‘career conversation’; looking back, then forward and creating a plan. The ‘get to know you’ conversations might feel a little intrusive as a manager initially but over time they build stronger and empathic relationships.
The first conversation that's required is learning someone's life story, so you can then understand what motivates them. As part of the radical candor framework, showing and actually caring personally about your direct reports is critical. Setting aside time to listen about one’s life journey will give incredible insights into what they care about and more importantly, why. If your doing this for yourself I recommend doing the personal journey map from BB#91.
The second conversation is about the future. What are your dreams? Most people will have obvious, sensible plans like paying off their mortgage but it’s your job as a manager to dig deep for a CAD - crazy-ass dream. I’m pretty sure every single person has some kind of crazy idea that if they could do whatever they wanted they’d probably do that. A EA might want to be a florist. A banker might want to be an organic farmer. A waitress might want to be a mechanical engineer. Encourage ideas outside of their immediate role today - that’s why you ask about dreams and not professional goals.
The third conversation is putting together an 18 month plan. Now that you have a pretty solid understanding of what motivates your direct report or, if you’ve done the personal journey map you’ll see the patterns emerge of what's important to you. It's now time to ask yourself or the direct report, some pretty self-reflecting questions.
What do I need to learn in order to move in the direction of my dreams?
How should I prioritize the things I need to learn?
Whom can I learn from?
How can I change my role to learn it?
Once people get clarity on the next steps that need to be taken it makes it easier for managers to identify opportunities at work that would help develop the skills that are required. Going to work every day and actively moving towards your CAD is so much more rewarding than just climbing the corporate ladder.
This is obviously a super board overview of what a ‘career conversation’ would look like. So much would depend on the relationship you had with your boss or direct report, or even how honest you’re being with yourself. One thing that struck me though is that these conversations could be happening right now. Even if your boss is a dickhead, you can have the conversation with yourself and look for opportunities that will help get you a tiny bit closer to your dreams! And just imagine being the type of boss that really, truly helps someone achieve those dreams! How rewarding would that be!
