How to have great career conversations with you team, and best support them in achieving their aspirations
Supporting your team’s development motivates them to do better work, and to stay and grow with your company.
Individuals develop rapidly when your company is growing, you know your team’s interests, and you can position individuals to take advantage of opportunities for promotion and success.
To do this well, you’ll need to do four things:
You can’t help someone progress in their career if you don’t know where they want to go.
Figuring this out is not a straightforward task.
Someone’s choice of career and what motivates it is a personal question. Given the amount of time we spend at work, it’s often really a question about their lives and how they want to live them in future. It can take time to build enough trust to discuss these topics in detail. But the only way to evolve your understanding is to get started.
This isn’t something which typically gets discussed over a few Slack messages. You’re going to have to talk about it. The good news is that having these conversations is one of the best ways to demonstrate your investment in your team and build better relationships.
This section is full of tips on how you can make those conversations a success.
We recommend having these conversations separately from your regular 1:1 meetings, particularly if it’s the first time you’re discussing these topics, for two reasons:
(If you’re working in-person, we’d also suggest doing these meetings over coffee or lunch. It can create a more relaxed atmosphere for discussion).
You’ll want to give each individual a heads up about what you want to discuss, either verbally or in an e-mail so they can come with some thoughts.
In our experience, beyond establishing the trust to have these conversations, the main issue team members have with them is feeling that in discussing their ‘career’, they’re meant to know all the answers and have a structured set of career goals they’re working towards. For most, that’s not the case (and isn’t necessary to building a great career).
In your messaging about the meeting, you can head off that concern, make your intentions clear, and set up a great conversation. You may want to use a template like the following:
Hi Sahil, I’d like to put in some time with you over the next couple of weeks to talk more about what you’d like to get out of your role at Kommon for your career and how I can help. If you have specific ideas and goals to discuss, that’s great. If you don’t, that’s also great - we can talk about the types of work you enjoy, the types of people you like to work with, the skills you want to build, and anything else that comes to mind. I’ve put in an hour initially, and then we’ll arrange further conversations in the coming weeks as we need to.
With the conversation set up, let’s talk about how it might go.
We’re going to go through a hypothetical set of career conversations you might have as a first-time manager at the start of your relationship with a direct report.
We say ‘conversations’ because it will almost certainly take you two or three meetings with each individual to cover off all these points. This is fine. There’s no need to rush it. We’re talking about laying the foundations for discussing long-term career goals, not chatting about the week’s work.
We’ll talk about:
(This framework is adapted from work by Russ Laraway and Kim Scott, which you can find references to in Further Resources at the end).
Your team member will typically expect you to take the lead and start the meeting. We’d recommend:
Then move onto the first topic…
What people want to do in the future is overwhelmingly influenced by what they’ve experienced in the past.
You’ll want to get a good sense of the key moments in each of your report’s lives and careers up to this point. You’re not looking to gather tons of detail, but to get a sense of what they care about and what drives them.
You may have got some of this detail from your initial 1:1s, but you’ll likely get further insight if you dedicate some more time to it.
You may want to ask some initial questions like:
‘Can you tell me the story of how you came to work for us, starting at school?’
‘Starting from your time at school, tell me about your life’
‘Tell me about the first job you ever had’
As your report starts to talk, listen for moments where they made key transitions in their life and ask follow-up questions to understand their motivations:
‘Can you tell me more about why you decided to move to the UK?’
‘I’m interested in why you took that job? Did you have other offers at the time?’
By the end of this discussion, you should have got to know much more about the key points in your report’s lives and careers, which you can use to think about how you can create some more.
Once you’ve covered off where they’ve come from, you can begin to talk about where they want to go.
This discussion will go very differently from individual to individual.
Some will have clear ideas about how they want to progress, and how their work at your company fits into a longer-term career plan. Some will have no idea at all (or think they don’t), but just want to be paid fairly for work they enjoy with people they like.
Most will be somewhere in between.
So in this part of the conversation, don’t go looking for specific answers if they’re not there. Be guided by the conversation and try to get some core insights about their long-term aspirations.
The key is to move the conversation beyond your existing company, and even beyond careers. In their dreams, where would your team-member see themselves in ten years time? Where would they be? What kind of work would they be doing? Who would they be hanging out with?
Russ Laraway suggests that you could open this conversation with:
‘What do you want the pinnacle of your career to look like?’
As the conversation progresses, look out for points where their answers jar with the understanding of their motivations you picked up from ‘The Life Story’ conversation. Where that happens, don’t be shy to ask some follow-up questions - it shows you’re paying attention and are invested in really understanding them.
Once you’ve gone through all this, you can let your team member know that you’re going to go away and give what they said some thought.
Suggest meeting again in the coming weeks to develop a plan (which we’ll discuss in a moment).
Some final tips:
Ok now you should be getting a clearer view of one side of the picture - what your team member wants to achieve.
In order to know if and how you can support them in that, you need the other side - what your company wants to achieve.
It’s only by understanding what your company values, and where the opportunities are to contribute to that, that you can pass those opportunities for growth onto your team.
If you’ve had the meaningful conversations with your boss from Alignment and Managing Up you should have lots of these answers already (if you haven’t, go and have them).
But even if you have, it’s likely that your conversations with your team members have raised further questions which you don’t have answers to. These are often around the availability of opportunities with your company, future strategy etc. You may need to go and do some digging to find those answers.
A specific piece of knowing your company relates to understanding how people get promotions and pay rises.
While career development doesn’t have to come in the form of promotions, they’re significant opportunities for greater responsibility, new challenges, and higher rewards, and play a key role.
In your conversations about their aspirations, team members may have already mentioned a specific promotion, or a desire for responsibilities which you know would only come after a promotion. Making sure you understand how and why people get promoted at your company is therefore crucial for supporting your team’s career development as you decide how to shape their work.
It’s also key to manage expectations with your team about when they can expect a promotion. One of the key reasons trust breaks down between managers and their teams is when team members have been led to believe they can expect a promotion, and it doesn’t come through.
The process is also sometimes not that clear. Some smaller companies have no process at all - it’s just an informal conversation with senior management. Some companies have a process, but it’s just theatre. Everyone knows it’s actually still about impressing particular figures in senior management. Some companies have rigorous career paths where you have to model certain behaviours and competencies as part of being put forward for promotion.
We’ll stop there, the examples are endless. The main lesson is to find out how it works at your company. And not just how the HR department says it does, how it really works. For example:
So when the time comes, and you know one of your team is ready, you know exactly how to play the game and win.
By now you have all the ingredients to support your team’s career development:
We’d make one final suggestion - collect all those thoughts into a plan for each team member which you can regularly review for progress.
This doesn’t have to be too formal. A career development plan should just be a list of three to five goals that you’re working on together which you both believe will advance the individual’s career in the next 6 to 12 months.
Writing them down makes the goals clear, and also gives you a document to keep you both accountable and track progress.
A typical career development plan might include goals related to:
You should write it up in a place that’s accessible to you both. Depending on the software your company uses, this could be something as simple as a Google Doc, or you may have dedicated tools to help with this.
You should aim to have career conversations with each of your team members every 2-3 months (at least quarterly). You may choose to have them more frequently if you’re working on specific shorter-term initiatives like a promotion push.
These conversations are an opportunity to revisit the career development plan, check progress, manage challenges, celebrate successes, and understand whether the team member’s aspirations have changed in any way since last time you spoke.