Career Development

Know Your Team

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.

‍Arranging Career Conversations

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:

• It takes time: you’re going to have a lot to discuss.  Your first conversation will likely run at least 45 mins - 1 hour. If you’re also trying to discuss the regular business of your 1:1s, you’ll end up trying to do two things in not enough time and do both badly.

• It shows your interest: by setting aside dedicated time to discuss each team member’s career, you’re showing your investment in their futures, and that never goes unnoticed.

(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.

‍Guiding the Discussion

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:

• Getting started: get the conversation off on the right foot.
• The life story: get the background on their life so far and how it’s influenced their choices.
• Aspirations: understand where they hope to go in the future.
• Next steps: what to do following these initial discussions.
• General advice: final tips on having good career conversations.

(This framework is adapted from work by Russ Laraway and Kim Scott, which you can find references to in Further Resources at the end).

1. Getting Started

Your team member will typically expect you to take the lead and start the meeting.  We’d recommend:

• Restate that the purpose of these conversations is for you to understand them better so you can support them in their career - both at your current company and beyond. It’s about you helping them.
• Note that this is just an initial chat and you look forward to having more conversations like it in the future.  

Then move onto the first topic…

2. The Life Story

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.

3. Aspirations

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.

4. Next Steps

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).

5. General Advice

Some final tips: 

• Be aware of your trust level: as mentioned before, these are personal conversations which touch on many different areas of people’s lives, not just their careers.  Choose your questions carefully, depending on the stage of your relationship with each team member.  If you’re unsure, you can begin questions with phrases like ‘Would you mind sharing more details about…’ or ‘Would you be comfortable telling me more about…’. 

• Tell some stories: it will help the conversation flow if you open up about your own background and your own career aspirations.  It will help model the type of conversation you want to have, and should encourage them to share more with you. 

• Take notes: whether during the session or shortly after, be sure to make a note of anything that you think will be useful for guiding the individual’s career.  There will be a lot said in these sessions, and it can be easy not to capture the important bits.

• Don’t worry about practicalities for now: some first-time managers shy away from these conversations because they’re worried they won’t be able to deliver on what the team member aspires to.  Don’t worry about this for now.  It’s invaluable for you as a manager to know what your team member wants, you can worry about doing it later.

Know Your Company

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. 

Understand Promotions

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:

• Talk to your boss.  Find out their role in promotions, and how they see the process working.  Are they involved in promotion decisions? Find out what typically impresses them.
• Find examples of previous employees who were at the same level as your team and ask what they had to do to get promoted.

So when the time comes, and you know one of your team is ready, you know exactly how to play the game and win.

Make a Plan and Keep Track

By now you have all the ingredients to support your team’s career development:

• You know more about their individual aspirations.
• You know more about your company’s goals and how each of your team could best support them.
• You know what’s going to be key for getting each team member promoted.

We’d make one final suggestion - collect all those thoughts into a plan for each team member which you can regularly review for progress.

Making a Plan

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:

• Promotion plans: if the team member is working towards a promotion, what are the key skills and behaviours they need to demonstrate in what timeframe to succeed.
• Experience: particular projects or workstreams the team member would like to work on to build their skills in certain areas.
• Training: learning and development initiatives the team member would like to complete.
• Relationship-building: individuals that the team member would like to build better working relationships with.
• Mentors: any mentoring relationships the team member would like to establish.

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.

Reviewing the Plan

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.