What do you want to be when you grow up?

How to have truly impactful, individualised career conversations

What did you want to be when you grew up? If you’d have asked me when I was 8 years old, I would have said a Marine Biologist — inspired by Anita Ganeri’s masterwork Odious Oceans. Unfortunately, this dream quickly took a knock when I realised that I was abysmal at science and was properly put to bed when I had my first panic attack whilst snorkelling.

My next idea was also inspired by a book (there’s a theme here!) — this time To Kill A Mockingbird, Harper Lee’s complicated classic. This time it stuck — I actually got as far as studying law at university, only to come to the crushing realisation about a year in that actually, it was nothing like what i’d imagined and just wasn’t for me.

In fact, whilst my employment law comes in useful from time to time, I couldn’t have picked a more different career. For one, legal career pathways tend to be pretty structured — very different from the squiggles and loop the loops that tend to characterise progression at startups. And whilst I do still love burying my head in a book, my career in People + Culture has involved tonnes of hands-on learning. Finally, what I do now depends less on exposition (thankfully — I certainly don’t have Atticus’ ability to command a courtroom)… and more on coaching, listening and responding to people’s needs.

The above isn’t what 8-year-old Hannah would have expected, but I suspect it’s a pretty common story — career trajectories are rarely as straightforward as popular culture and school guidance counsellors lead us to believe. This is particularly the case in startups, where progression can often happen at breakneck speed, but where there’s also often a lot of ambiguity around what growth opportunities will look like. Furthermore, even in scaleups and more mature businesses, peoples messy brilliance very rarely fits neatly into boxes described in progression frameworks.

So, if you’re a leader of people within a startup or scaleup, where does that leave you? How do you tackle conversations about your team’s career and personal development? There’s no doubt that the above context can make it challenging — but these conversations are far from skippable — so here are our tips for tackling them through coaching.

Ask the big questions

Too often career conversations can hone in on the specifics (what skills do you want to develop?) without looking at the big picture. Yes, mastering new things is exciting, but cutting straight to questions like this is pointless if you don’t understand what your team member is working towards long term — what excites them? What motivates them? What are they looking to get out of their role here?

Three questions to get you started:

• What do you want to be when you grow up? Yes, this question seems a bit silly on the surface — but it really gets people thinking about where they want to be long term and will tell you a lot about their motivations. Incidentally, so might learning what their answer to this question would have been when they were younger. I’m neither a Marine Biologist, nor a lawyer, but my motivations for wanting to explore these career paths (curiosity and championing people’s rights) have never left me.
• What really gets you out of bed in the morning? There is likely to be more than one answer to this — so don’t settle for something simplistic. And dig a bit deeper if the response is money — usually this is also a key to something — maybe getting on the property ladder, or providing for a young family. To get people to open up, reflect on your own why and share it first.
• Look forward 10 years from now, you’re at a party and someone is giving a speech about you. What would you like them to say? This question should tell you something about your team members values and the underlying motivation for their choice of career.

Stop putting people in boxes — help them leverage their unique strengths instead

Too often we focus solely on ‘areas of improvement’ in career conversations, often tying these into a career progression framework. Now, used well, these frameworks are useful for giving people clarity about how they can progress within an organisation and illustrating different pathways to develop (they often don’t do this, but that’s a whole different article).

We miss so much when we build career conversations entirely around these frameworks. Don’t get me wrong — used well, a progression framework can be a good tool to provide transparency and clarity on the opportunities available to an individual. However we shouldn’t use it to define the entire conversation — as leaders, if we’re really honest when using progression frameworks to assess people in our team and build development plans, it’s often messy and complicated (someone might be an L1 in one column, but have some L3’s elsewhere) — that’s not just you, that’s because people are messy and complicated (and brilliant!).

It’s now (I hope) clear to most leaders that hiring a bunch of people with exactly the same skills, abilities and characteristics — is a recipe for a homogenous team with tonnes of blind spots and at the extreme, toxicity. Therefore it baffles me that once we’ve put effort and intention into building teams with a diverse set of skills and attributes, we would try and wedge them into boxes indicating that there is only one way to be successful and base our career conversations around that.

However, in career conversations I’ve had, I’ve found it much more effective to focus on people’s individual strengths. What are they? How can they develop them more and leverage them better in their work? This approach not only benefits the individual — making it clear that their unique skill set is valued — but also the development of the team.

Three questions to get you started:

• What gets you excited about what you’re doing now? What would you like to do more of? (think about specific examples here of things that you do well or things that come easy to you? — what skills are you using?)
• Which strengths (skills/attributes) do you use more/less often? This is a good way to uncover whether your team member feels like their skills are valued and deployed in a way which is helping them reach their potential.
• How can you use your strengths more?

Lock it down

You’ll note that so far we’ve gone big (what do you want to be when you grow up), then we took it down a level to the practical (how can you make the most of your strengths) — now it’s time to take it home.

Career conversations are not impactful if they stay at the conceptual level. The conversation itself will be inspiring, but without a ‘what next’, progress can flounder. Once you’ve identified a couple of clear things to work on that are genuinely motivating and support your team members overall goals, it’s time to get specific and find a couple of clear actions to work on.

Do this by first clarifying what success will look like, then diving into a plan (P.S. our next newsletter is going to feature a lot about the importance of making those plans and getting clear on your ‘implementation intention’ to increase your likelihood of achieving the goals you set — until then, you’ll just have to trust me that getting specific works!).

Three questions (ok, 5 this time as this is where we get specific) to help you do this:

• What steps could you take to move towards this goal? Help your team member figure out some key actions/milestones that will support their personal development goals.
• What projects, tasks could you work on in support of this goal? Personal development goals are often seen as ‘extra’ work and therefore quickly deprioritised when things get busy. So helping your team member identify projects or parts of their day to day that are aligned with their longer-term plan really is a win-win.
• Who/what might be able to help you with this? You could discuss internal/external mentors, options for more formal training, conferences or events here. You should also define your own role in supporting your team member.
• When will you be taking these steps? The cycle you use to track OKR’s might not work for personal development goals- some of which are likely to be ongoing. Nevertheless, it’s important to put a timeline on the immediate steps you’ve agreed to maintain momentum.
• How will you know if and when you’re making progress? Some development goals — e.g. reducing imposter syndrome, can feel less tangible. As well as tracking actions attached to these — e.g. attending training or a workshop — it’s important to define what progress means to the individual.

That’s all folks

So there you have it! Career conversations that are individualised, impactful and result in tangible actions for your team members’ development.

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