• Tim Way


Instigating career conversations with your team is an important part of being a leader. But making time for those conversations is only the first step – making sure you’re having conversations of real value is the next.     

We all love progress

The connection between development, engagement and performance is proven. When people think they’re progressing it motivates them and increases their commitment to an organisation. So it’s no surprise development opportunities often feature highly in surveys asking employees what they value most from an organisation.

That’s why companies spend huge amounts of time and money to provide them for their workforce. They’re desperate to attract and retain the talent their businesses need to prosper and as a leader you’re a big part of the solution.

Your role as a leader

For too long career conversations have followed a box ticking approach. Many organisations rely on rigid frameworks that managers, understandably, work within. But this does little to make an employee feel their specific career progression is being addressed. You can change that.

Russ Laraway, co-founder of Radical Candor which helps companies build cohesive teams, calls these ‘imposter conversations’. There may be an intent to grow and develop a career but in reality the conversations focus on targets hit (or missed), performance and pay reviews, looking backwards rather than focusing on someone’s future.

If the talent in your team isn’t developing, they’ll go and do it somewhere else. By having a meaningful, sustained dialogue with them, they’re much more likely to stick around and grow with you.

Re-framing your approach

To start having more beneficial career conversations you need to reflect on and re-frame your role as a people leader. The urge to direct and manage is strong. After all managers are busy people with demanding clients and bosses, who are measured and rewarded on results. Getting things done is the overriding priority.

But to have a good career conversation requires a balance of boss, mentor and coach. That means listening to rather than directing someone, and an ability to step outside any box ticking framework your organisation uses.

Here are some techniques to try:

Hold up a mirror

Ask exploring questions to generate some self-reflection and actively listen to the responses. The aim is to understand what’s important to your team member and what is influencing how they feel about their career in the short and longer term. In many cases they may not have reflected on this before which makes it a good starting point.

By holding a mirror up your encouraging them to think clearly about what motivates them – why and how are they’re doing their role, where is it taking them and is that where they want to go? It’s important not to rush to judgement or offer solutions and advice. This is about taking time to understand the underlying influences on their career, so that they have confidence in the next steps you come up with together later on.

Share your experience

How have you dealt with similar challenges to those your team member is facing? As a leader you’re likely to have a few experiences under your belt, telling them how you responded to certain situations could trigger ideas they hadn’t thought of. Knowing others have been through something similar and thrived can also give them confidence and encouragement.  

As a more senior colleague you’ll also have a useful insight into the organisation at a higher level. What are senior leaders really looking for and what’s the direction and priorities of the company? This can be of real value when someone is reflecting on why they might commit to a develop goal.  

Again it’s not about telling them what to do, it’s about sharing experiences and knowledge they can learn from.

Plan actions

Greater self-awareness naturally leads to more relevant responses. Once you’ve identified their goals, influences, ways of working and so on, they’ll lean towards actions that address them. If you’ve heard the phrase ‘awareness is curative’ that’s what it means in a nutshell.

So when it comes to deciding what’s next, the awareness you’ve generated together will help them take ownership of their career and come up with an action plan to move it forward. As a manager you can use the company’s resources to help them achieve their goals and introduce them to people in your network who can support them.

Keep it up

These approaches aren’t meant to be a soft touch. Not only can investigating why someone is doing something be tough emotionally, it’s designed to lead to concrete career plans. Plans that are personal to each team member and give them the sense that their development is important and a priority. 

For these plans to really bear fruit, career conversations need to be ongoing. They don’t always have to be structured – an informal short catch up is sometimes all that’s needed, and the level of support required will vary as circumstances change – but careers are ongoing so the discussion needs to be too.  

First of all though, go back to the start and change the dynamic of the conversation. You don’t have to be an expert in career management to do it and you’ll find it has a positive impact on your team, your company and your leadership. 

Author: The Career Conversation editorial team.

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