Main illustration: Vinnie Neuberg
Imagine walking into the office one morning and having your star team member ask if you have a few minutes to talk. In person.
Your instincts tell you nothing good is going to come out of this conversation. And unfortunately, your suspicions are confirmed when they hand you their resignation and explain they’ve been offered “a new and exciting opportunity” that aligns with their career aspirations. You’re thinking, “How did this happen? What could I have done to prevent this?”
All managers deal with retention issues, but in my experience, those who deeply understand their team members’ long-term aspirations have a better chance of anticipating these changes – and influencing their team members’ decisions. Regular, open career conversations can be an effective strategy for this. These create more meaningful relationships with people on your team, uncover what motivates them and as a result increase their impact and engagement in their current role. After all, people who are highly engaged with their work are rarely thinking about leaving the company.
How to have effective career conversations
At Intercom, some of us use the following 3-step process for career conversations.
Step 1: Schedule recurring, timely discussions
We encourage managers to hold career conversations soon after performance reviews so they can look for ways to match development areas with long-term aspirations. These conversations can take place during 1:1s or as separate meetings. Once you’ve had the first conversation, it’s up to you and your team member to decide how frequent or formal these meetings should be. Just make sure you’re having these conversations regularly.
Step 2: Ask reflective questions
For your very first career conversation with a team member, start with questions about what the person wants to be doing, what they’re good at and what skills they want to develop. Stuck for questions on how to start this conversation? Here are some to get the ball rolling:
- What kind of work do you enjoy most?
- What are your superpowers as an employee? How can you leverage them to have even more impact on your work?
- What are the top two-to-three accomplishments you’re most proud of from the past six months? Why?
- What’s your current development focus? What skills are you working on in the short term and what are you doing to improve them?
- What would you like to see on your LinkedIn profile five years from now? What excites you about this idea?
- What are the crucial skills you’d need to be successful in your dream role?
Share the questions ahead of time so people know what you’re looking to cover in the discussion. This will encourage them to reflect on answers in advance, and free up time to dig deeper during the actual conversation.
Good managers find ways to encourage these moments of self-reflection
The goal with these questions is to understand what’s ultimately driving your team members. When we’re all busy building new features, meeting deadlines and navigating general day-to-day madness, career conversations can give your team a much-needed opportunity to pause and reflect on the things that give them the most satisfaction. Good managers find ways to encourage these moments of self-reflection.
Step 3: Connect aspirations to concrete opportunities
We follow up career conversations with Individual Development Plans. These one-page documents outline the skills and experiences people should focus on building. Both the team member and the manager work together to create this plan and check it regularly.
As a manager, you can help your team member build this plan by identifying projects and tasks that align with their aspirations. This doesn’t necessarily mean assigning work that takes valuable time away from the person’s core role. In fact, it’s a win-win when you find ways to use the current role to help the person grow skills that will make them successful in the long run. Some examples from my own experience managing the Customer Support team include:
- I noticed one of my team members was passionate about improving internal workflows and processes, so I helped her take on additional responsibility in this area for the team. She eventually became a compliance officer on a different team using many of the same skills.
- Another team member is fascinated by UI design, so he’s currently running a project to improve the way our team collaborates with the Research team and reduce customer confusion in our app.
By proactively helping people find these opportunities, I’ve seen increased motivation in my team because people can clearly see how their projects align with their long term goals.
But remember – it’s their career, not yours
You might be worried that you’re now responsible for driving your team members’ careers, but that’s not the case! Although you have a responsibility to be a facilitator and help your team members grow, at the end of the day it’s still their own responsibility to set these goals and pursue them. If people don’t know what they want to do or simply don’t seem to care, don’t feel like you’re the one who needs to do the heavy lifting. You should never invest more in someone’s growth than what the person is investing themselves.
That said, here are a few ways you can help people set more concrete goals.
- Ask them what are the things they’re currently doing that give them the most satisfaction. Offer additional suggestions based on their peers’ feedback and your own observations to build on their answer.
- Encourage them to look at opportunities on your company’s internal careers page.
- Arrange informal chats with people from different teams so they can learn about different roles.
By gaining a better understanding of the various roles available to them, your team member will have more clarity about the specific skills and experience they can start building to pursue the positions they’re most interested in.
An open conversation is a two-way conversation
I’ve also found I can help people test their aspirations against reality to make their goals more tangible. Let’s say you have someone who wants to become a people manager. Get them involved in interviews and training for new hires; give them a chance to run meetings to hone their communication skills. Use your own knowledge and experience to act as a mentor and help identify the skills they’ll need.
Remember, if you notice your team member is slacking in their core role because of these additional activities or has unrealistic expectations about their goals, let them know! After all, an open conversation is a two-way conversation. If the person’s goal is unrealistic or too vague, brainstorm smaller steps and experiences they can take that will get them closer to where they want to land.
Successful internal transitions are a win-win
Sometimes successful career development means accepting the fact that your team member is ready to move on to a new role. That’s not a bad thing, especially if they transition within the company. Although you might have lost a star performer, you’ve gained a new ally on a different team and best of all, you’ve helped the company retain great talent. So, how do you encourage internal transfers?
Here at Intercom we’ve recently improved our internal transfer policy, making the process more transparent and unified across all teams and offices. Our internal announcements page now contains a detailed, step-by-step guide for people interested in exploring other opportunities and recommendations for whom they can talk to. We also include a link to our internal careers page in the weekly company newsletter so employees can keep an eye on emerging opportunities.
As a result, we’ve seen greater success with transfers between different organizations, with experienced employees increasingly using their insights and skills from their previous role in a new context. For example, some of our customer support engineers have moved into product engineering roles, where they’ve leveraged real-life customer use cases and insights for the development of new features.
Celebrate development 🎉
It might seem counterintuitive at first, but having proactive career discussions with your team saves everyone time. Your team members will reach their growth goals faster, and managers are more likely to be spared from the stress and difficulty of the backfill they didn’t expect – but should have seen coming. Knowing what motivates your team members will help you keep them engaged in their current role while setting them up for success in the long run.
And when someone makes a successful move within your company, share that story! It sends a strong message to your team that you genuinely care about the people you work with, which will boost morale. The last thing you want is to have your valued team members feel like they’re stuck in a dead end career and a dead end team. Instead of fearing career discussions, choose to be proactive and embrace these conversations as a way to spur people’s growth over time – on your team and within your company.