How to Have Productive Career Conversations with Your Employees

Back to school or back to…gruel? For many of my coaching clients, the arrival of autumn brings about the work blues.

Where summer offers a little less structure and a little more lightheartedness, returning to routine can feel daunting for employees. There’s often a lingering apprehension (and lack of enthusiasm) about the busy end-of-year approach.

As such, autumn often spurs people to think about role adjustments, career changes, or general questions along the lines of: What’s next for me?

Leaders: How can you ease the seasonal transition and keep your team members engaged, inspired, and growth-oriented?

Q4 is the time to hold thoughtful, productive career conversations and get ahead of performance review season. I recently held a session for employees on owning and elevating their careers at L’Oreal UK, and I was impressed by the company’s commitment to equipping leaders and employees alike with tools to hold meaningful career conversations. They ensure managers are trained to support staff in these discussions — a crucial element in fostering engagement.

A 2023 Gallup study found employees were more engaged when they felt that their managers cared about their work growth. Too often, our culture looks at engagement as an ‘HR project’ that falls by the wayside — but engagement should be a core leadership priority. Engaged employees contribute to an energized, committed, and productive workforce.

A helpful approach that managers can use to support their employees is guiding them through a career audit — what I refer to as auditing their "work ecosystem." Like an ecosystem in nature, where all organisms interact to create a bubble of life, a work ecosystem is composed of various elements that shape one’s work life. A comprehensive audit helps employees take ownership of their career aspirations, and in turn helps leaders offer support and direction in targeted areas.

Here is a five-step approach to conduct 1:1 conversations with your team members, using this audit as a foundation for discussion:

Craft the Categories

Define the categories you want to explore with employees as they examine their work ecosystem. Here are some areas to consider:

  • Content: The topics and projects the employee is working on

  • Skills: The specific skills they’re using, such as analytics, coordination, leadership, etc.

  • Work milestones: Key performance achievements or progress points

  • Development needs: Areas where they could benefit from additional growth

  • Growth opportunities: Potential areas for advancement

In my coaching practice, I often include additional categories such as work/life harmony or team dynamics, and/or leave a blank category for them to choose. You should include categories that align with your company’s culture.

View as a Visual

Utilizing visual tools to bring the conversation to life can be helpful. In coaching, we often use the Wheel of Life: You can take this diagram and insert the categories that are most relevant to your work culture to use as a conversation-starter. It’s a way to break information down piece by piece and help employees explore their ecosystem with intention.

Reflect and Rank

Next, have your employee rate their level of satisfaction with each category on a scale from 1-10, with 10 being full satisfaction. An important step in this process is to have them define the criteria for a 10 in their own words, as a 10 looks different for everyone. Both the leader and the employee must have a clear understanding of each category’s definition to avoid misunderstandings.

For example: If a work milestone feels like a 7 to your team member, how might you support them in getting to a 10?

Inquire for Insights

Use open-ended questions to probe for direction. For example:

  • What aspects of your work have you found to be most fulfilling?

  • Where are you needing support?

  • What do you want to see happen x months from now?

  • How can I help?

The idea is to help unpack the information. As the manager, you are aiming to give each employee the opportunity to express their aspirations, while also guiding them in alignment with the business needs. You may need to provide concrete direction and have some asks of each employee; be sure to include those here as well.

Leave for Later

The purpose of a career conversation is to focus on the employee’s goals, successes, and areas for development — not remuneration. While bonus season might be on the mind of the employee, it’s helpful to hold a separate compensation conversation; oftentimes, that discussion is part of a broader team bonus review.

Wrap It Well

Whether the conversation is one that feels complete or still has some lingering questions, create an opportunity to revisit together. Your role as a leader is to ensure that your team members can carry out their roles to the best of their ability — to help course-correct and steer them in the right direction. Employees operate best when they are seen and their perspectives are taken into consideration, even if you can’t always provide all the answers from your managerial POV. At the end of the day, every employee has ownership over their career journey, but you can help them along this part of the journey: to feel fulfilled and successful in their current role.

Ideally, you should make time for these types of career conversations on a regular basis, so that you remain informed of what’s happening and build trust with your team. As a leader, you are in the business of people: the more you stay connected, the better equipped you will be to lead an engaged workforce.

“Pfizer has changed how managers are evaluated to reward how they lead. In addition to rating their business outcomes, performance ratings now focus on how managers achieve those results by measuring their positive impact on their teams. For example, Pfizer now assesses how well managers implement company values, such as excellence and equity, based on direct feedback from their teams.”Women in the Workplace Report, McKinsey, 2024

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