How to have career conversations that make everyone feel included

Organizations thrive when their people do. Helping employees grow in the direction of their professional dreams is key to making that happen.

Jane Horan
5 min readMay 25, 2023

How often do you have career conversations with your team? Not the standard performance review questions like, “What do you want to achieve in the next 12 months?,” but a conversation devoted exclusively to what your team member wants out of their career and life, and helping them to map it?

For leaders, having the conversations that matter is a key trend that’s shaping the art of people leadership this year. With the changing nature of careers in today’s society — from gig work and remote work to people working longer as they age — employees are increasingly looking at their longer-term career aspirations and including bigger dreams that potentially extend outside their current workplace and into new career areas.

Leaders can either engage in these conversations or be surprised when someone hands in their resignation.

What are the benefits of career conversations?

It’s clear from the data that people want to advance in their careers, rather than feel stagnant.

According to McKinsey’s 2022 Great Attrition study, the top reason for people quitting their company is a lack of opportunities for career advancement. Uncaring or uninspiring leaders also get an honorary mention as a demotivator that drives people away. This suggests that employees don’t just want a boss — they want a coach to guide their personal and professional development.

When done well, career conversations give employees a detailed understanding of where they are now, the dream in the distance, and the opportunities between so they can plan a path forward. The last thing you want is for good people to leave because they don’t know if a dream role might be available in the company or whether they can apply for it. By mentoring your team in this differentiated way, you create the mindset, “I’m developing and my manager has my back. The grass isn’t always greener on the other side.”

More fundamentally, your people need help to plan their growth trajectory! Certain groups come to work with lots of self-defeating tendencies, whether that’s imposter syndrome, flawed thinking, trying to live up to the expectations of others, or stereotypes of what “someone like them” can achieve in their careers. Well-structured career conversations help employees find the direction they’re craving but they also serve a bigger purpose, and that’s to consciously level the playing field for those who need more guidance towards the options available to them and support to amplify their voice.

Four tips for having inclusive career conversations

This all sounds great on paper. But how can you, as a manager, make sure the people under you are developing to their greatest potential? How can you become an inclusive leader who listens, coaches, presents opportunities and opens doors? The following tips may help.

#1: Leave your own career at the door

Your team members might not want your job or even a career in a traditional corporate hierarchy. They might view work in a completely different way — and that’s okay. As diverse humans with different backgrounds and identities, we will not follow the same paths to achieve our goals. Knowing what your team member wants, and not trying to fit them into your worldview, is key to creating inclusive talent development plans.

If a team member talks to you about plans outside the company, then you’re doing something right. It means they trust you enough to open up about future ambitions without feeling like it’s going to backfire on them in some way.

#2: Listen and ask questions, don’t give advice

Offering advice like, “When I was doing your job, I did this,” may sound like it is coming from a good place but it’s limiting. Conscious inclusion requires you to pay attention to the history, context and natural evolution of each person. The team member you’re supporting deserves a plan that gets them where they want and deserve to go, and they may be in a completely different place from where you were at this stage of your career.

A better approach is to ask open questions like:

● What do you want from your career?

● What might get in the way of achieving the career you want?

● What skills do you think you’re going to need to develop to achieve that?

● How can I help you develop those skills?

This article has 10 conversation starters to help you structure the conversations that matter. Use them to get to the bottom of the team member’s personal “why.” Above all, be reflective about the value you place on certain career paths and whether your own motivations and biases are leading you to treat someone’s ideas as exceptional.

#3: Advocate equitably for your team

When you’re in talent discussions with your coworkers or, for example, you’re putting together a project team, take care that you’re not always advocating for the safe pair of hands that always gets put forward for these things. Challenge your coworkers if they lapse into talking about the usual suspects. For example, you might ask, “Who else can we bring into this project to get a more diverse perspective?” “Who would benefit from the opportunity this role provides?”

Having career conversations is the first part of the process; actively pushing to align people and opportunities is the second part. Nobody should be overlooked.

#4: Integrate career conversations into daily practice

Career conversations are not performance reviews, they’re ongoing conversations about development, growth and opportunities. You should be having them with everyone in your team regularly and actively focusing your attention on doing so. You can think of this as a continual dialogue where every day you’re looking for alignment between opportunities and individual growth goals. Ask yourself,

● What are the skills that my team members are aspiring to develop?

● How will this opportunity help them?

● Are there other roles in the business that may interest them?

● Can I make an introduction?

● Can I recommend that my coworker bring this team member into their project?

The more you can help team members along their path, the more they’ll likely stay and help your company on its journey. Imagine how empowered you would feel if you were in their shoes!

Inclusive career conversations are a winning strategy

It’s not enough to have the conversations that matter, managers must intentionally invest in each employee, making sure they’re getting the opportunities and experiences they need to advance in the way they aspire to advance. Instead of empty promotions or someone else’s version of growth, aim for real, honest conversations that unearth each person’s hopes and dreams, and sheds light on their present and their future. Then be the connective tissue that unites the two.

Doing so can extend the life of employees at your company, but also ensure they feel noticed and valued while they’re here.



Jane Horan

Author. Helping people find meaningful work. I write monthly on inclusion, political savvy and careers and how these interconnect.