Career Conversations Matter
Years ago, I took over a team and inherited a Tier 2 tech named Alex. On paper, Alex was doing fine, hitting tickets on time, meeting SLAs, never missing a shift. If I had just looked at the metrics, I might have assumed he was content and planned the next 12 months around him staying put.
But in our first one-on-one, I asked a simple question:
“Where do you want to be a year from now?”
With some hesitation:
“Honestly? I want to be a network engineer.”
That answer completely changed how I managed him. Instead of treating Alex like a fixed piece of the puzzle, I started treating him like someone in motion. I got him exposure to network projects, paired him with our network lead for shadow sessions, and gave him stretch assignments that lined up with his career goals. Within a year, he was ready for the next step and our team didn’t lose him to another company.
Many managers meet their team for the first time and stop at performance metrics. If everyone is meeting expectations, it’s easy to think, “Great, I can plan out the next 12 months.” But if you never ask people what they want from their careers, you’re only seeing half the picture, and you may be setting yourself up for painful surprises.
People Are More Than Their Current Job
When I inherit a team, one of the first things I do is sit down for one-on-ones. I don’t just ask how work is going, I ask about their goals. And almost every time, I find something that would have been missed if I had just focused on performance.
Some employees really are happy staying where they are. They’re solid, reliable, and want to be a strong contributor for years to come. But many others want to grow. They might be a Tier 2 tech who wants to become a network engineer. Or a project manager who dreams of becoming an account manager. These are important things to know, because it means their “12-month plan” is not just about doing the same job but getting ready for the next one.
Planning the Future (For Them and for You)
Knowing your team’s goals helps you plan better. If someone wants to move into a new role, you can line up opportunities for them — shadowing, stretch projects, introductions to the right people. When they eventually move up, they’ll be more prepared, and the team won’t be caught off guard.
The opposite is true too: sometimes people want a promotion for the wrong reasons. Maybe they want to be a senior consultant because it pays more, but they’d actually struggle in that role. If you know that early, you can work with them to find another path, maybe a technical specialist track or a support role with better pay. That way they still feel valued without being set up for failure.
It’s good business.
Lower turnover costs: Replacing an employee can cost 1–2x their salary. Catching a flight risk early saves money and disruption.
Better succession planning: When you know who wants to grow, you can build your bench strength and fill roles internally instead of scrambling to hire.
Higher engagement: Gallup data shows engaged employees are more productive and less likely to leave. Career conversations are one of the strongest drivers of engagement.
Simply put: knowing your people is one of the highest-ROI activities you can do as a leader.
Why This Matters for Retention
One of the fastest ways to lose a good employee is to ignore their goals. If you don’t ask, they may quietly look for growth somewhere else. On the flip side, showing that you care about their development builds trust and loyalty. Even if you can’t promote them right away, they’ll appreciate knowing you’re helping them work toward their next step.
How to Put This Into Practice
It’s not enough to just ask, “Where do you want to be?”, many employees have never been asked and may hesitate to answer. Here are a few ways to make the conversation productive:
Start with curiosity. “What part of your work gives you the most energy?” opens the door without pressure.
Normalize ambition. Make it clear it’s safe to share goals, even if they involve leaving your team someday.
Ask about the why. If they want a different role, find out what they think it will give them: new challenges, recognition, better pay - so you can see if there are other ways to meet that need.
Be consistent. Ask every 3–6 months, because career goals shift over time.
These questions build trust. People start to see you as someone who cares about their future, not just their output.
Ask early. Within the first month, have a conversation about career goals.
Offer exposure. If someone wants a different role, invite them to a meeting or two where they can see what that role actually looks like.
Be honest. If someone’s goal doesn’t fit their strengths, talk about it openly and help them find a path that does.
Helping People Test Their Goals
Sometimes, employees want a promotion or a new role for reasons that aren’t quite aligned with reality. They might see the title and salary but not understand the day-to-day work. You can help them “try before they buy.”
Use low-stakes experiments. Let them shadow a senior person for a week or join a cross-functional project.
Give them a stretch assignment. A small taste of the new role’s responsibilities can clarify whether it’s a good fit.
Offer mentorship. Pair them with someone who can give honest insight into what the job is really like.
These experiments are a win-win: the employee gets clarity, and you avoid putting someone into a role where they may struggle or burn out.
Bottom Line
Managing a team is about succeeding today and preparing for tomorrow. When you know what your people want, you can help them grow, plan your team’s future more effectively, and keep your best talent from walking out the door.
