This Important Boss-Employee Chat Can Get Awkward. Here's How to Avoid That.

The biggest reason professionals switch jobs is to advance their career. Hence, if people believe they can advance their career at your organization, you greatly diminish the odds of them leaving.

It’s really that simple. But executing it is hard.

There are a few aspects to getting this right. You need to have a culture where you look within for leaders, instead of externally. You need to give your people both the time and the tools to learn the skills they need to advance.

And, you need to do something many organizations skip over: your managers need to have honest career conversations with their employees. Those conversations allow your managers to create development plans for their employees, which will go a long way to improving retention.

But having these conversations can be tricky. Managers need to set expectations, while also keeping employees motivated – not an easy balancing act. If handled wrong, this can get real awkward, real fast.

Don't worry, we’re here to help. In her LinkedIn Learning course Find and Retaining High Potentials, Leadership Development Consultant Kathrine Sharon outlined four steps for how managers should approach these career conversations, so they are as effective as possible.

They are:

Step 1: Get on the same page.

Here’s the big one.

Every employee wanted to be promoted yesterday, or at least get a hefty raise. Here’s where honesty really matters, and not just the employee being honest to the boss, but vice-versa as well.

In other words, this conversation often comes down to setting expectations. If a person wants to be promoted but is struggling in their current role, well, managers need to let them know they need to increase their own performance first. Or, if they are six months into a role and already want a new one, managers again need to reset expectations.

That said, saying no to everything isn’t the right solution either. Managers should go beyond offering just a lateral or upwards position change. Perhaps the person can take on a new project within their role or be given an opportunity to present to higher-ups – in other words, advance their career without necessarily getting a new role.

By being both realistic and pragmatic, your managers can set expectations that are honest, while still being inspiring.

Step 2: Create a specific plan.

Once you have a goal, it’s time to make a plan to achieving that goal.

The key when setting this goal is to be specific, in both actions and outcomes. Rather than just “improve leadership skills”, a better plan is “to successfully lead a project” or “to run two meetings a month.”

Additionally, a bad outcome is "be promoted” or to “run a team someday.” Instead, much more effective is to have something specific in mind – become a reliable project manager, become a manager of project managers, etc. – as that’s far more actionable.

Also, you want timelines here, as deadlines force action. So rather than saying you want to run a project eventually, make it a goal to run and complete a project within the next three months.

Step 3: Monitor progress.

Here’s where managers need to coach employees.

Once a plan is set, ultimately it’s up to the employee to execute it. But managers can keep them accountable by asking questions on their progress and uncovering areas they are struggling in.

Often, an employee will reveal several roadblocks in these conversations that are holding them back from reaching their goals – some legitimate, some excuses. Again, effective coaching techniques can help employees work around the excuses. For the legitimate roadblocks, managers can either see if they can help or alter the timeline.

Step 4: Give feedback and praise.

Along with monitoring progress and coaching along the way, managers should also provide feedback and/or praise after projects are completed.

This is motivating, particularly for high achieving employees. They want to know how they did. If you coached effectively along the way, feedback should not be a surprise. However, if they took that coaching and succeeded, praise is in order.

Do more than just praise their work though by saying they did a good job. Explain how it helped the organization. Maybe their project cut costs or expanded a market – that’s far more rewarding to hear than just “good job.”

How often should you have these conversations?

It’s not necessary to talk about an employee’s development in every one-on-one. But these conversations should happen at least once a quarter.

Additionally, monitoring progress can be something that happens nearly every day. If an employee is working on a project as part of their development goal, you’ll likely discuss that every time you talk with them, for example.

All told, the only thing worse than managers not having career conversations with their employees is managers having poorly managed career conversations with their employees. By following the four steps listed, you should avoid that.

*Image from Matt Pek, Wikipedia Commons