Career Conversation Tips and Questions to Engage Employees

PUblished on: 

April 17, 2023

Updated on: 

Written by 

Lucy Georgiades

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With fewer opportunities for upward mobility, bonuses or career security, having career conversations with employees can be quite daunting. Managers may worry that they don’t have the answers to their team members’ questions anymore. There are a lot of people in the same boat!

When you have career conversations, your people will feel so much more invested in and you will have clearer insights into what motivates them. It’s best to have the conversation and figure out how to make this chapter in their career as meaningful as possible, no matter how long or short it might be. So, don’t shy away from career conversations!

That’s why we designed this Career Conversation Checklist! It’s to help managers feel better prepared and ready to have meaningful conversations with their direct reports.

In this article, you will learn helpful tips for managers on what to do before, during, and after a career conversation. Feel free to share this with your people managers!

Want to build an environment that engages and retains your superstar employees? Watch ‘How to Have a Career Conversation’ free video training today.

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Want to build an environment that engages and retains your superstar employees?

Watch ‘How to Have a Career Conversation’ free video training today.

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Before the Career Conversation

As with all these kinds of conversations, preparation is going to be key. I’d suggest setting up the career conversation as a separate time to your regular 1:1s. Make it a full hour, at least, and schedule it at a time of day when both you and your direct report have the mental energy and don’t feel rushed going from meeting to meeting.

Prepare a list of career development questions that can help you understand your direct report’s motivations, feelings, and future plans.

Here are a few career development questions to help structure the conversation:

  • Where do you see yourself in 5 or even 10 years?
  • Where do you see yourself spending your time?
  • What type of work aren’t you doing?
  • What skills do you have?

It can be hard to come up with these answers on the spot, especially for those who appreciate a bit more time to prepare on their own. So it’s best to send these prompts to your direct report ahead of the conversation.

During the Career Conversation

When having a career discussion, it’s helpful to start the conversation further out in time and then get more immediate and specific. The conversation will have two parts: 1) Asking questions and 2) Setting development goals.

Part 1: Asking Questions

A great way to open the conversation is to ask a question like, “Where do you see yourself in 5 or even 10 years?” You might get a deer-in-the-headlights look from your direct reports, but that’s OK! Many of us don’t know exactly where we want to be in 5-10 years time.

The reason why we suggest managers ask their reports to imagine far out into the future is to allow them to think expansively and not be constrained by what might seem practical or even feasible.

You can help your report’s thinking by asking, “Where do you see yourself spending your time? What type of work aren’t you doing? Are you even in this industry?

Tip: Make sure to take notes in a shared doc - it will make your direct report feel heard, ensure they stay on the same page, and have shared accountability.

Now the idea is to move the timeline closer to the present. Once your direct report has taken a stab at 5-10 years, shorten the timeline to 2-5 years.

Ask questions such as:

  • Where are you spending your time now?
  • What skills do you have?
  • What do you feel confident doing?

The answers to these questions will help you understand what motivates your direct report in the nearer term. If one of their professional development goals is to be a manager, dig into what is driving that. Is it achievement and the next rung on the ladder or is it that they love to develop people and help them grow?

Once you have a sense for where your direct reports want to be 2-5 years from now, start to work back the timeline again.

Ask questions like:

  • In the next 12 months, what do you want to have learned?
  • What do you want to have experienced?
  • What do you need to do to set yourself up for your career goals?

Lastly, focus on the immediate time frame: ‘What is working now that is setting you up for where you want to go and the skills you want to develop? What’s not working?’

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Part 2: Setting Development Goals

Once you understand where your team members want to go in their careers, help them get there by setting growth and development goals.

Here are five basic rules to master when setting career goals:

  1. Set goals together. Help your team members feel empowered to own their careers. You can help set the stage for the conversation, encourage some goal-setting, and collaborate together. Your direct reports will feel a sense of ownership and accountability once they are achieved. It's also more engaging and fun to do it together!
  2. Write goals down in a shared doc. Writing goals help people remember them better because writing improves the memory storing process.
  3. Frame goals in the positive. It helps to focus on the right thing. A negatively-framed goal would be, "I need to stop being worried about giving feedback." A positively-framed goal would be, “I feel confident giving my team actionable feedback."
  4. Check if goals are aligned with overall team and company goals. It's much more motivating to see how one’s work has a positive impact on the company. The goals don't have to directly contribute to the company goals, but you need to help your reports craft goals that broadly align with them.
  5. Use a SMART framework to do a quick check of the goal quality. Goals should be Specific, Measureable, Achievable, Relevant, and Time-Framed.

As Jim Collins, well known author of Built to Last and Good to Great says, “Building a visionary company requires 1% vision and 99% alignment.”

Using the five basic goal-setting rules above, I'd recommend co-creating 1-2 near-term development goals (achievable in less than 6 months). Why? Research suggests as we get closer to reaching our goal, our brain releases dopamine and the more motivated we are to make it happen.

After the Career Conversation

Make sure you follow-up on development goals by discussing them once a month ideally, though quarterly is fine.  Your reports will need you to provide some accountability.

The American Society of Training and Development found that if you make a commitment to someone, you have a 65% likelihood of completing your goal. And if you have an accountability appointment with a person, i.e. your quarterly career development check-ins, you will increase your chance of success by up to 95%.

That's not all. Part of supporting your people's career growth is allocating work that's aligned to their goals. What can you delegate or what opportunities can you give them that map to their desired areas of growth?

Tips to Get the Most Out of Career Development Conversations

Here are a few other tips to keep in mind while preparing for and having career conversations.

Tip 1: It's Not The Managers' Responsibility to Come Up With the Actual Career Plans

Managers often hesitate to have career conversations because they don’t know what their report is going to say and they fear they won’t be able to deliver on it.

Reframe! It's not the manager’s responsibility to come up with the actual career plan.

Nor is it your responsibility to ensure your direct reports hit their goals. As I mentioned before, managers should empower their team members to own their own careers. You can set up the conversation, help their direct reports set goals, and help set up accountability.

Tip 2: Separate Career Conversations from Performance Reviews

Career conversations are not performance reviews. Each of them has a distinct purpose.

A career conversation helps managers understand what motivates their team-members, what their short and long-term goals are, and what will help them get there.

Performance reviews evaluate team-members’ work performance, identify strengths and weaknesses, and offer feedback.

I'd suggest carving out at least an hour for each, separately, to truly make an investment in growth.

Free 'How to Have a Career Conversation' Video Training

Elevate Academy is here to help managers feel more confident and ready in their day-to-day responsibilities, including having career conversations with their direct reports.

We're offering an 8-minute interactive 'How to Have a Career Conversation' class for free, which covers topics like:

  • How to structure a career conversation
  • What questions to ask
  • How to set goals
  • How to follow up

Lucy Georgiades

Founder & CEO @ Elevate Leadership

In London and Silicon Valley, Lucy has spent over a decade coaching Founders, CEOs, executive teams and leaders of all levels. She’s spent thousands of hours helping them work through challenges, communicate effectively, achieve their goals, and lead their people. Lucy’s background is in cognitive neuropharmacology and vision and brain development, which is all about understanding the relationships between the brain and human behavior. Lucy is an Oxford University graduate with a Bachelors and a Masters in Experimental Psychology and she specialized in neuroscience. She has diplomas with distinction in Corporate & Executive Coaching and Personal Performance Coaching from The Coaching Academy, U.K. She also has a National Diploma in Fine Art from Wimbledon School of Art & Design.