How to Ask the Best Employee Development Conversation Questions (+27 Examples)

Asking the right question can make all the difference when it comes to employee development.

People need to feel like their employer cares and that their career is going somewhere while working for them.

Which one of these do you think would prompt a more thoughtful response?

"Which job title do you want in five years?"

Or

"What do you feel passionate about achieving in the next phase of your career?"

It's undoubtedly the second one. 

Rather than prompting a short definitive answer, this one comes with an opportunity to explore feelings, aspirations, and possibilities. 

Asking insightful career questions is an opportunity for managers to help employees open up new paths to personal growth. 

Our guide to career development conversations offers an in-depth look at the thinking behind these conversations, strategies for getting the best out of them, and relevant advice from HR leaders.

Meanwhile, in the article below, you'll find invaluable tips for ensuring these talks go smoothly and inspire employees and their managers. We've also included a list of 27 career development questions you can ask to get the best out of your employees.

⚡️ Development conversations can supercharge employee performance

In short, career development discussions are conversations that managers have with their employees about their hopes for their careers.

They should be regular – around twice a year or more – and work best if the manager takes the back seat. 

Employees should be able to speak openly about what they really care about in their work and give constructive feedback about how their managers and teammates can better support them to progress within the company.

As a manager, you shouldn't aim to come out of a career development talk with an employee's wish list of promotion-related outcomes.

Instead, use these conversations to encourage honesty and self-reflection. 

The employee might envision a long-term future at a different company, which should be fine. But these talks should help you encourage their development while you still have them.

Also, these are distinctly not performance reviews.

While performance reviews look to the recent past to judge how well someone has done in their role, development conversations look to the future.

You can mention past performance, of course - performance does relate to how the future will pan out. 

In a typical group of workers, performance might range from "just getting by" to excelling on all fronts. So development conversations can also help employees reflect on the areas they need to improve to succeed in their roles.

But as a manager, in either scenario, you should be directing the conversation topic toward their desires and whether their development goals are realistic, whatever their current skillset.

💡 Check out 14 examples of developmental goals and ways to achieve them.

🗣 3 Benefits of having regular career conversations

- Developing positive relationships within your team

Managers and employees connect through a less formal exchange. So, by getting into "bigger picture" topics, there's a good chance they'll find common ground or a mutual understanding.

- Fostering self-awareness in the workplace

It's sometimes easy for employees to tune out and just go through the motions. But talking about what's possible in the future can bring them out of a slump and open their eyes to new paths.

Optimistic employees tend to perform better, as they have something to work towards. So by integrating employee enablement and development conversations, you can increase employee performance.

- Documenting employees' development over time.

You can also use these conversations to track development progress and check whether or not your employees are meetings the goals set by their growth plans. You'll be able to work with your employee to set goals, give them timelines, and return to them over time to see how things are progressing.

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💡 Tips for asking the right career development questions

Although we have some excellent example questions below, as a manager, you'll have your queries to pose, depending on various variables based on your business and the employee.

So if you're preparing for one of these talks and noting the topics you'd like to focus on, it's important to ask the right questions with the right intentions.

Your questions should:

• Give food for thought by being open-ended enough to prompt a good amount of introspection. A good measure for this is to ask yourself the very same questions. If the answers are too obvious, the questions may need to probe further.
• Help identify ambitious career goals. You need to nurture your employee's potential, not stifle it. Give them the freedom to talk about lofty ideals. Even if they seem a little outlandish, they can be helpful to start them on a path to improvement.
• Align their goals with company objectives. Their career progression may eventually lead outside of your organization. Still, until that happens, it's essential to nurture your employee's growth to benefit both them and your organization.

Here are the different types of questions you can ask. 

1. Trend questions ‍

Trend questions focus on the present and future and cover patterns they observe throughout their work. 

• What trends do you see in the industry? 
• What's the vibe been like at work since we moved office?

2. Assessment questions ‍

Assessment questions focus on recent past performance and events to gauge how and why they got there. 

• What has been challenging for you recently?
• What has worked well?

3. Priority questions

Priority questions focus on the future and identifying areas of concern and the next steps for them. 

• Where is there room for improvement?

4. Creative questions ‍

Creative questions are surprise curveballs that give your employee an opportunity to have fun, nurture their imagination, and spark interesting discussions. 

• What would you do first if you were made CEO tomorrow?

5. Practical questions‍

Practical questions deal with how to work together to make things happen. 

• How can we support you?
• What do you need from us to help take your skills to the next level?

Tip #1: Ensure you include a mix of these to find the most informative answers.

Tip #2: Make sure to identify previous wins and clarify the path to future success. 

Tip #3: Help employees carry the momentum of former wins forward to achieving new and exciting goals.

Now, let's look at some good questions to ask during career development conversations.

❓ 27 Questions for meaningful and inspiring development conversations

1. What do you love most about your role?
2. If you could change one aspect of your role, what would it be?
3. What are your short-term and long-term goals?
4. What accomplishment are you most proud of in your current role/ team?
5. What is your dream job? How far do you think you are from achieving that?
6. What drives you?
7. Who do you admire in this organization or industry? What is it about them that inspires you?
8. How connected do you feel to the organization's goals?
9. What do you find most challenging about your job? Is it stressful, or does it push you toward growth?
10. What would your perfect working day look like? Could we make it a reality?
11. Is there any skill that you need to develop? How would it help you in your daily tasks?
12. If we could invent an entirely new role that perfectly suits you, what would it be?
13. What's the best career advice you've received? How has following it made a difference for you?
14. What projects or responsibilities would you like to take on? What experiences or achievements do you consider essential for taking on higher-stake tasks?
15. Which method of learning do you prefer?
16. Is there anything that you are particularly passionate about right now?
17. What talent or skill are you not currently using in your role but would like to use?
18. Have you ever failed to achieve a career goal? If so, what did you learn from the attempt?
19. Would you benefit from having a formal mentor? If so, what role or department would you like them to be from?
20. What's happening in the industry that concerns you?
21. How do you think [industry trend] will pan out in the next decade?
22. What would you do first if you were made CEO of this company tomorrow?
23. What support can we provide over the next 6-12 months to help you get to the next stage in your development?
24. What activity would have the most significant impact on your development? Is there anything stopping us from starting right away?
25. Do you think this organization invests enough in employee development? 
26. What would you like to see done differently?
27. Are you happy with the development plan we've set out? If not, what changes would you implement to it?

🌱 Enable your workforce with Zavvy

Employee engagement and enablement are so much easier with the right system. And career-dev conversations benefit just as much from using one.

Even if you have an easy-going, informal company culture, it's crucial to build a process for having these talks.

By recording your discussion points within a specialized documentation process, your development chats are much more likely to have a positive impact.

Zavvy is an employee enablement platform that includes a comprehensive career development module. 

Our employee development software helps you record development chats, note progress over time, and connect people to help each other along their journey.

Book a free demo to discover how Zavvy can help you make career development talks fun, productive and uplifting.