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Learning & Development

35 career development questions to ask your employees, yourself & your company

Leapsome Team
35 career development questions to ask your employees, yourself & your company
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Promoting a growth mindset in the workplace pays off. According to Gallup, only 30% of employees believe someone in their workplace encourages their development. But if managers raise that number to 60%, they can see a dramatic increase in profits, productivity, and engagement.*

Asking questions about development shows employees you’re invested in their career growth. But it’s not enough to simply arrange one-on-one meetings with your reports — you also need to ask the right questions. Especially those that help you avoid discouraging employees through inequitable practices or unconscious bias.

To get you started, we’ve created this list of 35 excellent career development questions — based on current research and expert advice. We’ve organized it into categories for questions to ask yourself, your company, or during one-on-one meetings to clarify where your queries will be most valuable.

*Gallup, 2022

💥 Kickstart conversations with your people about career opportunities

Leapsome’s Development Framework visualizes your employees’ next steps and provides a robust framework for career development talks.

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One-on-one career development questions

One-on-one meetings are a great opportunity to discuss career development with your reports. You can help them set career goals, offer advice, and hear their concerns. Although every meeting should be employee-led, it’s still best to structure the session around a 1:1 meeting template and prepare your inquiries. That way, you can ensure the discussion runs smoothly and avoid posing leading or vague questions that may be counterproductive. A query like “How can I help you?” is too broad, and employees may struggle to answer it.

It’s also good practice to hold career development talks after a recent performance review. That way, the data from your performance review questions is still relevant and clear in your mind. Plus, separating career development meetings from employee appraisals keeps evaluations from stealing the focus.

You can start the meeting with questions about your report’s current role that gauge their job satisfaction and reaffirm what you learned from their performance appraisal.

  • Which recent projects have you enjoyed the most and why?
  • Which recent successes are you most proud of?
  • Do you feel like any of your skills are being underutilized?

Phrase questions about weaknesses carefully so they don’t come across as criticisms, which might put your report on the defensive. It’s a good idea to concentrate on how they deal with constructive criticism and learn from their mistakes.

  • Think of a project you worked on within the last year. What would you do differently if you did it again?
  • Can you tell me about a recent time when you received negative feedback and how you handled it?
  • Which tasks do your team members typically ask you to help them with?
Photo of a manager and their report during a career development talk.

Ask thoughtful questions that avoid criticizing your employees to facilitate a productive conversation

Development talks also provide a space to align your and your team’s expectations and hopes for their career path. Tim Toterhi suggests team leads ask: 

  • What does ‘career development’ look like to you?
“People rarely share the same definition of development. Until you know what the person is really after, you can’t help them blaze a path toward that goal.”

— Tim Toterhi, Performance Coach at Plotline Leadership

It’s crucial to ask employees this question early in their career development. Many people equate professional success with promotions, but some members of your team may prefer to make a lateral move instead.

You can use your report’s answer as a springboard to ask questions about their short- and long-term goals. Their answers will show you where their interests lie and indicate which departments and managers can aid you with their professional growth.

  • What role(s) do you see yourself playing in the company within the next five years?
  • What new skills would you like to learn or work on in the upcoming quarter?
  • Are there any areas of the company you’d like to learn more about?
  • Is there anyone in the company you’d be interested in learning more from?

For example, if a salesperson says they’d like to learn more from the head of quality control, they may consider moving to that department. The person they mention may be an ideal candidate for mentorship, too.

Once you have a clearer idea of your employee’s desired career path, identify what they need to do to achieve their professional goals. If your organization already has a development program, now’s the time to start or amend your employee’s plan. It’s also a great opportunity to listen to your report’s concerns and learn more about potential barriers to their career growth. 

  • What are the biggest obstacles that are preventing you from reaching your potential?
  • What additional materials and equipment would help you excel at your work?
  • Are there any areas of your work where you’d like more feedback?

Due to time and budgetary constraints, you might not be able to meet all employee expectations, like promotions, training, materials, and equipment. But these conversations can help you support your team in realizing their potential and planning a future with your company.

🔮 Help employees envision their future with your organization

Turn your team’s aspirations into concrete plans with Leapsome’s Development Framework and Learning Paths.

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Professional development questions to ask yourself

Between one-on-one meetings, take the time to reflect on each employee’s progress, assess your recent conversations, and think about what you could do to better support your people. This section includes some questions you can ask yourself to ensure you’re supporting your team’s development to the best of your ability.

Consider your team members’ motivation and commitment to their position, as your development planning won’t be as effective if you can’t engage your staff in the process.

“Not all employees respond to the same styles and techniques, so it’s important to consider each individual.”

— Laura Mills, Head of Early Career Insights at Forage

So, Laura Mills recommends asking yourself:

  • Are my employees engaged in their one-on-ones? If not, why? 

Employee feedback and engagement surveys may help you discover the underlying causes of disengaged staff. Although these surveys are anonymous, you may notice a pattern in the responses that indicate the problem. For instance, if half your team observes that you don’t offer enough feedback, you know that’s something you need to address. You can also ask yourself further questions to evaluate whether you’re meeting your people’s needs.

  • What is the most effective way of communicating with each employee?
  • How can I recognize and reward progress?
  • What’s the best way to deliver feedback to each of my team members?
  • How often should I check in with each employee?

Development talks are also a chance to strengthen the alignment between your team and your organization. Each employee should walk away from your meetings clearly understanding how their career path fits into the company’s long-term objectives. Perhaps the new responsibilities they want to adopt would fulfill one of your internal gaps. So ask yourself: 

  • Does each employee understand how their work contributes to company goals?
  • Am I making the reasons behind company decisions clear to each employee?
  • Am I effectively communicating our company values and mission?

Remember to ask yourself some hard questions, too. Some of your actions may be well-intentioned but feed into limiting beliefs that hold employees back. 

For instance, many leaders assume that professionals over 40 need more assistance with technology. This harmful stereotype might deter your older employees from expressing a desire to learn new technical skills or trigger accusations of favoritism toward younger employees. As a member of an employee-first organization, constantly question your thoughts and actions to ensure you’re as impartial as possible.

  • How can I avoid unconscious bias?
  • Does my entire team have equitable access to materials and equipment for professional development?

Questions to ask your company about career development

As the conduit between your team and management, it’s vital to hold regular meetings with other leaders. You can learn valuable information about available career opportunities and discover potential collaborations with other departments. Use this opportunity to gain insights into company objectives, so you know what new skills and knowledge may become a priority for your organization. 

Before any meeting with management or other department heads, prepare questions to ensure you get the information you need to take meaningful action.

Photo of a career development talk between an organization's managerial team.

Ongoing communication between management and leadership is essential for a dynamic, effective career development program

Your first questions should focus on what your business needs from its employees, as discovering skills gaps may present career opportunities for your team. Maybe an employee has shown an interest in management and taking on responsibilities like leading more projects as part of their development plan. If so, they’d be a great potential candidate for a managerial role in a new department. You could ask:

  • What skills gaps do we have at our organization?
  • Are there any current promotional opportunities within our organization?
  • What are the promotion criteria for these roles?

As well as aligning your department with company goals, initiatives, and priorities, you can practice internal collaboration, exposing yourself to fresh perspectives and letting you make pertinent, impactful decisions faster.

“It’s really easy for businesses to fall into the trap of working in silos with each department looking out for their own interests. If your teams fail to collaborate effectively, it can cause breakdowns in processes, which leads to inefficiency, delay, frustration, and disengagement. Use senior management meetings to raise these questions and to identify areas of improvement.”

— Natasha Maddock, Co-Founder at Events Made Simple
  • Is anyone aware of employees interested in learning about other areas of the company?
  • Are there any opportunities for professional development collaboration with other departments?

You may also be able to negotiate a ‘professional development trade’ between interrelated departments. For instance, the managers of sales and human resources may discover that they have different on-the-job wisdom and life lessons to offer each other’s teams. The department heads could give career development talks to the other team on topics like communicating with team members and effective time management practices.

In addition, ask for updates about new career planning resources and initiatives regularly. The field of learning and development is fast-changing, and your company may be planning to introduce new technologies or training programs you don’t know about yet. You may get insights from other departments if they’ve discovered helpful practices or free resources you can use, too.

  • What opportunities are there for growth within the organization?
  • What support can we offer employees seeking advice on career development?
  • What new materials and equipment can we offer our employees?

Before you leave the meeting, discuss what your organization is doing to provide equal access to career development opportunities. There may be extra resources available for underrepresented groups or employees with disabilities. Plus, there may be training for managers on how to reduce unconscious bias and keep employees involved in the career development process. 

  • How can we promote equitability?
  • How can our professional development program better promote diversity?
  • How can we adapt career development plans to better support struggling employees?

Develop your people with Leapsome

Questions are key to successful career development planning. They help you uncover what each employee wants to accomplish in their professional life, assist them in setting meaningful career goals, and get feedback about your existing people management practices. Asking the right questions helps guide your career planning process — and Leapsome’s platform offers the data and analytics to help you prepare them.

Leapsome also provides an in-depth but flexible framework for career development. Our all-in-one people enablement solution lets you build pathways your entire organization can follow. You can define what you need for each skill at each level in granular detail. And Leapsome combines development, performance management, feedback, and goal-setting in one place so you can move seamlessly between reviewing your people and planning your next career development meeting.

🖼️ Want a complete picture of each employee’s progress?

Leapsome’s Development Framework integrates with feedback and performance reviews, giving you all the data you need in one place.

👉 Book a demo

Written By

Leapsome Team

Written by the team at Leapsome — the all-in-one people enablement platform for driving employee engagement, performance, and learning.
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