Practical Career Development Questions to Ask Employees

Are you looking for career development questions to ask employees and develop your best people?  If so, you’re not alone.  The most frequently asked questions in our Confident Career Conversations Workshops relate to tools.  Questions like:

“What effective tools could I use in my career conversations?”

“Are there any particular tools you use that lead to great insights and actions?”

“What tools can I use to enable employees to alter their perspective on development?

That is why I developed the Career Conversation Toolkit.

What is the Career Conversation Toolkit?

The Career Conversation Toolkit

Drawing on principles of positive psychology, solutions focus and neuroscience, the toolkit gives managers, mentors and coaches a set of career conversation questions to:

  • Provoke reflection, insight, ideas and action
  • Keep the focus on the employee
  • Encourage them to take ownership

Career Development Questions to Ask Employees – 10 Tools

The career conversation questions are packaged into ten different tools.

  1. Career Platform – helps an employee determine what they want to change in their career and motivates them to take action.
  2. Your Journey So Far – allows employees to reflect on what they’re good at, what’s most important to them and how they like to work.
  3. Future Success – helps employees articulate their ambitions by describing what success will look like.  Find out more in the blog post, Future Success: 5 Powerful Questions to Think Creatively About Careers.
  4. Career Checkpoint – connects employees ambition with reality to identify how their current situation is satisfying their aspirations and the progress they have made.
  5. Career Kitbag – helps employees identify all the resources they have that will help them make progress.  Skills include technical skills, soft skills and career development skills.
  6. Career Routes – helps employees identify the options available to them in their current role and/or in new roles.
  7. Career Kitbag Additions – helps employees analyse the skills, experiences, information and relationships that they need to develop to progress toward their Future Success.
  8. Short-Term Milestones – helps employees focus on an achievable goal in the not too distant future.
  9. Setting Off – encourages employees to commit to do-able actions that will help them make progress, however small.
  10. Progress Review – helps employees learn from the experience.

Each tool provides a practical but flexible framework that can be used as the basis for a conversation that is only 15-20 minutes long.  You can use one tool or a number of tools in whatever sequence or order makes sense for them and their situation.

Why did you develop the Career Conversation Toolkit?

Quality career conversations are based on powerful questions.

The most powerful questions are strengths-based and solution-focused. In other words, they specifically ask about positives. What does the employee like about their current role? What would they like to do more of? What strengths do they feel they bring? What value do they contribute to the organisation?

Such questions provoke reflection, insight, ideas and action. They keep the focus on the employee while helping them see things differently. And they encourage them to take ownership of their own development. They help them recognise possibilities. They encourage them to create many alternatives and achievable action steps to build on their knowledge of how to progress.

Unless you are an experienced and qualified professional coach – and even when you are – it can be hard to always have the right question at your fingertips.  I created the Career Conversation Toolkit so it does the heavy lifting for you.

What is different about it?

When people think of career conversations, they often think about professional career coaching or counselling that involves a programme of in-depth discussions that take one or two hours at a time.  As a qualified career coach, I believe there is a place for that.  But not all career conversations need to take that form.  In fact, the most effective career conversations are often short and informal.  They take place with mentors, managers and HR professionals rather than external coaches.  They help employees develop their career within the organisation rather than by moving company. The Career Conversation Toolkit is designed to facilitate and enable those so that they happen more often and more regularly.

What problems will it solve?

The Career Conversation Toolkit gives you the practical tools, structure and questions to have effective career conversations that will engage, retain and develop your employees without taking up lots of time.

It will allow you to:

  • Have a meaningful career conversation in less than 20 minutes without any complex process or paperwork
  • Help employees feel more positive and satisfied with their current role no matter what their ambitions.
  • Encourage employees to identify development opportunities and take steps that will help them and the organisation.

It provides you with a flexible approach which means employees take ownership of their career development and you don’t have to have all the answers.

It allows you to have conversations that make employees want to stay with your organisation rather than go elsewhere.

It’s practical, simple and easy to use with all employees, no matter where they are in their career and what they want to achieve.

Where can I buy it?

You can find out more about the Career Conversation Toolkit and purchase it online at You may also be interested in our Manager’s Guide to Career Conversations which will help you put the toolkit into practice.


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