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Questions to ask

by Antoinette Oglethorpe
Indian Management August 2023

Toolkit to invest in your employees’ growth as well as fostering a positive corporate culture.

In an increasingly competitive corporate landscape, it is more crucial than ever for leaders to empower their teams to navigate their career progression. In my book, I describe a ‘Career Conversation Toolkit’, which provides a set of tools that managers can use to plan and structure career conversations with their employees. Drawing on principles of positive psychology, solution focus, and neuroscience, the Career Conversation Toolkit gives managers, mentors, and coaches a set of thoughtfully conceived questions to:

  • Provoke reflection, insight, ideas, and action.
  • Keep the focus on the employee.
  • Encourage them to take ownership of their career progress.

You can use one tool or a few tools in whatever sequence or order makes sense for the individual and their situation.

The tools are simple and straightforward, but very effective. They help the employee see the situation differently by acknowledging progress so far, identifying what is already working, detailing the preferred outcome, highlighting existing resources, and building employee self-efficacy. That, in turn, helps the employee to develop new behaviours. The tools help them recognise possibilities and turn challenges into platforms for opportunities. They encourage them to generate multiple options and identify small, achievable actions. They help them find ways to build on their existing knowledge of how to progress.

Let us explore the 10 tools:

  1. Career Platform. The ‘Career Platform’ tool serves as a starting point, helping employees identify areas in their career they wish to change and motivating them to take action. Through thoughtful questioning, employees can clarify what they want to change in their career and ignite the drive to take action.
    Typical Career Platform questions are:
  • What is going well in your current role?
  • What would you not want to change?
  • What would you like to be different?

2. Your Journey So Far. Reflection is a powerful tool for growth. The ‘Your Journey So Far’ tool encourages employees to reflect on their strengths, values, and preferred working style. By understanding what they are good at and what truly matters to them, employees can make informed decisions about their career path. Typical questions to help employees look back over their career are:

  • What are you most proud of?
  • What is it about that achievement that you found satisfying?
  • When was your most enjoyable time at work?

3. Career Kitbag. The ‘Career Kitbag’ tool enables employees to identify and leverage their existing resources for career progression. It prompts them to consider their technical skills, soft skills, and career development skills, helping them recognise the assets they already have.

Questions that help them identify their resources are:

  • What useful experiences have helped you get where you are today?
  • What valuable skills have you developed?
  • What positive qualities will help you make progress?

4. Future Success. Articulating a clear vision of success is crucial for career progression. The ‘Future Success’ tool guides employees to describe what their ideal future looks like, thereby encouraging them to envision their goals with clarity and purpose.

One way you can help employees think about their future is to ask them to imagine that a miracle happens. For example: Suppose you could wave a magic wand and develop your career in exactly the way you would like…

  • What would you be doing day to day?
  • Where would you be working?
  • What kind of people would you be working with/for?

5. Career Routes. The ‘Career Routes’ tool assists employees in exploring the various options available to them within their current role or in new positions. By understanding the potential pathways, employees can make informed decisions about their career options. Questions to explore the different options and possibilities include:

  • How might you make your current role more satisfying and enjoyable?
  • How might you broaden your role?
  • How might you gain specific skills and experience through special projects, responsibilities or assignments?

6. Career Kitbag Additions. Building on the ‘Career Kitbag’ tool, career kitbag additions helps employees analyse the skills, experiences, information, and relationships they need to develop to progress toward their envisioned success. It encourages them to identify areas for growth and the resources required to achieve their goals.

Questions you can use include:

  • What knowledge do you need to gain?
  • What skills do you need to develop?
  • What experience do you need to get?
  1. Career Checkpoint. Connecting employees’ aspirations with their current reality, the ‘Career Checkpoint’ tool helps individuals assess how well their current situation aligns with their goals. It enables employees to evaluate their progress and determine if adjustments or new strategies are necessary.

    One way to approach this discussion is to ask the following: on a scale of one to 10, where 10 is your picture of future success:
  • Where are you today?
  • What makes your score that high? What’s going well?
  • What elements of your future success are already in place
  1. Short-Term Milestones. Setting achievable goals is an effective way to maintain momentum and focus. The ‘Short-Term Milestones’ tool encourages employees to define tangible, short-term objectives that are within reach. These milestones provide a sense of accomplishment and motivate further progress.

    Typical questions include:
  • Where on the journey do you want to be in twelve months’ time?
  • How would you know you are there? What will you see, hear and feel?
  • What would be different for you and for others?

9. Setting Off. The ‘Setting Off’ tool is all about taking action. It prompts employees to commit to feasible actions that will move them closer to their goals, no matter how small those steps may be. By committing to these actions, employees establish a pathway for progress. Some questions you can ask are:

  • What steps will you take in the next three months to progress towards your short-term milestones?
  • What are the first small steps towards that?
  • What support do you need?‘

10. Progress Review. The final tool in the toolkit, ‘Progress Review’, helps employees reflect on their experiences, learning from both successes and challenges. By evaluating their progress, employees can refine their strategies and continue to grow throughout their career journey.
Questions to ask include:

  • What progress have you made?
  • What helped you make progress?
  • What have you learned?

Remember, for these conversations to be effective, they should feel natural and unscripted. While the Career Conversation Toolkit provides a structured framework, it should be adapted to suit individual preferences and circumstances. In essence, these tools empower employees to take control of their career development. They instil a sense of agency, highlighting that it’s their journey to undertake. It also enables managers to understand, empathise, and effectively mentor their employees towards a fulfilling career.

By using these tools, you are not only investing in your employees’ growth, but also fostering a positive corporate culture. And as we know, that is the key to an organisation’s success. I invite you to embrace these tools to build a workforce that is motivated, engaged, and future-ready.

Antoinette Oglethorpe Antoinette Oglethorpe is founder, Antoinette Oglethorpe Ltd. Antoinette is author, Confident Career Conversations: Empower Your Employees for Career Growth and Retention.

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