Any conversation with an employee will be more authentic if you have a trust relationship – and any conversation you have is an opportunity to strengthen that trust.
Are you already starting from a place of trust? Review the questions below and choose those that you feel will be helpful for your situation.
Are you still building trust? Review Building trust for leaders first.
These questions are listed in a recommended order but can be adjusted to fit your needs. Use those that are relevant and helpful in your unique situation. You could have these conversations once a year, or whenever you want to learn more about a particular employee.
General work review questions
These questions can become part of annual reviews. Wherever possible, share the questions with employees in advance of the meeting to allow them time to be prepared. This way they are less likely to feel interrogated and more likely to feel that their opinions matter to you.
Be prepared to hear any expressed needs or struggles and to ask what might help with that. Also, be sure to comment on both the effort and contributions the employee has made.
- How have you been feeling about work in general?
- Do you feel like you’re learning and growing here?
- If so, how?
- If not, what can I do to improve your experience?
- What skills have you developed over the past year?
- What skills would you like to develop this coming year?
- What are your greatest work-related successes or accomplishments this year?
- What were the greatest challenges you faced at work this year?
- What did you least enjoy working on this year and why?
- What coping strategies work best for you in dealing with workplace stress?
- What did you most enjoy working on this year?
- Who did you most enjoy working with? Why?
- What is your ideal work environment?
- Do you feel connected with your co-workers?
- Can you give me one or more examples of when a co-worker was supportive of you this year?
- Can you give me an example of when you were supportive of a co-worker?
- Can you give me one or more examples of when and how I could have been more supportive this year?
- Do you have any other suggestions that could improve your work experience or environment?
Work-life balance questions
- How have you been feeling about balancing work and home?
- What strategies help you in juggling work-life demands during the past year?
- What else might you need to have a healthy work-life balance?
Career goals questions
- What would you like to achieve in your career over the next few years?
- How can you move towards your career goals? What can I do to help?
- Ask for specific certification, education or experiences that will improve their qualifying for the career they desire. You can also ask them to consider actions that will improve their existing career, such as having better work-life balance or improving time management.
Wrapping up the conversation
Thank the employee for engaging in the conversation and share the specifics of what you heard in terms of:
- Contributions they have made and why you value them
- Challenges they are facing, the strategies and strengths they are using to deal with them
- How you will be supporting their development
- Next steps – any other actions either of you will be taking and when you will meet again
Next steps in supporting career development
If any of these situations apply to the employee, you can recommend the following helpful resources.
Is the employee looking to transition to a leadership position?
- Consider supporting their enrolment in becoming certified as a Mindful Leader to improve and demonstrate their knowledge and capacity.
- Suggest they subscribe to the free Bite-sized leadership strategies email series to learn more about resolving workplace issues.
Are they struggling with their mental health at work?
- Share the information, tools and strategies in Mental health at work.
Are they looking for personal growth opportunities?
- There are many ways to build resilience and social and emotional intelligence. Share the many free resources for Personal growth to help them improve work and personal relationships or develop leadership skills.
Are they considering retirement?
- Financial status is important, but so is proactively planning for the quality of life they desire in retirement. Planning for a mentally healthy retirement is a series of questions that will help them envision the relationships, purpose and well-being they want in retirement.
Additional resources
One-on-one discussion points. This example of a more compact and frequent discussion can be done virtually or in person.