5 Powerful Questions That Make Your Mentors Better

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Mentorship is a powerful tool that can help you achieve your business goals. When supported with the right frameworks, your cohort of mentors can help you take your business to the next level. 

Levelling up your mentors has never been more important. The great resignation has meant that employees are more likely than ever to go looking for a job they want if they aren’t happy. Mentors are a powerful force for reducing attrition.

In this blog post, we will discuss 5 powerful questions that any L&D manager can provide to their teams that will make your mentors better!

Set your mentors up for success

When you set up your mentoring program, it is important to make sure that your mentors are prepared for their role. You can do this by providing them with mentor training or by sending out a detailed mentor guide.

While you can always assume a base level of competence with your mentors, any such supporting materials should always seek to include a framework of questions you’d like your mentors to work through with your employees. You can’t assume mentors are mind readers and automatically know all the themes you wish to install throughout the workforce. You need to arm your mentors with the best tools you can.

Mentor tools

Mentors will vary their approach often depending on the department, type of work, level, priorities and mentor experience. Therefore the tools you provide them need to be useful across a variety of conversations and mentors facing different situations.

The most useful set of tools are coaching questions that a mentor can use in almost every situation they may face to coach their mentee through making progress with their goals.

One thing to note is the order – working through the questions in the order below does work nicely for running mentoring sessions. However, it’s not essential for a mentor to follow that order, mentors can use them in any way they think works best. Now let’s dig into them!

Question 1) What’s your biggest challenge right now?

Everyone always faces a challenge or multiple challenges. By starting with this question, you give the mentee an opportunity to open up about what they’re struggling with in a safe space. It also allows the mentor to quickly identify where they can provide the most value.

Sometimes this is an easy question for people to answer if they’re facing something that is consuming a lot of their time and energy. Other times, it may take a bit more thought. In those cases, the mentor can ask follow-up questions to help the mentee identify their challenge, such as:

  • What’s been on your mind lately?
  • What’s been taking up most of your time?
  • What goals have you been struggling to achieve?

Facing challenges upfront also means the rest of a mentoring session can be more positive. The mentor can also choose to spend as much time as necessary on helping the mentee if they both think that is wise.

Question 2) What goals are you working towards right now?

This question allows the mentee to share any goals they have, both work and personal. It also allows the mentor to understand what is important to the mentee and what they should be focusing on.

If the mentee is struggling to answer this question, the mentor can ask follow-up questions such as:

  • What would you like to achieve in the next month/quarter/year?
  • What are some things you would like to change or improve?
  • What would success look like to you in this area?

This question also allows the mentor to ensure that the mentee is working on goals that are achievable and realistic. By understanding the mentee’s goals, the mentor can help them create a plan to achieve those goals.

Question 3) What can you stop doing?

This is a great question for mentors to begin sessions with because it often takes people by surprise. Most people don’t take time to reflect on what behaviours, routines and actions they should cut out. This question allows the mentee to focus on streamlining their work and removing any unnecessary actions they may be taking.

We all have behaviours, routines and actions that we take that don’t lead to the results we want. This question allows your mentee to identify these areas of their work so that they can make changes to improve their productivity.

It also gives people permission to avoid being yes-people. In most lines of work you want employees to be adaptable and analytical of why things are done a certain way. Empowering employees to seek out improvements begins with identifying what’s not working.

Question 4) What can you start doing now?

This question is great for a few reasons. It allows mentees to identify small wins they can take now to improve their productivity or workflow. These small wins can be implemented quickly and lead to a feeling of accomplishment, which in turn encourages the mentee to keep moving forward.

Thinking about starting something new also prompts creative thinking. The question assumes something is absent, so in order to answer the person has to think creatively. This can lead to some amazing insights and new ways of approaching work.

It also instils a sense of urgency in the mentee to get started on their goals. Many people procrastinate because they feel like they need to have everything figured out before they can start taking action. This question helps the mentee to see that they can take small steps now and figure things out as they go.

Question 5) What’s working well?

This question is important for a few reasons. Firstly, it allows the mentee to identify areas of their work that are going well and helps them to understand what they’re doing right. This can be valuable feedback for the mentee, as it can help them to understand their strengths and how they can apply them to other areas of their work.

Secondly, it allows the mentor to understand what might be working well for the mentee so that they can share this information with other mentees. This can help to create a positive feedback loop where mentors are constantly sharing useful information with each other.

Thirdly, it helps to build a positive relationship between the mentor and mentee. This question allows the mentor to show an interest in what’s going well for the mentee, which can help to build trust and rapport. Having someone in your corner celebrating the wins is a massive boost in confidence.


Naomi Rothwell-Boyd is the founder of Tribe And Seek and an EMCC and CIPD accredited career and performance coach. She has coached people from a variety of backgrounds and industries, from graduates to senior executives, advising them on career change.

Guest Author Bio

Naomi Rothwell-Boyd is the founder of Tribe And Seek and an EMCC and CIPD accredited career and performance coach. She has coached people from a variety of backgrounds and industries, from graduates to senior executives, advising them on career change.

Naomi was also the first in-house learning and development lead at the HR consultancy Lane4 (the leading L&D consultancy in the UK). She worked alongside Olympic athletes to support clients like Kraft Heinz and TUI to develop their senior leaders. She also designed training at the Duke Of Edinburgh’s Award for both young and adult leaders.

No stranger to change, Naomi left a previous career in international development consulting behind and also fully overcame an accident that broke her neck.

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Grace Winstanely
Grace is the Senior Marketing Manager at Mentorloop. She is dedicated to making content that helps make mentoring more accessible to all and helping Program Coordinators deliver the best mentoring experience for their participants. She's also a keen cook, amateur wine connoisseur, sports fanatic, and lover of all things tropical.

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