Five killer questions mentors should ask

Stef Scott By Stef Scott, Senior Digital Editor

3 December 2015

Being a mentor is a rewarding experience: just ask any of the 250 mentors who have joined the ICAS career mentoring programme.

One of the great advantages of being a mentor is developing strong professional relationships with mentees.

Being a good mentor is not just about listening to your mentee, but asking them the right questions to prompt their thinking, encourage self-reflection and personal growth. We asked our mentors about the killer questions they ask their mentees to really get them thinking.

Here are five of the best ones.

1. Why are you looking for a mentor?

This is a great early question that mentors should ask their mentees. Not only will it help you understand where your mentee currently is in their career, but more importantly, the answer will give you a direct insight into the challenges they are facing right now.

Perhaps they’ve reached an important cross-roads in their career and need some guidance about which option to follow. Maybe your mentee is keen to make a step up the career ladder and is not sure how best to do it. Asking someone why they need a mentor will help you discover what they are lacking. Then you can use that information to think about practical ways you can help them fill in the gaps.

2. Where do you want to be in five years?

This is another good question to ask at an early stage in the mentoring relationship. You don’t necessarily have to stick with five years, as you could ask them where they want to be this time next year, or in 2 or 3 years’ time. Either way, the point of asking this question is to find out whether your mentee has a concrete plan for their career. It’s OK if they don’t have a plan as ultimately you can help them to create it.

If your mentee is clear in their own mind about where they want to go this provides a firm foundation for the mentoring relationship. You both have something tangible to work towards. Your role as mentor is to help your mentee reach their goals by breaking the journey down into discrete, achievable steps.

3. What are you good at?

This is a simplified version of the tried and tested ‘what are your strengths’ question. As a mentor it’s really important that you understand what your mentee is good at. For example, if someone is naturally good at motivating and inspiring others these qualities can help them lead bigger teams (or perhaps even organisations) in the future. If they have a strong entrepreneurial, innovative streak then this can be channelled into setting up their own business or getting involved in start-up ventures.

One of your key priorities should be to establish what your mentee’s core strengths are. Knowing this in conjunction with understanding their overall ‘plan’ will help you determine how well equipped (or otherwise) they are to reach their goals. If someone says to you they want to be running their own business in five years’ time, or be CFO of a blue chip company, it’s important that as a mentor you can recognise whether this is actually going to be realistic, and how much time, effort and commitment is needed for your mentee to get there.

4. What are you not so good at doing?

No surprises that asking someone about their weaknesses comes next. Don’t let your mentee dodge this question, give you a vague answer or get away with saying they don’t have any weaknesses! This is not a job interview so it’s important for your mentee to be really honest with you and open up about what their areas of weakness are. If someone can genuinely tell you about their weakness, then this shows that they have a good level of self-awareness.

To help dig a little bit deeper, ask them to think about the things that slow them down, that other people find challenging about working with them, or areas they’ve previously had negative feedback about. A good tip for this question is to give your mentee some time to think about it – don’t spring it on them without any warning. Let them know at the end of a mentoring conversation that you want to ask about areas of weakness next time you talk, and ask them to really think about what they will say.

5. How can I help you get to where you want to be?

This is probably the most important question of all. The previous four questions will help you establish where your mentee is right now in their career journey, their overall goals, their strengths as well as areas they need to work on. Now that you have this insight about your mentee, you can start to talk to them about relevant examples from your own experience that they can draw on as they work towards their own goals.

Asking these five questions provides a great starting point for any mentoring relationship. We’ll be following this up next week with five killer questions that mentees should ask their mentors.

Become a mentor with ICAS

Would you like to mentor the next generation of CAs?

  • We are looking for new mentors to join the scheme, so why not sign up and inspire fellow CAs to connect, and develop our profession? It’s simple and easy to register, and you can choose how much time you want to commit.
  • The ICAS Career Mentoring is a global virtual programme, free and accessible for all CAs.
  • For more information about the mentoring programme contact the Career Mentoring team at or go online for more details.


  • Career mentoring

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