What are the five questions every mentor should ask?
These five questions, originally shared in Harvard Business Review by Anthony K. Tjan, form a simple but powerful framework for guiding any mentoring conversation. Asked in order, they help you understand your mentee's aspirations, assess their strengths and gaps, and work out where you can add the most value.
- What is it that you really want to be and do?
- What are you doing really well that is helping you get there?
- What are you not doing well that is preventing you from getting there?
- What will you do differently tomorrow to meet those challenges?
- How can I help / where do you need the most help?
Why do these five questions work?
The questions follow a deliberate sequence. They start broad, with purpose and aspiration, then narrow towards specific actions and support. This structure stops mentoring sessions from jumping straight into problem-solving before the real goal is clear. It also puts the mentee in the driver's seat, which is exactly where they should be.
You can use these questions in a single session, spread them across your first few meetings, or return to them periodically as your mentee's goals evolve. They also work as a self-diagnostic, try answering them about your own career to see where you stand.
Question 1: "What is it that you really want to be and do?"
This question is about aspiration and purpose. It surfaces what's driving your mentee, not just their next career move, but the deeper motivation behind it. Someone might want to move into a leadership role not just for the title, but because they want to build teams that do meaningful work.
The answer here sets the direction for everything that follows. If you don't understand what your mentee is truly working towards, the advice you give may be well-intentioned but misaligned. Listen carefully, and don't rush past this one.
Follow-up prompts: What would you like to achieve in the next 12 months? What would make this mentoring program a success for you?
Question 2: "What are you doing really well that is helping you get there?"
This question spotlights strengths. It helps your mentee recognise what they're already good at and how those capabilities connect to their goal. Are they a strong communicator? A natural problem-solver? Detail-oriented? Identifying core strengths builds confidence and reveals what your mentee can lean on as they work towards their aspiration.
As a mentor, understanding your mentee's strengths also helps you give more targeted advice. You can focus your guidance on areas where they genuinely need development rather than reinforcing what they already do well.
Question 3: "What are you not doing well that is preventing you from getting there?"
This is about honest self-assessment. It asks your mentee to identify the roadblocks, gaps, or habits that are slowing their progress. This can be confronting, so create a safe space for the conversation. Your role as a mentor is to listen without judgement and help them see blind spots they might not recognise on their own.
Common themes that surface here include difficulty with delegation, avoidance of difficult conversations, lack of visibility with senior stakeholders, or spending too much time on comfortable tasks rather than high-impact ones.
Question 4: "What will you do differently tomorrow to meet those challenges?"
Questions two and three together reveal whether someone is spending the right time on the right things. Hard work alone doesn't guarantee progress, if your mentee is always practising their strengths while avoiding their weaknesses, they'll plateau.
This question tests whether your mentee has the willingness and aptitude to change behaviour. It moves the conversation from reflection to action. The answer should be specific and immediate, not "I'll try to be better at networking" but "I'll introduce myself to two people at next week's team event."
Follow-up prompt: What's one small thing you could start doing this week?
Question 5: "How can I help / where do you need the most help?"
By this point, you have a clear picture of your mentee's aspirations, strengths, challenges, and commitment to change. Now match that against your own strengths, experience, relationships, and resources. Where can you add the most value?
This might mean making an introduction, sharing a resource, role-playing a difficult conversation, reviewing their work, or simply being a sounding board. The key is that your support is targeted to what your mentee actually needs, not what you assume they need.
How to use these questions in Mentorloop
These five questions pair naturally with several Mentorloop features:
- Meeting agendas: Structure a session around one or more of these questions using Mentorloop's meeting agenda templates. Share the agenda with your mentee beforehand so they come prepared.
- Notes: Use the Notes feature to capture your mentee's answers and the actions you agree on. Share notes with your mentoring partner so you both have a record to refer back to.
- Goals: Once question 1 surfaces a clear aspiration, help your mentee turn it into a SMART goal in Mentorloop with tasks and due dates. The actions from question 4 become the tasks under that goal.
- Scheduling: Book your next session from within your Loop so there's always a meeting on the calendar. Consistent meetings keep the momentum going between conversations.