Mentoring Session Guidelines For People Leaders

By People Leaders | People Leaders Podcast

Mentoring Session Guidelines For People Leaders PL

These days a lot of people, particularly high performers and senior leaders, enjoy the benefits that coaching and mentoring provide. This podcast and post looks at a resource we offer our clients that delivers a framework to help mentors and coaches direct session discussions. Though you don’t have to follow it to the word, just having these questions in your back pocket, and following the structure loosely, gives you a pathway and will really help you make the most of your time together. Let’s dive in.

#1: What’s happened since our last session?

To encourage reflection, ask about the breakthroughs or insights your mentee has had, including feedback they’ve received from others. This could be about their style and characteristics, or a project they've been working on. Note that for some people, the idea of ‘breakthroughs and insights’ can be a bit woo-woo. In these cases, change your language and ask instead, ‘Have you learned anything about your management style?’ Or, ’Is there anything you would've done differently based on what you just told me?’ Remind your mentee that insights can be based on data or intelligence and don’t have to be about feelings.

Try asking, ‘Are there any new choices or decisions that you’ve made that you want to tell me about?’ Here, you invite them to articulate their decision-making process, which allows them to reflect and get a deeper sense of awareness around how they think, feel, and behave.

#2: What are you working on?

This is a very present focused question. In coaching and mentoring, we usually spend most of our time in the present getting the facts and then moving into the forward. Answers to this question might include progress reports on goals, projects, activities – really action-oriented stuff.

Remember that people have mentors for different reasons, perhaps for help developing relationships or progressing their career. Some people are new to a role and just need that extra bit of support. So, if your mentoring sessions are set up around career development, this question might be targeted directly, i.e. ‘What are you working on in relation to your career since last time we caught up?’ Alternatively, you can keep it very broad and general asking simply, ‘What's going on in your work right now?

The other question to ask here is, ‘What have you done that you're proud of?’ Now, with this one it’s important to recognise that for some people, it’s a really challenging question because we don't like to blow our own trumpet. However, it encourages the person to reflect on their strengths and capabilities and this is so, so important. If this is the case, swap out the word ‘proud’ for ‘satisfied’ to make the question less confronting, i.e. ‘What have you been really satisfied with having done in the last month or the last six weeks?’ And don’t forget to ask about obstacles which could causing them stress at the moment too.

#3: How can I help?

If you've noticed there are obstacles or issues in the questions you've just covered, your mentee might need some help. Of course, if everything's going swimmingly, you can still ask the question or ask ‘How could we progress this? How could this be even smoother for you, or even more satisfying? Is there anything you’d like advice on?’ There's always something you can offer. Then you can start to work on the next part, ‘So what's the plan of action?’ asking if there are any tweaks that can be made to the plan of action you talked about last time.

#4: What’s next?

Moving on to talk about what comes next, you can ask questions like, ‘Based on what we've just covered, what are you going to do and is there something I could do for you? Can I introduce you to someone? Give you some information?’ Without creating too much work for yourself, you always want to help them move forward. For moving into action, we always suggest you look at the next most logical step and ask what the path of least resistance is. When you can define that, you'll never be stuck.


In a mentoring relationship, you really want to grab the opportunity to deep dive into asking people, ‘What’s your head telling you? What’s your heart telling you? What’s your gut telling you?’ And a little bit of structure will really make your mentoring sessions more worthwhile and satisfying. So we hope you find the template beneficial and would love to hear from you if you have any thoughts or feedback. Let us know how you go.

Mentoring Session Guidelines For People Leaders

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