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How to Lead a Mentoring Conversation

This article is an extract from the forthcoming book by Ann Rolfe, The Mentor’s Toolkit for Career Conversations. Look for it on Amazon in July 2021

Increasingly, mentoring is integral to a leader’s role and many organisations have mentoring programs. Yet most mentoring happens in informal relationships, as a series of ad hoc meetings or casual conversations. 

Few people are properly trained to lead mentoring conversations, but you can learn to lead a mentoring conversation with the simple and easy to remember framework that I will spell out here. You will have the flexibility to adapt easily to any mentoring situation and you’ll have confidence because you’ll know what to say or ask next.

You don’t have to have the title mentor or manager to lead a mentoring conversation, but you do need understand how to help people create insight and empower them to act on it.

In a work setting you might use mentoring conversations with individuals for career development, performance feedback or building capability. You can use them with teams talking about goals and outcomes, to plan or debrief projects, or to manage or adapt to change. You can also use this type of conversation in spontaneous mentoring moments that present themselves.

You can also lead mentoring conversations informally with friends, family, colleagues or employees when a mentoring moment presents itself. You can watch the lightbulb go on as they get that flash of insight and you can observe or assist as they decide what to do with it. 

You lead a mentoring conversation keeping in mind four questions as a framework for the conversation. Before we get on to the framework for the mentoring conversation and what these questions are it’s important that we understand what a mentoring conversation is.

There is no single, correct definition of mentoring. I attended an international mentoring conference where an academic stated that her research had found over 600 different definitions of mentoring. Likewise, a mentoring conversation could be defined many ways.

Here is how I like to describe it:

A mentoring conversation is one where: 
people are safe to explore thoughts and feelings. 
They use critical, creative and above all reflective thinking to gain insight and generate possible options.
They make informed choices as they decide on goals and actions. 
They are assisted, as needed, to plan the way forward, and then they are

Mentoring relationships and conversations are not static, they are dynamic. They move and change because they are flexible and adapt to the person and the situation. There’s no “one size fits all” or rigid formula.

Traditionally, we’ve thought about mentors as “wise guides” Who share their knowledge and experience. While this is often useful, contemporary mentoring begins with a mentor asking questions and listening to a mentee. Mentoring is about offering support – encouraging and validating them, but it’s also about sometimes challenging them by offering a different perspective. This is not an either/or decision; rather, think of it as a spectrum. You will elicit AND impart, support AND challenge and move along the spectrum as needed.

Figure: The Mentoring Dynamic

I developed the framework for a mentoring conversation based on adult learning, action learning and classic principles of strategic planning. I call it a framework because, it’s like when you build a house, you start with a secure foundation (in mentoring that is the safe space of trust and rapport, which I’ve written about elsewhere). Then you put in place a framework for the walls and roof. Once the foundations and framework are in place you can go ahead and build the house, decorate the interior and create the home to suit the people. 

As you’ll see in the diagram below, I’ve laid the framework for a mentoring conversation out like an analog clockface, where we begin at the twelve o’clock position. We’ll generally move in a clockwise fashion, first getting the person to reflect on their current reality, the situation, issue or topic they want to discuss. Then we discuss the future and help them make informed decisions about it. We may then assist them to set goals and plan actions. Finally, we’ll support them as they take action.

Although I’ve suggested a clockwise cycle through this process, and I’ll continue that as I explain each of the four elements in more detail, keep in mind that in a real mentoring conversation you’ll likely skip back and forth, many times. And, although I talk about the mentoring conversation, it is more likely to be a series of conversations over a period of time. You can’t rush it and you need to remain flexible! This is about enabling people to make decisions and set goals that are right for them. The framework provides a supporting structure for you and for them. It is built on four questions. These are not the questions you ask the mentee, but the questions you hold in your mind to frame the questions appropriate to the person and the situation. So, I call them the “Umbrella Questions”

Where Are You Now?

In the noon to three o’clock position we want the mentee to explore their thoughts and feelings about the topic of the conversation. We want them to reflect, we want to draw them out, if we are successful, they will literally be thinking out loud. We will use open-ended questions to get them started, but essentially what you’re trying to find out is “Where are you now?” You want the mentee to reflect on what’s going on, clearly understand the current reality, problem, situation or event.

In the early stage of the mentoring conversation, we want to explore their thoughts and feelings, we’re going to use open-ended questions, we’ll start very broadly e.g. “What’s on your mind today? “What would you like to talk about? and then home in on the issue. It’s really useful to train your mentees to send an agenda prior to the meeting. This will help them focus and help you prepare.

It is quite possible that when they reflect on the situation, they’ll realise that there are deeper issues that need to be considered. The question on top of their mind is not the actual issue. Freud said: “The mind is like an iceberg, it floats with one-seventh of its bulk above water.” In other words, there’s a lot going on below the surface of our conscious mind. We are NOT trying to psychoanalyse our mentee, but we do want to increase their awareness of their own values, priorities, preferences and motivation.

We want them to talk so we’ll listen and use minimal responses like “mm hm”, “uh hu”, “go on” to encourage them to keep going. We might need to gently probe with phrases like “Can you say a little more about …” “Would you expand on that …” “Perhaps you’d like to say a little more about …” And, at times we’ll use reflective listening to help them clarify their thoughts, to check our understanding or summarise: “It sounds like you …” “So, what you’re saying is …” “What I’m hearing is …”

In this type of reflective conversation, the mentee may discover their own insights. You may see the lightbulb go on as they have that ah ha! moment. Have you ever had that? A sudden blinding flash of the obvious, or a slower dawning realization? Maybe an actual epiphany! Sometimes that’s all you need. It galvanizes you into action. 

It could be that your job as mentor is done – simply by listening!

Where Do You Want to Be?

You do want ensure that your mentee makes informed decisions about what they do. After all, Archimedes is said to have yelled “Eureka” and run naked out into the street after a flash of insight gave him the answer to a problem while he was in the bath! Not a good idea!

Also, some mentees may not know what they really want or what they’re capable of. So, our job is to help them generate options and possibilities. You can probably guess, after establishing “where they are now” we want to move to where do they want to be?”

You want to compare and contrast the current situation with the ideal one. You will continue using open questions, minimal responses, perhaps gentle probing and reflective listening. But we do have an additional objective now, we want them to make informed decisions before they take action.

If we go back to the Mentoring Dynamic I outlined earlier, this could be a time where you share some of your knowledge and experience. Or it could be a time when you suggest they go and do some research for themselves, or perhaps use a self-assessment instrument like Strengths Finder to open up more possibilities.

How Might You Get There?

When they are well informed and ready, the conversation proceeds so that they can decide on their goals and plan actions. So, the umbrella question, having asked: where are you now, and where do you want to be is how might you get there? 

If you can remember these three questions, you’ll never have to worry about what to say or do next. It will always be a variation of one of these questions. You want most of the planning to come from the mentee themselves. So as much as possible, keep asking them questions. Limit but don’t withhold your own input. Don’t be afraid to send them away with research tasks or let them go away to think about what you’ve spoken about and come back to you with ideas to discuss.

How Are You Doing Now?

It will be sometime later, when they have had a chance to do something based on your conversation, that they’ll come back so you can talk about follow-through and adjustment. You’ll lead a review of the action and outcomes and the question that frames that conversation is: how are you doing now?

Figure: Framework for a Mentoring Conversation

Practical Applications

I’m sure you can immediately se the application of the mentoring conversation framework to a career development conversation. The early meetings would help the mentee identify values, priorities, preferences and strengths. My next book, The Mentors Toolkit for Career Conversations will include loads of activities you could get mentees to do to discover these, before setting goals and creating an action plan.

Similarly, a manager giving performance feedback would use the same questions, along with sharing their observations of the gap between the employees’ current performance and the ideal or required performance, discover what’s in their way, help them set goals and plan for improvement and support change efforts. It would be very similar for building capabilities.

Project managers would call it over-simplification, and I agree, but essentially project planning uses these same questions. A project manager, renowned for bringing huge road and tunnel-building projects in on time and on budget told me his secret was the team project debrief. They always had a BBQ and a few beers to celebrate completion of a project. But a few days later the whole team gathered in a meeting room with white boards and lots of butcher’s paper for the project debrief. He explained to me that it had to be a non-threatening review – he had to have people’s trust as they discussed what went well, so they could replicate that in future and what did not go well so that they could avoid it. So, in this meeting there was no praise or blame, simply a critical review of the facts.

The key to a mentoring conversation is to remember it is a dialogue, a two-way process. It involves creating a safe space of trust and rapport, asking good questions, listening well and not jumping in to quickly with advice or solutions.

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About Ann Rolfe

Ann Rolfe is internationally recognised as Australia's leading specialist in mentoring, and is available for speaking, training and consulting. Here Ann shares her knowledge and allows you to ask your most pressing questions about mentoring.

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