The Surprising Truths Behind Good Mentoring
In September 2024, I gave a talk at YOW! Tech Leaders Summit Melbourne entitled The Surprising Truths Behind Good Mentoring. It built upon and extended on a previous article I wrote called How Not To Suck At Mentoring, and incorporated a bunch of new learnings as well.
Rather than rewrite the talk as a post, I thought I’d share the script for the talk, along with the slides. If you’ve seen me give the talk you might notice the map and the terrain diverge a bit - I can never seem to follow a script when presenting!
The Surprising Truths Behind Good Mentoring
This talk is formed from my own experience and journey in being a mentor, and in being a mentee.
At the start I wasn’t very good at it. I had a lot of assumptions as to what I needed to do, what was important.
As Jake from Adventure Time says: Suckin at something is the first step toward being kinda good at something. So I sucked.
And over time, through trial and error, many of my assumptions were invalidated, and I learned what good actually looked like.
Sometimes this was thanks to my mentee showing me what great looked like on their side of the relationship.
Sometimes this was through me growing as a mentor and learning what I needed to do to be better.
Some of you are likely on the same journey I have been on, and am still on. Hopefully some of these truths help you accelerate your growth as a mentor, and help you shortcut past learning some of these things the hard way.
Each slide will present a truth I have learned over time. Each truth, once understood, helped me be a better and more effective mentor, and mentee.
1. The Mentee drives
Mentoring is a two player game, and most of the time the mentee should be the driver.
Sometimes this won’t come naturally though, particularly for mentees who are new to this type of relationship.
They just might not know what to expect. What are their responsibilities here?
They probably have some deference to you and don’t want to come in guns blazing with questions and problems.
I encountered this a LOT when I started mentoring other engineers.
What it can look like is your mentee stating their goal to you, to build a certain skill or gain certain knowledge, and then putting you on the spot for how they might achieve it.
Where should they start? Do you have any good learning resources? What do I look like, a librarian?! How might they best achieve their goal? If the conversation starts at a blank canvas, your mentee isn’t driving.
When you see this happening, your job is to put them in the drivers seat.
You can do this by seeking first to understand: really orient yourself in your mentees world.
Get into the nitty gritty. Know their journey. Know where they are. Know why their goals are their goals. Be genuinely interested.
You need to feel well-aligned with them, like you can see their world through your eyes.
Once you feel well aligned, you’ll be well placed to start asking open ended questions that prompt them to reflect on what the crux of their problem is.
What are they working on at the moment? What does success look like for this thing? What are the current biggest risks? What is your mentee most worried about? Do they feel like they are set up for success?
You should be hearing things like:
“Oh Andrew I’m in the sixth week of the project we’ve been talking about, we’ve just finished building the walking skeleton, and I’m really struggling to convince our budget owner why we need to pay down technical debt before we continue to build”.
This is instead of something like:
“I really want to get better at stakeholder management, what learning resources could I use to get better?”.
Your conversations should feel specific, and concrete. If the mentee is not driving, and conversations are vague and oblique, you won’t be able to provide your mentee the value you otherwise could be able to.
Make sure they are driving.
2. Mentors don’t have to have all of the answers
With your mentee driving, you’re going to find they bring you all sorts of interesting problems. Often you’ll find you haven’t solved a particular problem, in a particular context, with a particular set of constraints before. You won’t have a perfect answer for them.
If you find yourself in this situation, resist the temptation to invent an answer on the spot. That never ends well. Instead, treat it as an opportunity.
It can actually be two opportunities.
Firstly, this is an excellent opportunity for you to work with your mentee. You have an opportunity to walk the walk with them, and show them first hand how you tackle problems you don’t have answers for.
How do you discover what is important? How do you learn about the things you are currently unsure of? How do you make progress on solving the problem? What happens when you encounter roadblocks?
Creating clarity in unclear spaces, and turning intractable, ill-defined problems into well-understood, solvable problems tend to be key growth areas for most aspiring leaders, and your mentee will benefit immensely from seeing how you tackle these sort of situations.
Mentoring doesn’t always just have to be conversations. This sort of “in the trenches” experience almost always has a stronger impact than just having conversations.
Secondly, this is an opportunity to direct them to OTHER PEOPLE to help solve their problem.
You can bring the strength of your network to your mentee. This might be your network within your organization, or it might be your broader network, where other leaders you know might be well suited to help your mentee solve their challenge.
One of the most valuable things your mentee can learn is to understand how to work with others to solve challenging problems. We all have strengths and weaknesses, and knowing when to seek the help of others when tackling big problems is an invaluable skill.
3. Be wary of vested interests
For people to grow, they need to confront their challenges head-on. They need to first-hand get the cuts on their arms that come from wrestling the beasts in front of them.
They need to fail, and succeed, and achieve the outcomes that lay in the grey areas in between these extremes.
If you have a vested interest in your mentee achieving a particular outcome, it might be tempting to coach them more explicitly, to give them very detailed guidance, to ensure they achieve the outcome you want.
This is going to limit their potential growth.
We learn best from our own exploration and ideation. You should be helping to broaden your mentees horizons and validate their thinking, but you shouldn’t be telling them what to do.
Your mentee will experience more growth by taking your input, and using it to formulate their own schemes and plans, to test their own ideas, so that they get deep understanding as to what works and why.
4. Mentoring, coaching, sponsorship: you do all three
You’ve probably heard these terms used, sometimes interchangeably.
I’ll provide some definitions to help frame this:
Mentoring is participating in a long-term relationship with someone else to help elevate the successes that person will achieve over that time.
Coaching is short-term, usually with a specific challenge or goal in mind. The context will be more limited, and your input more direct.
Sponsorship is showing up for people where they are not - making sure they are represented positively in the spaces where you have influence, and have access to opportunities they otherwise wouldn’t.
Any time you sign up to mentor someone, it is very likely you’ll do all three of these things. You’ll establish a long term relationship in which you’ll explore all kinds of challenges with your mentee. You’ll coach them on specific challenges they face, giving them detailed knowledge that will help them overcome them. You’ll sponsor them into opportunities, and celebrate their success.
This isn’t a problem - in fact its to be expected. The takeaway here is that it isn’t worth worrying about these definitions much, as you’ll naturally act under all of them if you are doing your job well.
5. Mentors need to grow too
I had found myself in a new mentoring relationship recently, and the person I was mentoring wanted to move toward a principal engineering role.
Now I’ve done that role for a while. I felt I was well placed to help them solve the types of challenges that came along with it.
But what I wasn’t confident about was how to provide them access to the opportunities they would need to grow. I’d had some feedback previously that we need to be conscious about who we provide opportunities to, and to ensure that we do that equitably to ensure everyone gets equal access to the opportunities available.
So there was a tension between me wanting to ensure my mentee got the opportunities they would need to grow and thrive, and our companies principles of ensuring equal access to opportunities, that I felt I just couldn’t resolve myself.
To solve this problem in my case, I went to one of my mentors within Octopus - Trish, to talk about the challenge.
The answer was in sponsorship. In this case to be a good mentor, I also needed to be a good sponsor. I didn’t really know what great sponsorship looked like, particularly at Octopus. I wanted to make sure I knew how to sponsor my mentee well while still upholding our values when it came to equal access to opportunities.
Working with Trish allowed me to gain clarity on how I could show up as a great sponsor for my mentee, whilst still respecting our companies values.
6. Mentoring is not a binding contract
This last one can be a tough one.
Sometimes, you and your mentee might just not be a natural fit. Perhaps you’ve struggled to find common ground to build a relationship around. Maybe they are looking for help in areas that just aren’t your strongest suit.
It might just feel like you’re not in a win / win situation for both your mentee, and yourself.
As a mentor, you are in the position of power, and are best placed to see this dynamic, and call it out. Be self aware. Do you really feel your mentee is getting value out of your catch-ups? Are they growing? Do you feel like you are getting along well? Is it a positive and energizing experience?
If not, you should be the person to call this out, and to help your mentee find someone who might be a better mutual fit for them, and their goals.
If you are running a mentoring program - Planning off-ramps and on-ramps in advance makes this process a whole lot easier. An example might be identifying other people in your network that might be better placed to mentor your current mentee.
If you are participating in an informal mentoring relationship, make sure you address this topic in your first catch up. By destigmatising it, you’ll be able to ensure you and your mentee are set up to be transparent with each other, and if the situation arises, for you to help your mentee find a mentor who is more strongly aligned with their ambitions.
7. My experiences as a mentee
I often know if I’ve found a great mentor when they tell me things that:
- Surprise me, and I know that I would not have come up with on my own
- That I strongly agree with
Usually these will be based on me bringing a problem to them that I’m not sure on. Or maybe I think I’m sure of, so I’ll give them my current strong opinion.
Often I’ll be facing problems, and I’ll talk to my mentors about it, and I’ll always come away feeling impressed by the new perspective they have bestowed upon me.
I know that I would not have come up with it on my own. I also know it strongly resonates with me.
This is the gold. This is where accelerated growth comes from. I would not achieve the same growth without receiving that input from my mentor.
Turning this around - this is what I want to do with my mentees. I want to be able to give them perspectives that they otherwise would not have come up with on their own - this is often perspectives born from my experiences, and I want to do it in a way that they resonate with, that helps them tackle the problems they are facing in new and more effective ways.