Building a mentoring relationship between delivery managers

Royal Greenwich Digital
Royal Greenwich Digital Blog
6 min readAug 10, 2023

Written: 28 July 2023 by Melanie Wong and Scott Drayton, Delivery Managers

Scott mentored Melanie as a delivery manager from August 2022 to February 2023. Scott has over 10 years experience in delivery management at different organisations and product teams. Melanie was new to the role of delivery manager, joining Royal Greenwich with a great set of transferable skills.

In conversation, here are their reflections on their experience of working together.

Illustration of a woman at a desk in front of a computer screen and a colleague in a suit standing next to her
Illustration by vectorjuice on Freepik

What were your first impressions of each other?

Scott: I was really excited and yet very nervous about coaching and mentoring you. I have helped people in this way before, but never worked directly with a Delivery Manager. I thought you were open minded, curious and keen to understand the “why” and the “how”. I got the impression you were nervous, so I tried to come across genuine and caring. I really enjoy watching people grow and become passionate about something and I definitely got the feeling that we could help each other!

Melanie: ‘This is someone I can learn from’. My first impression of you hasn’t actually changed since we’ve got to know each other better! From the very start you’ve been experienced, generous, competent and open. I’ve never had a coach or a mentor-like figure before, and I remember calling up my friend the night before our first proper Teams meeting and telling her my worries. She asked me if I thought you would be someone who would be open to hearing these (yes!) and reminded me even if I didn’t yet have a clear picture of how I wanted us to work together that could be shaped by both of us, and I’m so glad I took her advice.

What do you value most about the relationship?

Melanie: I really appreciate that you’ve never made me feel bad about things I don’t know, or take a while to figure out. Not that people generally do! But our chats feel like such a safe space which I don’t want to take for granted. I know that if I message you about something we talked about 3 months ago, admitting that I’m still not entirely sure about it, that you’ll simply offer a phone call and we’ll talk about it again until I understand it a bit more and you won’t ever ask me why.

Scott: You challenge me to question my own experience and theory! You make me share deeper thought about why something may have occurred or different angles to tackle a problem. I have learned so much about myself through working with you and subsequently how I tackle problems. You do not just nod and agree, ever! You pause, reflect and then are completely open about whether you have understood or not. I love this openness; it is so nice to work with someone who does not accept the text-book theory. The fact that you are so early in this journey has made me reflect on what I really learned when I started my journey!

What has been most challenging about the relationship?

Melanie: Figuring each other out, and learning where our boundaries are. I knew you were extroverted, and I wondered if I came across as too unsure, too quiet at times. I finally realised in one conversation that you were explaining something to me using 4 different examples because you thought I wasn’t understanding it, but I was just nodding and waiting for you to finish your point because I didn’t want to interrupt! Learning how I can make it easier for you to work and communicate with me has been a really unexpected and valued area of learning for me.

Scott: Adapting my style to suit how you communicate and learn. I have had to really think about whether I communicate effectively, and consciously consider my coaching and mentoring style. I sometimes (often) talk more in the hope that it becomes clearer, but I know that it not the case! I have had to learn to convey good information and knowledge with less words. I hope I have improved.

I have had to really try to understand and appreciate the stage of learning you are at and although this has been really interesting to discover, I initially found it really hard. I was regularly questioning my own knowledge and experience! I found out that I had to think more deeply about a scenario in order to explain and offer my experience in a certain area. Then to just shut up and let you digest it.

If you did this again, what would you do differently?

Scott: I would establish (as a pair) how we want to work together. We did this, but let it evolve naturally, which may have worked for some topics, but not all.
I would maybe devise a list of things to discuss, maybe some theory and high-level principles to have deep conversations about. These things fell out of some scenarios we encountered, but often had little structure and I was always worried you were not learning much from me!

Melanie: Not much, to be honest. I think I came into this ready to be open from the start, which matched your vibe and meant that we could honestly and openly work through whatever currently challenge I was worrying over! Perhaps I would try to remember earlier that learning goes both ways. I had to remind myself that I bring different skills and experience from my previous roles which can offer a different perspective to you.

What advice do you have for the other person in future?

Scott: Never stop being curious. Keep asking good questions. Consistent small steps of improvement. Value the view and opinion of the team. Understand why a framework adds value, then dismiss the barriers of the framework. Have deep conversations about value and improving. Learn to face complexity and ambiguity head on. Share your worries with colleagues. Write stuff down that frustrates you. Help your team ask “why?” more often. Allow room to experiment with an idea. Understand that the team are probably working within constraints already, find out what they are. Continue to visualise your thinking.

Melanie: This isn’t advice, exactly, because I don’t like giving unsolicited advice. But I wonder sometimes if you are so patient with accommodating the preferences of your teams that you don’t speak up often about what would make it easier for you. Like, letting people know if there is a preference is to think aloud and how that helps to generate more ideas, or if having information in advance helps if thinking on the spot is difficult.

What expectations did you have going into this?

Melanie: Its hard to say, because I had no previous frame of reference. I was determined to learn as much as I could, and try new things. I was confident in my own ability to learn, but its hard to get a sense of what one doesn’t know, and there’s so much I didn’t know(!). More than that, its felt really strange and sometimes uncomfortable having to learn something new so publicly.

Scott: I was so determined to help. I thoroughly enjoy this part of the role, whether it is Delivery Manager support or team support, I get so much from it. I was excited to work with someone so open and keen to learn. I did not expect to learn so much about myself! I did not expect you to help me reflect, as well as us helping each other to reflect on our work and improve it. I did not expect to get so much joy from watching you develop, challenge thinking and ask amazing questions so early in your journey!

Anything else you’d like to share?
Melanie: I feel like I’ve learnt so much from our time together. Our chats, the things we talk about and the way you explain things has broadened my perspective on how people think and learn. I also genuinely wonder if you’ve changed the way my brain is wired, I catch myself thinking about ideas or topics as questions now!

Scott: I have really enjoyed working with you Melanie. I hope that my odd explanations, occasional barrage of word-vomit and jaded experience has taught you that this role is hard and unappreciated. 😜

You have some really applicable and useful skills that I’m convinced will make you a success when working with and supporting teams. Continue to be open-minded and curious about what your next small step can be, and occasionally lift you head and scan the horizon for what to look out for next. Because we never really know!

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