Mentoring Through Conversation
Three styles (and a contract) to help your mentoring become an extended conversation.

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Three styles (and a contract) to help your mentoring become an extended conversation.

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https://youtu.be/5S959MblQAw Here’s my talk from Agile on the Beach on engineering career development that directly impacts retention and organizational success. In my career as an engineer, consultant, and mentor, I've found that growth isn't line...

Mentoring is often been essential to how engineers work and grow. It can bring knowledge, wisdom and experience to bear on an individual's progression and challenges.
Mentoring centers around an extended conversation: regular, focused one-on-one chats with the person you are mentoring.
Mentoring can vary a lot; often the key duties are:
👂 Be a person to speak to and listen
👐 Offer organizational support and comfort
🧭 Help people navigate the organization
🏋🏻♀️ Help people grow their capability
🎆 Celebrate success!
These conversations can range from a free-style catch-up or follow a questioning structure. Often these chats need a little structure to help with connection, learning, listening and growth.
At the heart of a successful mentoring conversation, there are a set of agreements.
It's all about the growth and success of the mentee. It's rarely the place for reporting up or collecting status updates. They should be done elsewhere.
The mentor should offer options and conversation areas, the mentee should say what they want.
If there is a timeline, or window for these chats, it should be clear.
The conversation starts from a point of trust, but if either party is dissatisfied it should be in the open.
Often these are not spoken about or checked in on. I very much think they should be discussed and clear.
Without chat there would be no mentoring - it all starts here.
There are a couple of formats I've found useful to lean on to get a chat going and to build shared knowledge and rapport.
Catch-ups are great to keep remote and timezone-distributed people in the loop. It's perhaps the MVP of mentoring. It's not about reporting to each other. Rather, you both get a slice of what's going on and what you don't know. It's a great way of syncing and learning about each other.
🎁 Share what’s going on in your world/team.
🐢 See where the conversation takes you.
👂 Keep listening.
The 4 Questions structure is great to help a mentor step into the mentee's perspective and talk things through. It's my go-to choice to get into what's going on in the mentee's world, once we have trust.
⚕️ 1. How are you?
👍 2. What’s good?
👎 3. What’s not so good?
🧩 4. Is there something we have not talked about that we should?
Mentoring is all about growth, and growth conversations are best if supported with goals, direction or even a plan. If your mentee has a clear direction they want advice and support on, your conversations can center around that. If not, you can build one together.
With this in mind. growth-focused conversations often take this shape:
🗺️ Check-in on progression and acquisition
🛣️ Ask them about how to progress a step
🚧 Discuss blockers
🎊 Throw in a good challenge
I've found this style also works well for onboarding and assisting new joiners learn about their role and how things function.
Mentor chats should be dynamic and adaptive. Mentors may choose a format to suit the situation and the mentee's needs, but they should also be listening to check if it's working for their mentee. Be ready to stop and reassess if you don't have the right format for the conversation.
A key to helping someone grow at work is helping them feel safe and happy. No one learns much for long without these. Mentoring conversations should start by helping someone into this position.
Beyond that, you, as a mentor need to build rapport and trust, so you can be told and tell critical information that might otherwise go unsaid.
Active Listening is a great way to do this, as well as a way to learn and guide without dominating a conversation.

There is a lot of depth in the ways you can use conversations to support guide and grow. Hopefully, these patterns will get you re-started if you stall.