Mentoring Through Conversation

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


4 min read

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:

  • ๐Ÿ‘‚ Be a person to speak to and listen

  • ๐Ÿ‘ Offer organizational support and comfort

  • ๐Ÿงญ Help people navigate the organization

  • ๐Ÿ‹๐Ÿปโ€โ™€๏ธ Help people grow their capability

  • ๐ŸŽ† 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.

The Conversation Contract

At the heart of a successful mentoring conversation, there are a set of agreements.

  1. 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.

  2. The mentor should offer options and conversation areas, the mentee should say what they want.

  3. If there is a timeline, or window for these chats, it should be clear.

  4. 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.

Mentoring Conversation Formats

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 up style

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.

  • ๐ŸŽ Share whatโ€™s going on in your world/team.

  • ๐Ÿข See where the conversation takes you.

  • ๐Ÿ‘‚ Keep listening.

Ask 4 Questions

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.

  • โš•๏ธ 1. How are you?

  • ๐Ÿ‘ 2. Whatโ€™s good?

  • ๐Ÿ‘Ž 3. Whatโ€™s not so good?

  • ๐Ÿงฉ 4. Is there something we have not talked about that we should?

A focus on growth and skills acquisition

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:

  • ๐Ÿ—บ๏ธ Check-in on progression and acquisition

  • ๐Ÿ›ฃ๏ธ Ask them about how to progress a step

  • ๐Ÿšง Discuss blockers

  • ๐ŸŽŠ 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.

Whatever style you use, listen and adapt

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.

Bring the warm blanket of trust and care, as well as the water-pistol of truth.

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.