I had the privilege of mentoring two junior software engineers over the past year. It was my first time doing something like this, so there was a lot to learn! To be honest, I don't think I got it quite right: many of the discussions meandered randomly around different topics, leaving an impression (on me, at least) that they didn't provide much value to the mentees. Having said that, I've learned a few tricks. These are pragmatic, simple tactics that helped me steer conversations in a direction that I think provides value to the mentee.

Build trust and personal connection

I'm lucky that I developed good personal connections with my mentees quite early on. I think none of the tactics below can work without that. I talk with my mentees about their hobbies, families, and activities outside of work. This all helps and makes the conversations much more engaging and interesting to both me and them.

Stay independent from company interests

Mentoring sessions should be a safe space. It means that my priority is the mentee, their growth, their feelings, etc., not the company. I try to make it very clear that they can speak freely about anything, even if it clashes with what the company expects from them. This is mostly done by building trust. There's no much point saying "you can talk about anything here". Make sure they can trust you, but if needed, make it clear that you are not a company representative in these mentoring sessions.

Do not shy away from discussing the purpose of mentoring

When I started mentoring, I tried to almost hide the fact that these meetings were there to help the mentee. I was trying to be attentive to what they wanted to talk about, without providing much structure or suggesting targets for these meetings. This led to many of the meandering discussions described above. Later on, I learned that it's OK to discuss the purpose of the meetings with the mentee and see what they think. Maybe they have clear goals they want to pursue, maybe they don't. This leads us to the next point.

Explore career direction and goals

Try to discuss career goals and aspirations, but accept that you might not get a clear answer. Also, accept that it's absolutely fine not to answer this question at all! If there's no clear purpose, it's absolutely fine. To be honest, I couldn't answer these questions for most of my life, and I don't think this is necessarily a problem.

Find ways to explore interests at work

A few months ago, I presented my manager a long list of technologies that I wanted to explore. He suggested going over the list one by one and figuring out if there were opportunities to explore each item within our work context. We asked: what other teams are using these technologies? Is there a way I can help these teams and learn something new along the way? That was a brilliant idea! I reached out to a few teams and got the ball rolling on things I wanted to learn. While I haven't used this technique yet with my mentees, I took note and plan to incorporate it in the future.

Retrospect

Don't run the tricks above just once. Go back to them. Ask the mentee what works. Make sure the mentoring sessions work for them. Make sure they trust you and can speak freely. The last thing you want is for them to say "it's useful" just to avoid offending you.

Take notes

Make sure to keep notes of the important points raised in these meetings. Personally, I don't share them with the mentee, because I think it can be overwhelming and suggest they need to do something about the notes, which is not the point. I take notes to help me ask questions about things they raised that are important to them. It helps with the retrospectives mentioned above.

Summary

Mentoring is a journey. While my first year of mentoring had its challenges, particularly with keeping discussions focused and valuable, I've learned a few effective tricks. Being transparent about the purpose of mentoring, understanding the mentee's goals, and regularly checking in on the effectiveness of the conversations are very useful. On the other hand, don't force these! Building trust and personal relationships should be the top priority, and it's fine to take it easy, have some meandering conversations, and have a good time.