Be Humble, Listen and Offer a Perspective: 7 Power Tips for Your Next Mentorship Session

Six months ago, Wix Engineering initiated a speed, open mentorship program, where a handful of our engineering leaders offered their time for mentorship and consultation to anyone, out there in the world, who desires to leverage it.

Since knowledge sharing in all its shapes and forms, and particularly mentorship, is one of my passions, I gladly onboarded the initiative and offered mentorship on self and organizational growth, dev culture, engineering excellence and anything in between…

After six months into the program with dozens of mentorship sessions under my belt, I’d love to share my lessons learned so far.

Speed mentorship and ongoing mentorship are not the same beast

The first thing I realized, as one might expect, was that a one-off, 30-minute mentorship session is very different from an ongoing mentorship program you give your mentees inside your organization.

You have no former knowledge of the mentee, their background, their position and what they are looking to achieve.

It’s a one-off session — no time to build a relationship and trust, no time for trial and error, or trying out and building techniques that suit you both.

On the other hand, since there’s no prior acquaintance, there’s also no bias or assumptions, nor potentially conflicting agendas. It’s a “no strings attached” experience, which allows for an Immediate and more open discussion with the mentee.

Once we (mentor and mentee) committed to these 30 minutes — there’s only something to gain, and nothing to lose from engaging in an open conversation.

Although very different, I feel that speed mentorship is a more condensed, objective playground to mentorship as a whole, hence the lessons learned from speed mentorship can be applied back on an any ongoing mentorship.

Mentorship is a two-way street

With my 25 years of experience in engineering management in global organizations & startups, I felt I had a pretty good exposure to different types of engineering cultures, challenges, growth paths & dilemmas out there, and the chance to surprise me with new dilemmas would be pretty slim.

Well guess what, I was wrong! There was something new and different to learn from each one of the mentees.

Whether it’s a different culture, organization structure, base assumptions and background of the mentees themselves, each of the mentees revealed a new and interesting world to which I didn’t get a chance to be exposed before.

I’ve eaten my humble pie and recalled once again that everyone and anyone is it’s own unique self, and has something interesting to share with me and to learn from.

And that in every mentorship session, we serve both as mentors and mentees, learning something new about the world and about ourselves.

So here come my tips and lessons learned:

1. Be humble

You don’t know it all! No one does and no one needs to.

You have added value as a mentor -not necessarily because you have all the answers and encountered all possible situations and dilemmas, and know the perfect recipe to resolve them all.

But because you’re wise, experienced, and ideally a good listener. You know how to help get to the real root cause of a problem/ dilemma and provide confidence and guidance to the mentee to carve a path on their own.

You are a facilitator in their journey, not a problem solving machine.

2. Spend more time listening than speaking

“If your mouth is open, you’re not learning.” — Buddha

You only have 30 minutes to get to know the mentee, understand together what it is that they are trying to achieve, and pave a way together that can assist them in achieving their goals. That’s a lot of learning you need to do in a very short time, and the only way to achieve that is to truly listen.

Remember that this session is about them, not about you. So don’t jump in telling your stories and giving concrete advice until you’ve truly listened and heard…

3. Don’t make assumptions

You don’t know anything about the mentee, their background and past experience.

Do not hurry and correlate their challenge to yours (it’s never the same) Don’t make assumptions on their past experience, abilities or constraints, nor on their interfaces or organization culture — just ask rather than assume.

4. Prefer asking questions over giving answers

Although, and sometimes since the session is short, mentees tend to come in with prepared questions / targets in mind after they spend time thinking about the problem, making a lot of assumptions about what are feasible options, what’s doable, and what’s not.

Therefore, in many cases, the question they ask at the beginning of the session is often not the actual problem they are trying to solve, or the goal they are looking to achieve.

You need to carve out the root cause, dissolving unrelated assumptions. And you can achieve this by asking questions. If you just answer the original question, most chances are, you didn’t address the real issue at hand.

One of my mentees came into the session with a question of “How to be a good architect”? After probing a bit with questions, it turned out that he was actually looking for a way to be more impactful in the organization while gaining better engagement from teams. While we were carving out the journey, he found that it was not actually via an “architect role”, but with a combination of a trainer and individual contributor.

We would not have gotten to this path if we didn’t go through the additional questions to clarify what it really was that he was looking to achieve, and why.

So here’s a list of questions which can help take your there:

• What are you trying to achieve?
• Why? (as many times as needed)
• What have you tried thus far? What succeeded, what failed, and why?
• Describe an ideal world

Once you believe you found the root goal together, echo it back to the mentee to verify it is indeed the actual goal.

5. Offer a perspective rather than an answer or advice

Once you’ve asked clarification questions (and truly listened to the mentee) and feel that you have a good grasp of the situation and the mentee’s goal, you can now help them pave a path to fit their needs and desires.

At this point, beware of giving them “an answer” — there’s never one correct answer, and remember that you had very limited time to understand the full complexity of the situation.

What you can offer instead, is a perspective from your personal understanding and past experiences.

Try avoid phrases like:

• “What you should do…”
• “What works / doesn’t work in this situation…”

Instead you can use:

• “Let me share what worked & didn’t work for me in a similar scenario”
• “An approach you can try…”
• “ if I was in your shoes. I believe that what I would try…”

It is also good to explicitly state that this is your perspective and that they will need to do trial and error to find out what best works for them.

6. The best advice is the one that comes from within

The most impactful conclusions are typically the ones that the mentee will reach on their own (with your guidance).

This is much harder to achieve in such a limited timeframe, as it requires a more in-depth process. However, you can try and help the mentee get there by asking guiding questions and helping them to see the situation from a different perspective.

You can use the following type of questions:

• How does your manager see the situation? What are their motivations?
• What is your interface motivation? Where do your motivations meet?
• What stops you from doing [something specific] today?
• What would you have done if this would have been a different organization / manager / position? (anything to exclude fear of implications from the equation)
• What would be a win-win in this case?

7. Get feedback

Most chances are you won’t meet again to hear what of the realizations of your conversation the mentee will take forward and try and apply in real life, and whether they fail or succeed. Hence, no time like the present (last minutes of your chat) to get the mentee’s feedback on the session you just had, so that you can improve as a mentor.

What I usually ask:

1. What are your takeaways from this chat?
2. How was the session for you?
3. I want to continually improve my mentorship, so would greatly appreciate your feedback on anything different / additional you suggest I do in future mentorship sessions.

The last one may be harder to ask since asking for sincere feedback takes courage on both sides. but keep in mind that the ”No strings attached” approach, allows the mentee to “pay back” in contributing to your growth. The more sincere the request, the more sincere (I believe) the answer will be.

Conclusion

Looking back at these 6 months of speed mentorship sessions, despite the fact that speed mentorship is completely different from an ongoing one, I believe that the lessons I’ve learned will make me a better listener and mentor. And I truly hope that you can leverage some of these tips as well in your next speed or regular mentorship session.

And if you’d like to chat about mentorship, engineering growth, engineering culture or anything in between, just go ahead and book a speed mentorship session, I’m always happy to chat, grow and learn together.