There are great examples of mentorship history in both the fiction and real world. In ancient Greece, Socrates mentored Plato, passing down his philosophical ideas and methods of inquiry. Plato, in turn, founded the Academy and became one of the most influential philosophers in Western thought. Plato then mentored Aristotle to pay it forward to his mentor. At the age of twelve, legendary guitarist Steve Vai started guitar lessons with Joe Satriani. Rocky Balboa had Mick to show him the ropes (pun intended) to become a champion.

In recent years, I’ve been critical of mentorship in software and tech. At times, it feels flawed and optimized for the wrong reasons. Mentorship isn’t something you scale. It’s a 1-to-1 and deep relationship. It feels performative and in service of the mentor over the protégée. My point of view doesn’t generalize everyone. There are great mentors out there who are of service to the next generation of builders. The intention of this post is to assist you with identifying what criteria and expectation to look for in a mentor.

The mentor is not a role you search for on LinkedIn. They could be a recruiter, designer, or entrepreneur. What’s core at the foundation is mentors are people providing useful guidance for your situation. They are invested in your success and what you can become, not who are today. What your mentor is not is a babysitter or responsible for bailing you out of desperation or despair. In any relationship between the mentor and protégée, it is the latter who is responsible for driving. It’s important to be vulnerable and talk about challenging topics with the mentor, but they aren’t therapists. Every second with a mentor is an opportunity to fast track insights and should not go to waste.

More importantly than what a mentor is not, let’s look at what to expect from a good mentor. I’ll use my personal examples in hope the experiences provide resonance for what you seek.

They ask powerful questions for your reflection
In 2016, I met one of my most important mentors. I arrived to the office along The Embarcadero in San Francisco. I recall being nervous meeting her because of the incredible track record she had. I prepared trying to impress with great answers. As she asked me questions to ponder about my career, team, and other topics, I was blown away. The 3-5 questions she asked invoked reflections I never thought about. That’s the power of a good mentor. They elevate your thinking by asking questions that aren’t solution-oriented but thought-provoking.

They get you to think bigger
The lived experience mentors have are the common insights you seek. This doesn’t mean they predict the future as prophets. Their experience is a data point for you to triangulate your navigation. Great mentors challenge you to think bigger than what you are thinking about. When you are thinking about the next few months, they ask you about the next decade. You’re going through a frustrating situation at work, they ask you how you can overcome it or if this adversity makes you stronger down the road. You have a future ambition and they ask you how you can make progress on it now. Those who’ve worked with Brian Chesky at Airbnb know his infamous question, “What if we add a 0 to it?” pertaining to scale and growth. All the mentors in my life have asked the equivalent of that as a force multiplier to think even bigger.

They give you access
Access is the game-changer. Mentors open doors that would take you years or never would attain. A mentor once invited me to a dinner with his former colleagues. The room was filled with former Apple, Pixar, and Facebook folks who worked on the most iconic projects. I had no business breathing the same air as those folks. However, my mentor wanted to make the introduction as he knew I was new to San Francisco and wanted to open up the connections. I’ve stayed in touch with many of them today. Another example was a different mentor who invited me to a design exec retreat with incredible leaders. I was clearly the baby of the group, yet she advocated for me to have a spot. That retreat elevated my thinking and became a transformative experience.

When mentors grant you this access, they are putting their credibility on the line for you to show up. Don’t be the person who is constantly asking for connections as it can damage the relationship. They will open the doors for you without you asking.

They give onset critiques
There is a fine line between being encouraging and a cheerleader; avoid slipping into the latter. Saying, “You got this” to someone who has a lot of work to do is a disservice for them in the long run. In mentorship sessions recently, I’ve been honest with designers that the market is a blood bath, and though it’s possible to land a role, it’s harder than ever at the moment. The critique is not to discourage but set clear expectations on what it’s going to take.

I entrust my mentors to be the biggest critic on what I need to work on in order to achieve my goals. One mentor worked with me rigorously on executive presence and gave me hard feedback on how I conducted myself. I was younger at the time and it was hard to hear, but what I needed to know.

They have conviction in what you can become
This one is the most important; great mentors believe in you, sometimes more than you do in yourself. They have seen many like you, and for them to commit time to help, they see something shining in your potential. None of the mentors in my life needed to help me. They chose to. Because of that high belief, I never wanted to let them down. As a result, I set higher expectations on myself and built the confidence to become what I sought.

On the flip side of the relationship, let’s consider the expectations of the protégée. The first expectation is the seeker of help should be the driver of the relationship. Though it’s not a one-way street, it’s up to the protégée to reach out when they need help. They find the time and the mentor makes the time. Make it be known what you want to cover and how your mentor can help. The second expectation is to practice discretion in order to maintain trust. Your mentor might share information or access that is rare. Do not broadcast it without their consent. I’m sharing you examples of my experiences with my mentors but not sharing the details (or even telling you who they are). The importance of this is not because of things being made public but focuses the conversations with you and them. Finally, mentors come and go. There is no obligation to have the same mentor for your entire life. This is why I believe it’s important to make most of the time as circumstances could change in the future.

There are a lot of people who may seem like mentors, but they may not be. Reflect and ask yourself:

• Is my mentor focused on my best interest in our relationship (vs. their own)?

• Am I making the most of the opportunities they are unlocking for me?

• How am I being challenged in my own viewpoints and bringing a higher altitude of thinking?

• What does my mentor see in me that I do not already?

I’m grateful for multiple mentors who invested me. Make the most of what you gained from them and commit yourself in helping someone else in their journey. That’s how you pay them back.

Hyperlinks + notes

A collection of references for this post, updates, and weekly reads.

• Happy 20th anniversary to Seattle Xcoders

• hyperspatial.ai

• Everything we launched at Webflow Conf 2024, congrats to those at Webflow on yet another incredible Conf!