A Guide for Mentoring — Introduction

Ray Berg
7 min readFeb 9, 2019

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Mentorship is a core value of the Python community and other healthy tech groups. While many groups are adopting mentoring patterns it’s becoming more apparent that the skills you need to be a good technical mentor are just as learned as the technical skills we hope to share.

This series is intended to outline some prospectives on technical mentorship to be taken or left as you find applicable. Here is the first part.

Motivation

Whether you start with ten learners or just you and a learner, the first thing to consider is your objectives. It’s great to consider the simplest case “a learner should gain more knowledge or skills than they have”, but there are other reasons to mentor. There are lots of ways someone can learn: watch a youtube video, take a class, online courseware, etc. Why is Mentoring useful at all?

Here are some motivations to consider:

You want to be a part of a community that mentors regularly

Part of altruistic action is saying “I will do this because I would hope it would be done for me”. All of us need mentorship at different phases of our careers and lives. This isn’t a zero-sum-game; it’s a choice to strengthen your community of influence with your service. It doesn’t mean you’ll get anything in return, but it does increase the likelihood that those values are mirrored back to you in the community you share.

Practicing mentorship is how we get better at being leaders

Forget whether you’ll be mentored some day, you might forget that you’re always sharpening your skills as a mentor. As you reconsider long-assumed ideas — as you explain things you didn’t remember you knew—you lay down new infrastructure in your brain. As you develop better methods to relate information to a learner you learn the same for talking to managers and executives. As you develop plans for your learner, you develop your skills as a leader for other teams.

Not all courseware is relatable

As a classic non-reader, the idea of sitting in front of a wall of text and hoping to learn is terrifying. There are so many ways for people to learn, and often the courseware designers are pitching you ideas from their place in the universe. Working in focused mentorship takes away the non-applicability. Focus on passions, focus on personal conflict, focus on the problems of the learner not the courseware.

Confidence and reinforcement is what most of us need most

This one is really important for me personally. Sitting and working on a problem for eight hours is usually only fun if you know there’s a value to it. How many newcomers do you know who think that programming or other technical challenges are that fun before they figured out how to get a program to run? They don’t; nobody does. In front of our keyboards we all sound a lot more like this:

> Should I be doing this at all? Is this right? Why am I so stuck? What if I’m bad at this? How does this even work? Is this useful? Am I going to find a job doing this? Can I ask a question about this in ____? What if they laugh at how much I don’t know?

Mentors provide — above all else — validation that we are not alone. We are not stupid. We are not bad. We are only learning. And that’s something of which we should be proud, not ashamed. Addressing those fears, helping someone find the tools to be self sufficient is where we find the magic.

Boundaries

Establishing a clear set of boundaries is not only helpful in guiding your mentee’s growth, but also preserving your emotional health to preserve you for future mentoring. Whether you are a part of a larger program or just setting out to do direct experience by yourself. Boundaries to consider:

When will this end?

The worst thing is being stuck in a situation where your energy is eaten up in a way that doesn’t satisfy you. Don’t let it happen. If the parent program doesn’t set an end date set one for yourself. Maybe you decide to re-commit to the learner for more time at that point, but you should both be aware that the end is out there; it’s coming. Mentoring beyond the end is a new obligation, not continuing the status quo.

What do I need to do to make this a useful experience?

Plan it out. Hours per week, include prep time. Make yourself a little uncomfortable with your initial estimate and dial it back later. If you start strong and need to taper off that’s normal; your learner will understand that. But think about what will make you proud before you start. Write it down!

What do learners need to do to make this a useful experience?

Again, whether the program has expectations or not, every Mentor brings theirs to the situation. If you expect a learner to spend five hours for every hour you spend together, tell them. And review with them whether they’re meeting that threshold. Revisit your expectations or provide feedback. A lot of Mentors stew over a mismatch between their expectations and what they see without talking to anyone. The only one you hurt is yourself.

If your expectations don’t align with the program, don’t join the program. Don’t use this as an excuse to not mentor; but remember that if you want someone to treat your time like that of a college professor you should apply to be a college professor.

Keep it professional

The time you meet is the most precious commodity you will share. Meetings and conversations in your mentorship should be serious and intentional. Be comfortable making agendas and sticking to them. Boundaries should apply to the time you take to meet, as well. If it’s 45 minutes, cut it at 45 minutes. If you can spend more time, and want to just be relaxed with your learner, all the better. Plan in time to not talk shop; plan in time to just be people in a room or on a park bench. But spend that limited commodity as best you can.

Reflect / Learn

You will be bad at this. If the things outlined in this document are scary or seem hard; it’s because they are. No one is good at mentorship without practice. Just like we’ve learned in technology, one really sound way to improve these skills is to retrospect and change course if something isn’t working. Whether that’s once a month or after each meeting, take the opportunities to learn as a Mentor.

Measure your Execution

You are responsible for your inputs to this process more than anything else. Be ready to review your own work.

> Are you proud of the way you’ve communicated? Are the meetings you scheduled effective and finishing on time? Are you as prepared for each action as you’d like to be? How well do you integrate this into your normal week?

You can ask your Learner(s) for feedback on this as well. Don’t hesitate to ask for feedback throughout your work together. Just be ready to hear it.

Measure your Outcomes

Being ready to collect and review outcomes along the way will help you track just how effective you are.

> Are they moving through topics? Are they gaining mastery? Are they building quality products? Is the learner able to apply the topics you discuss without your oversight? Is the program having the expected impact on their personal/professional life? What about yours?

This stuff is hard to plan ahead on, but really understanding baseline performance of a Learner, then providing opportunities to demonstrate proficiency down the road will help a lot.

Get Help

A great way to start as a Mentor is to ask for a seasoned person to help give you feedback and talk through how you approach things. I’ve found that it’s actually pretty easy to find Mentors to help you be a better one. They already believe in mentorship, so helping you is helping everyone you help. That’s a great use of a lunch or coffee.

Personal Background

I have served as the Director of the Chicago Python User Group (ChiPy) Mentorship program for the last three years, ending in December of 2018. It’s an incredible program that is well worth emulating, just as I emulated the first three offerings by the founder, Tathagata Dasgupta.

A few folks from my final cohort; that’s me between Patrick and Zax in the back, my two co-leads

After working under him for two terms as a mentor, I built my own team and ran six cohorts with 15–25 Mentor/Mentee pairs. We built a platform around this that is still under active development today and we hope to share with many other groups. Aside from that I have served as part-time technical teacher, classroom helper, music teacher, and other teaching roles since I was about ten years old.

The perspectives are generally taken from a 5 month, weekly meeting structure. The Mentor and a Learner are meeting on their own pace, working on a project the Learner has interest in for at least one-hour per week. This is provided only as context, all the content can be adapted to fit less/more frequent meetings.

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Ray Berg
Ray Berg

Written by Ray Berg

Programmer, Mentor, and generally mundane individual

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