Mentoring in Tech: Lessons Learned — Tasktop Blog

Tasktop Technologies
7 min readApr 16, 2019


Mentorship is not. . . . . .answering questions on Slack

I have learned many things working in tech, the most significant being the importance of mentorship. The strong mentors in my career have nurtured me into the professional I am today. Moreover, their tutelage has helped me develop a very strong personal philosophy on mentorship that is shaped by the successes and the failures of those relationships. Following is what I’ve observed so far about what mentorship is-and isn’t.

. . .easy

Many people tell their mentee early on: “Just ask me when you have questions.” Of course, a mentor should be 100 percent available to answer questions, but this is not enough. Too often, I’ve seen mentoring stall because the relationship never grows past answering basic questions.

. . .something everyone can do well-or at all

I’ve also seen people who are overloaded with work take on mentorship responsibilities, as if this is something small that they can do on the side. Mentorship is a real responsibility and takes a lot of work. If you don’t have the capacity to allocate the time and attention it deserves, it’s best not to do it.

Mentorship is. . . . . .a skill

Everyone should get a chance to learn how to be a mentor, but not everyone is well-suited to the role. Pushing someone who is not ready for such a responsibility can do a lot of damage to their mentees, not to mention dent the mentor’s confidence.

. . .important

Like any other skill, mentorship is something you have to practice, hone, and test. You should take pride in your mentorship skills and improve them as you work. Continuously take stock of your skill, use your company’s mentorship resources, keep abreast of the latest best practices, and evaluate your progress with people whose skills you respect. Like any skill, there will always be ways of improving.

. . .a complex, two-way personal relationship

Don’t approach mentorship flippantly; when you’re mentoring someone it’s likely the most important thing you’re doing that day. Great mentorship can really accelerate someone’s career, and poor mentorship can seriously stall it. When you give your mentee the attention they deserve you are signaling to them that their development matters, and they will be motivated to work with you and continue to grow and develop.

What are the goals of mentorship?

Too often, I’ve seen mentorship and on-boarding conflated when someone starts work. On-boarding is an incredibly vital process, but it’s usually focused on knowledge-sharing: learning tools, processes, conventions. Mentorship is just as much about building relationships and expanding one’s knowledge. Open yourself up to your mentee as much as they are open to you, you’ll both benefit from it. Your mentee shouldn’t see you as an information desk. Share your day to day experiences with them. If you are having trouble on a topic, ask them for help or just talk it through with them. It’s important that mentor and mentee work together closely so that the mentee can learn that everyone is always learning, growing, and struggling; don’t let them feel subordinated or alone.

I like to focus on ways to help someone become:

  • a next-level professional
  • a great teammate
  • the worker they want to be

Mentoring tips

You won’t really help someone reach these goals by telling them what Git repo contains what code, or how to fill out a defect report, or what testing patterns your team likes to use. Those things are important to know, but teaching those things isn’t really mentorship, it takes more than that.

Ensure that the mentee is comfortable in their work environment and with the team. To work effectively and happily, a worker must want to come into work and they need to feel that they are actually able to accomplish tasks and contribute value.

Guide them through tools, code, process, and conventions. It’s important to teach people technical and process details and subtleties so that they can feel empowered to do their work. It’s also important to encourage them to question the team’s processes, conventions, and patterns.

Teach them how to find information on their own in their environment. One of the end-goals of mentorship is for the mentee to become self-sufficient; teach the facts, but also teach them how to discover these things on their own.

Help them feel that they belong. As a mentor, you are likely interacting with your mentee more than anyone else, so you will have a huge influence on how comfortable and happy your mentee is feeling at work

Set clear expectations for the mentee, and for yourself. It’s important for people to have some points of reference for where they are in their development, and It should be clear what is expected from the mentee at various stages.

Provide milestones and check-ins. Expectations evolve with time, so that as your mentee progresses, they can continually evaluate how they are performing with respect to those expectations. Provide some reachable goals early on to inspire confidence. Also, ensure that the mentee has a chance to express what they expect of you as a mentor, such as your availability, where they most need your support, or the frequency of check ins. Your mentee should have opportunities to give feedback on your mentorship.

Give and solicit clear, open, and honest feedback. Setting expectations is the first step, but for people to know where they stand, they need to get solid feedback on how they are meeting expectations:

  • Don’t assume people know when things are going well-make sure to highlight when someone does something well or is just generally meeting and exceeding expectations.
  • Don’t hide or lie about real problems-have open and honest conversations about things that didn’t go well, so that together you can overcome those issues.
  • Solicit feedback from the mentee-solicit feedback from your mentee on a regular basis. Not only will this ensure that you can continue to improve as a mentor, but it will help establish and maintain the two-way nature of the mentor-mentee relationship.

Engage with the mentee in a way that works for them. Everybody is different, everybody thinks about things in their own unique way, and everyone will respond to different mentorship techniques in different ways.

  • Do not assume that what worked for you, will work for them-this is an easy trap to fall into without noticing it, so it’s important to keep it at the front of your mind
  • Start off by setting up some structured time with them. I’ve found that meeting daily away from where you normally work allows for dedicated time for mentorship. In the beginning, you’ll likely be going over a mandatory topic (team tools, process, conventions). By exploring these topics and monitoring how your mentee responds to them you’ll be able to learn what kinds of topics they care about most; for example, they may ask lots of technical questions, or want to learn how to do code review more effectively, or they need time to discuss different work interactions/relationships.
  • Find a cadence for these meetings that works for both of you. If regular meetings don’t work then drop them. It’s your job to figure out with your mentee the best way to mentor them.

Connect and refer your mentee with the people who can serve them best. Being the first point of contact doesn’t mean you should be the last or only point of contact. Reach out to colleagues and connect the mentee with the people who can serve them best. To be self-sufficient, people need to learn that it’s good and healthy to talk to and learn from everyone around them; this is a big part of ensuring your mentee feels comfortable in their environment and team, and sends them well on their way to self-sufficiency.

Recognize when the relationship is going poorly. If you’re having trouble with your mentee, reach out to someone who might be able to help you figure out ways to improve the relationship. A bad mentorship experience can be really damaging and set someone back quite a way, especially early in their career, so it’s important to try to address a poor mentor-mentee relationship as early as possible.

  • Talk with your mentee to find out if there are things you can change to improve the relationship.
  • Don’t be afraid to seek outside help if things are really not working; don’t go at it alone.
  • If you are supervising mentors, make sure to keep tabs on how things are going. If a mentor and mentee are a bad match, don’t assume that things will just work out; it’s your responsibility to intervene. Try to find out if there is anything you can do to help the mentor improve the situation, or find a new mentor for that mentee.

I look forward to learning more and more about how to be an effective mentor. But there are a few things I don’t foresee changing:

  • Mentorship is a skill-one you should hone and be proud of
  • Mentorship is about building relationships, as much or more than it is about building knowledge
  • Everybody is different, mentorship is personal, there is no one size fits all solution to mentorship
  • Clear expectations and clear honest feedback are the absolute keystones of an effective mentorship relationship

Written by: Jaxsun McCarthy

Originally published at on April 16, 2019.



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