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A Guide to Developer Mentoring – Interview with Rachel Ober

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In this interview with Rachel Ober, Senior Developer at Paperless Post, we discuss developer mentoring. Rachel teaches us the lessons learned from mentoring developers at Paperless Post, General Assembly, Turing School and beyond. These cover how to get started, tips on building successful mentor-mentee relationships, the benefits of mentoring as well as common mistakes. She writes more about teaching and mentoring on her blog.

Content and Timings

  • Introduction (0:00)
  • The Benefits of Mentoring (0:47)
  • Mentoring Myths (3:30)
  • Tips for new Mentors (6:20)
  • Successful Mentor-Mentee Relationships (7:52)
  • Finding Mentors and Mentees (9:53)

Transcript

Introduction

Derrick:
Rachel Ober is a Senior Developer at Paperless Post, and an experienced mentor. She’s a Ruby On Rails instructor for General Assembly, Co-organizer of the Write/Speak/Code conferences, and Founder of the New York chapter of RailsBridge. Rachel, thank you so much for joining us today. Do you have a bit to share about yourself?

Rachel:
Sure. I work as a a Senior front-end developer at Paperless Post. I work with a team of five other front-end developers building the different pretty things that you see on our website. I feel that it’s really important to kind of build your team around what you want to see in the work that you do.


“Be fearless and say, ‘Hey, I need help on this!'”


The Benefits of Mentoring

Derrick:
I kind of wanted to focus our conversation a bit around mentoring. You seem to have a lot of experience with that, so what are some of the benefits you’ve seen of mentorship?

Rachel:
Some of the benefits that I’ve seen about mentorship are a two-way street between the mentee and the mentor. For the mentee obviously the biggest benefits that you’ll see is that they will have confidence in their work, they have somebody that they can talk to or just sling questions back and forth. They trust this mentor relationship to be realistic, not just telling you what the mentor thinks the mentee wants to hear. You don’t feel as a mentee, that your trying to impress this other person. It’s a much more open relationship. For the mentor, for me it’s a gigantic reminder of where I’ve come from as well as … I’ve been working with Ruby on Rails now since I think 2005. Wow, that’s like a decade. Every time I meet somebody who’s just learning or is a few years behind me in terms of their career, I learn new ways of thinking about problems. I think mentoring is really a great relationship for both people.

Derrick:
How should people go about getting started with mentoring within a company?

Rachel:
As an individual person, it’s great to talk to people and to first gauge other people who would be interested in participating in something like that. Now at Paperless Post we are pretty equal between our Engineering Department as well as the other people in our company. We have people who design cards, people who are in charge of marketing, so it would be good as an individual to kind of weigh whether or not you’re looking for mentoring for the entire company or just to the Engineering department to figure out what your expectations are and what your goals are for your mentoring program. At that point you might get a group of people together to start some type of pilot program.

I would say even asking HR what their opinions are and whether or not doing some type of mentoring program, an official one, at your company, would be something that they would also support. Obviously having upper management is going to make sure that this is actually going to get integrated into your culture, you company culture. They will support you making sure that you’re following up with them. Maybe it can even be integrated into your review process that might happen once or twice a year.


“I would advise against having your mentor be your manager”


Mentoring Myths

Derrick:
What are some myths that stop people from getting into mentoring?

Rachel:
The biggest one is that people think that they don’t have anything to offer. I think it’s probably tied into Impostor Syndrome. That they think that they would instead hurt the other person maybe, or that they don’t have any accomplishments to really share with a person to be a role model. I think that is definitely not true. My most successful relationship with a mentor, was whenever I did admit to her my weaknesses and saying, “Hey, I had this issue right out of college. I worked at a place for a year and it was a really bad relationship for both ends. It wasn’t the right hire, it wasn’t the right fit.” She was able to admit to me that one of her biggest challenges, and after that mark in our relationship, I saw a great change in her where she believed then that because I had admit to this great failure in my life or this personal failure that I felt about, that she could kind of open up, admit that she was having difficulties in certain areas, and be able to regain her confidence, move forward, and do an excellent job.

I think especially with people who are just learning the program, they have this idea … It’s kind of strange because when I was learning how to be a developer, or learning about development in general, there was very stereotypically, you spend all day in front of the computer. Now it seems like it’s turned into something glamorous, because you have this ability to change your life and to earn a lot of money by becoming a computer software developer. My first class that I taught at General Assembly somebody asked me, “What does your daily life look like at Paperless Post?” I said, “Seriously I spend most of my day trying to fix bugs and most of the time it doesn’t work.” I think I blew his mind.

It was a very interesting experience, but you as a mentor, just by explaining what your daily life is and how you interact with other people on your team, is some really fantastic advice for somebody who is either thinking about becoming a developer, or about to take that step after either graduating college or taking one of these code boot camps. Just giving your experience is very valuable. They want to know how you go about interviews, and obviously if you currently have a job you’ve been through a couple of interviews. Nobody just gives you a job usually. That type of advice is just invaluable for somebody who really has no point in which to reference.

Tips for new Mentors

Derrick:
Any additional tips that you can give for new mentors about the types of things that they should be doing with their mentees to help them learn?

Rachel:
The tips that I give to people that are thinking about getting into mentoring, or people who are looking for mentors, is to really start off the relationship figuring out what the goals of the relationship are. Figuring out how often you’re going to meet, how long these meetings are, whether or not you’re going to have some type of assignment that that this mentee is going to give, and how involved your mentor relationship will be. I’ve had different relationships … Some of it is based on just talking. Talking through issues, and more of the social aspect of becoming a developer or navigating either their job or their learning environment. Other relationships have been very deep into code, working through problems, and learning how to break down problems.

I think figuring that out earlier, it really puts everything out on the table and saying like, “This is what I’m having issues with. This is what I’d like to improve on,” and just kind of like talking about each other, talking about yourself. I feel like it’s very hard at least for me to go in and start getting advice, if I don’t know at least the motivations for the mentee. What they want to learn, how they want to see themselves in a couple months after we’ve been working together.


“Having a whole network of people will really help you share your success in achieving your goals”


Successful Mentor-Mentee Relationships

Derrick:
What do you think are the essential elements of a successful mentor-mentee relationship?

Rachel:
I think that successful elements are definitely meeting regularly. I don’t think kind of having on the fly meetings is really helpful for either person. As a mentee you want to make sure that you’re checking in and goal setting. Making sure these goals are met and that you have this accountability person. Your accountability partner, that you are actually fulfilling the things that you set out to do. I think if you are a mentor and you see that your mentee is not fulfilling these requirements, then you have to have like a really good heart-to-heart and say, “Hey, I’m putting in this time. I’m volunteering, I’m not getting paid for this, and I chose to help you because I really believe that you can do some amazing things.”

Sometimes guilting them helps. If they’re part of a Code school you can contact their teacher or the administration and say, “Hey you know, we set up this relationship and I wanted to check in with them. Have you noticed anything on their side?” You don’t want to be meddling, but you also want to set yourself up for success both as a mentee and as a mentor. Keep assessing the relationship, making sure that it’s working, and also if you are a mentor, being knowlegeable of what they are learning or what their work entails, and anticipating questions that they may have. I think just being yourself and admitting whenever you don’t know what the answer is, or giving them advice on other people to talk to. Just being realistic about yourself, where you’ve been and giving that advice to somebody else, is really the crux of a relationship like that.

Finding Mentors and Mentees

Derrick:
Where can people find mentors, or people to mentor?

Rachel:
That is a very interesting problem. I don’t think it’s easy to find a mentor, because there’s a certain level of trust and understanding. For me, I have always mentored other people. I’ve found mentees with volunteering for Code schools. I’ve mentored students from the Turing School out in Colorado, which may sound odd since I’m in New York city, but I’ve been fairly successful working with people over Google Hangouts and Screen Hero, and Slack, and just leaving myself available over text message and phone. I’ve also mentored people either through organizations that I work through … I would say that’s mentorship even if maybe you haven’t said exactly what that relationship is, or have a steady schedule. Also through the classes that I’ve taught at General Assembly. People asked to meet regularly, they want really advice on where to go next. They become voracious and they want to learn as much as they can.

For me, I’ve been searching for my own mentor for awhile. I’m particularly looking for somebody who is five to ten years ahead of me in their career. It took me a little while to kind of formulate the idea of what I was looking for in my relationship. As a woman it was important for me to find a woman who was doing the type of thing I wanted to be doing. I had to really extrapolate and think about what I wanted to be doing in five to ten years. Really be honest with myself. Where am I going to be in my family life, where am I going to be maybe in the country. Assess these things that are important to you, and then see if there is somebody out there that you really admire and just ask them, and you don’t have to limit this to one person either.

Having a whole network of people will really help you share your success in achieving your goals, because you have more accountability partners and more opinions. There’s a couple online services as well. For women there is a site called Glass-breakers, which will link up people, via the LinkedIn Network. There I’ve had a couple introductions, and I actually met somebody in person who happened to be on a business trip from London. We had dinner and it was amazing how well we connected. I would be fearless and say, “Hey, I need help on this,” and admit that you need help, and these natural relationships will form.

Derrick:
Is there something in that relationship that says your mentor should or should not be your manager?

Rachel:
I would advise against having your mentor be your manager. Here we do have Technical Managers who are in charge of making sure our project is on time, making sure that everybody’s being productive, and basically are leading the projects, leading the teams. They’re also in charge of writing reviews for the team members. We then have other people who are available such as myself, who are really focused on making sure that the other employees are happy, they’re doing the type of work they want, and then also if there’s something they need to get off their chest, it’s a safe environment because you’re talking to somebody who isn’t reporting on you or needs to also … They’re kind of the neutral Switzerland or something. They’re to necessarily involved in the review process of you and your team, but they’re there to help focus on your happiness and the growth of your career.

I think whenever you’re the manager you have to constantly have that balance of the best interest of the company and the person, whereas I think an independent party really is concentrating on the person. It doesn’t mean that this relationship with your manager is bad, it just means that maybe you also need to take in a mentor who’s not in a manager role.

Derrick:
Rachel I think this was really great conversation. I hope a lot of people take the next steps to either find a mentor or become a mentor.

Rachel:
Great, thank you for having me.