“So…what happens in your ‘coaching’ sessions?” A few months ago, my older brother asked me this with a heavy dose of skepticism and curiosity about my newish career. He went through medical school, a long residency, and an additional fellowship, and now performs surgery on peoples’ feet and ankles, so the idea that I get paid to talk to people is a little baffling.
Five years ago, I probably would have treated coaching with the same skepticism myself. As my manager started to set me up to move into an explicit leadership role, I started to meet with a coach who was meeting with many of the leaders at Medium. Coaching was offered to me, and scheduled on my calendar — I just showed up. I’m not sure I would have sought it out before I had experienced it myself.
When I put myself back in past-Jean’s shoes, I wonder what I would have been curious to know about coaching, or specifically, coaching from present-Jean. So here’s a first round of Q&A that I think would have been helpful.
Q: How is coaching different from mentoring?
A: Coaching and mentoring are completely different beasts.
Mentoring is when someone — a mentor who has been-there-done-that and has expertise in an area — gives advice to someone else — a mentee who is usually younger. The mentor is perceived to have greater knowledge and experience, and they pass down this wisdom to the mentee.
Coaching typically means something very different — a coach helps a coachee explore possibilities, and tap into themselves to come up with creative answers to challenges. A coach holds the space and asks powerful questions so that the coachee can experience insights, and provides accountability to make lasting behavior change. It is not advice-giving.
Q: What does coaching with you typically look like?
A: It depends. With clients, we design the relationship upfront and iterate on it throughout our work together. Some clients, especially women in the tech industry, really do want an integration of mentorship and coaching. Other clients want more of the coach — someone to listen and reflect back what they’re hearing, ask powerful questions, and hold the space.
Most of the time, what I do is not coaching 100% of the time. People contact me and want to work with me because of the combination of coaching and my expertise running engineering teams. My training as a co-active coach helps me discern when to tap into my own expertise, and when to hold back.
I use frameworks and metaphors and stories to help explain some common patterns I’ve encountered on engineering teams and with engineering managers, and provide new perspectives to clients.
Q: What are typical issues you help people with?
A non-comprehensive list of topics often discussed in some form in coaching sessions: fear of failure, taking initiative, managing up, over-functioning as a new manager, the importance of building relationships, having difficult conversations, advocating for yourself in the workplace, self-management, giving feedback, coaching direct reports around interpersonal issues.
Some areas that dig deeper into my expertise and shared language in engineering leadership are: team processes, on-boarding new hires, product development cycles, relationship dynamics between PMs and designers, etc.
Q: How would I know if I need coaching?
Nobody needs coaching.
But you might want coaching if you’re in some sort of transition. For example, if you’re a founding CTO and have just raised a Series A round, and want help navigating your role at the company as you scale the engineering team (but you might not have much people management experience!).
Or if you’ve been more of a Tech Lead flavor of manager and now you’re managing managers and are struggling to prioritize and delegate so you don’t burn yourself out.
Or if you’re a first-time manager and you’re overwhelmed with the new role and how different it is from what you were doing before.
Or you’re an engineer struggling to figure out how to lead and progress in your career when you don’t have explicit authority on teams.
Coaching can help you get unstuck.
Q: How can you coach me as an engineer if you don’t know the technical details of what I’m working on?
I don’t coach anyone on technical details 😂. There are plenty of resources internally at companies, books, and classes for learning new languages, libraries, and technical frameworks.
We may have coaching conversations on how you decide what to work on, or overcoming the limiting beliefs that hold you back from taking initiative on projects, or avoid uncertain situations. That work is more about how you show up and lead.
Let’s be honest — engineers in the tech industry get a lot of technical training but virtually none on communication, leadership, and how to work with people. So that’s what I focus on, because it’s where I can make the most impact.
Q: How is coaching different from advice you hear from books, talks, and workshops?
Say you want to get more fit. You intellectually know that you should have some sort of plan — and you may also read some online fitness plans or watch fitness youtube videos — but instead do some at-home yoga about once every few months, sign up for a gym membership, but never quite get in the habit of going.
I often send links to books, talks, and workshops to my coaching clients to reinforce some of the conversations we have in coaching sessions. Those resources are super helpful in providing the initial insight of “ohhhh that makes sense. I should do that...” but putting it into practice and integrating it who you are as an engineering leader is a different story. Coaching provides focus and accountability on something you want to work towards.
Thanks to Twitter friends for contributing questions! Email me at jean@jeanhsu.com with other questions you might have, or inquiries about coaching packages.
