Leadership coaching

I spend a non-zero amount of time each month mentoring engineering leaders. Some of them are on teams I work with directly and some of them pay a nominal fee for mentorship. I dispense as much of this wisdom as I can for free (via this very blog!) and I am willing to give everyone a courtesy hour or two each year if they just have simple career questions. As a parent and professional I cannot afford to do more than that without material consideration. If you can accept that people are willing to pay for a dungeon master to play table-top games, you can probably accept that people are willing to pay for professional coaching.

There is a considerable spectrum for mentoring and professional coaching. At one point in the past I was working at a startup where we all received the benefit of a professional leadership consulting service from a wonderful coach named Sally Wilder. I greatly enjoyed that experience. There were a lot of takeaways for all of us from the experience. Today I am going to talk about one of those takeaways: The Binder of John Szeder.

If you have read some of my previous posts about t-shirts (link pending) or know anything about kids who grew up in the eighties, you know I have an ownership fetish. I love my physical goods. T-shirts, books and DVDs please. I get that the kids-these-days want subscription services and digital hats. It should come as no surprise that I treasured receiving a unique physical token as an outcome of our wonderful coaching session.

To be clear, Sally Wilder is not in the business of unique book publishing. Sally Wilder is an amazing professional coach for transcendent leaders. The months we spent together included some take-home assignments for personality tests, interviews with team members (peers, leaders, and subordinates), and multiple sessions where we took the outcomes of these meetings and tests and discussed them in deep, deep detail.

There were five of us who enrolled together to work with Sally, including my boss and three of my peers. It is safe to say that this put a significant dent into our company’s learning and development budget. It was absolutely worth it. At multiple times in your career you will hit a ceiling that is hard to penetrate on your own. External mentors and professional coaches help provide you with tools to break through that ceiling. I have observed that coaching and workshopping sessions are pretty common in sales organizations and sports, and hackathons are an individual contributor equivalent to these in how it helps you refine your craft.

It stands to reason that there are equivalent leadership growth tools—setting aside my own ringing endorsement of Sally and her coaching service.

It is hard to put into words what my binder means to me, and what that time we spent together entailed. I am not going to give a lump-sum review on a chapter-by-chapter basis. It would be too easy for you to go off and run your own online personality tests. You would be completely missing the point by doing so.

The value here is a blend of these assessments, the interviews with people on your team, and the results curated and discussed with an independent source. It is easy to take some leadership coaching courses and it is also easy to get feedback from your direct manager on things you can improve. 

There are questions in each case. 

In the case of a leadership course, do you know if it is helping to identify and provide targeted feedback for areas where you individually need to improve? Is it a generic course that gives you a general sampling of all the materials where you need mastery, or is there a meaningful framework included for how to apply that to your day-to-day on completion of the course?

In the case of your direct manager, I have more poignant questions from my own experience. Are you working in an organization where there is room for your professional experience? Are you working with a “zero-sum” manager who might not give you the best growth advice or leadership opportunities because they need you in your current role for them to be successful?

Those are hard questions to ask. I was denied an opportunity early in my career to take a senior role on a team because my existing manager wanted that role. Other times, I have seen people on career ramps that are slowed down because the existing leadership structures enjoy the scarcity of their rank. When you get to staff engineer and senior director of engineering, there are very few advancement opportunities for people to get to “engineering fellow” or vice president of engineering, and it does cross the minds of some managers and leaders that they need to make sure no one jumps their place in line regardless of ability or merit.

These are important questions to ask yourself. Not everyone has the luxury of a strong and trusting leader. It is valuable to get an independent assessment of your leadership growth path and a list of things to work on. It is a sign your company is willing to invest in you considerably if they are willing to spend learning and development dollars on hands-on professional leadership coaching and a sign they are willing to have you grow with the company.

Working with people (and companies) who are willing to give me transcendent professional opportunities is one of the most important things to me. Early in my career I tended to be reactive in pursuit of my career goals. After a certain point that became an obstacle for me and I started to think proactively about where I wanted to go from that point onwards.

My goals today include giving these transcendent opportunities to other developing leaders. One of the first engineers I ever hired is now the CEO of his own company and has closed series A funding for it. Other people I work with are not quite so far along. When I sit down with them as team members or as a mentor, I love to bring out my binder and talk with them about it. 

There is a certain vulnerability in sharing a printed assessment of your strengths and weaknesses and I think that it helps people to see that is okay. I find it constructive to be transparent about the journey I was on and things I needed to learn. I hope it assists them to go through their own transcendent professional change.

If they still struggle with it, I will do my best to send them to someone who helped me along the way.

Thank you as always for reading! Please feel free to share this on your socials or forward via email to anyone who you think could benefit.

Should I put up a Patreon for these articles? Should I continue to link to Amazon sites (Warning: This link has an affiliate code!) with the intent of making pennies on a Sunday morning?

Maybe I should just continue writing weekly out of the goodness of my heart and just know that it makes the world a little brighter and more abundant!