I’m pretty sure my claims in How to develop software, How to develop humans, and How to efficiently learn a programming language hold true for people who aren’t me. This how-to is similar, yet different, in that I don’t know enough to suggest anything you should believe or could try. All I know is what I believed, what I tried, and whether it worked. If something about my story helps you, I’d love to hear about it.
Why did I want to try coaching?
I’m not the most gifted programmer or project manager, and I have an academic background in neither. Of necessity, I’ve picked up some tricks that help me deliver results. I’ve built up skill at choosing the work that’s most needed, how to make it most predictable, and how to care for people.
As a perfectionist, procrastinator, and introvert, my at-work effectiveness does not come naturally to me. It has been, and continues to be, acquired through intellection; it is performed, when I manage to perform it, through intellection. The downside is that whenever I don’t have quite enough attention and energy, my effectiveness drops off pretty steeply. The upsides are that my best work is consistently trustworthy and valuable, I habitually observe and adopt techniques to make it more so, and I can almost always understand, verbalize, and demonstrate why I choose how I choose and why I do how I do.
I’m not singularly talented, but I compensate by being wily and by raising my team’s level of play. I’m no Michael Jordan, but maybe I could hope to become a Phil Jackson.
This isn’t the first time I’ve thought these thoughts in this order. I began to piece them together a couple years ago while leading a software team in a difficult environment, during which I felt both pride and pain while delivering exemplary work.
How did I give myself a chance?
A senior manager observed my frustration, suggested I’d do well at coaching software teams that needed to improve (of which there were many), arranged a test of our hypothesis (which went quite well), and set a move in motion. The new role represented for me not only an escape from chronic work-pain, but also a route to being appreciated, for my value could only become more significant and more evident. I had a lot riding on the move. So when a meddling middle manager blocked my transfer out of the department, he soon discovered that his authority stopped short of keeping me there.
Our plan, had it come to fruition, would have served my needs wonderfully. The team I would have joined was already 100% dispersed, and the teams I would have coached were all far from New York. Anticipating no further need for me to live far from Bekki and pay dearly for the privilege, I moved to Indiana. I would have had the chance to learn, under favorable and safe conditions — salary and benefits, an environment I knew well, plentiful obvious improvements to be made — the basics of how to be a coach.
But now it was time for Plan B. Having lowered my burn rate considerably, and having done enough coaching to validate pursuing more coaching, I could afford to wait up to 10 months for the established Agile consultancies to decide I’d help them serve their clients. (If I couldn’t make that happen in time, Plan C was to get another remote programming job, for which I began collecting links to promising remote-friendly employers.) To raise my profile, I sought to involve myself in conferences, conversations, blog posts, Twitter, LinkedIn, you name it.
A few months into my experiment, with several consultancies interviewing me, I warned each of them to see hiring me as a risk — because while I’d done a little coaching, and a lot of being a coach-ish teammate, I’d never been hired to be a coach — but that it’s a smart bet that’ll pay off for them. All of them thanked me for being honest; some of them continued to interview me in depth; and all of them ultimately decided they’d like to talk to me again after someone else had taken that risk.
When did I get that chance?
All of them, that is, except one. A couple months from bottoming out my savings, having just taken a practice interview for Plan C, I heard from Pillar. Like the others, they thanked me for being honest. Unlike the others, they didn’t need someone else to go first. Was I still available? How soon could I start?
How did I feel?
Jackpot! I get a chance to find out whether I can do this.
Crackpot! I have no idea whether I can do this. I haven’t done paying work of any kind in over nine months. I haven’t worked with the client’s primary programming language since 2003.
If I let the self-doubt stop me from accepting the job, worst-case scenario is I’m filled with regret and Plan C takes too long to work. Very not great.
If I accept but the self-doubt proves correct, worst-case scenario is I flame out in a few months and buy Plan C a little time. Somewhat not great.
If I accept and I figure out how to do a good job, jackpot.
How’s it working out for me?
I accepted, of course! Come back next week for the rest of the story.