Robin Williams playing a therapist in Good Will Hunting (my favorite movie)

On “doing a good job”

Dave Hoover
Red Squirrel
Published in
4 min readMar 17, 2022

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In 1997, I was a graduate student, working my way into a career in family therapy. A significant part of my graduate school experience was an internship (aka, a practicum) where I practiced counseling children or adolescents and their families. This was, naturally, heavily supervised via video recordings and weekly meetings with my supervisor. After a month or two of working with my clients, I expressed concern that I wasn’t doing my job well. My supervisor asked me what was leading me toward this negative opinion of my work. My response was simple: I couldn’t see much progress happening in my clients’ lives. What she said next has stuck with me for the last 25 years.

“You have to have your own definition of doing your best work. You can do your best work with a client and they can still struggle to make progress. You are not in control of their behavior; you are only in control of your own behavior.”

By 2004, I had switched careers, and had taught myself how to develop software. I had a few years of experience as a programmer, I had discovered some of the incredible work of Jerry Weinberg, and had just taken on my first consulting role as an employee at ThoughtWorks. My first client at ThoughtWorks was incredibly challenging. While the project was technically overwhelming for someone as inexperienced as I was, the fundamental challenge was dealing with the personality of our primary stakeholder. “He doesn’t suffer fools,” was a common description of this person’s style of interacting. In short, he was quite intimidating, and perpetually disappointed.

My first engagement at ThoughtWorks was one of countless seasons of my career in technology that I was thankful for my training and education in family therapy. Through my training, I had developed a fairly strong sense of what “doing a good job” looked like for me. With this foundation, I was able to navigate a consistently challenging client without feeling like I was constantly failing. This experience drove a more succinct point home for me:

Just because your client is unhappy doesn’t mean you’re doing a bad job.

To be clear, there is obviously some correlation between my clients’ level of (dis)satisfaction and how I do my job. The best consultants tend to have more satisfied clients over the long term, or they gradually find themselves struggling to find clients! I’ve spent 12 years of my tech career working at and leading various software consultancies, and my current business relies on our clients recommending us to their peers. I feel like my definition of “doing a good job” is working for me and a sufficient number of clients. Or at least I’m not sure how else to explain my survival in this field and Red Squirrel’s ongoing growth. That said, on any given day, one of our clients may be unhappy with us, and it’s important that we differentiate between their dissatisfaction and the quality of our work.

My definition of “doing a good job”

One of the most mind-bending experiences of my training as a family therapist was embracing what is called a not-knowing stance. This “stance” can be very uncomfortable for folks who have recently acquired knowledge and skill, finally feel like they are “getting it,” and then have to let go of that confidence and flip it around toward embracing a beginner’s mind. And so, a key ingredient of me “doing a good job” is showing up curious, with strong opinions, loosely held. The evolution of this “not-knowing stance” is embodied in one of our most important Apprenticeship Patterns: Expose Your Ignorance. Ultimately, I know I’m doing my best work when I’m being clear, caring, authentic, and vulnerable with my clients. And, as someone leading a company of 20+ people, I know I’m doing a good job when I behave the same way with my employees and subcontractors.

The double-edged sword of “customer obsession”

There are some incredibly successful companies who would likely take issue with my philosophy on “doing a good job.” Amazon comes to mind as one of the companies that is “customer obsessed.” To be customer obsessed is to put your customers’ needs at the center of everything you do. While this mentality can produce some delightful stories and generate mind-boggling value, I also believe that customer obsession tends to sacrifice the well-being of the people serving the customers. I am more obsessed with the well-being of people who work at Red Squirrel than I am about the satisfaction of our clients. We exist to unleash latent human potential, and that must start by unleashing our own human potential. To me, optimizing for short-term customer satisfaction is a losing game, since it will inevitably sacrifice the well-being of the people working to satisfy the customer.

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