Getting Started in Development Management:

“Peopleware” and the Imperative of Quality

In both my work and personal life, I’ve always enjoyed and tried to find leadership opportunities. In my non-work life it’s been easy — between volunteer opportunities like running Startup Weekend: Library Edition, or being a lead instructor for Ladies Learning Code to back in school when I ran the Tech Fund and started a peer-learning workshop series for the University of Toronto’s iSchool, or hey, when I was my elementary school’s first Class President, a role I suggested, and, I’m fairly certain, the school administration immediately regretted implementing.

And yet in my work life I’ve struggled to attain leadership roles. But that’s not quite true, actually. What is true is that I’ve simply never stayed at a company long enough for the idea of a leadership role to make any sense. Before working at my current employer, Shift Health, the longest I’d worked anywhere continuously was six months. These were summer jobs, research assistant gigs, student work dependant on the school year cycle, or simply places where I’d found that the furthest I could grow was the very bottom of the totem pole. And that just wouldn’t do.

So I listlessly roamed from one position to another for a dozen years of my life. Up until this moment — literally today — I considered this one of my major weaknesses. Clearly since I had never held a for-pay management level position, when I got my first one I’d be starting from absolute zero. My over decade-long experience in a plethora of settings not only had nothing to do with my ability to rise to the occasion of management and leadership at work, but it was in fact detrimental. I could have been spending those 12 years at McDonalds, slowly building up experience until eventually I’d…well I’m not sure, because I didn’t do it, but I’d bet there’s a fancy lapel pin involved.

Looking back at myself, several-hours-ago-me was very silly indeed.

Because of course this experience is valuable. In fact, it’s arguably much more valuable than staying in one place for that time would have been. Yes, I’ve never had the title “manager”, but I can replace that with over a decade’s experience in a ridiculous variety of workplaces with an equally ludicrous number of different people, clients, culture, politics, places, values, goals, histories, pain points, you name it.

Like the time I worked in a tattoo shop, where I learned the importance of culture — the fact that “company culture” bleeds over (aha ha) to your clients. If you’re having a good time while getting excellent-quality work done, people will not only want to come back, but they’ll choose you over the competitor down the street every time. I also learned that consistently high-quality work made with integrity matters more than anything else.

Or when I worked at a yacht club. I learned about class, yes indeed, a lot about it, and how people are very different, but I also learned how similar everyone is at the end of the day. I learned not to assume things about people and their wants and needs, but instead to listen and provide excellent service not because they threw money at something, but because they were people and this was their favourite place, their second home. I also learned that “lawn bowling” is a thing, and what a yacht actually looks like.

Because I think that doing a bad job is a huge waste of time, I’ve had to try to be an excellent employee in these positions and everything in-between — which means understanding what’s needed of me in such a wide variety of situations. This, above everything, has made me empathetic. And empathy, I’m becoming more and more certain, is a critical quality to have in management.

I could go on, of course. 12 years of work provides a lot of fodder for reflection. And I’m fairly long-winded. But what I’d like to segue into is what brought me to think about the value of diverse experiences and empathy in the first place. And that would be the (development) management classic “Peopleware” by Tom DeMarco and Timothy Lister.

Peopleware is a seminal look at how most problems in software development are “sociological”, not technical in nature. It’s a well-written and concise series of essays for those who, like me, are moving from development to management of software product teams. When I was promoted at Shift Health to the role of Development Manager I knew I had a long uphill climb in front of me, and more than anything I had to get all of the information I could on how to do this job as well as possible (see avoiding wasting time above). So I’ve started with the classic.

I learned a few key things from Peopleware:

  • trust your team. Hire those you can trust. Let them see that you trust them
  • quality and productivity go together
  • carry out leadership as a service
  • employees have strong personal motivations and reasoning to do and not do things in the workplace that are not the same motivations as the C-level’s
  • having high internal standards builds good teams that stay with the company
  • without an emphasis on quality, you can’t build a team of excellent individuals in the first place

These can be even further summarized into two main parts:


If you hire great people who enjoy their work, as a manager you need to be as hands-off as possible. You’re there to facilitate the process of work, and remove barriers. As the book says:

“The manager’s function is not to make people work, but to make it possible for people to work.”

One major impediment to this is a lack of trust in employees, assuming that they will take advantage of this freedom and fulfill Parkinson’s Law, which states that work expands so as to fill the time available for it’s completion, an obvious nightmare situation for upper management. This is something I’d only recently heard of, and had been thinking about its potential veracity when starting to read Peopleware. But DeMarco and Lister kindly did the thinking for me: this is nuts, they explain. It’s a baseless claim that started as satire, and if you hire good people and foster a culture of excellence, this simply won’t happen in software development companies.

A lack of trust in employees also betrays an insecurity in management. This management insecurity leads to “arbitrary standardization”, management defensiveness, top-down everything, and doesn’t allow the employees personal agency over their work. And without personal agency, they can’t possibly be proud of what they do. And this need for pride in work becomes critical when we look at the importance of quality.


Hand in hand with trust, the importance of quality is repeated throughout the book: quality people making quality things in an environment that does everything it can to foster this is critical to the company’s success. A key role of management is to build a team that “jells” — the individuals can work together so well they form a sort of clique that truly believes it is superior. Not in any purely negative sense, of course — the book is simply referring to that feeling that (at least I hope) we’ve all felt at one time or another when we’ve worked well in a team and truly believe that team and all of it’s members are brilliant, hard-working, and together created something that is The Best.

I felt this way, for example, in putting together Startup Weekend with three librarian colleagues. To this day I would tell anyone who asks about their individual and collective brilliance, and am exceedingly proud of what we accomplished. Even though it was unpaid work, we were completely motivated for months on end to succeed — because we wanted our event to be The Best, and we cared about the cause.

This second point’s importance is expounded upon in Peopleware as well:

“Teams are catalyzed by a common sense that the work is important and that doing it well is worthwhile.”

The authors also make the point that what is motivating to the employees is probably not the same thing that motivates middle and executive level management — if you’re in a large company and upper management tells the company that Q2’s profits exceeded expectations, while the C-levels may find this very motivational, it’s not “close” enough to the employees to be a thing that’s particularly motivational to them. One basic way you canmotivate employees is to show them that what they’re doing is going to be The Best Way to solve pain points they can understand the value of solving. That is, finding out how your employees can empathize with your potential customers.

To sum: expect great things. Communicate high expectations as a collaborative imperative. Make sure employees truly believe that what they’re doing is important and good employees will rise to the challenge (as long as barriers to exceptional work are removed).


While reading Peopleware I realized that although I don’t have for-pay management titles all over my resume, leadership (especially servant leadership — a concept DeMarco and Lister only mention once by name but I believe is the most accurate way to describe what they’re espousing) isn’t taught, and the experience to build it through empathy can come from everywhere — even a bakery, book scanning facility, medical clinic, tattoo shop, recruiter’s office, jewelry store, library, department store, classroom, yacht club, startup, and maybe even Marineland. Okay the jury’s out on that last one. But if you’re new to management like me, pick up a copy of Peopleware and read it cover to cover. The book focuses on employees as real human beings, and managers as facilitators of exceptional human work — something only possible through the cultivation of empathy. I’m greatly looking forward to a long future of applying my years of seemingly disconnected work towards leadership as a service.

One clap, two clap, three clap, forty?

By clapping more or less, you can signal to us which stories really stand out.