Inspired by the interviews in the Paris Review and Bomb magazine, “The Questions” in Sports Illustrated, and the regular interviews on the blogs of Tom Peters and Guy Kawasaki, Comment has asked a diverse group of mentors for their stories.

Comment: How would you explain what you do to an interested nine-year-old child?

Milton Friesen: I’m an inventor. Growing up on a farm meant I had lots of machines and projects to work on. I would have an idea for something (like a robot), and then I would look around to see how I could use old metal cabinets, springs, wires, and other bits to build one. Now, I turn my inventive passion toward ideas for making businesses, schools, churches, and other organizations cooler and more interesting, which makes me an organizational designer.

“You can pick me apart right down to the last neuron in my brain but you only get Milton when billions of neurons and other insanely complex elements are interacting together in the structured but highly adaptive entity known as a human being.”
 —Milton Friesen

Comment: What first drew you to this work?

MF: Like many designers, I am often motivated by frustration with what doesn’t work. I’ve had a chance to be part of a diverse mix of organizations and to see what was great about them and what wasn’t so great. I became intrigued by companies that were making shoes or selling coffee or designing hand-held devices in such a way that they delivered remarkable products while fostering dynamic and passionate organizational cultures. I learned, over time, that the great products were usually linked to great groups of people who had something bordering on the magical in their group dynamic. My perpetual disturbance of mind runs somewhere along the ‘why can’t we be better’ line of questioning. I believe we can be better, collectively, at the various kinds of work we engage in together. I’m an optimist who needs to know why some groups of people have, in Tom Peters’s parlance, the WOW factor.

The type of soil that my ideas have germinated in and grown from involves new research that is being done on complex adaptive systems. That’s a bit high octane but it is really as simple as trying to understand why we can’t predict earthquakes or avalanches with any precision. From that research, insights about similar dynamics in human organizations can be drawn. We need to improve our ability to understand complex interactions and part of that is being humble enough to say that some of our ‘common sense’ practices in leadership and business are, while common, not necessarily sensible.

Our typical response in trying to figure out that magic is to dissect it, reduce it, get down to the smallest bits and then say, “Ah, here it is.” That kind of chopping up does yield insight but is only truly valuable when it is held in tension against the unique qualities that are expressed when all the elements are working together. You can pick me apart right down to the last neuron in my brain but you only get Milton when billions of neurons and other insanely complex elements are interacting together in the structured but highly adaptive entity known as a human being.

Comment: As a novice, what were your most valuable learning experiences?

MF: I was raised in settings where I benefitted greatly from parents, schools, churches and other organizations that were lively and resilient. I had a chance to feel in my soul what that “it” factor feels like. That was and is tremendously valuable and acts as a magnetic north in pursuing my organizational design ideas and practices. I am only beginning to understand the profoundly formative experiences of being raised in such a unique setting.

I let my strong natural curiosity guide my approach in the various roles I’ve had. Saying that is a way of granting permission to yourself to be an explorer of ideas and practices. My early inventive habits gave me a comparative paradigm for approaching leadership challenges and organizational design problems—what do you have, how might it be used, what can be learned when it doesn’t work. You don’t need a degree to practice that kind of approach.

Comment: What is the best advice you’ve ever been given?

MF: Don’t stay too long where you abilities aren’t appreciated. I’ll need to add a couple of caveats to that. Taken the wrong way, it can feed your latent arrogance and create a condescending spirit. But the advice was given to me as a way of saying that you may outgrow some places or there may be some places you travel through that aren’t intended to be a final destination. Taken that way, it isn’t about being too good for a given organization or setting, it’s about needing to change the size or shape of the pot you’re growing in if you want to explore what you are capable of. Banana trees just don’t grow well in Canada so if you’re a banana tree born in a special nursery in Canada but want to get out, you’ll have to try and find a flight to the Bahamas. And risk is a constant companion in the exploration so that tends to sober things in a good way.

“I have found something that I consider important enough to invest my life in, something that I can honestly say is worth pursuing, even if I fail to achieve it.”
 —Milton Friesen

Comment: From what sources do you draw inspiration for your work?

MF: I’ve already mentioned the inspiration I get from complex adaptive systems. I have been challenged in my thinking by the work of people like Stuart Kauffman, the Santa Fe Institute, Margaret Wheatley, Tom Peters, Thomas Homer-Dixon, Ralph Stacey, Michel Serres and many more who are part of that galaxy. Some of the organizations that have deeply influenced the practice side of my work include IDEO, Apple, Mozilla, Starbucks, Nike and UPS.

Other important influences not directly connected to organizational design include novelists, painters, historical figures, scholars, magazine publishers, film makers, and other cultural creatives across a wide swath of western cultural life. The deep orientation to all of that comes from my having absorbed a significant part of the messy narrative flow of biblical narrative both formally and informally over the course of my life. I was raised and nurtured with the ethical and linguistic sensibilities of the most influential text in the western world and remain puzzled, encouraged, challenged, perplexed, and hopeful about the radical nature of that message.

Comment: What rituals and habits structure your workday?

MF: Currently, I am a bit of a nomad. I work two weeks in Hamilton and one week in Calgary and each place has a unique rhythm. In Hamilton, I walk a lot as I don’t have a car there. That pace of exploration has been given me a chance to see and experience things in a unique way. In Calgary, I walk from upstairs to my downstairs office.

I do my best work early in the day and then I have another good zone between eight and ten at night. I do my best to orient my thinking/ideation time around those zones and then focus on the project planning and administration elements outside of that. It almost never works that cleanly but I know myself well enough to recognize those are important patterns to pay attention to.

Comment: What are your favorite tools?

MF: I built my own canoe back a few years and I loved my little bullnose rabbet plane from Lee Valley. I also love MindJet because it allows me to visualize planning and ideas and then convert them into more linear bits as needed by different people. My core tool, however, is my cordless laptop, otherwise known as a bound, blank sketchbook, and a pencil—no batteries, no cords, no crashes, no airport security issues, no software upgrade costs, no frozen ink when conditions are bad. I write, sketch ideas, collect random thoughts, glue things in, rip things out, all to help translate the strange brew of thoughts that run through my head into something that might be of use to other people.

Comment: Tell us about a project that delighted you.

MF: A couple of years ago, I had a chance to take three days away from my office to work on a rebranding proposal for an organization with a deep legacy but a very uncertain future. I only focused on that project for three days, put together a PowerPoint presentation that threw most of the conventional wisdom on designing presentations out the window, and did a straight-up delivery of what I thought needed to happen to various leadership circles in the organization. One slide had pixilated GIF flames consuming a Norman Rockwell painting. I loved it. The project mattered deeply, it encompassed everything, and needed to be crushed into three days of research/development and a twenty-minute presentation at the end. That’s fun.

Comment: How do you plan your work?

MF: I borrow a phrase from Eugene Peterson to frame my approach: haphazardly intent. This recognizes that the most rigorously developed and detailed plans are subject to variations you cannot possible know or control. That doesn’t mean we aim at nothing. We aim clearly, but recognize that getting to the goal will mean running with a lightness of touch that has adaptability built in. One of the ways to do that is to pay attention to feedback loops and respond to them—that keeps you closer to the ever-changing real time that projects grow and live in.

Comment: How does your work connect to other aspects of your life?

MF: I have found something that I consider important enough to invest my life in, something that I can honestly say is worth pursuing, even if I fail to achieve it. We need better institutions. We need better practices for relating to each other within and between organizations of all kinds. This kind of better matters for me, my friends, my colleagues, my kids and, someday, their kids. Because of this clarity, I can connect the sacrifices of work with my desire to provide the best life I can for my family and people I care about. My learning is not static. My relationships are not static. My work is not static. My faith is not static. That means that they interconnect, through me, around me, beyond me in ever-changing ways. Our lives are, in the end, an adventure. I’m learning to embrace that.