This month, I talk to Aaron Schmookler about the seismic change that’s underway in our workplace culture. From places where people once more-or-less watched the clock, to places where many want real relationships and purpose. For Aaron, making that happen comes down to leadership. We talked about his eureka moment for getting into culture engineering; what taking teenagers into the wilderness taught him about motivation; what improv taught him about dealing with “difficult” people; how many people should report to a manager; how to create a culture of healthy failure; the fundamentals of effective communication, collaboration, and leadership; and how to learn.
Aaron is a culture engineer, who helps leaders build structures, habits, and mindsets that support an enduring high-performance culture, so both their profits and their people thrive. Aaron is co-founder and CEO of The Yes Works. He is the leader of two Giant Leap CEO peer mentoring groups in the South Sound and Kitsap County in Washington.
What follows are excerpts from our conversation, lightly edited for clarity.
‘I hate my job and love my work’
“A little more than ten years ago now, when my wife told me she was pregnant, I was doing work that I loved in a job that I hated. And I thought to myself, ‘This is not how it’s supposed to be. This cannot be how it is when my kid enters the workforce.’ So I started thinking about what it is that makes me hate my job despite the fact that I love my work.”
“One was people walking around the halls saying things like ‘TGIF’ and ‘I hate Monday,’ and ‘Same bleep different day.’ All the clock watching that goes on.”
“Another had to do with my direct supervisor. She was 20 years my senior, and had maybe been in the industry 30 years longer than me, and one day, she told me that I was a mentor to her – specifically with respect to leadership, and not knowledge of the industry. Then sometime later, two different colleagues of mine were really derogatory about her. Among other things, they said she was arrogant.”
“And so I thought, ‘How is it possible that my experience of this woman as fair and kind, didn’t jive with theirs? And how could I put their terrible behavior towards her in an understandable light?’ I think it had to do with the fact that she had too much work to do — she was managing way too many people and had way too many priorities to effectively manage us. I essentially got feedback from her once a year. And for most people, if you’re getting feedback from somebody only once a year, then any feedback is likely going to sound like it’s coming from some arrogant person who doesn’t know what they’re talking about.”
“And that got me thinking about both the skills I have that allowed me to build a strong relationship with her. And also the structural problems in the organization that created a greater likelihood of my colleagues coming to the conclusions that they did. And I thought, ‘I know stuff that can help organizations create environments where people and profits thrive instead of the kind of structures and skill gaps that led to this kind of terrible travesty of a situation.’”
On what teenagers taught him about leadership
“My resume is not a linear thing. And one experience I think back to is as an outdoor leadership guide. I was taking kids on a backpacking trip — it was one of the first leadership experiences I ever had. I wasn’t yet 18 years old. I was responsible for this group of young teenagers. And we were maybe a mile into the hike and 800 feet in elevation with another thousand or two to go. And this girl just sat down, and she just said, ‘I’m not going any further. I’m done.’ We had five days ahead of us, and the bus is gone, and she’s just done.”
“I tried everything I could think of. I cajoled her. I laid out the logic. I said, ‘The bus is gone. We’ve got 25 miles to cover in the next five days. If you don’t get there, you’re not gonna get picked up.’ I threatened, I cheer-led, and she just dug in her heels. There was nothing rational about it.
“It was a moment of leadership failure for me. And I remember just saying to her, ‘I’ve got to go.” And I walked off, you know, to stare into the trees and think.”
“And when I turned around, her peers, all these other young teenagers, had her backpack open, and were taking stuff out, and putting it in their own packs. After two minutes, her backpack was empty and eight other backpacks were a little bit heavier. And she was ready to go. And over the course of the next five days, she steadily took more and more weight back. I learned at that moment, what a poor leader I had been, and how to be better in the future.”
On how humility helped him lead with confidence
“Some of those things that I learned on that mountainside that day are the ones that helped me to get the best out of actors on stage – when it was early days in my theater company and we couldn’t pay them. These were actors who were used to being paid real money, and we were paying them $200 bucks for eight weeks of hard work. And, uh, they loved it. And I thank that girl, and especially her peers, for setting me up for the humility that it took to swallow a bitter pill of not knowing what I’m doing. And realizing I’d better figure it out.”
So back when my wife told me she was pregnant, and I couldn’t stand the idea that my daughter would inherit the prevailing work culture. I just asked myself what skills I’d gained from leading teenagers in the outdoors, some of whom didn’t want to be there and were afraid of bugs, and have them return from that trip, asking when they could do it again?
On dealing with ‘difficult’ people
“I remember going into a job once where I was replacing somebody. We had a week’s overlap, and the supervisor said, ‘You know, this person is a piece of work. You won’t be able to work with her; you’re going to have to figure out ways to work around her. And it’s not going to be fun.’ And I remember thinking, ‘Okay, that is your experience. It’s not going to be mine. This is going to be fine.’ And it was, because I had, by then, somehow absorbed understandings that let me deal effectively with people, and to enjoy working with people whom other people have trouble with.”
“A lot of those skills came from learning to be an improviser in theater. And from being a theater director and helping other people be better improvisers, even in scripted work. I realized these are actual skills, and they are transferable. The understandings that I’ve gained and that I continue to study are about what structures lead to effective teamwork, and how to convey these to other people.”
On how to improve culture
“One of the things that I learned in that interaction with my arrogant, not arrogant supervisor is the importance of management structures. Even as simple as how many people each manager supervises.”
“I remember talking with a CEO who said, ‘I’ve got great people on the front lines and I’ve got great people managing them. And I don’t understand why they’re at each other’s throats all the time.’ And what I swiftly learned just in a discovery conversation with him was he’d done a great job of hiring conscientious managers who were working hard to drive performance, but had 15 people reporting to each manager. And I said, ‘You don’t need to work with us until you have six or seven people reporting to each manager. If you still have trouble then, let’s work together.’
“Because one of the simplest structures is how many people are reporting to each manager, and whether they have time to build relationships of trust that can withstand the pressures of the manager working to drive good performance.”
On the fundamentals of good leadership
“When we start working together, we train teams on the fundamentals of effective communication, collaboration, and leadership. We put people through an experiential training experience that not just outlines and explains those fundamentals, but gives everybody on the team practice, so they already start to build habits. Each fundamental has a catchy phrase that becomes part of the vernacular of the team, so it’s self-reinforcing.”
“We call the first of those eight fundamentals, ‘Yay for failing.’ And the first exercise that we put a team through is designed to have them fail publicly, repeatedly. They fail 60 or 70 times together in an hour. And every time somebody fails, we raise our right hand, and we all chant together, ‘Yay for failing.’”
On failing fast and failing forward
“We talk about what it means to fail. What it means to fail fast. What it means to fail forward.”
“An example that I often use comes from Simon Sinek’s book, Leaders Eat Last. This story comes from a hospital in Providence, Rhode Island, where more than once, somebody went in for something like cardiac surgery but had their left leg amputated. And I’m not exaggerating about how wrong the surgery was that was conducted. And the thing that killed me in reading this story was that even though the surgeon thought he or she was doing the correct thing, the nurses all knew it was the incorrect surgery for this person. So this is not a ‘Yay for failing’ environment.”
“You could think of the nurses as being derelict. But really, they were terrified and neurochemically handcuffed. Their fear of ridicule and being lambasted by the surgeon who is god in this environment created such fear that they could not speak. They were neurochemically prohibited from speaking up.”
“In a ‘Yay for failing’ environment, they’d have been able to say, ‘Hey doc, you’re in the wrong room. I know you, you’re an orthopedist, and this is a cardiac patient.’ That’s a ‘Yay for failing’ moment that can be made possible in a ‘Yay for failing’ environment.”
“It makes me think about how many leaders I’ve spoken to who have said, ‘Why didn’t anybody tell me this was a bad idea?’ Their team knew it was a bad idea. They knew it was destined to fail. But it wasn’t an environment where people felt safe to speak up, to call out the fact that the CEO’s idea was likely to fail.”
“Fear of embarrassment is fear of death. ‘If my social status lowers far enough, then I’m going to be kicked out of the tribe, and I’m going to starve to death.’ That’s what our brains are doing.
‘We failed forward. We failed fast.’
“I think of a time when I was the leader of a team of lifeguards. There were a couple of different beaches on the waterfront. And if you wanted to swim out past the dock, you had to pass a swim test. Our process was to ask a kid, ‘How good of a swimmer are you?’ And if they confidently indicated some level of expertise, then you took them out into the deep water, and had them jump in and swim a certain number of laps to demonstrate their prowess, so we knew they could swim out to the dock in the middle of the lake.”
“Well, one day, I was way up on the beach, and was watching one of my lifeguards, Glen, talking to this kid, and the kid nodded and said something. And I watched Glen just kind of confidently march the kid out to the deep end of the dock. And the kid looked up at Glen who said, ‘Okay,’ and the kid jumped in. And I just watched Glen look around, and I didn’t see the kid, and Glen clearly didn’t see the kid. And after about three seconds, I saw Glen, belly down on the dock, reach down deep, as deep as he could, and pull the kid out by his hair.”
“It turned out that this kid knew he couldn’t swim. He knew there was no way he was going to be able to swim. He knew it, but he was more willing to die than to be kicked out of the tribe. Maybe being a non-swimmer was embarrassing to him. That’s how powerful the fear of embarrassment is.”
“Of course, as soon as that was done, I called an emergency five minute meeting. Everything stopped. And I said, ‘From now on, the process is that the kid walks into the water and swims to the deep area. There is no more jumping into the deep area for kids whom we have not seen swim confidently.’”
“That’s the failing forward. We failed fast. The lifeguard failed fast: after three seconds, pulled the kid out. I failed fast saying the process cannot stand. And then we failed forward by altering the process so that no kid would ever jump in and not swim again.”
For nearly 30 years, Aaron Schmookler has “helped leaders build structures, habits, and mindsets that support an enduring high-performance culture, so both their profits and their people thrive.” Aaron is co-founder and CEO of The Yes Works.
Aaron leads two Giant Leap peer mentoring groups in the Seattle area. Find out more about his groups.