I never went to business school. I never even made it to the end of that book that’s supposed to distill all the key insights of an MBA. Maybe I would have done things differently if I had anticipated building an 8-figure business with over 150 employees and more than 2,000 clients around the world. But in hindsight, I think I got lucky.
Thanks to my naïveté, I saw leadership through fresh eyes and gathered unexpected insights, many of which I share in my book, Lead Together: Stop Squirreling Away Power and Build a Better Team. It’s a business parable that’s grounded in psychology and laden with tools from my own experience, told in the form of a squirrely, page-turning story. Below are four of the surprising leadership insights that we learned as we built our business, even during the darkest days of the Covid epidemic.
Advertise your uncertainty
It was tempting to hide my inexperience, especially as our company grew and more people turned to me for answers. Sure, I occasionally scribbled down business jargon in my notebook to Google later, but for the most part, I was committed to being openly ignorant. If I didn’t have a good answer, I defaulted to: “I’m not sure. What do you think?” and “Let’s figure it out together.”
In time, I learned that this uncertainty-forward approach works best even when I am pretty sure I have a good answer. Advertising uncertainty creates space for others to figure things out, building their problem solving skills in the process. It also creates an atmosphere of possibility. If everyone is at least a little uncertain, then great ideas can come from everywhere.
1. Don’t make important decisions alone
Another unexpected benefit of my inexperience was that it pushed me to seek out input from others before making decisions. This practice began as a way to reduce my insecurity, but over time, I learned that the more confident I felt about a decision the more important it was to seek out other perspectives to challenge my own thinking.
I got in the habit of saying: “Here’s how I see it, but I have a feeling I’m missing something. What else do you think is important to consider?” As a result, I made better decisions and earned “build-in” rather than “buy-in.” In other words, I didn’t have to convince people to agree with my ideas because they already played a key role in building those ideas in the first place.
I sought input for most decisions and, for particularly important decisions (like hiring, budgeting, and business strategy) I never decided alone. In contrast to popular business practice, we either had two decision-makers and a tie breaker or used a consent model, giving everyone veto power. In this way, our decisions were stronger, everyone’s voice counted, and we were fully aligned.
2. Put checks on your own power
Our collaborative approach to decision-making didn’t just lead to better decisions and faster execution. I began to notice that it also created a sense of psychological safety on our team. Because nobody had the absolute power to make a hiring, promotion, or firing decision alone (not even me), our team members could voice their opinions and take risks without fear of retaliation.
So, I started to look for more ways to put checks in place on my own power and on other roles with formal authority. For example, we created a transparent and standardized compensation model, we designed a two-way assessment process between leaders and their teams, and we published success metrics and results for all roles to establish shared accountability.
Systems like these improved our decisions and expanded everyone’s sense of fairness. What’s more, just as psychology research shows, sharing power sparked greater empathy and thoughtfulness among leaders while activating greater participation and creativity company-wide.
3. Practice public displays of play
Last but not least, because I was so inexperienced, I had the surprising luxury of not being able to take myself too seriously. I made fun of myself on a regular basis, made no attempt to hide my flaws and embarrassments (like that one time my pants tore before a 300-person audience), and did my best to create a playful atmosphere for others.
In retrospect, I believe that what began as a coping mechanism for me turned into one of the best aspects of our company culture. It became the kind of place where people could laugh, be silly, and approach even serious work with a childlike sense of wonder. When people with influence or authority played in public, it put newcomers at ease. It served as a foundation for learning and creativity. And it turned colleagues into genuine friends.
By the time I left my company, we had 96% employee engagement and less than 2% attrition, we doubled in revenue and profits nearly every year, and the business continues to thrive. By now I have years of experience, and I am grateful for the lessons it’s taught me. And yet, I try to remember how much I still don’t know. How much I probably got wrong. And how much there is still left to learn.
