Letting Go

Once the decision was made to pursue this new opportunity, there was a cascade of implications and decisions to be made. How could we possibly step back from our roles in our companies? My role was CEO. The buck stopped at me. I had a dozen or so direct reports, and all of the strategic planning and decision making was under my control. I wasn’t completely engulfed in customer relations, as we had a sales staff, but my customers still knew who I was. My wife worked about half-time in the business looking after a host of things that would typically fall through the cracks in finance and administration. We didn’t have written job descriptions, we were just a catch all for anything and everything that a business owner needs to handle. We wrestled with how to tell our staff. We were still in the throes of Covid, and I had become close to many of them. I wasn’t sure how they would take the news that I was going to be stepping down from my role and backing away from the day-to-day of the business.

My new role hadn’t been finalized, nor had I even been officially offered a position. It was all very vague and conceptual and we were trying to do a whole bunch of things at the very same time, and some of them were interdependent. I found myself in a spot where I couldn’t really commit to this new role if I was still tied down to the business, but I didn’t want to exit the business if I didn’t have something truly great ready to go. We also needed to figure out our family situation, with 2 kids out of school and 2 still in school, we weren’t sure how we would manage our home life. After what seemed like weeks of agonizing, it finally hit me what I needed to do. Just like so many other things in my life, I had to commit and burn the ships.

In 1519, Spanish Conquistador Hernan Cortes de Monroy on most accounts wasn’t a really nice guy. He had a lot going for him, in that he had horses, dogs, and guns. That gave him a distinct edge as he and his cronies sailed around the Caribbean pillaging and conquering. But some of his antics weren’t completely legit, and he was a wanted man in Cuba. Going back there wasn’t a good option, but the other one wasn’t great either: Conquering the Aztecs of Mexico. Sandwiched between a rock and hard place, he knew his options were limited. Some of his men, fearful of the bloodthirsty Aztecs, wanted to return to Cuba to rather face the consequences there. Cortes knew he needed to get his men ultra motivated to take on the Aztecs, or he would surely face his imminent demise back in Cuba. He convinced them to land their boats on the shores of Veracruz, after which he promptly set them on fire. There was now only one option, and there would be no going back. He and his troops were fully committed to take on the Aztecs. Cortes and his men marched into the interior and slaughtered them.

This idea, of being so fully committed to something that it absolutely has to succeed, is another recurring theme in my life. I’m still not sure if it’s really the smartest idea, but it does seem to work most of the time. Making the decision to leave the safety of employment to start my own business was one of these times. We had no way of knowing if or how this would work – we just had to fully commit to it and make it work. There was no other option. I also know that in the early days of running our business I was constantly on the lookout for a back door – a way to get out if things weren’t working. Eventually I recognized I was putting too much energy into the back door. I burned the ships – borrowed a bunch of money, bought new equipment, and got to work with no option but to figure out how to make the payments. I quit putting energy into the backup plan, and my business launched ahead faster than I had imagined possible.

I’ve also been in this situation in the air. Normally as pilots our entire strategy is to have backup plans and redundancy in systems. We literally plot out what we can do when things go wrong and we try to create as many options as we can. But sometimes when you want to accomplish something, there just isn’t a solid backup plan, if any at all. On our trans-Atlantic crossing in 2018 in my Cessna 210, we found ourselves in this situation a few times. In order to accomplish our overall goal of making the crossing, we had to fly some legs where we would pass the “point of no return”, where we wouldn’t have enough fuel to turn back to our point of departure. The only choice would be to fly on to the destination, and deal with whatever weather or mechanical issues might arise on the way. We were fully committed to the destination. Airplanes are like that – taking off is optional, landing isn’t.

Video – St. Barths Landing: https://youtu.be/wS0SuqgOgzc

So without actually knowing if I would for sure have a job in California, if I could actually get a work permit to legally work there, or how we would continue to raise and educate our kids, I burned my ships and committed to exiting my company. It was a really crazy time. But the further I got into it, the more I realized that it was the right thing for us. I hadn’t known how ready I was to change things up and try something new again.

The process to do this wasn’t all that complicated. We picked a date when I would be done with my role as CEO. We whiteboarded and sketched and listed out all of the different things that would need to transition to the new CEO. There was still some uncertainty in our business from a recent drought, so we intentionally didn’t try to hire in anyone new at that time. With some help from a consultant, we drew up a transition plan with dates attached and specifics of roles and responsibilities. We knew that with the structure of our companies, even though things were a little slower at the time, it would be a big load and would stretch the new CEO thin. We knew that this situation would need to evolve as our business rebounded.

Telling our staff was another big deal. I knew that many, if not every single one of them would be blind-sided by this. Surprises in a business are generally not good things. Not many people like to be surprised. When you think about leaving your business you wonder how many people are there for what reasons, and if any are there because of you, what happens when you take you out. We gathered everyone in a group and I walked them through where I was at, what I was planning, and why. The discussion that followed, but more so the body language was encouraging and supportive, but they were shocked. And yet the ones who really know me, probably weren’t completely surprised. Overall it went over probably as good as I had hoped – there wasn’t a mass exodus for the door, but there were some questions and concerns we had to address. We walked everyone through it as best as we could, and in the end everyone was massively supportive and remains so to this day.

Learning to let go and let others run your business isn’t easy. There’s no way to cut it down to a simple formula. I’ve worked for micromanagers in the past and I know the pain they feel for their staff. I recall one time where I literally begged my boss to just allow me to fail for once, and he admitted he just couldn’t do that. He had to maintain enough involvement and control to ensure that failure was not going to be an option. This was a really formative moment for me. I learned from it, took that experience, basted it and cooked it in my mind. Then I burned it in never to forget. I knew that failure was my greatest teacher, but how do we fail quickly, easily, and cheaply enough not to inflict permanent irreversible damage to our business? I deeply believe in the value of failure (evidently by my track record!) and that we need to give people these opportunities. The hard part is standing back and watching it happen, or paying for the damage inflicted.

It’s not just about allowing people to fail. A big part of it is the small stuff. Few things will drive a staff to complete and total frustration as an owner nit picking the minor, inconsequential details. Yes, details matter, and they are what adds up to making the difference between mediocrity and excellence. But there is a balance to be had here – if you’re going to back away from your company, and let someone else run it, you need to be prepared that they might not choose Kirkland Signature toilet paper for the staff washroom. Walking this fine line – between getting involved or not is a constant struggle for us. We have had to become very vigilant about noticing – when are we concerning ourselves with minutia, when are we interfering with someone creating their opportunity to learn by careening toward a failure, when is it appropriate for us to step in and let our wishes be known. It’s a gentle, sometimes awkward dance, and all of us are learning the steps as we go. Above all, honest, open, and candid communication with leadership staff is absolutely crucial.

Our transition to becoming a board-run company is in process. We’ve started and we’ve made good progress. We don’t have bylaws or policies or procedures in place yet, but are working toward some really good guidance that is allowing us to know with clarity what the roles and responsibilities of the leadership team is, and what ours as owners is. So far we are small enough and accessible enough that we are maintaining monthly board meetings with a financial dashboard that gets updated biweekly. We’ve put in communications standards so that the leadership team knows and understands when we expect communication to happen. For example, if an employee ends up hospitalized or we get threatened by a lawsuit, I think someone should give me a call. If you’re interested in the complete list of our comms protocol, let me know and I’ll pass it along.

There is no magic bullet to figuring out how to let go and let others go. It’s a constant, daily habit that doesn’t come naturally to most of us. We want to be in control. We want to ensure that we get the results we want. But we just can’t be everywhere at once. The best advice I can give for anyone contemplating how to let go and empower others, is to just burn the ships and commit to it. Make it an intentional part of your thinking and conversations with staff to only concern yourself with details that really matter to the long term health of the business. If it won’t be remembered a year from now, it’s likely not worth talking about.