Reasons Leaders Disagree

In 2019, Perfect Search grew to new levels of revenue, survived a client’s bankruptcy, and leadership turnover. I learned more that year than in my previous ten years of entrepreneurship and leadership.

When evaluating our leadership, there were many disagreements on how to move the company forward and high-level strategy. It would be too easy to conclude some leaders were correct and others incorrect regarding a specific issue. This wasn’t the case.

Ten years of entrepreneurship have taught me that business decisions are extremely complicated. All of our leaders are intelligent and care deeply about the success of the company, however, we found ourselves in countless disagreements. When I reflected more on the disagreements, it became clear that they were caused by how we view risk and our perspective on timing.

Assess each other’s risk tolerance

Regarding risk, I’ve come to learn that everyone has a different risk tolerance.  As I continue to grow, I become more open-minded and less afraid of risk. From a business perspective, I often conclude that the biggest risk is not taking one or stagnation. Lack of innovation and testing has led to the demise of many strong brands in our culture.

In the summer of 2019, we were coming to the end of a 5.5-year lease in our amazing space in downtown Chicago.  I remember moving in and dreaming about all the growth our company would achieve in what I considered to be a “dream” space. This past year marked the beginning of the end of our lease agreement and we needed to make decisions to assess whether this space was still working for us or not. We hired real estate agents to consider other options to evaluate terminating or extending our lease.

The outside options didn’t seem as favorable as committing to our current space and so there was significant pressure for me to re-sign. I was told not signing was extremely “risky” because we could lose our amazing space. Some of this pressure had to do with the incentives for others involved in these decisions but I also thought losing our space was risky and that I should make a decision quickly.  Doing so meant committing to another five years at our space which was going to be an expensive investment of around $14k per month—you do the math.

My non-committal personality kicked in and I started to consider where our company would be in three or four years and if we would want to commit to a traditional, in-office culture or consider more remote flexibility.  I also had friends that showed me spaces that were significantly less in price but could offer the similar cultural benefits of our current space—this made me think more about cost-cutting in this decision.

At the end of the day, re-signing meant committing to another five-year lease at a large monthly financial investment. When I took this into consideration, I thought about where this company began and where I hoped for us to head next. The lives of my teammates were (and are) changing rapidly and I began to consider how our work environment should follow, too.

Looking to the future, we needed options for more remote flexibility and an office that wouldn’t sacrifice the culture we’ve spent so much time developing as a team.

Meet all parties with robust solutions

The pressure continued to build and so I asked our real estate agents if we could get a short-term extension in our current space to buy more time to make a long-term decision. They came back with the “great news” that our landlord had agreed to a 6-month extension at only a 5% increase in our current rental rate.

I asked if I could go directly to our landlord with my own extension request. They agreed but directed me to always have leverage when making such requests. I didn’t think this was necessary. I then emailed our landlord apologizing for my delay in resigning and mentioning the reasons why.

I didn’t want to commit while requesting a significant discount on rent closer to $5k in a month-to-month agreement.  They appreciated my candor and offered us half of our rental rate, month to month.

Perspectives in timing 

This lease decision occurred during a time when I wanted to offer more remote flexibility to our team. We first sent out a survey to gauge how our team would feel about this shift. There were a couple of team members in favor but many expressed concern about the impact this might have on our culture—which many would describe as the closeness of a family.

They were concerned about what the changes would do to our company over the next few months. I was excited about what this would mean in years two and three—when we would be able to vet talent nationally and globally, and how joining our culture would no longer require a Chicago address.  

To conclude, I found identifying differences in views on risk and timing to be the main cause of our leadership disagreements. Talking through these has helped us align into one cohesive vision for our company and our future.

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