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Jump off the cliff and build the airplane on the way down

Company Culture of Innovation! Pros vs. Cons

How does it effect a company culture when it’s leaders are willing to “jump off the cliff and build the airplane on the way down?” 

Entrepreneur: Someone who jumps off a cliff and builds a plane on the way down.

I can’t remember where I first saw or heard this quote, but I’m pretty sure it was on Pinterest back in the day when Jennifer and I first merged businesses. Needless to say, it resonated and it is something I’ve used a lot over the years in an attempt to explain our crazy culture.

To say Jennifer and I are comfortable with risk is the understatement of the decade, especially when we started in 2012. There is a blissfully naïve element to every entrepreneur, we’re sure we can make it work—no matter what. We’re sure we can overcome whatever obstacles building a business throws at us and as our Chief Revenue Officer, Ken Okonek, says—we always bet on ourselves.

I’ve heard it said that if an entrepreneur really knew what it was going to take to start a business then they probably would never do it; that our naivety is really the only reason we think it’s reasonable to build the plane on the way down, but call it what you will: eternal optimism, naivety, blissful ignorance…whatever: it doesn’t change the fact that being willing to “jump off the cliff and build the airplane on the way down” applies to so much more than starting a business, it is about building the business too. To scale a business, especially scale it aggressively, you are going to have to be constantly innovating. This means you and your teams are going to have to jump off the cliff again and again and again.

Bold. Innovative. Courageous. Daring. Visionary. Pioneering. Resourceful. Driven. Motivated. Determined. Adventurous. Risk-taking.

These are all words that inspire us. We like watching movies where the hero is all of the above and triumphs against all adversities and obstacles. It inspires thoughts of being a part of something greater than ourselves; of making a difference in our world. I have come to realize there is both a light and a dark side to this level of comfort with risk. There are challenges of course but benefits as well.

What are the cons or the challenges we’ll face?

Uncertainty: Embracing this approach means operating in a highly uncertain environment, which can lead to unpredictable outcomes and risks.

Resource Constraints: Building the airplane on the way down requires significant resources. Resources don’t just mean funding, thought that is usually the most important. Resources also means getting the right team togther as well as all of the other resources necessary to build a product or offer a service.

Adaptability: Companies must be able to pivot quickly and consistently in response to changing circumstances and new information.

Risk of Failure: People must be prepared to accept and learn from failure, and there is always a high risk of failure in this approach.

Pressure and Stress: The high-stakes nature of this approach can lead to significant pressure and stress for company leaders and employees.

Lack of Structure: Operating in a highly uncertain environment can lead to a lack of structure and clarity, which can be challenging for leaders and employees to navigate.

What are the pros? Are there benefits?

Rapid Innovation: Embracing uncertainty and taking bold risks often leads to rapid innovation and the development of groundbreaking products or services that can improve people’s lives.

Adaptability: Companies that embrace this approach are often highly adaptable and able to pivot quickly in response to changes.

Competitive Advantage: The bold and unconventional nature of this approach provides a competitive advantage and the ability to differentiate in a marketplace, even a busy or overcrowded one.

Learning and Growth: Embracing uncertainty and taking bold risks can lead to significant learning and growth opportunities.

How does that affect your team?

Here are some of the things we’ve struggled with and worked on improving and addressing over the years.

How do you find the right people who are willing to jump with you? Is always a significant challenge for several reasons. Firstly, people who are willing to jump and build the airplane with you are rare. Finding people as comfortable with risk as you are is understandably hard. There is a saying that if it was easy, anyone could do it. The fact that it is hard is part of the reason it is the select few that succeed at it. So have some grace with the people you recruit if they are less risk-tolerant than you. In fact, it is good to surround yourself with people who are a little more hesitant to jump than you. My co-founder, Jennifer, and I have always laughed that while we are both willing to jump off the cliff, she is usually first and I’m usually right behind her after I grab a few things or at least make sure I throw some tools down before me. It is actually vital to the success of any endeavor to have a balanced team and make sure to staff your weaknesses.

First, you have to identify and own your strengths and weaknesses as well as those of your team and then you have to staff them. The key is a balanced team. You want people with various levels of comfort with risk and change. If you have an entire team who is all rushing to be the first one over the edge there is a very strong chance you won’t have any tools or assets to build anything on the way down. A balanced team increases the chances you will have enough of both to make a pretty passable airplane before you hit the bottom. The challenge with a balanced team is that you are combining people with opposing strengths and skills to create balance and that can create friction. Now don’t get me wrong, I believe friction can be a good thing. But if you haven’t created a team that is comfortable with constructive conflict and has enough shared values to find the most creative and effective solution as a result of that conflict, then you will just have friction and nothing will get solved.

In an article published in the Harvard Business Review, Dr. Amy Edmondson coined the term “psychological safety” and it is a concept that has gained a lot of traction in recent years. While even Dr. Edmondson owns that it is more art than science, the idea of creating an environment that is safe for people to express their ideas, concerns, and to even try and fail is paramount to high-functioning teams. I would say that without creating an environment of psychological safety it is virtually impossible to have constructive conflict. Instead, you will have avoidance and a lot of drama going on under the surface that undermines the team’s ability to build that airplane, let alone be comfortable with jumping off the cliff.

Balance is imperative to every high-functioning team, but it is also important that you have the right combination of people and you understand each person’s comfort with change otherwise you risk burnout.

Our employees who are less risk-averse have told us over the years that they often feel a little more intimidated to raise their hands in various situations because they don’t want to hold the team back or be the wet blanket as it were. So as leaders, it falls to us to go the extra mile to seek out their thoughts and perspectives. We need to make a point of making sure they are heard.

Having a company culture that values risk-taking and pivoting frequently also leads to the potential for high burnout rates. Often the burnout first shows up in those less comfortable with risk and they are your warning sign of trouble ahead. I have found that when you have leaders who like to jump first and figure it out on the way down, sometimes they are halfway down before they realize half their team isn’t there with them, they are burned out at the top of the cliff. Leaders need to take steps to plan for the inevitable burnout for themselves and the team.

One of the ways to keep burnout from taking over is to keep the vision alive and your why in focus. There needs to be a very good reason why you are taking the risks and bringing everyone else along for the ride. If it is just the adrenaline rush of taking risks everyone is going to burn out, you included, and for what? What was the goal? What was the purpose for all of the stress and sleepless nights? As leaders, we must keep our why in focus for ourselves and our team lest we lose everything in the rush.

Most founders tend to be the type of people comfortable with a lot of risk, otherwise they wouldn’t have started a company in the first place. Keep in mind that you need to hire some balance into your team to be able to build a company that is successful in accomplishing the goal. As founders who are natural risk-takers, we need to own our weaknesses and hire to balance them out. Once you get the right team in place make sure you stay hyper-aware of the pros and cons and how a company culture that is comfortable with risk can lead to burn out.

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