“Together We’re Better Because of The Diversity of Thought” Lessons Learned With Chris Rawley

Chris: Thank you so much for doing this with us! What is your “backstory”? Can you tell us about your military background?

I’ve been fortunate to have exposure to a wide variety of assignments in the military in active and reserve capacities. I’ve served on a destroyer, worked in the Pentagon on various staffs, commanded a small boat unit, and deployed with naval expeditionary forces in Iraq. I deployed with special operations forces in Afghanistan, the Middle East, and Africa. I’ve done a lot of work in what the military calls the “interagency” which involves coordinating with various law enforcement, diplomatic, and intelligence organizations. The cultural challenges, not to mention the language barriers, involved with navigating the interagency can be daunting. In my latest reserve assignment, our teams partner with navies who are building their capacity to maintain security in West African waters.

Chris: What from your time in the military, do you think most prepared you for business?

Our business, agriculture investing, is mostly about risk management. Being an entrepreneur in a start-up is even more about managing risk. Across my military career I planned and executed a wide number of high risk evolutions, including special operations assaults, at-sea vessel boarding operations, and air operations. There’s always a fine line between mission accomplishment and losing lives and millions of dollars in equipment. In business, the stakes are usually capital or career-oriented, but the mechanisms for mitigating risk are generally the same.

Chris: How would you define your leadership style?

My leadership style is empower and entrust. I am very comfortable working with remotely located teams, so I’ve learned to trust people to get things done without a lot of supervision. I think most people do their best work and are most fulfilled when they are operating independently without micromanagement. That also means you have to expect them to fail sometimes and continue moving forward.

Chris: What are your 6 Leadership Lessons Businesses can learn from military experience? Please share a story or example for each.

  1. Understand risk to control risk. Most of the time when something goes really wrong, it’s because risk was misunderstood or underestimated. In 2013, when I was at Special Operations Command East Africa, I was on the periphery of an operation called Oaken Sonnet, that involved rescuing U.S. personnel from a besieged airfield in South Sudan during the civil war there. During the approach to the airfield, three aircraft full of special operators were attacked from ground fire and a few of the team members were badly wounded. To make a long story short, planners during the operation did not fully understand the risks involved and questionable decisions were made, resulting in an outcome that most likely could have been avoided. In making business decisions, managers need to think about possible worst case scenarios rather than just focusing on positive outcomes.
  2. Don’t confuse enthusiasm with capability. Everyone wants to win, but not every team is properly equipped to succeed. Getting the right players onboard and resourcing them properly are essential. In the case of Oaken Sonnet, enthusiasm to get the mission accomplished overrode sound planning and risk mitigation measures. If your team is not properly equipped to succeed, then the wise decision may be to not execute.
  3. Lead, follow, or get out of the way. This is an overused phrase, but it’s really true. The best teams in the military I have been a part of learned that if there are personalities or organizational bureaucracy impeding progress, sometimes it is best to just bypass the obstacles rather than confronting them head on. Of course, that’s easier said, than done, especially when a leader’s career might be at risk.
  4. Push your organization’s boundaries. If you don’t make big bets, you can’t win big. If an idea is legal, moral, ethical, and makes good business sense, go for it. Of course if you don’t manage your risk carefully, catastrophes can occur (see above).
  5. The boss isn’t always right, or forceful back-up. Many ship groundings or collisions at sea have been avoided because a navigator or junior sailor spoke up and prevented a ship’s captain from pressing on with a bad decision by supplying him or her with a critical piece of information or recommendation. Subordinates who feel empowered to question a decision can help an organization avoid disaster. On the other hand, can forceful back-up put your job at risk? Unfortunately, yes, there are bad leaders in every organization who feel they are the smartest people in a room or are equipped with the best information when they may not be.
  6. Think differently. In the military, it’s pretty obvious when you run across somebody who has done one sort of specialty or served in one type of unit their entire career. They tend to be pretty linear, inflexible thinkers. People who have a more varied background tend to be more open to new ideas. If you are building a team, look for people who have diverse life and business backgrounds. Our team at Harvest Returns spans three generations, multiple industry backgrounds, and different countries of origin. Together we’re better because of the diversity of thought we all bring to the table.

Chris: The future of many industries rely heavily on millennials and gen-z in regards to consumers and talent. Can you tell us something you or your company is doing to stay ahead with attracting both?

These generations want a flexible work environment. As a start-up, it’s much easier to be flexible on things like work schedules and locations, than it might be in a larger company. They also want to be trained and mentored, because like in every generation, not everyone is fortunate to have solid mentors growing up. From the customer side, the fact that we are a fully digital investing platform is attractive to consumers who grew up fully-connected.

Chris: Can you tell us one person in the world, or in the US whom you would want to sit down and have a drink or cocktail with? He or she might see this. :-)

I’d love to have lunch with President George W. Bush. He just seems like a nice guy to be around.


Authority Magazine

Leadership Lessons from Authorities in Business, Film, Sports and Tech. Authority Mag is devoted primarily to sharing interesting feature interviews of people who are authorities in their industry. We use interviews to draw out stories that are both empowering and actionable.

Chris Quiocho

Written by

Combat Veteran and Pilot by trade. Chris is a 4x Entrepreneur, host of the Jet Set Podcast, and Founder of offland.com

Authority Magazine

Leadership Lessons from Authorities in Business, Film, Sports and Tech. Authority Mag is devoted primarily to sharing interesting feature interviews of people who are authorities in their industry. We use interviews to draw out stories that are both empowering and actionable.