Bob Dougherty of Buckle: “Iterate quickly and capture lessons learned”

Take a “tactical pause.” By definition, a crisis means something unexpected has occurred, something in your assumptions or plans was wrong. It’s your job to figure out what. Give yourself the space to considerthe situation and gather additional information before moving forward. There is no set duration for a tactical pause — it could be as short […]

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Take a “tactical pause.” By definition, a crisis means something unexpected has occurred, something in your assumptions or plans was wrong. It’s your job to figure out what. Give yourself the space to considerthe situation and gather additional information before moving forward. There is no set duration for a tactical pause — it could be as short as a few seconds, or as long as a few weeks. Most crises develop slower than they first appear. You have more time than you think.

In this interview series, we are exploring the subject of dealing with crisis and how to adapt and overcome. The context of this series is the physical and financial fallout that resulted from the COVID 19 pandemic. Crisis management is one characteristic that many successful leaders share in common, and in many cases it is the most important trait necessary to survive and thrive in today’s complex market.

I had the pleasure of interviewingBob Dougherty.

Bob Dougherty is the director of driver advocacy at Buckle, provider of a financial services platform that focuses on insurance, credit and advocacy for the gig economy.

Bob is a career Army Infantry officer and veteran. From 2015 to 2019, he served on active duty as a company grade officer with both general purpose and special operations forces, deploying twice in support of combat operations in Iraq and Afghanistan. He currently serves as a Military Academy Liaison Officer with the United States Military Academy at West Point.

Bob has a bachelor’s degree in political economy from Princeton University and drives part time for Uber, Lyft, and Postmates.

Thank you so much for doing this with us! Before we dig in, our readers would love to get to know you a bit. Can you tell us a bit about your childhood “backstory”?

I was born and raised in a small town in Pennsylvania to wonderful parents and a family of service members, educators, engineers, and entrepreneurs. From a young age, this legacy of service inspired me to put the needs of others above my own. A mural on my grade school auditorium read that memorable challenge from John Kennedy’s inaugural address, “Ask not what your country can do for you — ask what you can do for your country.” I didn’t pay nearly enough attention during school assemblies, because my eyes were always drawn back to that mural. I knew then that I wanted civic action and service to define my life.

And what are you doing today? Can you share a story that exemplifies the unique work that you are doing?

I have the honor and privilege of leading Buckle’s advocacy program, which serves our customers (whom we call Members) with support programs, resources, and representation to help them achieve economic freedom.

One of the more meaningful initiatives for me is our response to the COVID-19 pandemic. Using our technology and data, we helped hundreds of our Members access unique relief programs available to them as sole proprietors. This program — which we did on an entirely pro bono basis — resulted in more than 3,000 dollars of incremental federal aid per Member, which is truly transformative for a family trying to make ends meet.

Can you tell us a bit about your military background?

I’m a 4th generation service member. My great-grandfather served with the AEF in World War I; my grandfather at Outpost Harry in Korea; my father as a naval science officer. There is definitely a tradition of service for the family and I took the bait: hook, line, and sinker.

After completing ROTC during my undergrad, I commissioned as an active duty infantry officer in the U.S. Army. I completed my basic officer training, Ranger School, and airborne training at Fort Benning, GA before joining the 82nd Airborne Division at Fort Bragg, NC, where I served as a platoon leader and company executive officer, including a 2017 deployment to northern Iraq in support of Operation Inherent Resolve. After returning home, I had the great privilege to be assessed and selected for service with the 75th Ranger Regiment and deployed to Afghanistan in 2018–2019 in support of Operation Freedoms Sentinel. I transitioned into the reserves in 2020 and currently serve as a Military Academy Liaison Officer for the United States Military Academy at West Point.

Can you share the most interesting story that you experienced during your military career? What “take away” did you learn from that story?

During the counter ISIS offensive in northern Iraq during 2016–2017, the coalition was having significant issues with ISIS drone attacks. Imagine that small little quadcopter that you bought off Amazon for your nephew’s birthday, but rigged up with an explosive chemical payload and flying 50 mph into concentrations of coalition troops. At the height of the attacks, we were experiencing double digit attacks daily. Using the normal procurement process, we tried iterating through a number of defensive countermeasures of varying efficacy, most of which were overly burdensome for soldiers, ineffective, or extremely costly. Ultimately, the solution came when DJI (the maker of the most common brands of these drones) simply issued an over the air software update which prevented its drones from flying in certain geofenced locations (like northern Iraq). Overnight, the number of drone attacks dropped from dozens per day to only a few every week.

These attacks were a complex problem — something novel, with a number of what Don Rumsfeld would call “unknown unknowns” — but we tried to solve it using the same systems, processes, and “if, then” playbooks we used for the complicated problems we had plenty of experience dealing with. When faced with a problem or crisis, stop and try to identify if the problem is complicated or complex. If it is complicated, rely on systems, processes, and experience — find the subject matter experts and rely on them to navigate the situation. But if the problem is complex, generally the “experts” are no better positioned to find the solution than the novices. Rely on creative and innovative problem solvers who think outside the box.

We are interested in fleshing out what a hero is. Did you experience or hear about a story of heroism, during your military experience? Can you share that story with us? Feel free to be as elaborate as you’d like.

Uncommon circumstances produce uncommon valor, but the people who inspire me most are the quiet professionals — the ones who show up every day and consistently do their job without praise or acclaim. Most of their names will never find their way into a newspaper article, but they are standing by across the world defending our country and those who can’t defend themselves.

Based on that story, how would you define what a “hero” is? Can you explain?

A hero is someone with the courage to act for the sake of others despite personal sacrifice. Courage is the first of human qualities, because it is the quality which guarantees the others.

Do you think your experience in the military helped prepare you for business or leadership? Can you explain?

At a very young age, service members are given significant responsibilities for the lives of their teammates, for millions of dollars of equipment, and — once all other options have been exhausted — the legal and legitimate use of force against their fellow man. These are serious matters, serious enough to paralyze someone to inaction. Yet, service members don’t have the benefit of “sitting out the game.” They are constantly forced in training and combat to decide and act. Do you go left or right? Shoot or don’t shoot? The sheer volume of repetitions in highly diverse and uncertain contexts builds fundamental attributes. Once formed and strengthened, these easily transfer from managing training to managing a P&L; from planning a major operation to planning a new product rollout. Plain and simple, the military is a leadership factory.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story?

My wife. Military spouses don’t volunteer to serve, yet their sacrifices are just as great. Thanks to her and all military spouses, without whom we couldn’t possibly do the job.

Ok, thank you for all that. Now let’s shift to the main focus of this interview. We would like to explore and flesh out how to survive and thrive in crisis. How would you define a crisis?

A crisis is an unexpected and quickly developing event, characterized by high risk and uncertainty.

Before a crisis strikes, what should business owners and leaders think about and how should they plan?

The challenge with “preparing for a crisis” is that, by definition, crises are unexpected; if not entirely, then at least in the specific context. So how does one plan for the unexpected? By (1) building a system of modular and responsive processes, rather than a defined set of playbooks and (2) populating that system with a team selected on fundamental attributes, rather than specific experiences or skills.

Interestingly, it is rarely the actual output of a planning process that equips you for success. Von Moltke the Elder said it well, “No plan survives first contact with the enemy.” Rather, organizations that are good at the process of planning can rapidly improvise in uncertain circumstances and thereby comparatively outmaneuver their competitors. I’ve found John Boyd’s concept of the “OODA loop” and Nassim Nicholas Taleb’s concept of “anti-fragile” to be instructive in this and their materials well worth the read.

There are opportunities to make the best of every situation and it’s usually based on how you frame it. In your opinion or experience, what’s the first thing people should do when they first realize they are in a crisis situation? What should they do next?

Take a “tactical pause” and question your assumptions.

What do you believe are the characteristics or traits needed to survive a crisis?

Calm, improvisational, confident, and decisive. We are inherently social creatures and subconsciously take our cues from the leaders and outlets we trust most. If the leader projects calm and confidence, the organization will follow.

When you think of those traits, which person comes to mind? Can you explain why you chose that person?

I think of Winston Churchill. He became the Prime Minister of Britain the same day that Nazi Germany launched their blitzkrieg against France and the Low Countries. Over the remainder of 1940, Churchill steeled his country in the face of overwhelming odds and rallied them to eventual victory, in the process delivering some of the finest oratory in history.

Did you have a time in your life where you had one of your greatest setbacks, but you bounced back from it stronger than ever? Can you share that story with us?

Failing a phase of Ranger School. When you’re a Ranger student, you want few things more than to earn your Ranger Tab and graduate in as short a time as possible. But every failure is an opportunity for growth. We can choose to let setbacks crush us, thinking ourselves incapable or without value; or we can choose to let them teach us, providing the necessary feedback to fuel new growth. With a different approach and newfound determination, I would later pass the course.

Here is the main question of our discussion. Crises not only have the potential to jeopardize and infiltrate your work, but they also threaten your emotional stability and relationships. Based on your military experience, what are 5 steps that someone can take to survive and thrive in these situations? Please share a story or an example for each.

  1. Take a “tactical pause.” By definition, a crisis means something unexpected has occurred, something in your assumptions or plans was wrong. It’s your job to figure out what. Give yourself the space to considerthe situation and gather additional information before moving forward. There is no set duration for a tactical pause — it could be as short as a few seconds, or as long as a few weeks. Most crises develop slower than they first appear. You have more time than you think.
  2. Assess and anticipate. When a crisis occurs, everything seems like a top priority and everyone wants answers. Don’t let the noise distract you — figure out what needs to happen now, what can wait until later, and what new challenges are likely to develop as the crisis matures.
  3. Make the best decisions you can with the information you have. After you figure out #3, don’t let the natural desire to gather more information prevent you from making a decision. A good plan, violently executed now, is better than a perfect plan next week.
  4. Communicate precisely. Crises are defined by uncertainty, and the natural desire for information often leads people to speculate. Fight that urge — communicate exactly what you know, what you don’t, and what your next steps are. Assume whatever you say will be disseminated broadly and taken as gospel. It’s hard to put that toothpaste back in the tube.
  5. Iterate quickly and capture lessons learned. Get the “minimum viable product” out the door, then iterate quickly — there is no better feedback than reality, and the lessons you learn from reality need to feed your next crisis response.

Ok. We are nearly done. You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

Bring an end to poverty. Many of the world’s ills are symptoms of this fundamental issue, rather than separate problems themselves.

We are blessed that some very prominent leaders read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this, especially if we tag them 🙂

Henry Kissinger. Talk about someone who has had the ear of American decision makers for almost six decades now and continues to influence world affairs directly through his personal relationships and indirectly through his writings and philosophy.

How can our readers follow you online?

Thank you so much for these amazing insights. This was truly uplifting.

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