Jack Butcher Of Hagerty: Five Things You Need To Be A Highly Effective Leader During Turbulent Times
An Interview With Fotis Georgiadis
Keep checking for tunnel vision and pathological certainty. Often, the first issue or solution isn’t always the right one to pursue. In COVID, we ran experiments. We found that the first approach often morphed into something else, something better and more effective. We kept checking our experiments and adjusting them. We did this with trading partner communication and engagement. It resulted in deeper relationships even during COVID.
As part of our series about the “Five Things You Need To Be A Highly Effective Leader During Turbulent Times”, we had the pleasure of interviewing Jack Butcher, President of Hagerty.
Jack is President of Hagerty, leading its global risk & insurance services businesses. He is also a member of the firm’s Executive Council and serves on the Board of Directors of Hagerty International Holdings, Ltd.
Prior to his current role, Jack was Senior Vice President of North American Markets at Hagerty, leading the build-out of the company’s regional strategy. Before joining Hagerty, Jack’s over 33-year career includes leadership positions in the commercial insurance and commercial transportation industries. As a Managing Director at Marsh & McLennan (Marsh, Inc. and Marsh & McLennan Agency, LLC), Jack led a number of Marsh’s businesses in Baltimore; Washington, DC; New York; and Chicago through growth and operational performance improvements. In his role as Executive Vice President & COO at TransForce in Alexandria, VA, this emerging-growth company saw a period of early-stage venture capital raises and rapid organic as well as acquisition growth. Today, TransForce Group is a leading provider of education, employment, and safety solutions to motor carriers across the U.S. and Canada.
Additionally, Jack has over twenty years’ experience as an advisor, board member, and investor to early-stage companies. He serves as a director of a rapidly growing insurtech firm and is an Advisor at a venture capital firm. In addition to his for-profit advisory work, Jack serves on several not-for-profit boards.
A magna cum laude graduate of the University of Richmond, Jack attended multiple executive education programs at the Harvard Business School. He actively serves his local community as a first responder and is an avid mariner and car enthusiast.
Thank you so much for your time! I know that you are a very busy person. Our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?
Thank you for having me here. Coming out of university, I was (and remain) insatiably curious about the world and about business. A mentor told me to search for jobs where it was my business to be an expert in other people’s business. That left me interviewing with one U.S. intelligence agency, with banks and with insurance companies. Since I needed a job, I took the first offer I received which was from a commercial insurer. Since then, I’ve enjoyed a fun and rewarding career across three different industries — in a start-up, a Fortune 500 company, in turnaround assignments, and in thriving high-growth enterprises. I’ve been a very lucky guy.
Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lessons or ‘takeaways’ you learned from that?
Funny now…but not-so-funny then. I have always enjoyed studying businesses and teams within businesses — understanding what makes them tick. When I was about a year into my first assignment and full of all the answers, my boss and I had a disagreement about a structural decision he needed to make with my input. Equipped with case studies and foundational textbook proof of my case, I went into his office, one day, with a textbook to show him how right I was. His reaction can only be described as animated (and loud). It was not at all funny at the time, but even to this day, he and I remain very close friends and we laugh about that. What did I learn? A few things: First a “tie-breaking” point with your boss generally goes to your boss. Second, the world does not operate in a tidy, textbook-like fashion. Third and finally, don’t wave a book around in someone’s face and expect it to be well-received. It’s funny to reflect on that hamstring pull, and I’m glad I learned those lessons early in my career. Unfortunately, many don’t.
None of us can 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?
I would go a step further and suggest that “no one can achieve success without a lot of help from a lot of different people along the way.” The best leaders I have worked with and studied have surrounded themselves with and listen to smart and insightful people. For me, these were my bosses, my peers, people who worked for me, my personal ad-hoc “personal board of advisors.” These are the folks who write a success recipe. Insights and advice can come from unorthodox sources as well. When I was 25, I made the occasional visit to a local shoe-shine stand. As time went on, I didn’t go for the shine anymore, I went for perspective. “Butch the shoeshine guy” was 92 years old and had more energy and lifetime experiences and hard-knocks than I could imagine: A battle-hardened US Navy World War II veteran with 26 grandchildren. He was one of the happiest, most outgoing people I had ever met. He was happy to be alive and had led a tough life. He was loaded with sound advice and life perspectives. Some of his gems: “Remember, no one gets there on their own.” And when I was complaining about something at work, he’d quip: “Hey! Always remember, you’re one of the lucky ones.” And I’ve never forgotten that. The point is, great insight and perspectives comes at us from unexpected sources, be alive to them all.
Extensive research suggests that “purpose driven businesses” are more successful in many areas. When your company started, what was its vision, what was its purpose?
We have always been entirely purpose driven — mission driven. Our mission is to “save driving and car culture for future generations.” That remains the centerpiece of the investments we make, the people we hire, and the initiatives we undertake. It’s not a simple slogan. We live it: For example, we teach hundreds of teenagers how to drive manual transmissions each year (on our fleet of collector cars…and they love it!). Our employees have access to an automotive restoration program, where they restore a collector car and get it on the road. We have committed millions over the years to preserve automotive heritage and history, including the creation of the Historic Vehicle Association (now part of Hagerty Drivers Foundation,” whose signature effort is, in partnership with the U.S. Department of Interior and the Library of Congress, annually adding vehicles to the National Historic Vehicle Register, which documents the invaluable history of our automotive past.) The net effect of all these efforts? It brings passionate people to work every day to serve our members and partners who share the same passion for the mission, and they feed off each other.
Thank you for all that. Let’s now turn to the main focus of our discussion. Can you share with our readers a story from your own experience about how you lead your team during uncertain or difficult times?
I would start by making an important distinction, here, between uncertain times and difficult times. Uncertainty is simply a daily reality — the environment business operates in and leaders lead through every day — it’s a constant and has been omnipresent long before I got into business and requires us to continually learn and evolve as leaders. Difficult times, on the other hand, are episodic and can range from moderate problems and challenges up to stock-price moving or organization-threatening crises. These times are [hopefully] not a constant, but leaders better be ready to confront them along that spectrum at some stage of their tenure. They are also learning opportunities, but not always in the most pleasurable sense.
I’ll focus on one crisis that befell an organization I worked for. The company became the subject of a regulatory investigation which caused the stock to lose over $9 billion of market capitalization over just two days. Employees were fearful and preparing resumes, clients were uncertain and seeking alternative providers, plaintiff lawyers were lining up, and competitors were licking their chops over all this. It was a business crisis by any definition. In the ensuing weeks and months, we overcommunicated with our stakeholders. We were transparent with what we knew and what we were doing to cooperate in the investigation, what we were learning from it, and what we were doing to fix it. It took several years to resolve and to demonstrate that our deeds matched our stated intent. Particularly in the early hours and days of the crisis, it was vital that we didn’t fill the air with “corporate-speak,” or quixotic platitudes about how all was going to be OK. Early-on, it was uncertain, and we were honest with employees about that. The unvarnished truth was not easy for them to hear at the time, but they trusted we were dealing plainly with them even if it was hard to hear. Over time — a long time — we earned back the confidence of regulators, pride of employees, trust of clients and approval of shareholders. That brand is very strong today.
In a crisis, it’s important to move toward the sounds and sights of chaos and fear, then lead honestly and steadily through it. It’s what leaders do.
Did you ever consider giving up? Where did you get the motivation to continue through your challenges? What sustains your drive?
Give up? No. Strangely, the opposite happened. I found exhilaration, energy, mounting fortitude, and determination as we waded more deeply into the crisis together. To me, it’s easier to lead when things are going great. However, leaders (and strong leadership) are most relevant when things are tough and uncertain — when people need steady and thoughtful direction and action. I also learned so many things from what the company asked me to do during this time, and it opened-up job promotion opportunities I never expected as a result. So, yes, giving up would have been easier, and I would have never forgiven myself.
What would you say is the most critical role of a leader during challenging times?
Several are vital, but if I picked just one: Steadfastness. If the pilot is freaking out, what will the passengers think? If you are steady, mindful and focused, you will make better decisions, engender greater confidence, draw more people to you and to help, and you will lead more mightily through the hard stuff.
When the future seems so uncertain, what is the best way to boost morale? What can a leader do to inspire, motivate, and engage their team?
A few things are important in my view: First, be authentic. People need to see you as human. They will test you to see if you are the “real deal” or a pretender. Next, be honest. People sense it when someone tries to sell them false security and unbounded rah-rah platitudes. Don’t misunderstand me, I am by nature an eternal optimist and I signal that. I believe good things can happen if you do the right things. That said, when people are uncertain or even scared, they are searching harder to find real humanity and truth in their leaders.
During the early days of COVID, things were uncertain. I was asked on a “townhall-style” employee call: “Can you guarantee we will get our bonuses this year?” My answer: “No. I can’t guarantee that.” There was silence. But after that call, I got dozens of emails and calls from people thanking me for my honesty and for not trying to sweet-talk them into a false comfort. The good news: business recovered and we were ultimately able to pay those bonuses.
Next, communicate frequently and transparently — and don’t stop. Finally, stay on-mission. Napoleon Bonaparte, when asked about the secret to his military prowess, said simply: “If you set out to take Vienna, take Vienna.” Be true to your purpose in the first place. Your team will so appreciate that the purpose they joined endures. If people can go home at night knowing they can trust that what you tell them aligns with what you do, chances are they’ll be back tomorrow. Employees and customers, alike.
What is the best way to communicate difficult news to one’s team and customers?
Be straight. Don’t dance or sugar-coat. Just go there. Borrowing from Churchill, he said that if you are going through hell…keep going. He was right. Power through the issue and get to the punchline. There will be time to fill in the background and answer questions later. But “soft” or indirect messaging is not the stuff of leadership.
How can a leader make plans when the future is so unpredictable?
Leaders have no choice. The future is and has always been uncertain — since time immemorial. That’s what they pay us for. Great leaders who embrace and leverage uncertainty are always in high demand. Thriving and growing in an unpredictable world is a hallmark of great leadership. How many predicted 24 months ago that the entire world would close for months on end. Who was ready for that? Yet, look at the amazing adaptations so many organizations made. From proprietors to Fortune 50 companies to hospitals to airlines to your own businesses. So many were able to adapt and overcome. It was inspiring. The evolution of nature and of business tells us that it’s not the mightiest of species that survive, rather it’s the most adaptable.
Is there a “number one principle” that can help guide a company through the ups and downs of turbulent times?
Stay fiercely on-mission and true to your culture. Over these past two years we’ve seen cultures pressure-tested. Some galvanized and grew, while others sadly shattered. It’s been a fascinating study to watch and learn from the ones that flourished.
Can you share 3 or 4 of the most common mistakes you have seen other businesses make during difficult times? What should one keep in mind to avoid that?
It’s not fun to talk about, but it is vital to talk about. There are many, but, sure, I’ll pick three. First mistake: believing your past success will automatically carry you through. Pathological certainty is hubris and it’s dangerous at any moment, but particularly in difficult times. Second mistake: discounting threats and risks and failing to plan “what if” contingencies for them. Finally, I see teams grasp at “silver bullet” thinking — the idea that if we “just do this one thing, we’ll be fine.” I rarely see a business challenge or a surgery or a flight go well because of just one thing. It’s always a mosaic of interdependencies that weave together to drive a positive outcome. Jim Collins talks brilliantly about some of this in his book “How the Mighty Fall.”
Generating new business, increasing your profits, or at least maintaining your financial stability can be challenging during good times, even more so during turbulent times. Can you share some of the strategies you use to keep forging ahead and not lose growth traction during a difficult economy?
Again, stay on mission. As we saw these past months, if market conditions are tough for you and your enterprise, they may be tough for your customers and partners as well. After you have focused on the well-being of your own employees, stay close to customers and partners. Be there for them. Stay focused on helping them overcome their challenges. Stay close to their needs and keep innovating for them. Keep trying, as Steve Bezos puts it, to invent on their behalf. These are the moments your stakeholders are most likely to lean on your mission and value it, so its needs to remain sturdy.
These times also remind us to stay close to KPIs and remain open to new ways of operating. For my company, an example is that we learned about and modified new ways to utilize physical spaces/offices and who needs to be in those spaces and when. We also learned how to communicate more broadly and more efficiently by leveraging technology and building new rhythms and habits.
Ultimately, don’t wait until things get back to “normal.” Across my lifetime, things have never gone back to “normal.”
Here is the primary question of our discussion. Based on your experience and success, what are the five most important things a business leader should do to lead effectively during uncertain and turbulent times? Please share a story or an example for each.
- Confront reality. Never waste a crisis. When COVID hit our organization, we admitted openly to our team members in the moment that we were unclear about the path of the pandemic and where it was going to take us, but that we were positioning for a number of possible outcomes. They believed what we told them going forward because we didn’t try to do what too many organizations do by trying to create false security. No one at the time in the world of business knew how this would all unfold. But here is what I did know: If you shoot straight with people and are transparent with where you are — together — and share what you’re doing about it, they will trust you more. Despite the challenges of the pandemic, we kept planning for contingencies — long lockdowns, prioritizing ongoing operations, reducing non-essential operating costs. A word about the term “non-essential.” At no time are people non-essential. Too many leaders don’t get that. We went after non-people operating costs and found new methods of getting things done more efficiently. By doing that, we did not lay-off or furlough anyone. The wonder of crises — they make you a better and smarter leader for your organization, if you don’t waste the moment.
- Surround yourself with diverse and candid counsel. Our team gathered in the early stages of the lockdown and we traded ideas about how we needed to react and adapt. We invited-in cross-functional points of view beyond the core team to generate more creative ideas. Cyrus the Great (the famed first leader of the Persian Empire circa 550 B.C.) had a powerful saying: “Diversity in counsel; unity in command.” I love that. You need diverse voices and perspectives around you all the time — including people who do not agree with you. “Creative abrasions” are the best scrapes to get. You debate, decide and do — together. You move decisively as one. When people see that, it strengthens their trust in you and resolve to stand fast and work with you.
- Communicate reality and steps you are taking — frequently. One result of COVID was that we launched new rhythms of team communications — weekly video and routine live “townhalls” that will survive well into the future. We also created a “What’s Up Doc[ument]”. The What’s Up Doc is a monthly compilation of one-page summaries from each leader in the organization, shared across to every other leader. It includes a quick-hit summary of what’s up? What’s next? And what’s stuck or standing in your way? Originally intended as a triage approach, it’s now a routine status summary we use to help each other out. We are more connected to a more distributed workforce than ever. During the lockdown, we also launched an intensive (and fun!) member [customer] outreach campaign that engaged our team (who appreciated the distraction) and it created new dialogue with customers, partners, and prospects at a time when they, too, appreciated the outreach and care (they were anxious, too, so it created an affinity experience with them.) The results? We initiated more collaboration and new paths of revenue growth that were not anticipated. Check in with your stakeholders — relentlessly.
- Use both a microscope and a telescope. In virtually all times of turbulence or crisis, our teams needed to keep watch for signs and signals of near-term performance and change. The microscope (constant customer and partner contact plus a watchful eye on KPIs) helps there. As a colleague says: “operate in the weeds.” The telescope keeps one eye on the mission and the horizon. I have found that in troubled times, near term noise can drown out or distract a team from the main mission and take an ear off the long-term track. When that happens it creates brand confusion, blindness to emerging trends and more trouble. Once you are satisfied that your mission is still relevant in the marketplace, double-down on it, and scan vigilantly for emergent trends.
- Keep checking for tunnel vision and pathological certainty. Often, the first issue or solution isn’t always the right one to pursue. In COVID, we ran experiments. We found that the first approach often morphed into something else, something better and more effective. We kept checking our experiments and adjusting them. We did this with trading partner communication and engagement. It resulted in deeper relationships even during COVID.
Can I add a 6th? Lather-rinse-repeat, even outside of tough times. These are habits and disciplines for routine times too.
Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?
Picking one is the toughest thing you’ve asked me today. I love so many, but here’s one: “If you never ask questions, you be seldom correct, but never in doubt.”
This one ties together so much of what we’ve talked about today. Particularly in turbulence, it’s easy to get tunnel vision, or hunker down. Under stress, leaders can fall prey to withdrawing into what they already “know” at the expense of reaching out for what other people or the market knows. Of course, a leader is ultimately accountable to decide and take action, and it can’t all be about “group think.” What I’m talking about, here, is that pathological certainty trap we discussed earlier. I am surrounded by really smart people, and shame on me if I don’t seek their counsel. Also, keep listening hard for the quiet voices. Sometimes they’re the ones that know the unforeseeable will happen. So, listen to the data, the marketplace, stakeholders and voices loud and quiet.
That quote speaks to me in uncertain times and in all times.
How can our readers further follow your work?
I hope we can follow each other’s work. I have much to learn from your readers. We all seem to confront the same opportunities and challenges, simply in different contexts. I try to share concepts and learnings (and hard lessons!) with business colleagues and peers on LinkedIn. I also have the privilege of spending time with other organizations where I can trade ideas and approaches with leaders. I wish all your readers good health and good fortune. Thank you for having me.
Thank you so much for sharing these important insights. We wish you continued success and good health!
Jack Butcher Of Hagerty: Five Things You Need To Be A Highly Effective Leader During Turbulent… was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.
