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“Good Leaders Value Diversity Of Ideas and The Input Of Others” with David DeWolf CEO of 3Pillar Global

I had the pleasure of interviewing David DeWolf, CEO of 3Pillar Global, a software-development firm based in Fairfax, VA. David founded his company just 12 years ago and it’s since stretched across 3 continents with nearly 1,000 employees. 3Pillar Global builds customer-facing digital products for some of the biggest brands around, like Carfax, PBS, Equinox, […]



I had the pleasure of interviewing David DeWolf, CEO of 3Pillar Global, a software-development firm based in Fairfax, VA. David founded his company just 12 years ago and it’s since stretched across 3 continents with nearly 1,000 employees. 3Pillar Global builds customer-facing digital products for some of the biggest brands around, like Carfax, PBS, Equinox, and National Geographic.

Thank you so much for your time! What is your “backstory”?

Before I started 3Pillar, I’d worked as an independent consultant as a software developer. Contacts would often ask if I knew anyone else I could recommend to help them out with particular needs. I played matchmaker for a number of companies looking for software developers before someone asked how much they should pay me for the services of one of the developers I recommended. From there, everything grew organically, and quickly. Before I knew it, I had six employees.

It didn’t take long to dawn on me that six people — each with a family, a mortgage, and real responsibilities — were now depending on this business to succeed. I truly embraced my role as the CEO and recognized that I needed to start thinking structurally, not just about our product. That meant finding new ways to delegate work, building a board to advise us, and defining what we wanted our company to be.

Can you share the funniest or most interesting story that happened to you since you began leading your company?

One of the most interesting stories for me happened shortly after we’d made an acquisition in India. Our leadership team there was struggling. There were lots of office politics and people were jockeying for position. There was a lot of conflict between our company culture and the culture they’d known in the past, which was very hierarchical. I’d caught wind of some of the issues they were having, but one trip in particular stands out.

Almost as soon as I got to Noida, I started hearing stories that made me think the situation was even more dire than I’d been led to believe. I cleared my calendar and everything I had on the books that week. I decided to spend it solely with the leadership team to help them get to the bottom of the issues they were having. As we started to dig in, it became clear that one of the big issues was a lack of communication. People were just not willing to have hard conversations with one another.

So I gathered our leadership team in a room, and I told them that we had to get more comfortable being open and honest with one another. I asked them to go around the room and each tell me one thing that they appreciated about my leadership and one thing they thought really held my leadership back. I asked our head of HR to go first and she was scared to death. I think it took her 10 minutes to get something out of her mouth. But she did, and then we went around the room and got feedback from everyone on my leadership. Then we did the same for each and every person in the room. It helped teach us all how to have a safe, non-political environment where you can really share your thoughts, feelings, and opinions.

What is the top challenge when managing global teams in different geographical locations? Can you give an example or story?

3Pillar has offices on three continents and employs nearly 1,000 people, so we have to work efficiently and cooperatively no matter where we’re located. I think one of our keys to success in that regard is figuring out what to delegate, avoiding micromanagement.

We hire amazing people, but we don’t hire them just so we can constantly peer over their shoulders. If one team is sending an assignment to another team, especially if it’s being sent across an ocean, we want to make sure that the constituent components can be completed where they’re at.

So give your teams the autonomy they need to complete projects without unnecessary oversight.

What advice would you give to other CEOs or founders to help their employees to thrive?

I try to lead with humble confidence, and I’d encourage other business leaders to take the same approach. This means having the confidence of your convictions but acknowledging that as leaders we aren’t untouchable, we aren’t infallible, and we are going to make mistakes.

People can detect authenticity — or the opposite — much better than they are given credit for. Show your team your true colors. Show them your passion and your drive, and own up to mistakes when you make them. Good employees will match your enthusiasm and join you in the trenches if you’re willing to lead the way and be yourself with them.

Most times when people quit their jobs they actually “quit their managers”. What are your thoughts on retaining talent today?

We place a huge emphasis on leadership training at 3Pillar for precisely this reason. The cost of hiring and training new employees is so high that you have to wonder about any company that doesn’t place a premium on keeping employees satisfied.

I’m a big believer in the concept of servant leadership. We want our leaders to be approachable, to be fully invested in helping the people they work with get where they want to go in their careers, and to be involved in helping them get there.

One key point that we also look to reinforce every chance we get is that there’s a very real difference between leading and managing. It’s a subtle difference but it’s a very important one. Leading is about painting a vision of a future that inspires others to action. That’s a core tenet of what we try to teach in our leadership training programs.

Based on your personal experience, what are the “5 Things You Need To Know To Successfully Lead a Team?” (Please share a story or example for each, ideally an example from your experience.)

We have a Leadership Manifesto at 3Pillar that lays out five qualities we expect all our leaders to demonstrate. So rather than spelling out 5 things to know to lead a successful team, I would lay out 5 qualities I think it’s important for any leader to display. To truly succeed as a leader, I think you must be:

  • Compassionate — Leaders must genuinely care about those they lead. They seek to understand others and they demonstrate this understanding through their interactions and actions. They act in the best interest of others and sacrifice themselves for the good of the team. They see their leadership as a responsibility to serve, not a privilege to take advantage of. They do not rely on title or authority for effective leadership.
  • Collaborative — Leaders value the input of others and diversity of ideas. Their humility creates an environment where ideas are shared openly and treated with respect. They seek to understand and genuinely consider what others are intending to communicate before they dismiss or embrace an idea. They make timely, firm decisions that integrate a variety of perspectives in order to drive desired business outcomes. They are open to re-evaluating decisions when new facts or circumstances warrant.
  • Responsible — Leaders take total responsibility over their team’s success or failure. They own their decisions and the actions of the members within the team. They continually inquire “what is it about my own leadership?” that caused this result. They recognize their limitations and rely on the team to compliment their strengths. They hold others accountable and encourage extreme ownership within their team.
  • Courageous — Leaders set aggressive goals and challenge others to stretch and grow. They set aspirational objectives and pursue them passionately. They take risks and rise to the occasion. They do not back down from a challenge or yield in the face of adversity. They face their fears, share their fears, and overcome their fears. They make hard decisions and have tough conversations. They set the highest standards of character, behavior and execution and demand exceptional results.
  • Developmental — Leaders embrace a growth mindset. They recognize the ability of individuals and teams to learn and grow. They invest in growth, for themselves and others, across a variety of performance areas. They focus on improving their own skills, evolving their leadership and expanding their business acumen. They teach others to lead and refine their craft. They provide opportunity for others to rise to the occasion.

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.

Leading with humble confidence. This means leading with humility, of course, but it’s more than that. It also means leading for the benefit of others and taking a real interest in seeing others succeed. I’d like to see more genuine, authentic leadership where those who are in positions of power truly have an interest in seeing their charges succeed and aren’t just in it for themselves.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

Leaders eat last. It’s the title of Simon Sinek’s 2014 book on teamwork, and I’m a big believer in the concept. Leaders who are more concerned with the well-being of those they lead than they are with their own accolades are the ones who are going to be the most successful — and the most fulfilled — in the long run.

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