The Evolving Leader

For the final episode of season 1, we look back at some of the common threads and leadership themes that we heard from numerous guests over the course of the season. Among those were the importance of: People. Effective leaders truly care about investing in and developing the individuals and teams that they lead. They don't see them as cogs in the machine, or assets that can be easily replaced. Humility. As David recounts from the leadership classic Good to Great, the difference between level 4 and level 5 leaders is humility. The best leaders know that it's not all about them, and they think and act accordingly. Being coachable. It can be easy to fall into the trap of thinking you have all the answers or don't need any help when you're put in a position of leadership. For leaders to continually evolve, they must also find ways to get feedback and work on their own weaknesses. We also ask David to look into his crystal ball to see where he thinks he (and 3Pillar) will be in 5 years. The answer? Tune in to find out... Also listen to hear us address an elephant in the room. There is another podcast called (The Evolving Leader). And it's quite good. If you've made it all the way to the end of Season 1 with us, you may want to give it a listen to pass the time until our next season. You can also watch the (full interview of episode 10 on YouTube).

Diversity — of thought, experience, and opinion — ultimately forges stronger leadership teams and companies. Tune in to this episode to hear: Why it's always good to have tension between visionary leaders and operational experts who will be responsible for helping bring the vision to life How The Product Mindset went from an idea David had for a book one night at 2 AM to a reality, complete with a stage appearance at CES, a traveling breakfast series, and a series of workshops Why the 3Pillar value of "open collaboration" doesn't equate to blanket agreement on everything, and a healthy amount of debate is actually good David DeWolf talks with Heather Combs to unpack these topics and more. Heather served in several C-level roles over the course of 5 years at 3Pillar before recently departing to become CEO of (StraighterLine). StraighterLine is a student success and college readiness company focused on helping colleges and universities improve retention and admit more college-ready students.

Acquisitions are an important, potentially vital tool that evolving leaders may well need to use at some point in their leadership journey. Along with acquisitions, however, come an entirely new set of leadership challenges. Think of the acquisition as the wedding day, and "real life" as everything that follows. David DeWolf talks with Dan Henderson, 3Pillar Global's Head of Corporate Development and M&A, about how acquisitions can fuel a company's growth and what to look out for when considering acquisitions. Among the topics David and Dan discuss on this episode are why: You should never fall in love with the deal when looking at acquisition targets One criterion when considering acquisition targets should be the strength of the culture the leaders have created It has never been more true or applicable that the world is flat Leaders should look for complementary cultures that can mesh well with their company's existing culture Prior to 3Pillar, Dan's roles included serving as Investment Director at (CIT GAP Funds), where he managed a portfolio of investments in high-growth tech and life-sciences companies based in VA. The 26 companies in his portfolio represented hundreds of millions of dollars in combined enterprise value. You can watch the (full conversation with Dan Henderson on YouTube).

For any leader of a growing company, there comes a time when cultivating your culture through osmosis just doesn't cut it any more. Whether it's because you're adding more team members, expanding to new locations, or a combination of both, there will come a time when you have to be purposeful and intentional about what kind of culture you want your organization to have. David DeWolf and 3Pillar's Chief People Officer, Jamie Whitacre, discuss some of the ways they've worked to carefully craft and scale 3Pillar's culture as the company has grown to 2500 team members in 9 countries. Just a few of the topics David and Jamie cover are: Why ensuring there's a shared understanding of expectations throughout an organization is a must The importance of frequent communication that recognizes and rewards those who actively live your values How 3Pillar's attention to culture pre-pandemic has helped the company accelerate its growth trajectory during the pandemic David and Jamie also take time to discuss Jamie's own evolution as a leader. Today, she is 3Pillar Global's Chief People Officer. Twelve and a half years ago, she joined 3Pillar in an Accounting role as her first job out of James Madison. She quickly switched to Talent, and Jamie has repeatedly risen through the ranks at 3Pillar in no small part because she understands the important role culture plays in attracting and retaining some of the best talent in the world. You can watch the (full conversation with Jamie Whitacre on YouTube).

Mark Timm joins David DeWolf to discuss the importance of mentorship in evolving one's leadership abilities, as well as how to find the right mentors for each season of your life and career. As Mark says during the episode, "The world is divided into halves. The haves have mentors; the have nots don't." Tune in to this episode for more on why mentorship is such an imperative for leaders to continually grow. You'll hear about the role mentorship has played in the evolution of two successful business leaders who have served as mentors to one another and were first introduced by a mutual mentor, Michael Hyatt. Mark Timm is co-author of the book (Mentor to Millions). He co-wrote the book with Kevin Harrington, one of the original sharks on the hit TV show Shark Tank and one of Mark's most influential mentors. Mark and Kevin were both mentored by the legendary author and speaker Zig Ziglar.

Alan Stein, Jr., keynote speaker and author of the recently released book (Sustain Your Game), joins 3Pillar Founder & CEO David DeWolf to talk about the importance of mastering the fundamentals of leadership. Without nailing leadership basics like building trust, developing mutual respect, communicating effectively, and being responsive to a fault, any leader will struggle to take his or her leadership game — and the teams they are charged with leading — to the next level. Alan shares stories from his decades in and around the game of basketball that any leader can learn from as they seek to bring the right mindset to the workplace and beyond. Tune in to hear why, in this age of infinite distractions, it's more vital than ever to "be where your feet are" and develop the capacity to focus on the next play, no matter what has happened in the recent past. You can watch the (full conversation with Alan Stein, Jr. on YouTube). You can learn more about Alan's latest book, Sustain Your Game, at and you can visit his website at

Jennifer Stanford joins David to talk about the necessity of leaders developing their own emotional intelligence. We discuss why self-awareness; authenticity and psychological safety; and a willingness to continually work on oneself are key cornerstones of development for anyone in a leadership position. For David, learning that authenticity was just as much a necessary character trait for leaders as charisma was an eye-opening realization. David and Jennifer mull over whether there is such a thing as a natural-born leader and discuss why true leadership means leading people up, down, and across, not just down. (Jennifer) is famous within 3Pillar for her company's Identity Mapping and the 4 Ways assessment, which helps teams understand one another better, collaborate more effectively, and more rapidly develop the all-important dynamic of trust within teams. You can also (tune in to the full episode with Jennifer Stanford) on YouTube.

Bobby Christian joins us to continue our discussion on how and why your leadership focus and capabilities must adapt as your company moves through various phases of revenue growth. We learn in this episode that the entrepreneurial journey isn't always as rosy as it's portrayed to be. Early in 3Pillar's history, their largest client was acquired and ended their contract with 30 days' notice. Because the client was responsible for 50% of 3Pillar's revenue, David had to learn how to sell — and quickly. David and Bobby's early working relationship was solidified by their experience working together to land a new client that prepaid their SOW 6 hours before 3Pillar would've missed payroll. Tune in for some hard-earned wisdom from Bobby and David around the importance of cash flow, how to deal with the challenges of melding cultures after an acquisition, and learning to accept that people leaving your company, while difficult, can also present opportunities for growth. You can also tune in to (the full video of episode 3 on YouTube).

Bobby Christian, a serial entrepreneur and technology executive, joins David DeWolf for the first installment of a two-part conversation. They give listeners a look into the various phases of startup growth and the mindset shifts that are required for leaders to successfully navigate their companies through each phase. An email that Bobby sent David in 2012 outlining the various challenges startups and entrepreneurs face at a number of revenue phases sets the stage for the discussion and was one of the germinating ideas that helped spark the podcast. (Bobby) is the COO of (Deepwatch), a company that provides early detection and response to cyber threats. He served as 3Pillar’s Chief Growth Officer from 2009 to 2013, and he was an informal advisor to David in the very early days of 3Pillar. In an official capacity leading 3Pillar’s sales organization, he helped the company grow from $5MM in annual revenue to $25MM. You can also tune in to the (full video of episode 2 on YouTube).

For the first episode of The Evolving Leader, 3Pillar Founder & CEO David DeWolf talks about his continual evolution in going from a software developer writing code 80 hours a week to a successful entrepreneur at the helm of a rapidly growing global company. David discusses how he's been able to make leadership leaps at various points along the way as he has guided the company 3Pillar through numerous growth phases. 3Pillar has grown from 6 team members in 2009 to around 2500 today. In setting the stage for the rest of season 1, David shares how impactful other people have been on him throughout his leadership journey, which was one of the things that gave him the impetus to start this podcast. He also talks about how discovering his true passion of building high-performing teams ended up changing the trajectory of not just his life but the lives of many others as well. You can also tune in to the (full video of episode 1 on YouTube).