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Becoming CEO: Journey and Reflections with Chris Painter

Chris Painter is the president of Logikor and a longtime client and friend of Mike’s. Throughout his career, Chris has always wanted to be the one at the helm of an organization, leading the way. And it shouldn’t surprise you that he started near the bottom and worked his way up. Today, Chris and Mike talk about how he worked his way up to a CEO position. They share advice on how to identify if you have the right team and how to build the right team. This includes inside the organization and outside the organization with advisors. The conversation really heats up with insights when they begin discussing the impact of self-evaluation and how imbalance can impact a leader, their family, and the organization.

  • Chris started his career with an internship at Dow Chemical. He learned that while he isn’t a ‘transactional guy,’ he loves business. The travel, the people, the wheeling and dealing – Chris knew he’d found what he wanted to do with his life during his last year and Dow and his time at Transfreight: transportation and logistics.
  • During the late 90s, Chris committed himself to transportation and logistics. If you recall, this is also when Japanese manufacturing was taking North America by storm, and Chris was more than a fan. He was an adopter of the practices and chose his next position based on which company was doing the ‘just in time inventory.’
  • Chris’s first position was nothing glamorous; he was a front-line supervisor dispatching trucks and drivers. But Chris was ready when his first big break came, and he shares how exactly he landed on the path to leadership and his current position as the president of a company. It was one of the most challenging roles he took on, but Chris flourished.
  • Chris had aspirations to run an organization, even when he was a frontline supervisor. Even though he didn’t have a plan for it, he had a very effective approach: find opportunities, don’t wait for others to present them and give everything you have to succeed at them. Very often, this meant raising his hand and volunteering to fix things that were broken. But there came a time when it was about building something.
  • Chris understood that his role was something new in the company, so that meant there wasn’t a lot of support for him. This points directly at how transportation and logistics were changing drastically in North America. This worked in Chris’s favor; all around the world, companies wanted to adopt what Toyota was doing. But when the industry caught up, Chris realized he needed to be more proactive in driving the growth strategy.
  • If you’re interested in being a CEO yourself, Chris has some wonderful anecdotal advice for you. The parent company had previously used a rotational leadership role. They realized that things were broken badly, and they couldn’t continue that way. As CEO, Chris faced unique challenges; the staff was used to having someone in to maintain rather than the drastic changes he had in mind. He shares the three-year journey and his success.
  • Getting the right leadership team in place is one of the biggest challenges companies face. Chris worked extensively with Mike to lay out what the organization should look like, even down to the roles that each member of the team would fill. It wasn’t an easy process; they ended up having to let several people go, building an entirely new executive suite and Chris explains why.
  • Starting with the end in mind they had to define what success ultimately looked like and had to focus on getting the right people in the right seats on the bus. Chris and his executive team had to set a new vision for the future state of Transfreight. They had to assess the leadership gaps and define the differences in success for positions across the organization. This included hiring executives and leaders across the organization that would allow them to achieve success of the desired state. This ultimately led to building a $300M+ revenue organization, 1,200 employees spread across 32 facilities in Canada, United States of America and Mexico. Ultimately this also led to the organization being sold to Penske Logistics.
  • Chris has always focused on making himself a better leader, and this led him to begin a 360-degree evaluation and attending the Center for Creative Leadership: Leadership at the Peak program. It was a life changing experience. Chris shares many of the ways the program helped not just him, but also his cohort, recognize how they were leading their relationships, work, community, and life. It was an experience of brilliant minds and Chris realized that one of his biggest problems was trying to be good at everything. He encourages us to reflect on where you get your energy, where you get your passion and what will allow you to become the greatest person you can be. He also shares the concept of ‘white space’ and balance in leadership and relationships. The drive to run an organization and throwing yourself into the organization can create significant challenges and imbalance.
  • Chris eventually went from CEO to entrepreneur after reflecting on what he was truly accomplishing at Transfreight. While it was a great place to work and he was fairly compensated, the passion wasn’t there for him anymore. But it wasn’t a quick decision for him. Chris lays out the strategy he used to make the single biggest decision in his life.
  • During his time at Transfreight, one of Chris’s teammates left to start a company called Logikor. This new company was driving growth and very nimble, to the point where Chris was interested in acquiring them for Transfreight. That didn’t come to pass, but when he left Transfreight, Logikor was a very natural candidate for Chris to consider. He shares what convinced him to become an owner and the President of Logikor.
  • Chris and Mike discuss the impact of allowing your advisors to understand the vision, the values and the desired future state of your organization. It is an important approach for successful business leaders. A strong network of outside resources, who are along the journey with you, is a winning strategy when you are at the top. It will fuel your growth and success.

Chris Painter



Center for Creative Leadership

Leadership at the Peak Video

Book Recommendation

No Man’s Land by Doug Tatum