If I could turn back time: 6 lessons I wish I knew earlier

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By Colleen Killen-Roberts

Our chairman has a passion for investing in the next generation of leaders, and earlier this year, he launched a “meaningful leadership” program for our organization. Five individuals have been invited to be part of this 12-month program, which offers leadership lessons from both internal and external speakers. I was honored to be the first guest speaker, and as I prepared for the session, I reflected on my professional journey and wondered what parts might be beneficial to this group. In other words, what is the shortcut to how I got here? Further, can knowledge be a substitute for experience? To the latter question, I am not certain. But it’s worth a try. So here goes. The following six lessons are things I learned the hard way:

  1. Manage the environment — I wish I would have known that it is not my job to make my team members happy. People are complicated. They are holistic in nature and have both personal and professional lives. In addition, they hold the keys to their own happiness. But what I can do as a leader is to create a positive work environment that fosters a team spirit and honors the values of the team.
  2. Don’t take things personally — Situations that I thought were about me often were not. Let me explain. I was in my early 30s and part of a senior leadership team: the CEO, two male partners, one female leader and me. For whatever reason, the female leader did not show me a lot of love. At first her unsupportive remarks took the wind out of my sails. But as time passed, I realized it was my choice to either be offended by her or to choose to not to be offended. So, I decided I would be a good team member even though she wasn’t. The decision turned the momentum of the relationship around, and four years later we actually got along well. Many years later after I left the organization, I learned that she was even harder on herself than she was on me. As it turned out, it was never about me at all. Go figure.
  3. Underpromise and overdeliver — This concept is an interesting one and can create a lot of internal stress. For example, at one organization I worked in we were under intense cash pressure (we didn’t have any). I told my boss that I would handle all the incoming creditor calls and find a way to keep the materials we needed coming in. I overpromised to him. It was a huge burden for me to carry alone. In hindsight, what I should have done is tell him, “I will be the lead contact for the creditors and do what I can to keep you out of it.” In this scenario, the emotional pressure is much less intense. But if I did end up carrying the burden alone, I became the hero. In summary, if you overpromise, you can be a stress box, and if you underpromise, you can be a hero. Tough choice.
  4. Leverage your boss — Simply make their job easier. In the organizations I have worked for, my direct supervisor often has been the head of the organization. As such, they have a big job with a lot of responsibility. If I can proactively offer solutions and anticipate problems, I help leverage them and they become more effective. For example, I once worked for a CEO who was a serial entrepreneur and wore a lot of hats — including several that didn’t fit so well. To ease his burden, I took on human resources and finance, areas where I was strong, so he could concentrate on sales and being a rainmaker. As a result, company revenue increased 250% in three years.
  5. Integrity is everything — This segues from the previous lesson: Don’t make promises you can’t keep. Walk the talk. Let your team members know they can count on you. If you can’t do something, be honest and admit that you’re spread too thin. Remember, it takes a long time to build trust, and trust is a critical component of healthy, long-term relationships.
  6. Know thyself — I wish I had been more comfortable in my own skin and embraced my strengths and been aware of my weaknesses. Early in my career, I often tried to turn myself inside out and be all things to all people, which was a very stressful road. Over time, gaining much experience on many different teams, I realized my superpower is making things happen. Yet what I’m not so good at is slowing down and dealing with details that sometimes need to be addressed. Some things I overlooked blew up on me. Today I stop and ask myself, “Is this something I should give more time and attention to?”

As I finished my presentation to the group, my hope was that I gave them some sort of CliffsNotes on how to make their professional lives better. But deep down, I realize leadership journeys and lessons are personal. My experience of walking through situations created meaningful lessons for me. My guess is that it will be the same for them.

(Published Oct. 15, 2021)

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Colleen Killen-Roberts
Divisional Vice President of Entrepreneurship
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“Entrepreneurs need a bridge between their dreams and reality,” says Colleen Killen-Roberts, Divisional Vice President of Entrepreneurship at the Edward Lowe Foundation. “And that’s where operational expertise comes in. Operations is about creating the necessary infrastructure to take the entrepreneur’s ideas and make them happen.” In this series of articles, Killen-Roberts shares insights gleaned from more than 25 years of operational and fiscal management experience at second-stage companies.