1. What have you found most challenging as a CEO or executive of a large enterprise?

One of the challenges is ensuring you're still accessible to encourage communication and engagement. One of the greatest advantages of startups is the ability to build flexible, cohesive teams. In a larger organization, that sense of cohesiveness and flexibility requires more deliberate effort to establish in the organization culture.

2. How did you become a CEO or executive of a large enterprise? Can you please briefly tell the story?

The first time I was promoted to an executive title was at Kaiser Permanente, at that time a $50B organization. I had applied for a role that opened, and my boss asked me why I wanted the position and how I would feel if I was not selected. I told him that I had thought through that possibility and felt it was a win/win situation. The other applicants already had executive experience, but I knew the selection process would expose me to senior management and present my qualification and career aspirations. The interview process provided access to stakeholders I did not have access to in the ordinary course of work. My boss was satisfied that I had thought through the decision to apply and was an outstanding advocate for my selection. I was fortunate to have him as a mentor and sponsor.

3. How do you structure your work days from waking up to going to sleep?

I'm not a morning person, so I like to start my day with exercise, whether at the gym or a simple walk outside during the pandemic. Physical activity helps me clear my thoughts, then I like to refer to the list of Open Items I created the previous day. I find the act of creating the list ensures nothing falls through the cracks but also helps me prioritize my open items. Then I like to tackle the most urgent or important items before opening emails or other distractions. Getting the urgent or most important items complete provides momentum in my day before the normal process of meetings. During the day, I check the list to continue checking off items and adding items as issues come up. At the end of the day, I review what's leftover and prioritize my list for the next day.

4. What's the most recent significant leadership lesson you've learned?

An important leadership lesson is how to use work as an opportunity to develop others. It's easy in the course of the day to focus only on getting things done without stopping to think about whether a meeting or a project could be a development opportunity for someone else. It's tempting to get things done yourself because it's quicker, more efficient, and gets done the way you want. However, we all benefited from someone slowing down their own work to bring us along, and we need to be deliberate in providing that same opportunity for others. Even when it creates more work for us.

5. What's one book that has had a profound impact on your leadership so far? Can you please briefly tell the story of how that book impacted your leadership?

A book that I still like to review sometimes is Crucial Conversations. Many of us have had situations where a discussion had derailed and wondered how did this happen? One of the things taken from the book is the importance of preparing for a crucial conversation by looking within to ensure I'm clear on my intentions for the conversation and leading with the facts.

6. How do you build leadership capacity in a large enterprise?

Leadership capacity in a large enterprise is done through teams rather than individuals. I work as an advisor for startups and I always emphasize this importance for scaling up. It's easy when an organization is small to think there is one leader, one person with all the answers. In a larger enterprise, you have to trust that the collective experience, knowledge, and diversity of a team will provide better results in the long run than depending on one individual.

7. What is one meaningful story that comes to mind from your time as a CEO or executive of a large enterprise so far?

Recently, I transitioned from an organization and provided a public note of appreciation to everyone there. What really surprised me was the outpouring of sentiment not from the people I spent time with the most, but from many people whom I saw less frequently who took the time to reach out and say what they remembered about working with me. This was done verbally with a phone call or a simple note through email, note, or card left at my desk. The volume and generosity in those heartfelt messages really touched and truly reminded me of the size of the team I had been lucky to work with but also the importance that all interactions leave an impression with others. I was humbled.