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

What I have found to consistently be the most challenging aspect of being a C Level executive has been the odd sense of isolation and loneliness that can come from leading. Many times your teammates won't, or don't feel comfortable sharing the brutal truth with you so many times you operate on partial information and when difficult decisions need to be made you can feel very isolated and alone. It's part of the territory, and it's your responsibility, but I feel leaders aren't honest enough with themselves that this isolation from things can create a sense of loneliness that can be tough to navigate. You might be surrounded with people all day, and still feel disconnected from what is actually happening if you are not careful. I have combated this by trying to be open, and welcoming of feedback, criticism, and harsh truths. This opens the door for more honest conversations and gives me the chance to truly connect with people and be more connected to what is happening. It's never the actual work that is hard, it's the need to make decisions with less than perfect information and taking risks of being misunderstood. Having a group of trusted advisors who will "keep it real" with you can help ensure you aren't disconnected from the work on the ground and you are a relevant force in the business.

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

As I traveled along my journey as an Enterprise Salesperson and began achieving greater and greater heights, I began sensing more of a desire to see others succeed even more than seeing my own success. A mentor came alongside me, and called out this sense of leadership that was apparent to others as well as myself. As I leaned into that, I began to be given opportunities to lead, and I took on a "learning attitude". I looked at every opportunity as an opportunity to help others succeed, and to learn something new. Step by step, as I executed on the roles and the objectives in front of me, I went from being good at leading myself, to being good at leading others, to be good at leading leaders. With each new opportunity, I began to build a sense of inertia. Both in success, and in some failures, I began to live the principle that if you are a good steward of small things, you will be given more. Before long I found myself in larger fields of responsibility, and leading large groups of people along the way. If I rewind the clock, my story is one of dedicating myself to doing regularly and on purpose the things that some people only do occasionally, took advantage of every opportunity to learn, tried to work smart but was willing to outwork my competition when needed, and treated people how I wanted to be treated. Taking this path opened doors, set me apart from other leaders, and earned trust from other senior leaders that would afford me the opportunities I have had in my career.

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

I try to wake up at the same time every day. I have a pretty standard routine every morning to get my head together, prepare my mind for doing quality work, and also to keep a cadence. I Usually try to do my very thought provoking and difficult tasks or meetings on the first of the day when I am fresh. Get through emails that need action, and prioritize any major decisions that need to be made. I like to have at least one structured break of 10-15 minutes at mid day to grab lunch, reprioritize the second half of the day, and check in with my teams. I like to then use the second half of the day to do routine tasks, review content or documents that need my feedback, and knock out the mundane pieces of work. I then close my day off with making or returning phone calls. I follow this cadence because it uses the most productive parts of my day to solve big problems, and the least productive to do less meaningful tasks. At the end of the day I like a little thinking time to remind myself of what I accomplished and what I need to solve tomorrow, as well as a reprioritization of the rest of the week. The "thinking time" is crucial. You need time where you are not making decisions, and can be creative with what's next, and what deserves or needs attention. I finish my day with a family dinner. Every day I strive to be at the family dinner table. It's a balance we need as a family, and a place to refill my tank. I do not sacrifice this especially during the times of this pandemic where I am not traveling. This grounds me, and reminds me what is important. It does not get hijacked, it does not get interrupted. Then I try to spend time with my wife Susan to reconnect on the day, and do at least one thing that fills my tank before the evening gets too far along. Music, some reading, a walk with the family, or a project that gives me a sense of accomplishment. Filling the tank is important to stay mentally on track. I then will usually review my calendar before bedtime to ensure I am ready to go the following day. This actually helps me sleep. If I know I am prepared for the next day, I can easily head off for a good night's sleep. One thing that I have learned. Rest is a weapon. Having a cadence through your day that ends with solid rest (both sleep and some downtime) allows you to run at a high pace and not succumb to burnout. Pace, discipline, and a sense of priority will take you places sheer powering through will not. Every now and then you have to just power through, but it can't be the norm. Rest is a weapon.

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

Listen more than you speak. I by nature have a lot to say. It's in my DNA, and I love to engage in dialogue and ideation with people. But I have learned that when I listen, truly listen to the people around me, and wait to speak until the others have been heard, and I have thought through my feedback, that I make better decisions and I am better at leading people. I have made many less than great decisions when I either have not sought wise counsel, or have simply spoken over top of people. It's a constant struggle, but I have trained myself to try to listen more, and speak less. Your words have more power, and you will HEAR what others are saying and answer root cause issues not merely address high level objections. Good leadership listens more than it talks.

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?

Leaders Eat Last (Simon Sinek). It reinforced those initial ideas of servant leadership. As leaders we aren't in charge of the work, we are in the business of caring for those that do the work. It's a mindshift that caused me to stop looking at metrics alone, and focusing on supporting and growing my team to do the work that ultimately drives those all important metrics. If I care for the people, and I strategically lead towards a north star, with common purpose, great things happen to those who follow that model. It turned my thoughts upside down on how to be an effective leader. Build safety for people to learn, grow, and achieve, and that is what makes for an effective leader.

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

Decentralizing decision making. If all decisions fall to the few, then you aren't building the capacity for others to lead. You learn to lead when you have to make decisions. Leadership is not just strategy, and execution. It's learning how to make decisions, and how to influence to make those decisions count. If you aren't pushing decisions downward within the business you aren't building capacity, you are just building processes. If people are given the chance to make decisions that have impact, you are effectively building leadership capacity. It's actually a simple principle that always seems too simple. Leadership training is important, but giving people opportunities to learn and make mistakes through decision making builds capacity in the business to grow.

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

One way to know if your leadership is effective is to see what happens when you are unable to lead and the team has to step in. Several months back I had to step away from the business for 6 weeks to recover from an illness. It was brutal. For several weeks I was unable to do any work whatsoever. I literally had to walk away. For a "Type A" leader this was not only difficult mentally, but emotionally. I had the utmost confidence my team could survive my absence, but what would the implications be? The net net of the situation is that not only did my teams move on without a hitch, they executed the greatest quarterly performance in company history. This showed me once again that if you empower people to do their jobs, and show trust, that they will achieve great things. They didn't "need" me to do their jobs, I learned that I am merely a facilitator of direction, capacity, resource, and encouragement. My team's ability to operate without me, proves the strength of my leadership. An idea that might be counterintuitive to some. It gave me great pleasure to see them take the spotlight and show up when the company needed them. Great leadership empowers.