1. What have you found most challenging as a leader?

I did not work my up from the inside. My first CEO-type job, as president of a nationally ranked finance company, was my first-ever job in the finance industry. Nobody including me saw it coming. I had to figure out how much I needed to learn about finance to succeed in that role while simultaneously trying to earn the confidence of my colleagues and institutional partners about my ability to lead the company into the future.

2. How did you become a leader? Can you please briefly tell the story?

I was at a transition point in my career in the Defense Department, trying to decide where the next good opportunity for professional growth would be. Out of the blue, a former classmate reached out to tell me he had a role for me at his finance company, because he needed someone with a big-picture strategic mentality.

After considering a number of options, eventually I decided to take his offer, and moved to NYC to begin working for the first time in the private sector. My first month on the job, my former classmate, now my boss, sent me out to visit his company’s various subsidiaries. My first visit was to the largest subsidiary, a nationally ranked independent equipment finance company in Nebraska.

I spent a day and a half there getting a feel for the business, and upon my return to NYC wrote my boss a short confidential report on what I had seen, including recommendations on some structural and managerial issues that I thought needed to be addressed urgently. I never expected that my boss’s reaction to reading the report would be to conclude that the right way to address the issues I identified was to make me president of that subsidiary.

That is not what he originally brought me on board to do, but he recognized that I was able to see things from a perspective that others hadn’t, and propose solutions. In effect, my confidential report to him ended up being my own job description.

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

I wake up naturally every morning with the sun (which means I’m usually more tired in summer because I get a lot less sleep). I usually stay in bed for a while reading news headlines and checking email. I don’t have a set routine every day.

Some days I sit down at my home desk at 7AM, get started on my day, and end up working from home the whole day. Other days I get a later start, have lots of meetings at multiple locations, and spend a lot of time driving back and forth. Sometimes I have evening events. Usually I’m at work quite late. I don’t take a lunch break, and it’s quite normal for me to have dinner at 9PM or later.

My inbox and my meeting schedule dictate how my day unfolds. I try to never have more than 20 unread emails in my inbox. I don’t fit exercise into my schedule on a daily basis, but I am pretty disciplined about disconnecting from work as much as possible on the weekends, when I usually do a full day of something fun and strenuous like a long-distance rugged hike in a remote area.

4. What's a recent leadership lesson you've learned for the first time or been reminded of?

To stand your ground. Often leaders have to make decisions that may not be popular or well-understood. If people express opposition, know why you made the decision you did, and make sure it was grounded in your values and the values of your organization. Listen to people and engage with them, and take constructive criticism on board, but don’t change course if your decision was truly made for the benefit of the institution and was based on its values. Don’t cave in to negative opinion. Don’t become an appeaser.

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?

“The Beast in the Jungle,” a short story by the great British-American author Henry James, with an implicit moral: don't let fear or doubt paralyze you from taking hold of the opportunities in front of you. I first read this story the year after I graduated from college, and can't overstate how much I took it to heart.

I - and many people - hesitate to move forward towards our goals or desires because of any of a variety of fears/doubts (uncertainty about our abilities, or whether it will work out in the long run, or what the unforeseen consequences will be)... In essence, this kind of hesitation is actually an active choice to remain in the status quo; we disguise it to ourselves as just being careful, but in reality we are limiting our options and our own potential based on intangible and often ill-founded fears.

It has impacted my leadership insofar that ever since reading it I have very deliberately thought about how to take thoughtful risks. A lot of leadership is about effective risk taking, and because of this story, I have spent a lot of time not shying away from risks, but instead being cognizant of the danger of doing so. It has left me open to a lot of unconventional possibilities.

6. If you could only give one piece of advice to a young leader, what would you say to them?

Having extremely well-defined areas of responsibility and very clear chains of command actually can do more harm than good: it creates boundaries and isolated silos. It’s hard to cultivate meaningful creativity and organic leadership inside an unambiguous rigid hierarchy. Another way to say this is that true learning - by people and by organizations - doesn't usually happen in a place where everything is already defined, whether by structure or tradition (ie "we've always done it that way").

Bringing in the latest models of the most advanced technology won't change that. Organizational culture - the ways in which people interact - determines what your organization is capable of. If you want to build leadership and a culture of innovation, you have to enable people to interact in innovative ways, which goes far beyond creating a few spaces where ideas can be pitched to senior leaders who continue to sit atop a bureaucracy that by definition can't absorb the innovation it purports to want.

Think about the true definition of your organization - it should be defined by its values, not just by its structure. Make sure that a company org chart isn’t the main driver in your decisionmaking because if that is the case, you are actively degrading leadership capacity. Empower subordinates at every level to have a stake in institutional outcomes, and create opportunities for them to be creative and share ideas. This enables leaders at every level.

7. What is one meaningful story that comes to mind from your time as a leader, so far?

It’s hard to pick, but what comes to mind is the way that one of my employees relied on me during a very difficult time in her life. That was extremely meaningful. Her ex, an abusive man, showed up unexpectedly in the workplace. We immediately put into place additional safety measures to remove his ability to access the space, and ensure that she and all our colleagues felt safe at work.

She then decided to talk to a lawyer about her personal options, and asked me to accompany her for moral support. I worked closely with HR to ensure she had as much time as she needed to explore the options that were right for her, and I immediately cleared my schedule so I could go with her to the lawyer. It was an eye-opening experience. I felt grateful for the opportunity to support her and deeply humbled by her willingness to ask me to do so. She ended up continuing with the company, and we were successfully able to keep her ex away.