1. What have you found most challenging as a leader of a small or medium enterprise?
Balancing home life and worklife. As a husband, and as a father of two, and working remotely for the past 16 years, the lines between the two can blur. It's important to set boundaries, and KEEP THEM.

2. How did you become a leader of an SME? Can you please briefly tell the story?
My current role represents my third leadership role, and each one built on the one previous. My first SME leadership role came about when I was tapped to become the Executive Director of a small nonprofit educational association.
I had distinguished myself as an entrepreneurial thinker at a County Office of Education, bringing an innovative approach to professional development opportunities to support the 20,000 teachers within the county. Two of the nonprofit's board members encouraged me to apply and I spent the better part of a month preparing my presentation and researching for the interview process. I went through a three-step interview process with a written response, panel interview (9 panelists and 9 questions in 45 minutes!) and a 20 minute presentation responding to a prompt.
I was offered the job that evening, and by accepting, became the organization's youngest ED in its 30+ year history. My wife took some convincing, especially given it was for 1) less pay, 2) had lower health coverage, 3) required me to be out of town 3 days/week and 4) The organization had about 6 months of reserve left before it would be forced to cut expenses (again) or shut their doors. At the time, we had a two year-old at home, and it was a stretch for all of us to make it work. So - it was a leap of faith.
The organization had dwindled from eight staff to two, dropped from 8,000 to 2,000 members and had recently had to cancel its Fall Conference for the first time since 1978. The good news is that by the time I left (as CEO, btw), we had grown the organization to 13,000 members, re-established the Fall event, and increased our impact to reach nearly 30,000 educators.

3. How do you structure your work days from waking up to going to sleep?
I live in the Pacific time zone and my company is based in Minneapolis, so I wake up at 6am and quickly check my inbox, slack and other notifications for any colleagues from time zones east of me to catch any major issues. Then I shower, eat, grab my coffee and get to my desk by 7am (ok - sometimes I don't get there until 7:30). I work until 8:15, drive my daughter to school and check on the rest of my family (including getting the dog outside). I'm back at my desk by 8:45 and work until 12 or 1pm (sometimes, I go straight through until 2pm). Most of my meetings are in this window due to the timezone situation. I eat lunch, stretch and make sure I'm not staring at a screen for at least 15 minutes.
The afternoons allow me to get head-down work done, prep for the next day, and go out and meet with business contacts for an after work drink. This type of networking is essential in the work I do, as maintaining relationships is key to my success.
I leave the evenings to relax and be with family. Around 10-11pm I'll check back into my inbox/calendar to mentally prepare for the next day before I go to sleep, often accomplishing incomplete tasks on a mobile device from the couch/bed just before midnight.

4. What's the most recent significant leadership lesson you've learned?
Hire good people with a positive attitude. You can always train them to have the skills they need to succeed.

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?
Monster Loyalty: How Lady Gaga Turns Followers into Fanatics by Jackie Huba
I met Jackie when she was hired by Discovery Education to build their educator community. She inspired me with her deep understanding of customer evangelism and how to engage a community to do your marketing for you. I had no idea how powerful her ideas would be just a year later when I became an executive director of a nonprofit with zero advertising or marketing budget.
I would later go on to join the marketing department the same day that they launched a customer advocacy team and would soon be tapped to lead the team myself. I bought every team member a copy of the book and we had discussions around her ideas. The 'seven lessons' were valuable throughout.
I reached back out to her several times after that chance meeting in 2004 and have had great conversations over coffee since then. I make a point to reach out to her nearly every time I'm in Austin.

6. How do you build leadership capacity in an SME?
For every position, I hire for leadership ability. I am always looking for someone that can step up and then give them opportunities to learn the skills they will need to succeed when they do step up. I teach everyone to accept failure as a learning environment. Iteration is key.

7. What is one meaningful story that comes to mind from your time as a leader of an SME so far?
Early in my SME leadership, I had a board member that was constantly pushing and prodding me at every turn. I thought she was not a fan, and was challenging my leadership from a perspective of doubt that I was the right candidate for the job.
I kept working with her and taking her advice throughout my first year, earnestly taking her suggestions and applying what I could. But underneath it all, I sensed she was not a fan, against my success and ultimately not confident in my work.