1. What have you found most challenging as a leader of a small or medium enterprise?

Prioritization is always the greatest challenge when leading a SME. With finite time and resources, it's critical to

1) have a focus

2) ensure activity is aligned with that focus

3) ensure alignment - with your team and cross functionally

4) eliminate all activities that are not aligned with that focus

5) de-prioritize the aligned activities that do not create the most outcomes

This is not much different from leading larger organizations. Only with smaller organizations, you must be more ruthless with the time management and alignment.

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

I've always considered myself someone who creates and grows organizations. And I've always believed that sales and marketing belong together.

Joining a smaller organization provided me the opportunity to bring sales and marketing together. When I interviewed, the board asked why I wouldn't take only sales or only marketing. "It's simple, I said. Sales always blames marketing for not enough leads, and marketing always blames sales for not properly following up on their leads. You want me yelling at myself at 3AM if we're not driving revenue and a pipeline that powers predictable revenue."

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

I usually start early by scanning email and social media for urgent actions or landscape changes. After that a workout and/or meditation. From there, it's reviewing the plan, eliminating critical to-do's, and executing the plan.

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

When I was moving from a software engineer to a consultant, towards my journey to sales and marketing, a mentor changed my life.

He looked at my bookshelf, and commenting on all my Java books mentioned that "English, too, is a programming language. If you focus on English like you've focused on Java, you'll be able to connect your heart, your passion, and your mind to motivating others to join you in any mission you accept."

To this day, I attribute that 5 minute conversation to changing my career, and fueled me with a passion for the art and science of messaging as a vehicle for achieving business missions.

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?

Non-zero, by Robert Wright taught me that game-theory - non-zero sum games specifically - is what separates us from monkeys. Specifically, that my managing increasingly complex and high-yielding win-win interactions where 1+1=5 is what leads to the greatness of our species, and is a unifying thought in building and motivating teams to achieve deeply meaningful and challenging missions.

6. How do you build leadership capacity in an SME?

Effort.

Understand your process and the activities needed to generate needed outcomes.

Understand the outcomes' most wildly important leading and lagging indicators.

Understand skills you'll enable and those you must hire.

Pick the right team based on values and skills.

Align and Enable.

Trust and Delegate.

Trust and Verify against the leading indicators.

Lead from the front.

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

none come to mind right now