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

Cash and scaling. As a leader you want to provide for your employees and give them the benefits and perks they need and deserve, but you have to balance that with being financially viable and responsible. So the balance of growing and scaling your business while keeping an eye on the financial side to ensure you stay fiscally prudent is both a challenge and necessary.

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

Throughout my career, I have taken inventory of both the good and the bad that I have been a part of. I have also identified that people and the culture will make your job (or life) great and is also likely the main reason in a negative environment. I feel culture starts at the top. Once it has been defined, it is hard to change it, so establishing the right culture and environment with my core values of trust, transparency, honesty and accountability become a motivating factor for me. With all of that being said, Covid was the true driving factor for me. Covid flipped the industry upside down, which created new challenges, but also opportunities. So when Covid hit, coupled with my desire to build something on my own, I decided the time to make the move was now and together with my co-founder Joe, we started Sellstack together.

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

When I wake up (usually around 6am), I grab a cup of coffee and read Twitter to see what Donald Trump has done today. I then get right to email and see what urgent matters have occurred overnight and run through my email before the day starts. Generally speaking your calendar is going to take charge between 8am-5pm so that will determine my next 9 hours. I tried to block off some time during the day to ensure I get outside to walk my dog Josh, or go for a run. Getting some fresh air or exercise is mandatory. I try to disconnect for a few hours at night, have dinner with the family and relax. As the day ends, make one more trip to the laptop, clean out the emails that came in after 5pm and send off some responses to get the next day going. Last thing; check the calendar to see what the next day looks like. Rinse and repeat.

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

Communication and feedback is critical. Ensure you are meeting with your teams. Communicate up and down and sideways. Let the team know what you are doing and what you are working on. Get feedback on this as well to ensure alignment. Without proper communication and feedback the opportunity to "lose control of the vehicle" is likely.

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?

Who moved my cheese by Spencer Johnson. This is a book about dealing with change and more than likely your business, and how you operate, is going to change. This book is short read that can be read on an airplane for a business trip and is a good way to get the team or company aligned on what we can expect going forward and how we should react.
I used this book to align a past global organization (2008) which was reluctant to change. This book served as an icebreaker of what was to come and in some ways helped ease the fears of the folks that were resistant to change.

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

I think both employees and customers need help/guidance. They need a plan. They need a path to success. So sit down with the customer or employee and understand what success looks like to them. Listen to them. Plan for success with measurable goals. Check in regularly to ensure you are on track to achieve your personal success and hit those goals. If you steer off course, then get back on track. If you have a change of heart then create a new path for success.
Building leadership and success takes hard work, but for starters it takes a desire to sincerely want to help someone as well as good listening skills and empathy. This is critical. Everyone can sense a phony or if you are doing this to just "check a box" or ultimately just make yourself successful. If you don't put others first, you aren't a good leader and more than likely don't have the skills (or desire) to build leadership properly.

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

Find something you are GOOD at and then focus your time on getting GREAT at that task. Once you are great at something, you will achieve success, relevance, camaraderie and self worth which will in turn make you passionate, which is the key to life and success. So don't follow your passion, find something you are good and become great at it!