In installment 2 of the CEO Insights panel, we will share each CEO’s perspectives on day-to-day focus and priorities and their best and worst days as a CEO. They provide key takeaways for aspiring CEOs and leaders.

Revisiting part 1 of the 3 part series, let’s review who the panelists are:

I moderated the CEO Insights panel which included: Adam Cole – Founder and CEO of SIPPIO, Eric Hernaez – CEO of RabbitRun Technologies, Tom Joseph – Founder and CEO of White Label Communications, and Tony Lewis – Founder and CEO of Clearly IP. These four distinguished CEOs have all been a CEO multiple times and have founded and exited a multitude of companies.

The panel provided a behind-the-scenes look into the journeys each took to become a CEO, the challenges they face every day, and over the past 16 pandemic months. Each provided tips and guidance for those who wish to become a CEO or a senior executive leader in their career.

Focus and Execution

The question to each CEO panelist was, “Given the top-to-bottom list of responsibilities you have as a CEO, how do you determine what to focus on and how do you execute on that focus?”

There are some gems to learn from the panelist’s responses to this. Having experienced these scenarios with 9 rookie CEOs, on which I base my book, The Rookie CEO, You Can’t Make This Stuff Up!, this will be enlightening to some readers.

Eric: It’s a gut feel on what to focus on. As I am not a numbers focused leader to determine priorities, I know what needs to be done. My effort is inspiration of the team towards my vision and they will come up with the solution.

Tony: I agree with Eric, it’s a gut feeling. I know where we are going, what we need to do, and we march forward as a team. My team has many folks who have been with me in multiple companies and we know what to do. I don’t want “yes-men” but I do encourage discussion, if necessary. This is why I hire smarter people than me. I am a true believer in not being the smartest person in the room. I do not believe in laser focus, because if you are too sharply focused, you could miss what’s going on out there in the market with customers and competitors.

Adam: I have a great team, a hierarchical structure, and I trust my people to lead and align with my vision. We get laser-focused on the key priorities in front of us and meet on a regular basis. Since the pandemic, with remote workers, we have had more meetings and longer for operations, management team, and staff but recently we are working to cut the meetings in half to free up more time to get things done and for people to be available as needed rather than be in meetings.

Tom: Every project brings with it opportunity costs, so we evaluate each priority against the strategy to determine the return on investment for the customer and the company. Once we decide the priority, we execute lead by my great leadership team, great people, and metrics to measure progress.

Worst and Best days

This question was simple to ask, but I could see on the CEO’s faces the challenge of answering the question. Some CEOs know off the bat their highs and lows, while others had to consider how to state those days!

Adam: I have had no “terrible” days that I can recall, even though some days were not as good as others. As a seasoned veteran, Adam normalizes these days and takes things in stride. Get an interruption? Take care of it. In the SaaS world, the great days are the very first signed contract – the highest of highs. Any win, or closed deal, after a longer sales cycle, is a great day!

Eric: His worst day was easy – the data center and network were down. He was at the data center feeling helpless with no answers. Customers kept calling. He said he did whatever he had to do to keep customers. It was a learning experience for him, and he learned after that event, that things always get better. That event has helped him be prepared for the future.

Tom: Tom “takes it in stride” when things go bad. Bad moments always get better. He has a similar perspective to Adam. He too normalizes the issues which allows him to process any issue, build or follow a process around it, and make the experience better.

Tony: Outages, lawsuits and losing a staff member contribute to his worst days. They are all equally bad, with the loss of a team member being the worst days, but he believes to be your best to succeed. His best days were being acquired and launching new products or services that have taken a long time to develop and test.

In general, each CEO downplayed their worst days as “something always goes wrong, and we have to address it as soon as possible in the best positive light!”

What’s next in the series

The 3rd and final installment in the 3-part series will discuss advice each CEO might give today to themselves in their pre-CEO days, tips and advice for aspiring CEOs and leaders, and their final words. Please come back for this final installment for the best and final takeaways!


The journey of each CEO is different. I write about this concept in my book, and these CEOs shared their stories on the panel. One of the strong assets of solid proven CEOs is being vulnerable. All 4 CEOs provided insights into their vulnerability by both being on the panel and responding candidly. I am forever grateful for these distinguished CEOs who give their life and passion to their companies, their leadership teams, their employees, and their customers. Once again, a special thanks to the CEO panelists and to ITEXPO for supporting and promoting the panel!

Thank you for stopping by the CEOInsights blog, and I hope you come back soon to read part 3 of this series! Plus, much more CEO Insights content is planned for the days and weeks ahead including guest CEO posts, tips to gain back lost time and more.