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“5 Things I Wish Someone Told Me Before I Became a CEO” With Matt O’Grady

As part of my series about the leadership lessons of accomplished business leaders, I had the pleasure of interviewing Matt O’Grady. Matt is the Founder & CEO of Matt O’Grady Coaching, specialists in corporate gratitude and employee appreciation programs. Working with companies of all shapes and sizes across all industries, his meaningful approach has provided a […]


As part of my series about the leadership lessons of accomplished business leaders, I had the pleasure of interviewing Matt O’Grady. Matt is the Founder & CEO of Matt O’Grady Coaching, specialists in corporate gratitude and employee appreciation programs. Working with companies of all shapes and sizes across all industries, his meaningful approach has provided a measurable impact on employee engagement and retention. Under his leadership, Matt O’Grady has helped dozens of organizations attain new levels of connection, happiness, and success while also guiding them in management of stresses and challenges of today’s world.


Thank you so much for joining us Matt! Can you tell us the story about what brought you to this specific career path?

Becoming an entrepreneur and corporate gratitude coach was a natural fit for me as I have always enjoyed leading a team. Whether on the field or court in sports or during my time in the military, establishing camaraderie and making connections through achievements has always given me a strong sense of fulfillment. Now in business, coming together as a team and guiding the direction, I can bridge my passion with purpose.

Can you share one of the major challenges you encountered when first leading the company?

It would be juggling so many moving parts. As the leader, I need to have both an understanding of the day-to-day as well as what it takes to complete the big picture. There was a time when I would get most excited about driving the company direction or growth strategies. but I quickly realized I need to be focused on all areas from soup to nuts. While I hire specialists to manage these areas like accounting, insurance, HR, property management, etc. I have found it important to be briefed regularly on these matters while motivating my team in sales, customer management and growth.

What lesson did you learn from that?

I learned being a successful CEO will require me to become a better planner in terms of both time management and delegating duties. And, by solving my own challenge, I have become more efficient and focused which has provided a smoother vision for my team. Regardless of the issue or obstacle I am faced with, I approach it as a creative project or puzzle that needs to be figured out rather than a difficulty that has to be overcome.

What are some of the factors that you believe led to your eventual success?

Two factors stand out to me. First was having tremendous mentors who were kind enough to talk with me about how they approached business, success and life. That is invaluable for any new leader. Second, is being an eternal optimist. Even when the chips are down, I believe there is always a way, to get back up and begin again. The only thing that ever stops us from our greatness is giving up on ourselves.

What are your “5 Things I Wish Someone Told Me Before I Became CEO”? Please share a story or example for each.

  1. Become an Expert Time Manager. That was a tough learning curve for me but once I got it down it make a big difference in our success.
  2. Accept that you will be running a Marathon and not a Sprint. One of my mentors used to make me take a long relaxing lunch every few weeks, I never wanted to do it but I saw the value in the long run. It allows us to relax enough to get creative to think outside the box and enjoy the journey.
  3. Recognize everyone on your team. It’s very important to make sure that your whole team feels engaged and part of the overall success. While top sales performers may have contests for their own departments, demonstrating employee appreciation by managers to all employees, should be part of the culture. Everyone from, regardless of position, needs to feel a part of the whole and it is up to the leaders to make sure that happens.
  4. Be more Coach and less Boss. I see many leaders running their teams into the ground and they burn out, quit or stay but become unproductive. Our workforce will always be our key to success so leaders need to know how to motivate and build morale. We have to learn how to get the best out of our team while making sure they are enjoying their work, getting support from top down and bottom up. Learning how to coach up our team with the best intentions and the highest integrity will produce fantastic results.
  5. Enjoy the Journey. Running a business will always have challenges and unanticipated situations. They key is to enjoy the process and learning how to do that really allows the day to day to be so much more fulfilling and rewarding rather than just waiting for the end of the year trophy and suffering every day until then. That is no way to live in our work life. Embrace it all!

What advice would you give to your colleagues to help them to thrive and not “burn out”?

Recognize you will have both ups and downs. Find ways to take breaks, to have fun, be creative, and be grateful for what you have in your team, at your job, as a leader. If you are enjoying the journey, living in the moment of your career you will be more productive and more in tune with what needs to get done.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story?

There are too many to count, however, one of my early mentors taught me how important it is to be able to focus on your tasks, your goals, priorities without being stressed. In fact, focusing, directing our attention towards our goals while actually enjoying the process, letting go of the worry and anxiety that can come up and simply coming back to an important question: “What can I do in this moment to simply and easily move this forward?”

What are some of the goals you still have and are working to accomplish, both personally and professionally?

My first book, Living Gratitude: A Simple Path to Happiness, continues to be in demand as this is a topic people want to understand better to apply to their own lives. After receiving so many comments and questions online and at events, I am now working on a sequel to provide more insights. I am excited about the growth of my coaching business and how well the corporate gratitude programs have been received. We look forward to bringing the message of workplace appreciation to more leaders, executives and employees across even more industries.

What do you hope to leave as your lasting legacy?

I hope to leave a legacy of joyful success. Life is too short to sweat the small stuff. If we look hard enough there is always something to be grateful for in our work life and our personal lives. I hope to leave the legacy of teaching people how to focus on what they want without stress and in fact enjoying their work so much that it becomes a foundation of happiness and success in their lives.

You are a person of great influence. If you could start a movement that would enhance people’s lives in some way, what would it be? You never know what your idea can trigger!

I want to start an institute that teaches all the above philosophies to young leaders so that they can also pass this legacy of successful stress-free working and living to be successful in both their business and personal lives.

How can our readers follow you on social media?

Matt O’Grady Coaching is onFacebookTwitterInstagramLinkedIn, and on YouTube

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