We were lucky to catch up with Drew T. Jackson recently and have shared our conversation below.
Drew T. thanks for taking the time to share your stories and insights with us today. Coming up with the idea is so exciting, but then comes the hard part – executing. Too often the media ignores the execution part and goes from idea to success, skipping over the nitty, gritty details of executing in the early days. We think that’s a disservice both to the entrepreneurs who built something amazing as well as the public who isn’t getting a realistic picture of what it takes to succeed. So, we’d really appreciate if you could open up about your execution story – how did you go from idea to execution?
When I began my business, I started out with a bang! I immediately found success in onboarding clients to my executive coaching and leadership training business. I continued to dream big and believe that everything would come together because I wanted it; unfortunately, that is not how it works. In executing on building a business, you inevitably run into walls. This was something that I experienced early on, and it was a painful experience. Fortunately, I had access to an international business and leadership expert from whom I could reach out and receive mentorship. I will share a portion of our conversation in the following few paragraphs.
“I want to ask you a question specifically about business building. I know that you have built multiple businesses and I want to ask you whether you have ever had a time when you hit a wall? If so, how did you push through?”
My mentor was very gracious in his response to me. He reassured me that he is constantly hitting walls; he estimated that he hit walls weekly, if not daily. He called it a part of business and especially business building. He gave me six bits of wisdom that have been a touchstone for me over the last several years.
My mentor shared, “I’ve always said problems surround every opportunity you have, and every problem is surrounded by opportunity. When I go into a problem, I look for the opportunity; I know there might be some walls or issues when I go into an opportunity.
You must assess the wall. Now when I hit the wall, instead of backing up and running harder to hit it again, I ask myself, ‘Okay, what’s the wall?’ I try to define what the wall is. I try to determine where I hit it. If I can do those two things, I can probably knock the wall down or go around the wall or put a door in the wall. I can do something to get through it, but I’ve got to figure out what it is and why I ran into it in the first place. Those are the first two things I do, and I have found that there’s an answer for every wall I hit. There’s a way to get over it, around it, under it, or through it.”
He said, “You must appreciate the wall, and I think many people don’t appreciate their problems. Being an impatient person, problems feel like a delay to me, but that often gives me some great lessons. The Law of Reflection states, ‘Learning to pause allows growth to catch up with you.’ I like to say: I must slow you down to speed you up. Too many businesses are running back into the wall as fast as they can get up, never taking a moment to pause and figure out why they are running into the wall, to begin with. Reflection turns experience into insight.”
“Something else to remember is that it’s uphill all the way. You must understand that it’s uphill all the way in business, and it’s never going to be easy, and there will always be walls. Expect walls. When you hit a wall, if you think, ‘I didn’t expect this to happen,’ then get out of business. Mark, the CEO of my five businesses, and I talked today for five minutes. He told me two things that are both bad news. Okay, well, the only difference between that call and yesterday’s call is that yesterday he only told me one piece of bad news. Tomorrow he may tell me three things, I don’t know, but it’s business.”
He continued, “Life has problems and walls, and I have discovered that the people who succeed have a mindset that says this is what Life is all about, looking at problems, figuring them out, and fixing them. That’s what I do and what I’ve found is that once you become a wall scaler or put a door in a wall, you get through it. The next wall doesn’t intimidate you. Since I’ve had thousands of walls in the progress of my Life, it’s just a wall. There’s an answer, and I will find a way like thousands of times before this.
With emotional tenacity, you will be successful. That’s emotional tenacity and stability. If you have it, you’ll be successful. If you don’t have it after a few hits into the walls, you’ll quit. I have found that emotional tenacity and the pure realization that I will have problems allow me to get through those problems a lot quicker.
One of the things I noticed about builders is that they spend very little time rehearsing their life issues; they leave them behind because they know that none of that will solve anything in front of them. I’ve never gone back and camped and nursed myself and, at the same time, made progress. I’ve got to leave the camp and go back and tackle the war. When I tackle one thing, I’ve got to know that as I knock it down, I will see another behind it and that, my friend, is Life.”
Each time I read those notes from my time with my mentor, I am inspired to pursue my dream and reach my potential. This book was written because, in my 20-year career working with people, I can tell you that those in the highest positions of power and influence still run into walls. Running into walls is part of the human experience. I have seen people act out and self-sabotage when they hit walls, and I have seen clients break down and cry due to the feeling of helplessness.
I wrote The Executive Leader’s Handbook for those who feel like they can confide in no one, those who believe they can show no signs of weakness, and those who are supposed to know it all. I know you; I have been you, and I meet with wildly successful people like you every week. I desire to provide you with a quick reference guide that you can use to solve problems that executives just like you face every day. If you have ever tried to Google your way to solving an executive leadership problem before, then my book, The Executive Leader’s Handbook, is for you.
I am so passionate about this that I want you to have my book for free, and you can download it at theexecutiveleadershandbook.com
Know that I am here to support you on your journey, and as I write this, I am compelled to tell you that I believe in you and your success. My dream is to help you live yours.
When you discover your dreams, it inspires and motivates you to move forward in life. I know that dreams give you passion for living, and passion for living is the fuel that wakes you up and drives you to persist until you reach your full potential.

As always, we appreciate you sharing your insights and we’ve got a few more questions for you, but before we get to all of that can you take a minute to introduce yourself and give our readers some of your back background and context?
WHAT I DO: I help leaders and managers at small businesses with 50-400 employees create leaders team members love to follow. As a John C. Maxwell certified coach, I’m able to utilize tools and training that help increase revenue, boost morale, and retain top talent.
WHO I WORK WITH: I’ve spent the last 15 years serving clients including:
🐔 Chick-Fil-A
🏦 Colonial Bank
🏠 Habitat For Humanity
🤝 LendersOne
👨🏭 Lennox
⚕️ Medical City Fort Worth
💉 Metro Anesthesia
💳 Pinnacle Bank
🏡 Plaza Home Mortgage
WHAT MAKES ME DIFFERENT:
Chick-fil-A works with me because I help them increase sales by 20% year over year. Top Lennox Dealers work with me because I help them gain buy-in from their team and build leaders that enable them to grow exponentially.
I knew from the age of five that I wanted to be a public speaker. My passion for public speaking has fueled my results-oriented approach. I get results through coaching and training by identifying the result my client is looking for, and come hell or high water, achieving it.
SPEAKING TOPICS:
📈 Increasing Sales in ANY Market: Master the art of selling by learning how your sales style influences buying decisions.
💫 360 Communication: Discover the 4 keys to increase your effectiveness and influence in your communication.
🔓 The Law of Intentionality: Identify and destroy the 8 growth gap traps that are stopping you from reaching your full potential.
🏆 The 21 Irrefutable Laws of Leadership: Discover and learn how to apply the 21 irrefutable laws of leadership required to create world-class leaders.
WHAT OTHERS SAY:
🗣️We have generated an increase of over 23% in sales since we began working with Drew this year! The two years before we worked with Drew, we had not broken through 6% growth year over year, and currently, we are up 23.1% in sales. – Philip Browne, Owner and Operator of Chick-fil-A Waxahachie
🗣️Drew’s executive coaching has helped me strategically think through challenges and various communications I need to have in my role over operations. I have grown in my ability to empower my team and focus on items at the executive level. I highly recommend Drew for executive coaching. – Christine Watson, EVP Of Operations at Trinity Oaks Mortgage
How do you keep your team’s morale high?
Imagine one of your key employees decides to leave your company today.
Suddenly everything will seem to collapse around you. Her absence will cause the loss of opportunities and a general malaise in the rest of the team, who will no longer feel eager to work.
Even customers will notice.
The company will suffer a crisis because replacing such a person will be difficult and expensive.
Could you have kept this employee?
Daniel H. Pink (author of the book “Drive: The surprising truth about what motivates us”) demonstrates through various experiments that intrinsic motivation is based on three pillars:
Autonomy: achieving enough flexibility to feel that we are in control of our lives, our decisions, and our work.
Mastery: having the possibility of achieving mastery and excellence in the tasks we perform.
Purpose: to understand that our role is part of a plan and that we are an essential part of it.
Do you keep these three factors in mind when motivating your employees?
Many companies do not.
They focus the commitment to economic incentives.
Money is a motivator, sure it is, but not the only motivator and maybe not even the most excellent motivator. What counts is what we call “emotional salary,” which includes flexibility and other non-financial incentives.
On the other hand, it is common to think that talent retention is exclusive to the Human Resources department. Do you still think that way about talent retention? You’re mistaken.
Many underestimate the potential of leaders, placed in high positions and especially in middle management, to generate commitment in their teams and retain their employees.
Unfortunately, many individuals in these middle management roles are highly qualified in their area of expertise but do not have the skills or emotional intelligence to lead teams.
They do not communicate well enough what the company’s mission is, or the purpose of the work carried out by their team. They neglect the needs of employees to continue training and progress in their professional careers. They forget that you don’t leave a job; you leave a boss.
For this reason, having qualified middle managers aligned with the company’s goal of retaining talent as a company asset is so important. The impact of the leaders on the rest of the squad is incredible.
If a manager treats his team well, he has a much greater chance that these people, in turn, will treat the people with whom they interact well, be they other employees, suppliers, or customers.
Two steps you can take to retain key employees
Create leaders who move masses
A leader must be well equipped if he wants to get his people to commit. His qualities include active listening, empathy, and the courage to involve and challenge his team to go one step beyond their capabilities. Allow them to have the possibility to stand out and make a difference within the company. An engaging leader does not speak in terms of “me,” but of “we,” giving meaning to why we do what we do.
Measure leadership ability
Putting numbers on what you do is always a good idea. Therefore, if you measure the leadership capacity of your middle managers, you will be able to understand better how to involve your employees. What does an ideal leader look like in your organization? Does your leadership team know the answer to this question? If not, how are they supposed to measure themselves and if they are succeeding as a leader?
Take these two steps to develop your leaders, and you will see an immediate boost in your ability to retain top talent.
If you’re interested in discussing how I may help you increase revenue, boost morale, and retain top talent, here is a link to a quick survey to give me a better handle on how I can help: https://zr3tenl02nb.typeform.com/drewjackson. Once you complete it, I will be in touch to schedule some time to chat.
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Contact Info:
- Website: https://drewtjackson.com
- Instagram: https://www.instagram.com/drewtjackson1/
- Facebook: https://www.facebook.com/drewtjacksoncoaching
- Linkedin: https://www.linkedin.com/in/drewtjackson/
- Twitter: https://twitter.com/DrewTJackson1
- Youtube: https://www.youtube.com/drewtjackson
- Other: The Executive Leader’s Handbook on Amazon: https://www.amazon.com/Executive-Leaders-Handbook-Challenges-Leadership/dp/B09VWSKF52/ref=tmm_hrd_swatch_0?_encoding=UTF8&qid=1651077479&sr=1-1
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