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7 Questions on Leadership with Luke Sheffield

Updated: Jan 5

Name: Luke Sheffield

Title: Entrepreneur / Owner

Organisation: Port-A-Go, Empower Rental Group, and Luke Sheffield.coo

My expertise is in empowering business owners, sales professionals, and operational leaders to achieve remarkable success through the art of deal-making, the cultivation of core values, and the strategic development of diverse pathways to prosperity. In my role as a Co-Founder at Empower Rental Group, I spearheaded the successful completion of 22 acquisitions, a testament to my proficiency in the realm of mergers and acquisitions.

Furthermore, I played a pivotal role in orchestrating the remarkable expansion of a modest rental company, catapulting it from just 3 locations to an impressive 40 locations within a mere 3 years. With a solid foundation of 20 years of experience in sales and operations, I've honed my skills in crafting innovative strategies that drive substantial revenue growth. For instance, I led a national account team that achieved remarkable results, elevating revenue from $54 million to a staggering $100 million in just 3 years.

In addition to my other achievements, I've also demonstrated a proven track record in building a highly successful brokerage division from ground zero to $40 million in Corporate America. My approach hinges on fostering dynamic teamwork, leveraging extensive industry connections, and engaging in collaborative efforts with exceptional leaders and teammates. I take great pleasure in assisting entrepreneurs embarking on their business journey and professionals striving to elevate their capabilities for scaling new heights of success. While keeping in mind the importance of Faith, Health, and Family.

Thank you to the 2,000 leaders who’ve generously done the 7 Questions on Leadership!

I hope Luke's answers will encourage you in your leadership journey. Enjoy!


Jonno White

1. What have you found most challenging as a leader?

Probably balancing the demands of communication within a team and maintaining a healthy work-life balance.

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

At the age of 22, fresh out of college, my journey with Hertz Equipment Rental commenced in the realm of inside sales. Armed with a hunger for learning and a tenacious spirit, I quickly made my mark in the challenging world of sales. The dynamic environment, coupled with my relentless drive, propelled me to consistently exceed targets and stand out among my peers.

Recognizing my potential, the leadership team at Hertz Equipment Rental provided me with an opportunity to transition into an outside sales role. This shift not only expanded my skill set but also exposed me to a broader spectrum of clients and challenges. Navigating the intricacies of outside sales, I honed my ability to build relationships and provide tailored solutions to meet the diverse needs of our clientele.

My dedication and results in the sales domain did not go unnoticed. Just a year and a half into my professional journey, the organization saw fit to entrust me with the significant responsibility of leading a team as a Branch Manager at the age of 23. This rapid ascent was a testament to the faith the company had in my capabilities and leadership potential.

As a Branch Manager, I embraced the challenges with enthusiasm. I can’t say I was very good then. Leading a team required not only the application of my sales acumen but also the development of strategic planning, operational management, and team leadership skills. My role involved overseeing the day-to-day operations, ensuring customer satisfaction, and fostering a collaborative and high-performance culture within the branch. It was challenging for me.

My leadership philosophy centered on expecting everyone to work as hard as I did. Which isn’t the best strategy. Over the years, I developed more open communication, and empowerment, and fostered a sense of shared ownership among team members.

I learned that encouraging continuous learning and innovation while leveraging the strengths of each team member to drive collective success is what's best. The fast-paced environment of the equipment rental industry served me well in that it demanded adaptability, and I thrived on the challenges that came my way. I would also say the same about the storage container rental industry as well.

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

4:00 AM - 6:00 AM: Morning Prayer and Reflection.

The day begins with a moment of introspection and gratitude. Starting with a morning prayer sets a positive tone for the day ahead, prayer, journaling, reading the Bible, and almost strategy on task management. Which can lead to more journaling.

6:00 AM - 7:00 AM: Energizing Workout

Next comes a commitment to physical well-being. Engaging in a morning workout, whether it's a brisk run, lifting weights, a peloton ride, or a sauna helps boost energy levels and enhances mental focus for the day.

7:00 AM - 8:00 AM: Family Connection Time

Prioritizing family, the morning is dedicated to connecting with loved ones. Whether through breakfast with family members or a phone call while traveling, maintaining strong family ties is an essential part of the morning routine. I also try to journal and write out family things that need to get done or think about date ideas or family ideas. Is there anything not on the calendar that needs to be done? That kind of thing.

8:00 AM - 12:00 PM: Strategic Work Block

Entering into the workday, the morning is dedicated to strategic tasks and high-priority projects. Eat the frog-type things of doing the most painful things first. Leveraging the early hours allows for focused and undisturbed work, maximizing productivity. I also like to do any kind of YouTube recordings or podcast recordings then because I generally have the most energy earlier.

12:00 PM - 1:00 PM: Lunch and Recharge

A break for a nutritious lunch not only fuels the body but also provides a mental pause. This time can also be used for a short walk or moments of relaxation, enhancing overall well-being. About 1.5 years ago I started doing 10-minute walks around this time frame or try to.

1:00 PM - 5:00 PM: Afternoon Work Block

The afternoon is structured for meetings, collaborative work, and addressing tasks that require creativity and innovation. Maintaining open communication with any team that I’m working with ensures alignment and progress toward shared goals.

5:00 PM - 7:45 PM: Family and Personal Time. Prioritizing family once again, this time is dedicated to family activities, dinner, or any personal pursuits that contribute to a healthy work-life balance. Put kids in the bath and then my wife and I put our 3 to bed. The oldest is at the age where she can do so herself and sometimes she will hang out with us after putting our younger boys to bed.

7:45 PM - 8:30 PM: Flexible Work Block

Recognizing the flexibility needed in a dynamic work environment, this time can be utilized for tasks that require attention or responding to emails. If not required, it serves as additional personal time. Planning for Tomorrow. Reviewing the day's accomplishments and failures. Planning for the next day ensures a smooth start. Setting priorities and organizing tasks contributes to a sense of control and preparedness.

8:30 PM - 9:45 PM: Wind-Down and Relaxation

Engaging in activities that promote relaxation, such as reading, listening to a podcast, or spending quality time with my wife helps transition from the workday to a restful evening.

9:45 PM: Lights Out

Recognizing the importance of adequate rest, the day concludes with a commitment to a good night's sleep, setting the stage for another day of purposeful and balanced living.

Note: For those wild hair moments, if the urge strikes me to enter the office at 3 AM, flexibility is maintained, allowing for a customized schedule that accommodates bursts of productivity. Sometimes I just wake up and go.

4. What's a recent leadership lesson you've learned for the first time or been reminded of?

Transitioning from personal to business in the online world can feel peculiar, yet it's crucial to recognize that many offline business principles apply. Balancing professionalism with authenticity is key; sometimes, taking ourselves less seriously can open up new possibilities and foster genuine connections.

The leadership lesson here is adapting offline business principles to the online world. Balancing professionalism and authenticity is crucial, and embracing a less serious approach at times can lead to genuine connections and new opportunities.

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?

Atomic Habits" by James Clear. This book is about the science of habit formation if you haven’t read it yet and it’s how small changes can lead to remarkable results.

While it primarily focuses on personal development, many of its principles apply to leadership.

Here's how I applied the book;

The book introduces the concept of the "aggregation of marginal gains," emphasizing the power of tiny improvements over time. I focused on this principle by starting to focus more on continuous improvement in daily tasks, leading to significant progress over the long term.

Where in the past I focused more on big-picture continued improvement and big needle movers when I was involved in the day-to-day of our equipment rental business.

He also discusses the idea of habit stacking, where new habits are integrated into existing routines. He talks about positive habits within teams by incorporating them into established workflows. I’ve started to do this in our toilet business by breaking down habits into really what he would call a loop cue or reward. Which is also applicable to the family I’ve found.

Clear also talks about these Identity-Based Habits. Which is what I have been exploring online. It involves focusing on identify-based habits vs. outcome-based habits. I’m learning that identities based on values are different than they used to be. It’s taking a different perspective while still performing at a high level.

6. If you could only give one piece of advice to a young leader, what would you say to them?

That’s a good question. I would say embrace a mindset of continuous learning and adaptation. This is kind of one of the reasons I’m creating courses online now and eventually at a university.

It’s important to seek knowledge, be open to new perspectives, and view challenges as opportunities to grow. The ability to adapt and learn continuously not only enhances your leadership skills but also empowers you to navigate the complexities of leadership with resilience and agility.

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

It would probably be a friend outside of my existing company. This was a guy named Ken who had been an integral part of a thriving business venture. His commitment to the company's success was unwavering, yet there came a moment when he sensed a shift within himself. It was a moment of introspection, a quiet realization that the path the business was taking no longer resonated with his core values.

Ken was never one to compromise his character for success. He believed that one's integrity and personal values should stand firm, even in the face of professional challenges. Decisions were being made that Ken found increasingly difficult to agree with.

With grace and poise, he approached the leadership team, expressing his concerns and acknowledging the misalignment between his values and the direction of the business.

Ken calmly explained his decision to step away. His words were not fueled by resentment or frustration, but rather by a commitment to personal authenticity.

He spoke of the importance of aligning one's professional journey with one's values, of the profound impact it could have not just on one individual, but on the entire ethos of a team and a business.

His departure was marked not by discord but by mutual respect. The leadership team, recognizing Ken’s unwavering character, wished him well on his newfound path.

For me, witnessing Ken’s graceful exit became a pivotal moment in my journey.

His conviction in prioritizing personal values over professional success left an indelible mark on me. It sparked a journey of personal value development, prompting me to reflect on the significance of leading a life that authentically reflects one's beliefs.

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