Growth Through Delegation: Caitlyn Wells Of Upwell Strategies On How Relinquishing Control Is The Path To Growth

An interview with Dr. Bharat Sangani

…In my experience, successful delegation comes down to finding the right balance between empowering your team and staying connected to their work. I’m a firm believer in regular team check-ins, as they create natural touchpoints where we can discuss progress, work through any roadblocks, and make sure we’re all moving in the same direction. One thing that’s been absolutely essential for me is having a solid project management system in place. It keeps everyone on the same page and makes it easy to track what’s happening across different projects and team members. As a founder, you get real peace of mind in knowing nothing is going to slip through the cracks…

Many leaders struggle with the idea of letting go, believing that holding onto control ensures success. However, effective delegation can unlock new levels of growth, creativity, and scalability. In this series, we are exploring how leaders across industries have learned to delegate effectively and the transformative impact it had on their organizations. As a part of this series, we had the pleasure of interviewing Caitlyn Wells.

As the founder of Upwell Strategies, Caitlyn has devoted her career to empowering impact-driven CEOs to scale their businesses with efficiency and heart. With a vision to transform how leaders engage with their team, she founded Upwell Strategies to serve as a strategic partner to leaders who are aiming for sustainable growth in their businesses. Through developing systems tailored to each unique business’ needs & goals, Upwell Strategies has helped numerous entrepreneurs align their business operations with their overarching vision & goals.

Thank you so much for your time! I know that you are a very busy person. Our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?

My journey to starting Upwell Strategies is likely deeply rooted in my upbringing. I come from a family of small business owners and have always had an entrepreneurial spirit. You could probably say that entrepreneurship runs in my veins. The next step in my journey was in college when I pursued a degree in business and digital marketing, which gave me a strong foundation and knowledge for where I am now.

After spending time working at an agency, I took the leap to start Upwell. Initially, I focused primarily on providing marketing and sales funnel services. As the business evolved, I found myself often helping clients with their operations as well and discovered my true passion for systems and operations. There’s something incredibly satisfying about creating systems and automations that help businesses run more efficiently, so I pivoted to focus entirely on operations — it’s where I truly thrive and can make the biggest impact for our clients.

Today, I wear many hats both within the business and outside of it — I’m a business owner, a mom to an amazing toddler, and a wife. Balancing these roles has actually made me better at what I do, as I understand firsthand the importance of solid systems and efficient processes in creating a business that supports your life, rather than consuming it.

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

When I think about the key people who’ve helped me get to where I am today, my husband, Luke, immediately comes to mind. His unwavering support has been absolutely crucial in my entrepreneurial journey, from the very first moment I shared my dream of starting a business to where we are now with Upwell Strategies.

One of his biggest moments of support that stands out to me is how he supported my vision before I had even really started much. When I first shared my desire to leave my job and fully commit to growing Upwell, there wasn’t a hint of doubt from him. We made a deliberate decision to adjust our finances at the time to rely solely on his salary during those first couple of years of running the business. I was extremely grateful and privileged to be able to do this and it gave me the freedom to leave my job and focus entirely on building the business — even with it being very early stages of the business.

Through every pivot and every challenge, Luke has been my rock. His steady support has given me the confidence to take necessary risks and the security to know that it’s okay if everything doesn’t go perfectly according to plan. I’m incredibly grateful for his partnership in this journey.

You are a successful leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?

In reflecting on my journey as a leader, three key characteristics have been particularly crucial to my success. First is organization. I’ve always believed that having strong systems and clear processes isn’t just about keeping things tidy — it’s about creating a foundation that enables growth and scalability while driving high performance and trust on your team.

The second trait is determination. Business isn’t always smooth sailing, and there have been plenty of challenges along the way. But I’ve found that consistent, determined effort, even in small steps, ultimately leads to significant progress. It’s about showing up every day and doing the work, especially when things get tough, and setting that as an example for everyone on your team.

Third, and perhaps surprisingly to some, is simply kindness. In leadership, I’ve found that treating people with genuine kindness and respect not only creates a positive work environment but also builds stronger, more resilient teams. People perform at their best when they feel valued and supported by those around them.

Ok, fantastic. Let’s now turn to the crux of our interview. Can you tell us about the point in time when you realized that you would need to learn to delegate?

I actually would say that my delegation journey had two distinct points where I found myself having to learn (and then re-learn) the importance of delegation. The first was when I had my first child. The experience of preparing for maternity leave and then also navigating motherhood while continuing to grow Upwell Strategies made me acutely aware that time is our most precious resource, and I needed to find a way to be both present for my family and effective in my business. The only way that was going to be possible was through effective delegation.

The second key moment came during a period of significant business growth. We were getting busier, and I found myself at a crossroads: either figure out how to delegate more effectively or risk sacrificing either the quality of our work or my work-life balance. I wasn’t willing to compromise on either front so learning better delegation was my only option. This was when it really hit home that delegation wasn’t just a nice-to-have skill — it was absolutely essential for sustainable growth.

These moments taught me that learning to delegate isn’t just about managing workload; it’s about creating space for what matters most while ensuring the business can thrive. It’s about finding that sweet spot where both personal and professional goals can co-exist and support each other.

What was the most challenging aspect of learning to delegate effectively, and how did overcoming it impact your personal leadership style and business growth?

Being completely honest, my biggest hurdle with delegation was coming to terms with my perfectionism. I used to have this mindset that if I wanted something done exactly right, I needed to do it myself. Looking back, I can see how this thinking was not only limiting my growth as a leader but also holding back the business and my team’s development.

Learning to release control was a journey for me. It required a mental shift from focusing solely on having tasks done “my way” to appreciating that there might be different — and sometimes better — approaches to achieving the same goal. The most challenging part was building that “trust muscle” and accepting that while someone else’s method might be different from mine, it could be equally effective or even bring fresh perspectives I hadn’t considered.

This evolution in my thinking has transformed my leadership style. I’ve become much more focused on outcomes rather than controlling every step of the process. It’s allowed me to empower my team members to bring their own creativity and problem-solving skills to the table. Surprisingly, this has often resulted in innovations and improvements in our processes that I might never have discovered if I’d kept everything under tight control.

The impact on our business growth from this has been significant. By letting go of the need to personally handle everything, I’ve been able to focus on higher-level strategic initiatives while fostering a more engaged and confident team. It’s created a positive cycle where team members feel trusted and valued, which in turn leads to better performance and more opportunities for growth — both for individuals and the business as a whole.

Can you share a specific example of a time when delegation led to an unexpected breakthrough for your company? What did you learn from that experience?

One of the most significant breakthroughs we experienced came from delegating our marketing creation workflow. For three years, our marketing efforts were inconsistent — we’d have bursts of activity followed by periods of silence, mainly because I was trying to manage it alongside everything else.

Taking the leap to delegate almost all aspects of our marketing creation was transformative. I had to push past my initial hesitation, but once we had the right team and processes in place, we achieved something that had eluded us for years: true consistency. Our marketing went from being sporadic to becoming a well-oiled machine, with regular content creation and campaign execution.

The results really opened my eyes. Not only did we start seeing measurable growth, but the quality and creativity of our marketing actually improved with dedicated people focusing on it. It was a powerful lesson that sometimes what a task needs most isn’t your personal touch — it’s the focused attention and fresh perspective that comes from having the right people dedicated to it.

This experience taught me that effective delegation isn’t just about maintaining the status quo — it can actually elevate your business in unexpected ways. It reinforced for me that when you give capable people the space and trust to excel in their areas of expertise, they often exceed your expectations and take things further than you might have on your own.

How do you decide which tasks or responsibilities are essential to delegate versus those that require your personal involvement? Do you use any frameworks or decision-making processes?

When it comes to delegation decisions, I always start by looking at the potential ROI. I ask myself: What could I accomplish with the time this task currently takes me? What’s the cost of having someone else take it on? This helps me make clear-headed decisions about where my time is best spent and where I might be creating a bottleneck by holding onto tasks that could be handled effectively by others.

I’ve also learned to take a step back and really evaluate whether certain tasks are truly moving the needle for our business. Sometimes we continue doing things simply because we’ve always done them, so I make it a point to assess if each activity is still contributing meaningful value before deciding how to handle it.

The existing skillsets within my team play a huge role in these decisions. I look at who has the capability, interest, or potential to take on different responsibilities. But I also think it’s important to be realistic about our current capacity and expertise gaps.

If I identify important tasks that no one on the team can currently handle, I go through a careful evaluation process. Can we invest in training to build this capability internally? Is it time to consider bringing in someone new with these specific skills? And critically — can our business support that investment right now? These questions help me make strategic decisions about growing our team versus developing existing talent.

I’ve found this approach helps me make more objective decisions about what to delegate, while ensuring we’re building a team that can sustainably handle our key business needs. It’s not just about getting things off my plate — it’s about thoughtfully distributing responsibilities in a way that helps everyone, and the business, grow.

What advice would you give to leaders who struggle with the fear of losing control when delegating critical tasks? How can they build trust with their teams?

I think this is something many leaders struggle with, myself included in the beginning. I’ve found that building a strong foundation is key to feeling confident when delegating critical tasks. For me, it all starts with having solid processes in place and documenting them. It’s one thing to know how you would do a particular task in your business. It’s another to have it documented where you can easily hand it off to someone else. And these aren’t just documents that sit on a shelf — they’re living guidelines that help ensure consistency and quality, making it easier to trust that work will be done to the right standards. Weaving these SOPs into your systems and workflows helps to ensure they are followed and easily accessible at all times.

Proper training is absolutely crucial in delegating important tasks. I’ve learned that investing time upfront in comprehensive training pays huge dividends in terms of both quality and confidence — for yourself and your team member doing the work. When you know your team members have been thoroughly trained, it becomes much easier to step back and let them take the reins.

I’m also a big believer in the gradual approach to delegation. Rather than diving in with both feet, I start by handing off smaller responsibilities and gradually increase them as team members demonstrate their capabilities. This step-by-step process naturally builds trust and confidence on both sides.

One thing that’s often overlooked but has been invaluable in my experience is really focusing on the hiring process itself. I’ve learned to look for specific qualities and indicators that tell me whether someone will be a good fit — not just for the role, but for our team culture and working style. When you bring in the right people from the start, the process of building trust and delegating responsibilities becomes so much more natural.

And one big thing to remember is that effective delegation isn’t about “losing” control — it’s about increasing your impact through others while maintaining high quality standards. It’s a journey that takes time, but the results are worth it when you see your team members growing and succeeding in their roles.

This is the main question of our interview. What are “5 Things You Need To Know to Successfully Delegate for Growth”?

How do you ensure accountability and maintain high performance after delegating responsibilities to others? What systems or processes have worked best for you?

In my experience, successful delegation comes down to finding the right balance between empowering your team and staying connected to their work. I’m a firm believer in regular team check-ins, as they create natural touchpoints where we can discuss progress, work through any roadblocks, and make sure we’re all moving in the same direction.

One thing that’s been absolutely essential for me is having a solid project management system in place. It keeps everyone on the same page and makes it easy to track what’s happening across different projects and team members. As a founder, you get real peace of mind in knowing nothing is going to slip through the cracks.

I also build in review stages throughout our projects, but I’m flexible with how these work. As team members grow more confident and show they’ve got things handled, I’ll dial back the frequency of reviews. It’s important to me that people feel trusted to run with their responsibilities while knowing they have support when needed.

To maintain high performance, I make sure we have clear metrics in place per role and schedule regular monthly or quarterly reviews with each team member. These conversations, paired with data, help us celebrate wins and spot areas where we might need to adjust our approach whether that’s through more training, adjusting a few processes, or something else entirely.

How can our readers further follow your work?

You can connect with me on LinkedIn, where I regularly share industry insights and updates about my work. For a deeper dive into what we’re doing at Upwell Strategies, visit my website at https://upwellstrategies.com/.

Thank you so much for sharing these important insights. We wish you continued success and good health!

About The Interviewer: Dr. Bharat Sangani is a cardiologist and entrepreneur with over 35 years of experience, practicing in Gulfport, Mississippi, and Dallas, Texas. Board-certified in Internal Medicine and Cardiology, he specializes in diagnosing, treating, and preventing cardiovascular diseases, including heart disease and hypertension. In 1999, Dr. Sangani founded Encore Enterprises, a national real estate investment firm. Under his leadership, the company has executed transactions exceeding $2 billion, with a portfolio spanning residential, retail, hotel, and office developments. Known for his emphasis on integrity and fairness, Dr. Sangani has built Encore into a major player in the commercial real estate sector. Blending his medical and business expertise, Dr. Sangani created the Life is a Business mentorship program. The initiative offers guidance on achieving balance in health, wealth, and relationships, helping participants align personal and professional goals. Now based in Dallas, Texas, Dr. Sangani continues to practice cardiology while leading Encore Enterprises and mentoring others. His career reflects a unique blend of medical expertise, entrepreneurial spirit, and dedication to helping others thrive.