Implementing agile methodologies can be a game-changer for businesses, but it comes with its own set of challenges. This article presents valuable lessons from experienced business leaders who have successfully adopted Agile practices. Their insights cover crucial aspects such as managing expectations, fostering team dynamics, and overcoming cultural barriers.
Manage Expectations for Long-Term Agile Success
One major challenge we faced when implementing Agile practices was being a little too impatient and, to a certain degree, having unrealistic expectations. Like many, we expected immediate results; however, the process is not something that takes effect overnight. It does deliver, but it takes time.
Overcoming this challenge was not easy, but we did it. Instead of focusing on big wins, we changed our perspective to focus on smaller wins and learning experiences. We celebrated specific instances where Agile principles assisted us in preventing larger problems and those instances where following the methodology led to better outcomes.
When it comes to Agile, it’s all about managing your expectations effectively. Yes, you may think this is the silver bullet you needed, and it is. But it is not going to make any major changes in the short term. This is a long-term strategy that constantly delivers results. A simple change in perspective allowed us to see the value that Agile practices have to offer.
Mike Falahee, President, Marygrove Awnings
Embrace Redistribution of Control in Teams
What surprised me most about adopting agile practices at Redfish Technology wasn’t the process, but the psychology behind it.
At first, it felt like a loss of control. I had to let go of the rigid, top-down planning that provided a sense of order. Suddenly, things were moving in smaller increments, my teams were making more day-to-day decisions, and priorities shifted constantly based on real-time feedback.
It felt chaotic compared to our previous structure.
But over time, I realized it wasn’t a loss of control; just the redistribution of it.
Agile gives more ownership to the people closest to the work. Recruiters have more clarity on their priorities, more input on how to solve problems, and more room to adjust based on what’s actually happening, not just what was planned weeks ago. It empowers teams to work smarter and stay aligned without waiting for someone at the top to hand down the next step.
So while taking that first step was a challenge for me personally, I’m glad I went through with the shift, because I gained a more engaged and more accountable team able to handle their own tasks with less micromanagement.
Rob Reeves, CEO and President, Redfish Technology
Foster Flexibility Through Clear Communication
One major challenge we faced was getting the entire team, especially those in warehouse operations and customer service, on board with the idea of “constant change.” While Agile sounded great in theory, in practice, it felt chaotic to some. People were accustomed to long-term plans rather than quick sprints and frequent adjustments. To overcome this, I ensured we had clear and transparent communication. We explained why changes were occurring, celebrated small victories, and incorporated feedback loops into our daily routine. Once the team realized it wasn’t about rushing—it was about staying flexible—they embraced it.
Chris Putrimas, CEO, Teak Warehouse
Shift Mindset with Cross-Functional Collaboration
One of the biggest challenges we faced when implementing agile practices at Level 6 Incentives was shifting the mindset around planning and project management. Our business revolves around custom-built incentive and rebate programs, which require a significant amount of upfront strategy work. Moving to a more iterative and flexible way of working initially made some team members uncomfortable. They were accustomed to building a comprehensive blueprint, executing it from start to finish, and then delivering the final product. But agile doesn’t work like that. It’s messy, fast-paced, and built around continuous improvement.
What helped us push through that discomfort was bringing everyone into the “why.” We didn’t just announce a process change. We explained how working in shorter sprints and getting faster feedback would make our programs stronger, more aligned to client goals, and quicker to market. We also paired people from different teams to collaborate early, so sales, marketing, and operations weren’t just handing work off but building together. That cross-functional trust took time, but once we saw the results – more responsive programs, happier clients, and fewer misfires – it started to stick.
Agile wasn’t a one-size-fits-all fix, but adapting its principles to our world made us more nimble and better equipped to deliver value.
Ben Wieder, CEO, Level 6 Incentives
Address Cultural Resistance with Empathy
When we first transitioned to Agile in our healthcare IT organization, the biggest challenge wasn’t technical—it was cultural. We were asking developers, testers, clinical advisors, and compliance teams—many used to traditional waterfall hierarchies—to suddenly collaborate in self-organized, cross-functional squads. The pushback was immediate. Some felt exposed without long-term plans; others struggled with the pace and ambiguity of sprints.
Based on my analysis of similar healthcare environments, I realized we needed more than Agile coaches—we needed empathy-driven transformation. We started by running empathy workshops to identify specific discomforts. For clinicians, it was about losing control of the scope. For engineers, it was story churn and unclear definitions of done. Armed with that feedback, we implemented two changes: 1) Embedded a “Clinical Product Owner” into each team to align medical insights with user stories, and 2) Introduced Agile Playbooks tailored for compliance-heavy domains—mapping HIPAA and regulatory checkpoints into sprint cycles.
One of our breakthrough moments came during the development of a remote patient monitoring module. The team, using Agile, released an MVP in just 6 weeks, compared to the 4-month average under waterfall. But more than speed, it was the cross-functional trust that stuck. Teams began demoing stories to actual patients, iterating based on feedback loops, and gradually, Agile stopped being a method—it became muscle memory.
A study by McKinsey shows Agile teams in healthcare tech see a 20-30% increase in productivity when cultural resistance is addressed upfront. We saw similar results, plus a marked improvement in team morale and clinical stakeholder satisfaction.
Agile isn’t a plug-and-play methodology. In healthcare, especially, it must be translated, not just taught. And once you get past resistance with empathy and structure, Agile becomes less about process and more about people trusting each other to build better care solutions, faster.
Riken Shah, Founder & CEO, OSP Labs
Introduce Agile Anchor Points Gradually
One major challenge was integrating agile practices into a team accustomed to rigid, top-down structures. People were resistant to change, especially when it wasn’t just about adopting new tools but shifting their entire mindset. To tackle this, we introduced the concept of “agile anchor points”—a sort of mental pivot that allowed team members to gradually shift focus from old ways. We did this by identifying small but impactful tasks that showcased the benefits of agility, like rapid feedback loops via quick debriefs. By highlighting these anchors in weekly huddles, team members began to see the tangible benefits, sparking curiosity and encouraging incremental change. This allowed us to weave agility into the company’s fabric without overwhelming people, making the transition smoother.
Shannon Smith O’Connell, Operations Director (Sales & Team Development), Reclaim247
Cultivate a Learning Mindset Through Coaching
The biggest challenge we faced when implementing Agile was getting the whole team to shift from a ‘delivery mindset’ to a ‘learning mindset.’ Initially, sprints felt like mini-waterfalls; we were just cramming tasks into two-week blocks. We overcame this challenge by investing in Agile coaching and making retrospectives non-negotiable. Once the team started seeing failure as feedback, not blame, our agility became real, not just in name but in mindset and outcome.
Marco Manazzone, Chief Executive Officer (CEO), Zzone Homes
Balance Flexibility with Safety Using Tools
Agile practices are proven techniques to enhance efficiency within all business operations — with automation and AI, it’s a complete no-brainer to capitalize upon. Our company adopted Asana to transform how we plan and deliver an amazing expedition experience. One of our primary challenges revolved around last-minute customer preferences that changed our plans.
These changes usually intersected with local safety guidelines and permits, which caused chaos within the tour guide teams, disrupting the entire flow. To overcome this challenge of balancing agile flexibility with safety norms and permits, we used a fresh approach. We used the tool to create task dependencies and also created a task checklist with priorities and a “deviations allowed” checklist.
This helped all our team members ensure no task was left undone, while also allowing for a broader outlook on which requests could be considered. For instance, last-minute changes cannot accept route deviations, since they’re dependent on permits. Using this approach reduced ambiguity and last-minute chaos, which not only brought greater clarity but also saw a surge in responsiveness rates.
These deviations were highlighted in red, using the agile features. Every team leader must leverage an agile tool to streamline their workflows for smart and efficient workflow management. This brings the benefit of clarity, reduction in unnecessary meetings and delays, while increasing overall performance.
Brian Raffio, Senior Travel Coordinator & Specialist, Climbing Kilimanjaro
Demonstrate Value Through Pilot Sprints
Teams were used to traditional project planning, and the idea of working in short, iterative sprints felt unfamiliar, even uncomfortable. That was the major challenge in adopting agile practices.
How did we overcome it?
We didn’t try to push it all at once. Instead, we ran a few pilot sprints in smaller teams, to learn, not convert. We paired each sprint with open retrospectives, providing space to talk about what felt clunky and what actually helped.
The shift came when those same teams started delivering features faster and with fewer revisions. Once the value became visible, the Agile adoption became fully successful.
This wasn’t a one-and-done shift. We had to keep reinforcing the “why.” But that early investment in patience, transparency, and proof made all the difference.
What I learned from this is the need to treat Agile not as a process you install, but as a habit you grow. Start small. Show results. Respect people’s discomfort, and let the practice prove itself.
Alexander De Ridder, Co-Founder & CTO, SmythOS.com
Brett Farmiloe is the founder of Featured, a Q&A platform that connects brands with expert insights.
