Most leadership development programs focus on outcomes. But what about the thinking, listening and strategic decisions that shape effective, successful programs?
Trina Huntley is the Manager of Learning & Development at Payworks—a Canadian-owned and operated organization that provides workforce management solutions and is a client of ours here at Padraig. In her role at Payworks, Trina has focused on growing employee engagement and performance through learning, development and coaching.
The Payworks—Padraig connection
Payworks ran a nationwide competition to find a service provider who could design and deliver a custom leadership development program for their company. They approached us because they had seen our model of The Network, which is Padraig's in-house, ready-to-go, cohort-based leadership program and they liked the format and the approach. They also had heard good things about our skill in leadership development.
We went through a process where Payworks met with several vendors, talking about the values that their company lives and how they translated those into leadership pillars that they would want reflected in the leadership development program. Our Padraig team outlined for them the model that we currently have and adjusted it to provide workshops aligned with their pillars. In cases where we didn’t already have a workshop in our library of courses that aligned perfectly, we worked with them to design customized courses for leadership at Payworks.
The leadership learning is now ongoing, and we’re concluding Padraig’s second year of delivery for Payworks. We’re constantly monitoring and continuing to adapt courses, if needed. As part of the Payworks program, we facilitate one-day workshops, conduct group coaching sessions and pair participants into dyads to work together on homework assignments and to support each other. In this way, the program is also building a network of people geographically dispersed throughout Payworks.
Additionally, the program brings a shared language of leadership to Payworks. It gives folks something to aspire to, as well as the confidence and knowledge to be able to lead effectively.
Reflecting on the planning process
We enjoyed reading a blog Trina wrote that summarized what she’s learned about leadership training, notably her candid reflections on what surprised her when planning a leadership development program, what worked well and what she’d approach differently in future.
Trina’s reflections of her work behind the scenes showcase Payworks as an example of how thoughtful program design can create real transformation.
As executive coaches, we believe exploring the process—not just the product—gives valuable insights to other L&D and HR leaders.
Payworks challenge: Scaling with intention
One of the biggest challenges Trina has faced at Payworks was scaling up and scheduling a meaningful leadership development program to 87 (and increasing) leaders amid rapid national growth.
“We had to be thoughtful in our execution,” explains Trina. “We knew from the beginning that mixing leaders across departments would enhance peer learning and broaden perspectives, but we had to balance that vision with operational needs—we couldn’t pull too many leaders away from their teams at once.”
A second key challenge was managing the potential for scope creep—not from a lack of direction but from the sheer passion and energy behind the initiative.
“To keep the vision focused and sustainable, we mapped out a phased approach rooted in strategy, starting with current leaders and following with emerging ones. This helped align resources while building momentum over time,” says Trina.
Padraig insight: Intentional cohort design and balancing access with capacity is one of the keys to successful leadership development programs.
Designing for connection, not just content
Trina emphasizes cross-functional learning, group coaching and topics such as emotional intelligence and inclusion as among her top priorities going into the process.
“At the heart of the program was a single, people-focused question: How can we empower our leaders— new, seasoned or emerging—to lead in a more connected, inclusive and adaptive way?”
As the Payworks teams grew in size, diversity and geographic spread, a goal was to equip their leaders with the tools and mindset to engage and retain talent while driving business outcomes.
“The first step was to deeply understand where we were starting from. I spent a lot of time listening— through one-to-ones, group sessions and informal conversations,” says Trina. “What emerged was a clear desire for more cross-functional connection, better alignment among mid-level leaders and a break from siloed ways of working. Those insights shaped every aspect of our design.”
Padraig insight: Successful leadership learning must address both relational and strategic dimensions because leaders must think clearly and connect deeply in fast-moving, people-centred workplaces. Relational leadership builds trust, engagement and culture while strategic leadership sets direction and drives outcomes.
Staying agile and grounded in feedback
When designing a leadership development program, Trina’s approach is to leverage input from leaders and feedback loops.
“One of the most impactful decisions I made was designing the program around cohort-based learning with leaders from across the organization. This directly addressed the desire for more collaboration and communication, and it created a real sense of shared experience,” says Trina.
“I also built in structured group coaching, led by certified professionals, and anchored the curriculum in practical topics: how to navigate tough conversations, increase emotional intelligence, lead through change and foster inclusion and belonging. These sessions have already shifted how our leaders show up for their teams.”
Most importantly, she says: “I’ve stayed close to the experience—gathering feedback regularly and adjusting as needed. That agility has been essential in making sure we’re delivering real value.”
Padraig insight: Responsiveness and iterative design are hallmarks of our impactful leadership development programs because they ensure that programs stay relevant, learner-centred and aligned with real organizational needs. Content,delivery and most importantly, retention are meaningful when connected to the actual work and challenges faced by leaders. Putting new skills into practice makes leadership development stick. Some leaders also benefit from a gentle nudge to start (or refine) their own process, which is where coached peer leadership groups keep them learning and growing.
Alignment with organizational strategy
When designing a leadership development program, Trina focuses on values alignment and leadership as a business driver.
“I started by reconnecting with the core purpose and values of our organization,” says Trina. “That clarity helped us ensure that leadership development wasn’t a side project, but a direct driver of our business strategy.”
To accomplish this, Trina says she focused on questions like: What kind of leadership will move our business objectives forward? What behaviours do we need to model as we serve an evolving marketplace?
“That alignment allowed us to anchor every part of the program—from topics to outcomes—in our long-term goals, while still making room for enthusiasm and innovation in the delivery,” explains Trina.
Padraig insight: Leadership behaviours set the culture of an organization and the culture will ultimately determine the success.
Making it work: Sponsorship & a cultural shift
According to Trina, finding enthusiastic sponsors is a key to getting buy-in and building momentum.
“A big part of our success came from securing executive sponsors – senior leaders who believed in the vision and weren’t afraid to champion it across the organization,” Trina explains. “Their support sent a clear signal that leadership development wasn’t just ‘nice to have,’ but mission-critical.”
Their advocacy also helped Payworks manage the change side of this initiative: shifting priorities, reallocating time and building new habits.
“That kind of cultural shift doesn’t happen overnight, but having visible, committed leadership at the top made a world of difference,” shares Trina.
Padraig insight: For any leadership development program to succeed, it has to be seen as more than a HR project. When senior leaders from the top down visibly champion learning, it allows other leaders and staff to make the time and give the effort needed for it to be successful. Active engagement by mid-level leaders is also critical because they bridge the gap between vision and execution, modelling and reinforcing learning through their own interactions.
Takeaway for HR and L&D leaders
When we asked Trina what’s one piece of advice she’d share with other L&D professionals designing leadership programs in their own organizations, she shared:
“Be patient, and stay agile. Leadership development is transformative work—it ripples across teams, cultures and outcomes.”
Trina suggests leaders give themselves permission to learn as they go and stay connected to the people they’re designing the program for.
“Create feedback loops, listen actively and don’t be afraid to adapt. The more human you make the process, the more lasting the impact will be.”
Padraig reflection: Nothing is ever perfect and, of course, trying to deliver perfection prevents making progress along the way. We work closely with Payworks to assess all aspects of the leadership development program and to modify content or the order of things to ensure the program is delivering results in the best way.
Coach’s Questions
Where in your organization is leadership being tested right now? What kind of support would make the biggest difference? How would a well-designed leadership development program change the organization? How are you listening to the people you're designing leadership development for—and what are they telling you?
