What Happens After the Leadership Retreat?
Photo Credit: Harshit via Unsplash
Why the real work of leadership development begins when we go back to work.
Leadership training tends to stick when leaders practice what they learned inside their real workday, with steady follow-up and a group to return to in the months after the retreat.
Leadership retreats and trainings can be incredibly powerful. We step away from the urgency of our work long enough to see ourselves and each other differently, and in that space, there are breakthroughs and hard conversations that finally get to happen. We leave carrying real commitments and a genuine determination to lead differently.
And then we go back to work …
Where the inbox is full, and the problems that waited patiently for us all need attention at once. What we left behind is largely unchanged, and the familiar ways we have learned to operate await us. Insight can help us see a different way forward, and a new habit asks for something more, the slow work of practice and repetition, with support and enough time for it to settle.
Henley Leadership Group coach Melanie Cossette saw this play out again and again over nine months with leaders at a travel tech company in the Seattle area, where a three-day leadership training was followed by small group sessions and ongoing conversations. What she noticed was how often the change took hold in the weeks after those inspired moments, as leaders returned to the ideas and commitments they had made and began practicing them in the midst of their actual workday.
Key Takeaways
Much of the change from a leadership retreat takes shape afterward, as leaders practice new behaviors in their everyday work.
Henley Leadership Group coach Melanie Cossette saw this across nine months and roughly 12 deep-dive sessions with leaders at a Seattle-area travel tech company.
A 2024 review of 91 studies found that people need the capability, the opportunity, and the motivation to apply training at work.
Small, consistent steps shared with a group, along with regular follow-up, helped leaders build momentum over time.
When the Real Work Begins
Several years ago, I participated in a large body of work inside a travel tech company in the greater Seattle area. The deep dive was a three-day leadership training followed by ongoing conversations with those leaders and facilitated small group discussions. There was also a portal with information that supported the leadership concepts we were embedding, along with conversation starters to keep the work going once our team was no longer directly involved.
I spent 9 months in that organization, facilitated approximately 12 deep dives, and got to know and engage with many leaders across the organization, both horizontally and vertically. In these larger group settings, breakthroughs were achieved, awareness was shared, tears were shed, and commitments were made, both individually and collectively. The company and the people were committed to the program and to positive change.
After the glow of the deep dive, that is where the work really began. It is in our daily lives that we are given “grist for the mill” to test our learning and try on new behaviors. It’s not easy. Often, in the first group follow-up session, I heard people report not having grabbed "the bull by the horns" because the flood of work after a three-day offsite felt all-consuming. Also, they fell back into their regular work rhythm, and it felt hard to incorporate the new learnings. The best of intentions can lie on the side of the road as we hurriedly work to “get it all done”.
Encouragement was given, often, I'd say, "Small steps build momentum." (Thank you, James Clear!) We continued the journey together, sharing challenges and wins, with my role being to reinforce learning and explore implementation. When did change take hold? Not immediately, but over time. It was the consistent revisiting of ideas, and the sharing that each individual contributed - honesty, trepidation, triumph, failure, and learning, which shaped the experience of success.
Small steps consistently applied build momentum. Small steps that could be shared, acknowledged, and celebrated. The change took hold for different people at different junctures along the road we traveled together. And, in full transparency, there were always a few who stopped coming, usually with an apology citing their workload.
So to answer the question, “What does it really take for people to grow?”, I would say it takes more than anything else, a desire to do so. Not lip service to wanting to grow, but the deep-in-the-gut desire for something different. Then it takes exposure to new ideas, a willingness to stretch into something new, and a commitment to the process, with the understanding that it won’t happen immediately. It also takes trust, trusting that if I commit to this growth and apply myself to it, it will happen!
— Melanie Cossette
How Does Leadership Development Actually Stick?
Leadership development sticks through practice in the real workplace, supported by follow-up that keeps bringing leaders back to what they learned. Melanie's experience reminds us that inspiration and new learnings are only the beginning. We can recognize a habit like being highly reactive and genuinely want to change it, knowing full well what it costs us, yet still return to the familiar when the grind and demands of everyday work take over. When that happens, the retreat has still done its part, and what remains is the patient work of practicing a new way of leading in the very environment that helped create and reinforce the old ways.
This is where new ideas and the tools to practice them go hand in hand. Stepping onto what Ronald Heifetz and Donald Laurie call the balcony, the vantage point where we can see the patterns we are usually caught inside, or simply taking quiet time for self-reflection can help us see what no longer serves us and imagine a different way forward. From there, the insight has to be carried back into the workday, where each attempt at something different teaches us a little more about the next one.
Research on training transfer points in the same direction. A 2024 systematic scoping review published in the European Journal of Work and Organizational Psychology examined 91 studies on how soft skills carry from training into the workplace. The researchers organized what they found around the conditions that help learning travel into daily work: people need the capability, the opportunity, and the motivation to apply what they have learned. Melanie's story adds something the research also names, which is the quiet power of follow-through, of having someone who returns to the learning with us and helps us find our way back when the week pulls us off course. Her small groups gave leaders a place to bring honesty and failure alongside their wins, and that kind of shared candor is much of why we build our own leadership program as a nine-month cohort.
The changes themselves may not look dramatic. A leader might listen instead of immediately solving the problem, ask another question instead of giving an answer, trust someone else to take the lead, or have the difficult conversation instead of putting it off. Each choice may seem small on its own, and over the months they gather into a different way of leading.
Leader Reflection
What happens to your intentions once you return to work after an offsite?
What helps you put new ideas into practice?
When you look back at changes you’ve made as a leader, how did they happen?
How have other people helped or gotten in the way of changes you’ve tried to make?
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Learning something new is only the beginning. Without practice and follow-through, it can be difficult to apply what we learned once we return to the demands of everyday work.
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Practice. This gives leaders a chance to try out new tools, different responses, and other approaches in real situations, to see what happens and to continue learning and growing.
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Follow-through provides leaders with continued support as they apply what they have learned, work through challenges, and make changes in their day-to-day leadership.
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There's no fixed timeline. During Melanie Cossette's nine-month engagement, change took hold at different points for different leaders, and it grew through revisiting the ideas consistently over those months.
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Training transfer is the degree to which what people learn in a training shows up in how they actually work afterward. A 2024 review of 91 studies organized this research around people's capability, opportunity, and motivation to apply what they learned on the job.
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In Melanie’s work showcased, it meant facilitated small group sessions and ongoing conversations with a coach, supported by an online portal of resources and conversation starters.
Seeing a pattern clearly is often where growth begins, and the changing of it unfolds slowly, across many ordinary days. If you have a leader in your organization who is stuck in that gap between insight and real change, we'd love to talk about what coaching could do to help close it. A 30-minute conversation with our team is a good place to start to see if we’re the right fit.