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Summary
Should we expect the most recent customers or students to be the most deeply engaged? Experience suggests otherwise. Put it down to human behaviour. In a world fixated on real-time metrics and instant feedback, we should remember that the deepest and most durable loyalty could take long to form.
There is a small puzzle I have been sitting with for some time. When I invite alumni to a flagship programme event—one meant to celebrate learning, community and shared journeys—it is not the most recent graduates who sign up first. Instead, registrations tend to come from those who attended classes many years ago.
This is puzzling because, on the surface, everything points the other way. Faculty relationships with recent alumni are warm and conversations are ongoing. If loyalty were a simple function of proximity, they should be the first to respond. Yet, getting recent alumni onboard for such events often proves harder than engaging those who graduated a decade or more ago.
Over time, I have realized that this pattern has little to do with teaching and much more to do with how human beings relate to institutions, leaders and even one another once time enters the equation. Leaders often seem to assume that the most recently enrolled, such as fresh hires and newly onboarded customers, would be the most engaged, since the memory of their experience is vivid, relationships are still active and the value proposition seemingly needs no reinforcement.
Behaviourally, the opposite tends to happen. When access feels easy and ongoing, people tell themselves ‘not now.’ There is no urgency when no loss is perceived. Older alumni, by contrast, experience distance. What was once routine now feels rare and returning to a familiar but no longer everyday space holds emotional weight, turning participation into an act of reconnection rather than continuation.
Business leaders encounter this pattern all the time, even if they do not consciously label it. Long-standing customers are often more responsive to renewal conversations than newly acquired ones.
Similarly, former employees turn into stronger brand advocates a few years after they have moved on, while current employees remain ambivalent. In family businesses, it is not uncommon for elders to feel more emotionally attached to the enterprise once they step back, rather than when they were fully immersed in running it day-to-day. Time changes how value is perceived.
A common misunderstanding among leaders is the assumption that identity forms at the same pace as experience. People do not become ‘alumni,’ ‘partners’ or ‘legacy carriers’ the moment a programme ends or a role changes. Identity needs distance to crystallize.
Recent graduates, much like newly appointed leaders or successors, are still focused on proving themselves. Their orientation is tied more closely to their immediate cohort or role than to the broader institution or its history. Older alumni have had more time to connect the dots. With distance, they can look back and see how early conversations and even mistakes quietly shaped later decisions. Things that once felt like course material begin to register as context and what once felt like hard work starts to feel truly formative.
Similarly, in organizations, it is only after leaders have moved through cycles of success and failure do they begin to appreciate the institutions, mentors and early structures that shaped them. Such appreciation begins to grow once the pressure to perform eases and the urgency to prove oneself recedes, with loyalty following much later.
Perhaps the most counterintuitive realization is that strong relationships can actually dull urgency. Maybe the old adage should be tweaked: familiarity breeds complacency. When access to a leader, an institution or a community feels guaranteed, people tell themselves there will always be another chance. It is only once that access begins to feel finite that they act, echoing another well-worn truth that distance often makes the heart grow fonder.
This explains why former colleagues reconnect years later, why retired leaders suddenly become much sought after and why alumni return at a point when they no longer need anything in particular. This is really just human psychology at work.
For business leaders, the lesson is not to complain about delayed loyalty, but to plan for it. Engagement does not always show up immediately or on cue. Some relationships need space before they deepen; others reveal their strength only with time.
Different stages also call for different invitations. Early on, people respond to opportunity and a sense of agency; later, they are drawn to meaning, legacy and a chance to give back. Creating moments that feel irreplaceable matters, because people tend to show up if they sense how special it is. And finally, we must resist reading absence as disengagement. Sometimes, it simply means the relationship is still unfolding.
When people return years later without any obligation or incentives, it tells us something important. The experience did not merely inform them; it stayed with them. In a world obsessed with real-time metrics and instant feedback, we must remind ourselves that the deepest forms of loyalty operate on longer timelines. For leaders, the real test is not who shows up right away, but who comes back when they no longer need to. That’s when you discover what truly lasted.
These are the author's personal views.
The author is professor, economics and executive director, Centre for Family Business & Entrepreneurship at Bhavan’s SPJIMR.
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