Every organization hits milestones worth celebrating—a big anniversary, a major initiative achieved or a moment that deserves more than a quick shoutout. But here’s what we’ve learned from working with clients on these moments: They don’t automatically resonate just because leadership sees their importance.
The celebrations that stick are the ones where people see themselves in the story, feel closer to their team and leave energized about what they’re building next.
To unpack what really makes milestone celebrations land, I sat down with three JPL leaders who’ve spent years in the trenches helping clients get this right:
- Jill Sailer, Lead Account Manager
- Jon Bishop, Manager of Client Leadership
- Frank Rowland, Director
Here’s what came up in the conversation, along with some honest insight into what works and what tends to fall flat.
Lindsey Williams interviews Jill Sailer, Jon Bishop and Frank Rowland (left to right).
1. Start with why anyone should care
“You can’t assume a milestone matters to everyone just because it matters to the organization,” Jon Bishop points out. “If people can’t see how their work connects to it, or how it moves the business forward, it won’t land.”
Before you plan how to celebrate, ask a more fundamental question: Why should employees care about this? How does it connect to what they’re working on right now? What does it say about where you’re headed together?
When you make that connection clear, the milestone stops being just a date on the calendar and starts to feel meaningful.
But don’t stop there. Define what you want people to feel afterward. What should employees walk away thinking? What should partners or customers understand differently? Breaking goals down by audience—employees, leadership, customers, community—helps you design a celebration that’s a reflection of your brand strategy, not just a checklist of activities.
2. Bring employees into the story first
A lot of organizations get this backward. They focus on the external moment—the press release, social posts or community event—and loop employees in at the last minute.
Here’s the problem: If employees feel like spectators to something they helped build, you’ve already lost them.
“When employees see their actual work reflected in the narrative, the moment feels genuine, not staged,” Jill Sailer says. “It doesn’t matter who’s delivering the message if people recognize themselves in it.”
Let employees experience the story first. Better yet, let them help shape it. Share the milestone story, video or announcement with key contributors before it goes public. Early access signals trust and respect—it tells employees they’re insiders, not spectators.
Then take it external, knowing it’s rooted in something real.
Frank Rowland points to a client’s successful 100-year anniversary as an example of getting this balance right. The celebration worked both externally with the public and internally with employees because the internal story came first and shaped everything that followed.
3. Use small moments to build the big ones
The milestones that deliver the biggest impact don’t come out of nowhere. They feel earned because there’s been an ongoing narrative and a steady cadence of recognition leading up to them.
But there’s a balance to strike.
“When recognition turns into a parade of trophies, it stops feeling special,” Frank says. “People want moments that feel considered.”
You don’t need more recognition. You need better recognition. Frank recalls a client who cut their awards programs in half and saw employee engagement increase. A few meaningful moments that build toward a larger organizational win will always beat constant recognition.
Jill adds another perspective: “If you get the smaller moments right, you’re building a rhythm. So when it’s time for a big celebration, you’re not scrambling. You already have great content, stories and mini milestones that naturally build into the big one.”
One client Jill works with built an ongoing peer-to-peer recognition program tied to their performance behaviors. JPL helped them create the nomination process, gift options, newsletter placements and video components. It’s the kind of program that creates a steady drumbeat of recognition throughout the year—so when bigger milestones arrive, they feel like natural peaks rather than isolated moments.
4. Make room for it
Want to kill a milestone celebration fast? Squeeze it into the last 10 minutes of an already packed meeting.
People can tell when something is an afterthought. What they respond to are experiences that feel intentional—moments where they can participate, not just sit and listen.
That might mean a dedicated event. It might be a hybrid experience where remote employees can genuinely engage. It could also be something physical or digital created during the celebration that sticks around afterward, helping sustain energy and momentum.
Frank shared two client examples that show what this looks like in practice. A large healthcare system created surprise recognition moments for employees doing exceptional work. They filmed the employee’s day behind the scenes, captured peers talking about what made them special and then surprised them with a recognition lunch. “It was a different way to approach it,” he says, “and it really worked.”
On a larger scale, another client hosted an annual awards event celebrating employee milestones from 5 to 25 years, combined with performance recognition. Attendance was 100% voluntary, and Frank saw firsthand how employees reacted on an emotional level. “It wasn’t just about employee recognition,” he says. “It was about being part of the brand’s legacy and seeing people truly celebrated in this big, incredible way.”
The key to this in today’s workplace may surprise you: Plan hybrid-first, not in-person-first. Ensure remote employees can contribute beforehand, participate live and engage asynchronously. Avoid “watch-only” experiences—design interaction for everyone from the start.
Equity in celebration signals equity in culture.
Whatever the format, the message to employees should be clear: What this person or team is doing matters to the success of all of us, and we should pause to recognize them and celebrate it as a special moment.
5. Mix up who’s telling the story
Milestones often feature the same voices—executives and senior leaders we hear from all the time. That’s a miss.
“There’s an opportunity to bring in a range of people within the company, or even someone totally unexpected, in a milestone moment,” Jon suggests.
He points to a global client who brought in a highly animated brand manager to kick off an enterprise-wide event. “They really equipped him to seize the moment,” Jon says. “It worked because employees heard from someone they didn’t usually hear from.”
When people hear from peers across roles, levels and parts of the organization, the story feels richer and more believable. Those lightly produced, authentic moments land harder than polished speeches.
And don’t forget the people working behind the scenes. Highlighting contributors who aren’t typically visible reinforces that the milestone happened because of many hands, not just a few.
6. Use the milestone to look ahead
The best celebrations don’t just look back. They pull people forward.
Invite employees to share ideas about what should come next. Ask for input. Then, when those ideas take shape, celebrate them. That’s when a milestone stops being about the past and becomes a launchpad for future growth.
Jon shared an example of a client that created a program where any employee could submit ideas to improve the business, discuss them as a group and build on them together. Jill notes that other clients have run similar programs around driving innovation where employees meet regularly to discuss and develop ideas that move the business forward.
The key to success, he says, is closing the loop. “If leaders ask for feedback and ideas, they need to report back: ‘We heard you, we listened, and because of your input, here’s what we’re doing.’ That connection reinforces that employee voices actually matter.”
As Jill puts it, when employees contribute ideas, they become part of what’s next. “They’re building it, creating it and then they get to celebrate the success of it.”
7. Don’t let the moment end when the celebration does
By treating the milestone as a chapter, not a finale, you can sustain energy long after the celebration.
Reference the milestone in future communications and decisions. Build follow-up moments—thank-you messages, content recaps, team discussions. Ask employees to reflect: What did this moment mean to you? How does it shape what’s next?
Turn the celebration into a content ecosystem. Share internal recaps, employee spotlights and social storytelling. Let the milestone live on through onboarding materials, town halls and internal communications.
Jon mentioned a client who marks each year with a Founder’s Day celebration. It’s become an annual milestone with internal, external and community components that reinforces the company’s legacy and culture year after year.
When celebrations are documented well—captured through the employee lens, not just polished brand footage—they become cultural anchors. Archive milestones so employees can see how they’re part of a longer legacy. Culture strengthens when people can look back and recognize themselves.
Here’s what it comes down to
Milestone moments are happening whether organizations leverage them or not. Making these moments meaningful by pausing to celebrate them takes intentional planning. But it pays off big.
When you connect milestones to people’s work, bring employees into the narrative and give them a voice in what comes next, you’re not just marking time. You’re building something together.
You’re saying thank you in a way that lands. You’re strengthening the team. And you’re giving people a reason to be excited about the next chapter.
