In-person events are back — here are 4 steps to improve the planning process
This blog is based on an article that was originally published in SUCCESS. It has been updated for 2025 and beyond
Large-scale events like sales kickoffs and leadership summits have long been a staple of business strategy. They’ve served as annual milestones—moments to align, inspire, and energize teams around the path forward.
But in today’s environment, their role has become even more vital. As organizations navigate dispersed teams, shifting strategies, and relentless change, these events are no longer just ceremonial—they’re one of the few chances to create clarity, connection, and culture at scale.
How you bring people together is now just as important as why.
Virtual fatigue, rising costs, evolving team structures, and hybrid expectations have transformed event planning from routine to strategic. The most effective companies are moving beyond default formats and asking: What does this moment demand—and how do we design for it?
There’s no one-size-fits-all anymore. The best events flex—tailored to your business, your people, and the outcomes that matter most.
So is there a gold standard? In-person still delivers unmatched energy and connection—but in 2025, the smartest strategies are context-driven.
- In-person builds energy you can feel. It’s unmatched for connection, culture, and rallying teams around big shifts.
- Hybrid expands reach. It connects distributed teams while maintaining presence and participation.
- Virtual is fast, inclusive, and cost-effective—perfect when timing or accessibility is the priority.
- Hyper-local brings people together in smaller, regional gatherings—minimizing travel while maximizing face time and relevance for specific markets or teams.
The question isn’t which format is best—it’s what does this moment call for?
This updated post explores how to design high-impact events—tailored to your context, your people, and your goals.
Let’s dive in.
Set the tone—and build something that lasts
It’s not just the format that’s shifting. Structure, length, content, and tone are evolving too—which creates a powerful opportunity for leaders to shape more meaningful, memorable experiences.
To make these moments count, it helps to pause and consider:
- What do you want this experience to be remembered for?
- How do you want people to connect with it—and with each other?
- What kind of follow-through do you want to inspire?
Approaching event planning through this lens turns it from a one-off activation into a long-term investment. As a leader, you don’t have to manage every detail—but you do need to set the tone. When your vision is clear, your team can build something truly intentional.
Here are four strategies to help you get there:
1. Empower teams to make the right decisions.
Many meetings are unproductive or a waste of time, and meetings involving event coordination may become nothing more than project updates. Though these aren’t without merit to gauge progress, it shouldn’t be the sole focus. For execution teams to act on the right decisions around every detail, the meeting agenda should also touch on the vision, benchmarks, next steps and any obstacles that might require additional support, among other topics. And it should do so at a cadence that makes sense for you, the team and the event itself.Perhaps all that’s necessary is to meet once a month until the event date closes in. Maybe every two weeks is a better option. Information is power, as they say, and you can empower your team to take initiative on their own. Research has shown that empowering team members may lead to innovative behavior and improved work performance, among other benefits. This potential boost to innovative, proactive and knowledge-sharing behaviors may be especially useful when it comes to the team developing innovative ideas and the wherewithal to put those ideas into action. Engage all team members early in the planning process. Provide them with the freedom necessary to make decisions on their own so that when things deviate from the plan, they can adjust accordingly instead of being left unsure of the next steps.
2. Find a balance between internal vision and external engagement.
You’re essentially building a legacy for how you want to be remembered. This can have a sizable impact on not only creating a memorable and lasting experience for your audience, but encouraging them to return year after year.Just look at the Consumer Technology Association’s CES® event, which claims to be “the most influential tech event in the world.” At this year’s event, CES welcomed nearly 120,000 attendees from around the world and offered massive visibility (print and social media) to its exhibitors and presenters. The planning and execution of this event, which showcases other companies’ solutions, requires months of vetting potential exhibits, working with venue and event teams and organizing high-profile keynotes.While staying true to your vision is critical, make sure that you don’t lose sight of the customer in the process. Get boots on the ground and make a habit out of listening, relaying what’s learned and even following up with customers. Then, it’s just a matter of striking a balance between your vision for the event and what the audience is saying. It’s important not to go too broad or too narrow when homing in on your audience and vision; it’s more about finding something in between that speaks to what’s really going on in the business and what attendees want in an event.
3. Create a purposeful, intentional atmosphere for meetings.
All discussions should be connected to the company strategy—“connected” being the operative word here. Think about the purpose and desired outcome. What conversations do you need to initiate? What is the red thread or throughline for everything you’re doing at the event?Without that connection, the focus can shift away from the strategy. Our company uses a pyramid diagram to divide ideas into sections and organize the meeting structure to ensure all discussions are intentional and purposeful.At a recent sales kickoff for a large client, we ensured the client’s new methodology and customers were at the core of every design element. Everything from the digital solution to the scenarios that participants engaged in to how facilitators led debrief conversations was designed to reinforce the new methodology and drive the effectiveness of a cross-functional team in service of customers. As a result of that intentionality, the client saw a 54% uplift in their pipeline coming out of the event and a 40% adoption growth of a newly introduced scorecard for account executives.
4. Reflect on operational successes and failures.
You may not think of reflection as a competency, but research shows that such a habit can be the differentiator between extraordinary and mediocre workplace performance and engagement, and it may serve to benefit your team as well. As such, make after-event discussions more than just debriefing sessions. Did the experience lead to the desired outcomes? Were there any unanticipated outcomes? More importantly, how do you plan to track results over the next few weeks or months?Our company worked with one client who was exceptional at this process. Naturally, the event’s theme fed into the experience from start to finish, and the outcomes were as expected. But instead of checking off that box and returning to business as usual, the client took reflected on the outcomes. They found ways to incorporate that specific experience into their organization so they didn’t lose any traction made with the target audience.
Thinking more strategically about how to execute an event and incorporating these event planning tips will put you a step ahead of the competition. It will also help you create an experience that’s both memorable and a critical part of establishing a legacy for you and your company.
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Global spending on AI is forecast to reach $2.52 trillion by 2026, a 44% year-over-year increase, according to Gartner. At the same time, only about 10% of AI pilots scale beyond proof of concept.
What’s the disconnect?
Why aren’t most organizations seeing the ROI they hoped for, despite making such large investments?
It’s not because the technology isn’t ready. And it’s not because the use cases are unclear.
The disconnect exists because many organizations are investing in AI as a technology upgrade and expecting a business transformation in return.
The tools are advancing at breathtaking speed, and most organizations already have AI in motion. But the work itself often stays the same. AI gets layered onto existing tasks instead of being used to rethink workflows end to end. Adoption metrics go up, while decisions, operating models, and value creation remain largely untouched.
When teams first start using AI, they do what makes sense. They try to recreate today, just faster. Can it help me write this? Analyze that? Save a bit of time?
That’s a smart place to begin. But it’s not where ROI, or reinvention, actually shows up.
Getting over the hump
Real returns begin when teams experience what we often call “getting over the hump.”
This is the moment when two things click at once:
- AI can fundamentally change how work gets done.
- People don’t need deep technical expertise to make that change happen.
When teams see weeks of work compress into hours, or watch an end-to-end workflow suddenly run in a new way, something shifts. Confidence replaces hesitation. Curiosity replaces caution. The questions change, from “How do I use this tool?” to “What’s possible now?”
That shift matters, because ROI doesn’t come from using AI more often, it comes from using it to work differently.
Why ROI stalls as AI scales
As AI initiatives expand, many organizations discover that the limiting factor isn’t the technology itself. It’s the environment surrounding the work.
ROI shows up when teams are able to explore and redesign workflows, not just automate steps. That requires clarity on outcomes and guardrails, but also room to experiment, learn, and iterate. When AI is tightly controlled or narrowly deployed, pilots stay pilots. When people are trusted to rethink how work happens, value starts to compound.
Organizations that unlock ROI don’t chase perfect use cases upfront. They focus on learning faster and applying those insights where they matter most.
The early signal that ROI is coming
Long before AI shows up in financial results, there’s an earlier indicator that organizations are on the right path.
People are energized by the work.
You see it when teams start sharing experiments, when ideas move across functions, and when learning becomes visible rather than hidden. Progress feels owned, not imposed.
That energy isn’t accidental. It’s a signal that people feel trusted to rethink how work happens, and that trust is essential to turning investment into impact.
Reinvention happens closer to the work than most expect
AI reinvention rarely starts with a sweeping rollout or a multi-year roadmap. More often, it begins with one meaningful workflow, one team close to the work, and a willingness to ask a different question.
With the right support, that team gets over the hump. What they learn becomes reusable. Patterns emerge. Over time, those insights connect, creating enterprise-wide impact and sustained ROI.
That’s how organizations move from isolated pilots to real returns.
What this means for AI investment
No organization feels fully “caught up” with AI, and that’s true across industries.
The organizations that will realize ROI aren’t waiting for certainty or the next breakthrough tool. They’re reinvesting their AI spend into new ways of working that scale human potential alongside technology.
Handled thoughtfully, AI doesn’t distance people from the work. It brings them closer - to better decisions, stronger collaboration, and better outcomes.
For many organizations, that’s where the real return begins.
Technology choices are often made under pressure - pressure to modernize, to respond to shifting client expectations, to demonstrate progress, or to keep pace with rapid advances in AI. In those moments, even experienced leadership teams can fall into familiar traps: over-estimating how differentiated a capability will remain, under-estimating the organizational cost of sustaining it, and committing earlier than the strategy or operating model can realistically support.
After decades of working with leaders through digital and technology-enabled transformations, I’ve seen these dynamics play out again and again. The issue is rarely the quality of the technology itself. It’s the timing of commitment, and how quickly an early decision hardens into something far harder to unwind than anyone intended.
What has changed in today’s AI-accelerated environment is not the nature of these traps, but the margin for error. It has narrowed dramatically.
For small and mid-sized organizations, the consequences are immediate. You don't have specialist teams running parallel experiments or long runways to course correct. A single bad platform decision can absorb scarce capital, distort operating models, and take years to unwind just as the market shifts again.
AI intensified this tension. It is wildly over-hyped as a silver bullet and quietly under-estimated as a structural disruptor. Both positions are dangerous. AI won’t magically fix broken processes or weak strategy, but it will change the economics of how work gets done and where value accrues.
When leaders ask how to approach digital platforms, AI adoption, or operating model design, four questions consistently matter more than the technology itself.
- What specific market problem does this solve, and what is it worth?
- Is this capability genuinely unique, or is it rapidly becoming commoditized?
- What is the true total cost - not just to build, but to run and evolve over time?
- What is the current pace of innovation for this niche?
For many leadership teams, answering these questions leads to the same strategic posture. Move quickly today while preserving options for tomorrow. Not as doctrine, but as a way of staying adaptive without mistaking early commitment for strategic clarity.
Why build versus buy is the wrong starting point
One of the most common traps organizations fall into is treating digital strategy as a series of isolated build-vs-buy decisions. That framing is too narrow, and it usually arrives too late.
A more powerful question is this. How do we preserve optionality as the landscape continues to evolve? Technology decisions often become a proxy for deeper organizational challenges. Following acquisitions or periods of rapid change, pressure frequently surfaces at the front line. Sales teams respond to client feedback. Delivery teams push for speed. Leaders look for visible progress.
In these moments, technology becomes the focal point for action. Not because it is the root problem, but because it is tangible.
The real risk emerges operationally. Poorly sequenced transitions, disruption to the core business, and value that proves smaller or shorter-lived than anticipated. Teams become locked into delivery paths that no longer make commercial sense, while underlying system assumptions remain unchanged.
The issue is rarely technical. It is temporal.
Optimizing for short-term optics, particularly client-facing signals of progress, often comes at the expense of longer-term adaptability. A cleaner interface over an ageing platform may buy temporary parity, but it can also delay the more important work of rethinking what is possible in the near and medium term.
Conservatism often shows up quietly here. Not as risk aversion, but as a preference for extending the familiar rather than exploring what could fundamentally change.
Licensing as a way to buy time and insight
In fast-moving areas such as AI orchestration, many organizations are choosing to license capability rather than build it internally. This is not because licensing is perfect. It rarely is. It introduces constraints and trade-offs. But it was fast. And more importantly, it acknowledged reality.
The pace of change in this space is such that what looks like a good architectural decision today may be actively unhelpful in twelve months. Licensing allowed us to operate right at the edge of what we actually understood at the time - without pretending we knew where the market would land six or twelve months later.
Licensing should not be seen as a lack of ambition. It is often a way of buying time, learning cheaply, and avoiding premature commitment. Building too early doesn’t make you visionary, often it just makes you rigid.
AI is neither a silver bullet nor a feature
Coaching is a useful microcosm of the broader AI debate.
Great AI coaching that is designed with intent and grounded in real coaching methodology can genuinely augment the experience and extend impact. The market is saturated with AI-enabled coaching tools and what is especially disappointing is that many are thin layers of prompts wrapped around a large language model. They are responsive, polite, and superficially impressive - and they largely miss the point.
Effective coaching isn’t about constant responsiveness. It’s about clarity. It’s about bringing experience, structure, credibility, and connection to moments where someone is stuck.
At the other extreme, coaches themselves are often deeply traditional. A heavy pen, a leather-bound notebook, and a Royal Copenhagen mug of coffee are far more likely to be sitting on the desk than the latest GPT or Gemini model.
That conservatism is understandable - coaching is built on trust, presence, and human connection - but it’s increasingly misaligned with how scale and impact are actually created.
The real opportunity for AI is not to replace human work with a chat interface. It is to codify what actually works. The decision points, frameworks, insights, and moments that drive behavior change. AI can then be used to augment and extend that value at scale.
A polished interface over generic capability is not enough. If AI does not strengthen the core value of the work, it is theatre, not transformation.
What this means for leaders
Across all of these examples, the same pattern shows up.
The hardest decisions are rarely about capability, they are about timing, alignment, and conviction.
Building from scratch only makes sense when you can clearly articulate:
- What you believe that the market does not
- Why that belief creates defensible value
- Why you’re willing to concentrate risk behind it
Clear vision scales extraordinarily well when it’s tightly held. The success of narrow, focused Silicon Valley start-ups is testament to that.
Larger organizations often carry a broader set of commitments. That complexity increases when depth of expertise is spread across functions, and even more so when sales teams have significant autonomy at the point of sale. Alignment becomes harder not because people are wrong, but because too many partial truths are competing at once.
In these environments, strategic clarity, not headcount or spend, creates advantage.
This is why many leadership teams choose to license early. Not because building is wrong, but because most organizations have not yet earned the right to build.
This article was originally publish on Rotman Management
IN OUR CONSULTING WORK with teams at all levels—especially senior leadership—my colleagues and I have noticed teams grappling with an insidious challenge: a lack of effective prioritization. When everything is labeled a priority, nothing truly is. Employees feel crushed under the weight of competing demands and the relentless urgency to deliver on multiple fronts. Requests for prioritization stem from both a lack of focused direction and the challenge of efficiently fulfilling an overwhelming volume of work. Over time, this creates a toxic cycle of burnout, inefficiency and dissatisfaction.
The instinctive response to this issue is to streamline, reduce the number of initiatives, and focus. While this is a step in the right direction, it doesn’t fully address the problem. Prioritization isn’t just about whittling down a to-do list or ranking activities by importance and urgency on an Eisenhower Decision Matrix; it also requires reshaping how we approach work more productively.
In our work, we have found that three critical factors lie at the heart of solving prioritization challenges: tasks, tracking and trust. Addressing these dimensions holistically can start to address the root causes of feeling overwhelmed and lay the foundation for sustainable productivity. Let’s take a closer look at each.