6 Planning Habits That Hold Events Back (And What to Do Instead)

Every new event is an opportunity for new thinking.

The start of a new show cycle — it’s when event planning teams are feeling empowered with knowledge from the past event, unbound by constraints, and optimistic about all that’s possible. Unfortunately, however, it’s also when many of these well-intentioned teams begin to drift off course.

Having been brought in to lead strategic planning efforts, often after organizations expressed frustration with past methods that fail to reflect how events, audiences and industries are evolving, I’ve found a different approach to planning that consistently produces better outcomes. Below are six planning habits worth stopping, along with practical advice for what to do instead.

1. Stop assuming everyone shares the same understanding of reality. Start grounding the group in the same facts before planning begins.

One of the fastest ways to derail strategic planning is to incorrectly assume everyone enters the process with the same understanding of performance, audience behavior, and market conditions.

Before asking people to imagine the future, take time to clearly show them the present. Share post-show data, attendee behavior trends, exhibitor feedback, and relevant industry context. When you create a common foundation and align on a shared truth, strategy gets sharper and the process becomes more productive.

2. Stop prioritizing neutrality over relevance. Start working with professionals who understand your event and audience.

There’s often a desire to bring in an impartial consultant or facilitator with a fresh perspective. While that instinct is understandable, neutrality without context can slow progress. When outsiders don’t understand your audience, your business model, or the history of what’s already been tried, your planning often defaults to generic exercises (think mission statement tuning, high-level SWOTs [strengths, weaknesses, opportunities, and threats], broad vision statements that don’t feel actionable, etc.).

A better approach is to work with someone who understands your space but is not embedded in internal politics. That combination allows the work to go deeper into growth opportunities and constraints, audience shifts, potential partners, and collaborators, etc.

In practice, this often means spending less time orienting people to the problem and more time helping them make informed, forward-looking decisions.

3. Stop confusing activity with strategic depth. Start designing the planning process for thinking, not performance.

Many planning sessions still rely heavily on games, sticky notes, flip charts and rapid-fire exercises. These tools are not inherently bad, but they often limit the depth of thinking required for real strategy. Complex challenges rarely fit neatly on a sticky note.

Consider fewer activities and more time intentionally allotted for deep thinking, provocative conversations, and visioning. Also, consider how pre-work (advanced reading, surveys, one-on-one conversations, etc.) can be utilized to make a planning session more productive. The goal should not be to keep people busy. It should be to give them space to think clearly and contribute meaningfully.

4. Stop treating volunteer leaders like event operators. Start tapping into their industry expertise and letting staff translate.

Far too often, event staff ask their volunteer boards, made up of accomplished industry leaders, to weigh in on event logistics, pricing models, or operational details that are not even close to their realm of expertise. This leads to frustration on both sides and time and expertise wasted.

A more productive approach is to let volunteer leaders do what they do best. Share insight into industry dynamics, customer behavior, emerging challenges, and other inside perspectives. Event staff can then use that information to translate intelligence into event decisions. When roles are clear, boards feel heard and respected, and staff can make stronger, more informed choices.

5. Stop starting with last year’s plan. Start beginning with a clean slate and harder questions.

Incremental change feels safe, but it often locks organizations into outdated assumptions. When planning begins by tweaking last year’s plan, innovation is constrained before it even starts.

Last year, Freeman released research comparing Innovators and Conventionalists, noting that Innovators are more likely to challenge existing models and rethink core elements of an event, while Conventionalists tend to optimize what already exists, even as audience behavior changes. And, at the start of a new show cycle, that difference matters.

Early in the process, ask questions that temporarily remove constraints. What would we do if we were launching a competing event today? What would we recommend if budget, legacy decisions or internal processes were not immediate concerns? These questions are not meant to ignore reality. They are meant to surface ideas that would never emerge if the conversation starts with last year’s plan.

6. Stop trying to do everything at once. Start aligning on priorities before debating tactics.

Many planning processes fail because there are too many good ideas. When everything is a priority, nothing truly is.

Start by aligning on a small number of strategic priorities. Then evaluate ideas through that lens. This applies equally to marketing plans. A plan that tries to address every competitor, channel, and audience often becomes unusable. Depth beats breadth. Fewer priorities, clearly defined, lead to better execution and clearer decision-making throughout the year.

Why This Matters

The habits we bring into strategic planning shape what we get out of it.

When planning is focused, intentional and grounded in reality, it creates clarity, confidence and momentum. Teams leave aligned around priorities and energized about what comes next.

At the start of a new show cycle, the greatest opportunity is not to work harder. It is to work differently.

Kimberly Hardcastle is chief strategist at The Freeman Company.