How to Plan a Leadership Workshop: 8 Proven Tips

You’ve been asked to plan a leadership workshop, and the stakes couldn’t be higher. If it falls short, you're looking at disengaged participants, wasted budget, and zero impact on your organization. Get it right, and you have the potential to transform how your team leads, collaborates, and performs. Here's how to make sure your workshop falls into the second category.

1. Define Crystal-Clear Objectives

Every decision you make about the venue, activities, speakers, and duration depends on knowing exactly what you want to achieve. Skip this step, and you risk making random choices that fail to create a coherent experience.

Ask yourself what specific leadership skills participants need. Are you developing emerging leaders who require foundational abilities like communication and delegation? Or supporting experienced managers refining their strategic thinking?

Talk to your target audience before finalizing your objectives. What challenges do they face every day? What skills do they wish they had? The same approach you use to identify client needs applies here. You can create content that truly resonates by focusing on your audience’s most urgent challenges and offering solutions that address them directly.

Write two or three measurable learning outcomes. Avoid vague goals such as “becoming better leaders.” Instead, set clear, specific targets such as “Participants will demonstrate three active listening techniques” or “Leaders will create action plans to improve team feedback.”

2. Choose the Right Format

Leadership workshops come in various shapes and sizes. Match yours to your objectives and audience availability.

Half-day workshops work well for focused skill-building on single topics like giving effective feedback or running productive meetings.

Full-day sessions allow deeper exploration of interconnected topics with time for multiple activities.

Multi-day retreats work best when you want participants to leave daily distractions behind and fully engage in learning and team-building experiences.

Weigh the choice between in-person and virtual formats carefully. In-person sessions foster deeper connections and allow for hands-on activities that are hard to replicate online, while virtual sessions provide flexibility and cost efficiency for teams spread across different locations.

‍
3. Build an Engaging Agenda

Here's where planners go wrong: they pack schedules with back-to-back presentations and wonder why participants disengage by lunch.

Adults learn through active participation, not passive listening. According to studies, experiential learning outperforms traditional methods because it enhances motivation and allows for better knowledge retention by actively engaging learners in the process.  Structure your agenda to include short presentations (15-20 minutes max), group discussions, hands-on activities like role-playing, individual reflection time, and regular breaks every 60-90 minutes.

One approach that consistently energizes leadership events is bringing in entertainment that doubles as engagement. Mentalists like Christophe Fox blend psychology, storytelling, and audience participation to keep attention high while reinforcing leadership themes around communication, connection, and performing under pressure. Interactive experiences can boost engagement by up to 40%.

Start with a relevant icebreaker, not a generic “share a fun fact” exercise, but an activity connected to leadership themes. Finish with action planning to ensure participants leave with specific and actionable next steps.

4. Select an Inspiring Venue

Where you host your workshop signals its importance. A cramped conference room says "check the box." A thoughtfully chosen venue says "this matters."

For in-person workshops, look for spaces that offer:

• Enough room for both classroom-style seating and breakout activities
• Natural lighting (it genuinely affects energy levels and engagement)
• Reliable technology, including projectors, screens, and strong Wi-Fi.
• Comfortable temperature control
• Minimal outside distractions

Think beyond traditional conference rooms. A retreat center or unique event space can boost creativity and show that this experience is different from regular meetings.

5. Choose the Right Facilitator

Your facilitator makes or breaks the experience. This is not just about finding someone knowledgeable. It is about finding someone who can command a room, adapt on the fly, and create psychological safety for vulnerable leadership conversations.

Internal facilitators are familiar with your organizational culture and can draw on relevant examples from within the company. External facilitators offer new viewpoints and foster an environment where open, honest conversations can occur without the pressure of colleagues’ presence. The same strategies used to lead creative teams effectively are also relevant in this context. Leadership workshops require someone who can balance structure with flexibility and draw out each participant's strengths.

Whoever you choose should read the room, handle difficult participants diplomatically, and model the leadership behaviors you're teaching.

6. Design Activities That Stick

Activities should be designed to achieve the learning goals rather than simply occupy time. Choose formats that give participants practice with the skills you are developing.

Case studies present scenarios requiring decisions and reasoning. Use situations relevant to your industry or combine real challenges your organization has encountered.

Role-playing lets participants practice difficult conversations like giving feedback or navigating conflicts in low-stakes environments.

Team challenges reveal natural leadership styles and build collaboration under pressure.

Peer coaching sessions pair participants to work through real challenges they're currently facing.

Whatever you choose, debrief thoroughly. The real learning happens in reflection and discussion, not the activity itself.

7. Plan for Different Learning Styles

Participants absorb information differently. Some learn best by listening, others by reading, and still others through practical experience or collaborative discussion.

Incorporate various learning methods into your agenda: use visuals such as slides and charts, facilitate discussions for those who learn by hearing, offer hands-on exercises for experiential learners, and provide written resources for readers.

You do not need to cater to every style in every segment, but ensure there is variety throughout the day. Switching formats also helps maintain energy. Prepare takeaway materials such as summary handouts, reflection worksheets, and resource lists to extend the impact beyond the event itself.

8. Build in Follow-Up

Here's the harsh truth: Published research replicated Ebbinghaus's forgetting curve experiments and confirmed that memory retention drops quickly in the hours and days following learning. Without reinforcement, people can forget as much as 70 percent of new information within 24 hours.

Build accountability into your workshop design from the start:

Action planning during the final session ensures everyone leaves with specific commitments—2-3 concrete actions they'll take in the next 30 days.

Peer accountability pairs keep participants connected and checking in with each other.

Manager involvement amplifies impact when supervisors are briefed on workshop content and can reinforce new skills.

Follow-up sessions 30-60 days later let participants share wins, troubleshoot challenges, and continue learning together.

Measurement. Survey participants immediately for reaction data, then again later to assess behavior change. This helps you improve future workshops and demonstrate ROI.

‍
FAQs

How long should a leadership workshop be?

Half-day sessions work for focused skill-building. Full-day workshops allow deeper exploration. Multi-day retreats are best for comprehensive development or team bonding.

What's the ideal group size?

Most workshops work best with 8-20 participants, allowing meaningful discussion and personal attention while remaining manageable.

How much does a leadership workshop cost?

Costs vary based on duration, venue, and facilitator fees. Internal workshops might cost a few hundred per participant; multi-day retreats with external facilitators can run several thousand.

Key Takeaways

• Define 2-3 specific, measurable learning objectives before any other decisions
• Match format and duration to your objectives
• Choose venues that inspire and support active learning
• Build agendas around participation, not presentations
• Select facilitators who create psychological safety
• Design activities with thorough debriefing
• Include multiple learning modalities
• Plan follow-up and accountability from the start

Cover Photo by Matheus Bertelli