Beyond Theory: How to Effectively Facilitate an Eisenhower Matrix Workshop That Actually Works

Authored By Bernard Agrest

Earlier this week, I published an article on utilizing the Eisenhower Matrix to help stakeholders manage task overload in complex projects.  One of the steps I suggested to develop buy-in with this framework was to facilitate a workshop with stakeholders to bridge the gap from theory to practice. For those who are interested in promoting this type of session, here’s the typical agenda that I use (complete with pre-work and discussion questions) to help:

Pre-Work

Identify 2-4 key stakeholders who:

1. You have an existing relationship with
2. Have authority/ability to influence change
3. Ideally, know each other.

Ahead of the meeting, share the Matrix concepts and ask each stakeholder to bring 5-10 current work priorities.

Share the Desired Outcome for the meeting. Sample Language: “The goal of this session is to map our current work patterns, identify prioritization disconnects, and understand the gap between what we say matters and where we are spending our time.”

Offer opportunities for stakeholders to connect and engage in advance.

Meeting Agenda

Kick-Off (5-10 Minutes):

1. Lay the groundwork to establish trust and psychological safety in the room. Examples: "We're not judging anyone here. We're challenging ideas, not people."
2. Connect to the Business Value. "Every hour in a meeting costs us 'X' and comes with the opportunity cost of not focusing on 'Y."
3. Establish the logical progression of this facilitation:
   1. Understand current prioritization patterns and trends
   2. Surface true project priorities and map them to the current work being done
   3. Identify one practical way to close the gap, and celebrate wins as they're identified.

Framework Explanation (1-2 Minutes)

This should be a brief knowledge check with stakeholders to ensure they are comfortable with the concepts introduced in the Eisenhower Matrix.

Big Action Item Identification (5 Minutes):

Ask each stakeholder to write down three action items that they know, if completed, would propel them forward in their work. These action items do not have to be connected. Make sure that they don't share these out, yet.

Mapping Exercise (10-15 Minutes):

Each stakeholder takes 2-3 minutes to plot their pre-work items on the Eisenhower Matrix.

Discussion and Reflection (15-20 Minutes):

Take this time to discuss any trends that you're noticing as a group. Here are some guiding questions to engage with:

1. What are the biggest disconnects in how you're categorizing work?
2. What type of 'less' important work consistently gets prioritized? Why?
3. What habits or pressures (internal or external) are pushing work into 'urgent' territory?

Invite stakeholders to reflect on where they've placed their tasks on the matrix and how those initial tasks connect to the three action items they've identified. How many of them are directly related?

Reflections (10 Minutes):

Pick one of the following reflection questions, or use your own:

1. What one identified action item that wasn’t listed can be replaced with one or two of the pre-work items that stakeholders initially identified. What should be done with those other items? Are you still feeling pressure around those items? Why?
2. Is this what you expected from this facilitation? Why, or why not? What was/wasn’t helpful?
3. Are there any actionable insights you’ve identified? What are they?

Afterwards, each participant identifies one specific task they will commit to prioritizing based on the meeting’s insight to push the project forward.

Reinforcement and Next Steps (After-Meeting)

1. Now that you’ve successfully led this workshop, you need to follow up with a strong synthesis of the discussion. Ideally, include a visual representation of the mapping exercise that was conducted so that it can be referenced later.
2. Schedule a 30-minute individual review session with each stakeholder two weeks after the facilitation to check on the progress of the action item they committed to at the end of the meeting.

Contributor Bio

Bernard helps organizations make better decisions, manage change, and scale sustainability—without losing sight of their people. Currently, he leads the Workday Implementation for the UW-Madison Health System, impacting over 10,000 employees across seven service lines. His background spans building a PMO, leading data and learning initiatives at Teach For America, and consulting with startups and nonprofits on governance and organizational change. He is certified in both change management and project management. 

Connect on LinkedIn: Bernard Agrest