top of page
Leadership Retreat.jpg

By Amy Eisenstein 


Is it time for your nonprofit’s leadership to have a retreat? Ideally, you ought to have a leadership retreat annually.

The team at Capital Campaign Pro is preparing for a three-day retreat in NYC. For several weeks leading up to the retreat, we wrestled with how it should be structured, who should facilitate, and more.

We started with fun!

In other words, team building and bonding. One member of the team hasn’t been to NYC since he was a child, so he created an amazing list of things he wanted to do… like eating pizza off a paper plate, riding the subway, and visiting all five boroughs!

Why a Leadership Retreat?

Capital Campaign Pro is a remote company, and our team only comes together once or twice a year. Normally, we see one another on Zoom only. Although we check in with one another about family and personal lives, we don’t have many opportunities to engage at a deeper level.

While your organization may not have the same challenges (staff all over the country) or opportunities (a budget for fun) that we have, I hope this post will help you generate some ideas which would resonate with your team.

For example, when having a staff retreat, get out of the office!

Ask for ideas of things people have never done before or feel would be fun to do as a team. Consider renting an Airbnb for a night up to an hour away! Even if most people don’t sleep there, you might find one with a nice living room or a big dining room table. A change of scenery will do wonders for your brainstorming.

After we determined our location and some of the fun activities (a tasting tour in China Town and walking over the Brooklyn Bridge to get pizza on a paper plate), it was time to schedule the planning work of the retreat.

Leadership Retreat Agenda: SWOT Leads the Way

After several weeks of discussion about how to create the agenda for our work time together, who / how to facilitate our brainstorming, we settled on the side of less rigid. (I advocated for a more structured agenda, but I got overruled.)

Here’s how we landed:

Day 1: SWOT Analysis Brainstorming and Discussion

Everyone was asked to do their own SWOT analysis in advance of coming together so we would be ready to compare and discuss on the first day.

If you’re unfamiliar with SWOT, it’s a well-known planning tool to help organizations evaluate their Strengths, Weaknesses, Opportunities, and Threats.

  1. Strengths and weaknesses focus on internal things happening at your organization.

  2. Opportunities and threats are external to your organization.


This simple, yet effective analysis tool will help kick off our retreat and set us up to discuss the near- and long-term future of our organization.

Day 2: Implementation

On day two, we’ll focus on how to go about implementing plans based on the SWOT analysis discussions on day one.

Day 3: Next Steps and Planning

At the end of each day, we’ll review how the day went and how the next day should be structured (if at all). I am confident that this break from the daily hustle and bustle of running a business will be productive for planning the next three years.

Questions for the Leadership Team

In addition to the SWOT analysis, I’ve prepared a list of questions to ask the team and discuss while we’re together. Here is part of the list.

  1. What impact do we want to have? How big do we want to grow?

  2. What big challenges do our clients face? How can we better support them?

  3. What happens when we have twice as many clients? (What are the staffing and other implications?)

  4. What is standing in the way of growth?

  5. How do we want to work? How do we avoid burnout and keep staff happy?

  6. What do the next three years look like?


Hopefully these ideas will help you as you plan your next leadership retreat.

Are there any other questions I should add to my list? What other questions might you ask your team as you look toward the future? Leave a comment below.

Amy Eisenstein, ACFRE is one of the country's leading fundraising consultants. She speaks internationally at fundraising conferences and in nonprofit board rooms about raising major gifts and capital campaigns

bottom of page