Seasons of change: Five critical conversations for nonprofit leaders

OCTOBER 4 / Mike Grogan


IntegralOrg has launched the Critical Conversations Toolkit to help staff and board leaders of nonprofit organizations better understand their current and anticipated capacity to operate through inclusive, creative, and thought-provoking questioning. Find the toolkit in IntegralTools

“For one it’s the change of seasons, for another, it’s the season of change.”  

The early days of fall are, to me, the most poignant time of the year. With the waning days of summer and the turn of the leaves comes an array of thoughts and feelings - there is always a touch of sadness that comes with the end of a summer that usually seems all too short. But fall is invigorating, a time of change charged with excitement and anticipation of what lies ahead. In ecological systems, fall is the time for both a harvest of past work and preparation of the ground for the next growing season. It is a season of both letting go and planning for what is to come.

For nonprofits entering the fall, it’s challenging to gain a clear sense of what comes next. While this fall will (hopefully!) look much different than last, it will almost certainly look very different than the years before. The ongoing pandemic and challenging financial environment are, and will remain, pressure points for many organizations. As the folks at Leap of Reason1 warn:

“If the virus continues to surge and the restart of the economy sputters into late fall or
winter, the next 12 to 18 months may well be the most trying time for our sector….
These are the realities we face:

      • The demand for many core nonprofit services will skyrocket.
      • The supply of funding for nonprofit services will come under heavy pressure.”  

Making plans of any sort is challenging in a world of change and uncertainty. The COVID pandemic and associated interventions have shown us that what is a certainty one day is gone the next. These days it’s plan, plan, plan, throw out the plan. For many nonprofits, the road to recovery may not necessarily be a road to “restoration of how things were before COVID.” Making plans set in stone may not be possible. However, there are routes we can take as we go forward, routes that help organizations think strategically. For leaders, both staff and boards, it is imperative to monitor and understand the impact these changes have on our current and anticipated capacity to operate.  

“All change begins in conversation."

Before we strategize, we talk. Now, perhaps more than ever, it is time for nonprofit leaders and leadership teams to make time for a variety of conversations about areas of critical importance to ongoing sustainability. Engaging in such conversations is an activity that all too often gets sidelined in the face of seemingly never-ending day-to-day challenges.

There are fiduciary conversations to be had about how we will steward organizational assets and strategic conversations to help us chart a course forward. Perhaps most importantly is that these critical conversations be generative in nature. Generative conversations shift our leadership role from problem-solver to sense-maker. Generative conversations are an inclusive, creative, and thought-provoking style of working together where questions and issues are reframed to allow new, often deeper, insights to emerge. The result is that strategies for attending to problems and opportunities emerge and are shared.

The five guided question sets in the Critical Conversations Toolkit are offered for nonprofit leaders to critically examine their organization’s capacity to deliver service and their place in the sectoral landscape. Some of these conversation areas, such as finances, may be perennial, but have taken on a nuance in the current environment. Others, like vaccinations and hybrid workplaces, may be entirely new ground. Some conversations may help us prepare for scenarios that may or may not come to be. Prioritizing time for discussions of all types will inevitably provide insights into areas that need to be refined or retuned, while others may challenge the core functions of our organizations. Wherever they may take us, these conversations are opportunities for us to learn.

“As the days grow shorter, we acknowledge the changing season and understand that
we too, are in transition.”


Mike Grogan is the President and CEO of IntegralOrg. Mike has worked in the nonprofit sector for over 25 years and is recognized for his ability to create effective and adaptive solutions to organizational and community issues. His skills and experience stem from a diverse background that encompasses building organizations from the ground up to developing leading-edge nonprofit collaborative, public policy, and capacity building initiatives.