2025 Free Learning Series
This year’s free learning series will work through aspects of the Flying Whale Organizational Maturity Matrix. In each workshop we will:
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Take a self-assessment of where your organization lands on the spectrum for the given topic.
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Analyze your results.
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Plot the way forward.
View the 2024 Learning Series
The Archive
Workshops by Month
January 29th
11am MST
Anti-Racism: What are we ready for?
Curious Idea: The speed of our organization's anti-racism journey can only go as fast as the speed of our leaders' individual racial identity development.
Description:
One of the most difficult and essential parts of building an organizational culture is the fact that we are all on our own individual racial identity journeys. Some of us are just beginning to notice that whiteness equals privilege. Some of us are tired of working with white people. Some of us are tired of wokeness. Some of us are excited about a new partnership we just forged with an indigenous community leader. And some go home in tears from the impact of white supremacy. And yet we all long to make progress. We often don’t know what progress looks like.
In this workshop, we will complete a self-assessment to locate ourselves on Flying Whale’s Organizational Maturity Matrix on the topic of anti-racism. We will look at the stages of white identity development as guides for the stages of developing an anti-racist organization. We will explore how the stages might differ for organizations led and operated by people of color. In both cases, we will discuss what it takes to move to the next stage.
Side benefit: This workshop will help you build an answer to the often-asked funding questions about the status of your organization’s equity work.
Guest Co-Host: Dina Bailey, CEO of Mountain Top Vision. Before opening her consulting practice, Dina was the Director of Museum Experiences at the National Underground Railroad Freedom Center as well as the inaugural Director of Educational Strategies at the National Center for Civil and Human Rights. Dina most recently served as the Director of Methodology and Practice at the International Coalition of Sites of Conscience and she currently works as the Director of U.S. Programs for the Auschwitz Institute for the Prevention of Genocide and Mass Atrocities. Dina is a proud board member of the American Alliance of Museums. Dina has been published in both formal and informal education fields and has served as an adjunct professor for Johns Hopkins University’s museum studies graduate program. Dina is excited to currently be working on her doctorate through NYU Steinhardt.
February 26th
11am MST
Building a culture that people come to study
Curious Idea: Most organizations accept that the personality of its leader should determine the culture.
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Description:
Nonprofit organizations rarely prioritize building a strong organizational culture, unless it's a holiday or there’s a crisis. This might stem from an assumption that culture is built by a shared passion for the mission.
In contrast, for-profit companies recognize that a strong workplace culture is essential for attracting and retaining top talent. They compete to be recognized as “the best workplace,” often investing heavily in perks to enhance employee satisfaction and productivity. And yet they have also been known to create flat org charts, give employees time to work on pet projects, and set compensation based on peer reviews.
In this workshop, we will complete a self-assessment to locate ourselves on Flying Whale’s Organizational Maturity Matrix on the topic of cultural commitments. This will clarify how clear we are on the features of our culture that are most important and how consistently we reinforce those commitments. We will look at for profit and nonprofit cultures that attract the best talent in the world and determine your next step in moving forward on the matrix.
March 26th
11am MST
Building a data collection plan that we don’t dread
Curious Idea: Data collection is dreaded because it’s for your donors more than yourselves.
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Description:
When I speak with nonprofit program leaders across the country, there are two things they commonly dread the most: fixing the van and collecting data (yes, most of you have a van that causes you a lot of trouble). Data collection is tedious and unwelcome to many of you because it has been about finagling people to fill out papers that must be manually entered into a database that only one person likes. And yet our funding relies on it.
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In this workshop, we will complete a self-assessment to locate ourselves on Flying Whale’s Organizational Maturity Matrix on the topic of program evaluation. We will identify a data collection system that you will not dread. Furthermore, we will discuss how to build routines for learning from your data so that you collect it primarily for your own benefit, second for your donors.
April 30th
11am MST
How to make hiring decisions for your programs
Curious Idea: You can staff your programs in order to generate impact rather than relieve pressure.
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Description:
Our program staff deliver the program or services that our mission promises. We often hire them to relieve pressure from others on the team. When someone is at capacity, it’s time to expand the org chart. This results in an ever-increasingly complicated org chart. Instead, we can make hiring decisions based on the talent needed to meet aspirational outcome goals.
In this workshop we will complete a self-assessment to locate ourselves on Flying Whale’s Organizational Maturity Matrix on the topic of the program staffing model. We will evaluate how to shift from your existing hiring model to one that is more focused on achieving impact. You will identify the focus and timeline of your next three hires.
May 28th
11am MST
How to know when you’re ready for your next strategy
Curious Idea: You know your current strategies are working when donors are coming to you. When that happens, you’re ready for the next revenue stream.
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Description:
The current socio-political-economic landscape demands our careful attention on our fundraising strategies. At Flying Whale, we talk a lot about doubling down on one or two fundraising strategies until they are scaling: major gifts, annual giving, events, grants, and corporate sponsorships. Now is the time to determine if you are ready for a third or fourth strategy which will fortify your revenue through the next 5-8 uncertain years.
In this workshop, we will learn exactly how to determine when your current strategies are operationalized and scaling. We will specifically talk about scaling by generating exponential revenue that comes from donors who are attracted to your organization. What does it require to shift from promotion to being an attraction? We will then offer tips for assessing which strategy will come next. We will also complete a self-assessment to locate ourselves on Flying Whale’s Organizational Maturity Matrix on the topic of development.
June 25th
11am MST
How to get donor reports under control
Curious Idea: A quarterly impact reporting routine can relieve the pressure on all other reports.
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Description:
Donor reports are in the same category as janitorial tasks: they are often dirty jobs. We struggle with collecting the necessary data, we feel annoyed with the questions, the power dynamics, the rationalizing. This is the case for grant reports, but also our major donor, corporate sponsorship, and our annual impact reports. We can get ahead of these when we build a routine for generating a quarterly impact report. This can serve as the content you copy and paste from for all other reports.
In this workshop we will complete a self-assessment to locate ourselves on Flying Whale’s Organizational Maturity Matrix on the topic of the program evaluation. We will create a template for a manageable quarterly impact report for your organization and discuss next steps to getting it done.
July 30th
11am MST
Am I ready for big bet philanthropy?
Curious Idea: Investors are looking to take big risks on organizations that have developed something game changing in their sector.​
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Description:
Big bet philanthropy is the practice of making large donations with the goal of transforming an issue, sector, or the organization itself. Big bets are typically multimillion-dollar grants or initiatives that can be high-risk and potentially high-reward. Think the Audacious Project, MacKenzie Scott, Melinda French Gates’ Pivotal Ventures, and others.
In this workshop, we will assess what it takes to be ready for this type of investment. We will complete a self-assessment to locate ourselves on Flying Whale’s Organizational Maturity Matrix on the topic of programming as well as development to determine how close we are to readiness for these investments. We will also discuss how to attract big bets and land on their radar.
August 27th
11am MST
Supervisors as teachers not bosses
Curious Idea: Excellent on-the-job training requires bringing the qualities of an adult education classroom into your workplace.​
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Description:
So much is required of supervisors of entry level positions. They are schedulers, project managers, quality controllers, van drivers, supply orderers, report writers, guest speakers, and often lastly: trainers. And yet, we know that the quality of training entry level staff receive is directly correlated with their output. And this impacts your supervisors’ retention.
In this workshop, we will discuss how to train supervisors in the tenets of adult education and equip them with meaningful on-the-job training exercises, routines, and workshops for entry level staff. We will complete a self-assessment to locate ourselves on Flying Whale’s Organizational Maturity Matrix on the topic of programming and determine how improving your supervisors’ training routines generates more impactful programming.
September 24th
11am MST
Developing a less hierarchical org chart
Curious Idea: Hierarchical organizational charts are safe but expensive.​
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Description:
Flat organizational charts often feel like an unattainable ideal—something to admire but not emulate. Good for them” we shrug. Meanwhile, we continue to invest heavily in maintaining traditional hierarchies, overlooking their hidden costs: the time spent reporting up, waiting for decisions to trickle down, and enforcing compliance. In this workshop, we’ll challenge these norms by exploring structures that empower leadership to support innovation without relying on compliance. We’ll examine successful for-profit models where staff have the autonomy to define their priorities, projects, and workflows. Through this lens, you’ll complete a self-assessment using Flying Whale’s Organizational Maturity Matrix to pinpoint where your organization stands and identify steps toward building a more agile and innovative structure.
October 29th
11am MST
The daily routines of our favorite leaders
Curious Idea: Great leaders begin the day identifying the highest value tasks to complete that day. They are often on a different list than those which generate instant gratification.​
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Description:
Leadership isn’t just about grand philosophies—it starts with the small, daily routines that shape how we show up in every aspect of our work. As the saying goes, “How we do small things is how we do everything.” In this workshop, we’ll dive into Steven Pressfield’s book Turning Pro to explore the critical differences between the routines of “professionals” and “amateurs.” Through guided discussion and reflection, we’ll uncover how adopting professional habits can transform your leadership practice. You’ll also complete a self-assessment using Flying Whale’s Organizational Maturity Matrix to evaluate your current leadership routines and identify how to move forward.
November 19th
11am MST
Shifting the role of the board when its time
Curious Idea: The board’s governance structure should match the organization’s stage of maturity. Shifting the governance structure is as easy as clarifying expectations.​
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Description:
One of the biggest sources of tension between boards and staff is mismatched expectations on the role of the board. In this workshop, we will complete a self-assessment using Flying Whale’s Organizational Maturity Matrix to pinpoint where your board stands on this topic. From there, we’ll clarify board roles, identify your organization’s current needs, and craft a realistic plan to transition toward a governance structure that truly works.
December 10th
11am MST
A guided reflection on your year
Curious Idea: We can become organizations capable of solving impossible problems when we know our current status on Flying Whale’s Organizational Maturity Matrix.​
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Description:
Throughout the year we have been using pieces of Flying Whale’s Organizational Maturity Matrix. As we end the year, we will have an opportunity to select a segment of the full assessment and take it: programming, leadership, culture, operations, or development. Then I will guide you through a process of planning how to move forward based on your results. This will set you up to begin a new year with a clear set of next steps toward organizational maturity.
Workshops by Topic
Part One: Assessing Our Organizational Culture
January 29th Anti-Racism: What are we ready for?
FEBRUARY 26th Building a culture that people come to study
Part Two: Assessing Our Programming
MARCH 26th Building a data collection plan that we don’t dread
APRIL 30th How to make hiring decisions for your programs
Part Three: Assessing Our Development Strategy
MAY 28th How to know when you’re ready for your next strategy
JUNE 25th How to get donor reports under control
JULY 30th Am I ready for big bet philanthropy?
Part Four: Assessing Our Operations
AUGUST 27th Supervisors as teachers not bosses
SEPTEMBER 24th Developing a less hierarchical org chart
Part FIVE: Assessing Our Leadership
OCTOBER 29th The daily routines of our favorite leaders
NOVEMBER 19th Shifting the role of the board when its time
DECEMBER 10th A guided reflection on your year