Calibrating Risk in a Shifting Landscape

By: Tim Cynova // Published: January 27, 2025

How Your Organization Can Stay Agile, Adapt, and Lead with Values When the Rules Keep Changing

Ever play a game where the rules keep changing… even while you’re playing it?

Last Fall, I read Michael Lewis' Going Infinite: The Rise and Fall of a New Tycoon about the recently-convicted Sam Bankman-Fried and the rapid rise and quick demise of his company FTX. Lewis details the interview process Bankman-Fried went through for an early internship. It consisted of a series of games that kept changing and where candidates were constantly given opportunities to wager based on various uncertainties.

Reading that passage in the wake of the U.S. presidential election, I felt like that was what we were heading towards. We didn’t know the specifics of what would happen after the inauguration; however, we knew enough about the incoming administration’s priorities to surmise that organizations doing values-based work would likely be required to quickly assess – and likely recalibrate – some key pieces of their activities. In recent days, we’ve started learning about how the new administration plans to move forward via a series of Executive Orders.

Understanding and Navigating Shifting Lines

Nonprofit executives know that boundaries, or lines, exist between what a 501(c)(3) can do and what activities might jeopardize its tax-exempt designation. Some of the lines nonprofit organizations need to navigate are drawn by the IRS, others by public perception, some by state Attorney Generals, and still others by new laws and regulations.

As nonprofit executives we face questions like: “Which side of the line is this activity on: the advocacy side or the lobbying side?” “Are these workers W2 employees or independent contractors?” “Can we confidently continue our equity-based fellowship program without fear of getting sued or should we change or discontinue it?” These are questions that ripple across organizations, shaping everything from strategic plans to daily operations to cash flow to an organization's reputation and its integrity.

Yet, sometimes fear, misunderstanding, and uncertainty about what and where those lines between what a nonprofit should or shouldn’t do—and how those lines might move under different circumstances—can lead to a few extremes. On one end of the spectrum, organizations steer so far from any line that they avoid risk altogether, thereby often creating *new* risks that threaten their relevance to the communities they serve when they fail to adapt and evolve. On the other end of the spectrum, they push right up to the edge of those boundaries, assuming they’ll be fine… until the line shifts or their activities are deemed to cross it because the line itself might be blurry.

Who Holds Decisions of Consequence?

For much of my career, I’ve occupied roles where the stakes of many decisions were relatively high: CEO, COO, CHRO. Each scope of responsibility comes with its own focus, but they all have one thing in common—being tasked with making decisions with consequences that could expose an organization to real, potential, or perceived risk. Risks in categories like legal, reputational, HR, financial, mission-related, or even that overarching risk: the existential threat of losing your 501(c)(3) determination. 

When you’re operating in organizations that are values-driven and constantly innovating, adapting, and testing new ideas, and that creativity can often clash with rigid, and in many times outdated legal and regulatory frameworks. And often, “risk management” and “decisions of consequence” are concentrated in those executive roles above and the Board of an organization. All of this has had me thinking:

What would happen if people throughout an organization knew, understood, and discussed related risks, how they are evaluated, which risks are worth the, er, risk, and who ultimately has decision-making authority?

Moving Forward with Moving Lines

Risk isn’t binary. It’s not about whether something is risky or not—it’s about understanding the spectrum of risks, the likelihood of them occurring and, maybe most importantly, what organizations will do if and when they materialize.

Organizations often lack even a simple structure to guide them through this important work. So, I’ve been sketching out a Risk Calibration Blueprint – decision making models, facilitation framework for understanding and communicating, scenario simulation, etc. – that can support organizations as they work to build understanding that supports risk assessment and an agile response.

Some of the fundamentals and highlights include:

  • Get Curious About Risk: What’s the likely spectrum of risks your organization might face? Look at everything: legal, reputational, operational, financial, etc. Think about both the predictable risks (audits) and the wild cards (pandemics).

  • Build for Agility: Organizations that can pivot quickly are the ones that thrive. How can you invest in the infrastructure that supports this adaptation—clear policies, strong decision-making processes, and the right legal and financial counsel.

  • Values-Centered Decisions: When things get tough, your values are your foundation. What matters most? What are you willing to compromise on, and what is non-negotiable?

  • Creating Space for Dialogue: Risk conversations shouldn’t just happen at the executive level. Make it easy for anyone to ask difficult questions, share concerns, practice simulations, and talk about the moving lines they’re navigating in their day-to-day work. Host regular conversations between staff and board. Invite anonymous questions. Lean into the uncomfortable questions that will emerge. Transparency builds trust.

  • Decide Who Owns the Response: Be clear about who is responsible for a risk if it materializes. Knowing who’s leading the effort helps ensure you’re ready to act when the unexpected happens and helps “non-owners” calibrate their relationship with it.

  • Understand Personal Calibration: Acknowledge that comfort with risk varies—what’s daunting for some may be the daily for others.

When the Rules Shift, Values Anchor

Your organization's values should be at the root of navigating uncertainty, if not, they’re aspirational values at best. Values ensure decisions remain mission-aligned, even under pressure, and provide a steady guide when fear or ambiguity threatens to derail progress.

Risk doesn’t have to hold your organization back. It can highlight creative constraints that help to identify where the boundaries are letting you meet those constraints with creativity, not fear. By understanding risks, preparing for agility, and grounding your actions in values, your organization can confidently adapt, innovate, and create meaningful impact—no matter how the lines shift.


Check out our online Quick Courses and Epic Explores.

The courses include everything from how to reimagine your recruitment and hiring process, to creating distributed leadership and decision making models, to introducing race-based affinity groups. You can quickly get up-to-speed on easier ways to scope roles than traditional job descriptions, and consider if creating a Core Curriculum would aim your onboarding process.


Tim Cynova is an HR and org design consultant, an educator, and podcaster dedicated to dusting off workplaces to (re)center values-based approaches where more people can thrive. He is a certified Senior Professional in HR (SPHR), trained mediator, principal at WSS HR LABS, on faculty at New York’s The New School, Minneapolis College of Art & Design, and Hollyhock Leadership Institute. He has held executive leadership roles in a variety of nonprofits for the better part of the last 20 years

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