Striving for Liberatory Supervision: Reflections from the Field

By: Cassie Whitebread, Senior Consultant at Healing Equity United

Photo via [Martin Wahlborg/Canva]

Here's a question: Did anyone actually train you to be a supervisor before you became one? If you're like most people, the answer is some version of no. We learn on the job, borrow from the managers who shaped us, and hope for the best. The problem is that when we aren't intentional about that process, habit and history can quietly take the wheel, and we risk perpetuating harmful managerial practices we experienced — especially for employees who identify as People of the Global Majority (PGM) and other historically oppressed identities.

As someone who has had supervisors who ran the gamut from "meh" to toxic, I didn't have many positive examples to draw on when I became a supervisor myself. I built the plane as I was flying it, and I was by no means an amazing supervisor. It's part of why this work feels so personal to me — and why HEU created a Liberatory Supervision Cohort. Now in its second iteration, the cohort recently wrapped up with a group of 30 supervisors from nonprofits across the country and globe. It's a brave space for supervisors to reimagine their leadership practices as ones rooted in trust, transparency, and collective care. The following themes emerged from our workshops and peer coaching sessions this year.

At the beginning of the cohort, we ask folks to reflect on their worst and best supervisors. We heard that the worst supervisors micromanaged, insisted on tasks being done their way, were discouraging, failed to take accountability for mistakes, were unclear about expectations, and took credit for work that wasn't theirs (for more on this last behavior, see Jess Ayden Li's recent blog post). On the other hand, the best supervisors were advocates, showed up as their authentic selves, were transparent, trusted their team to make decisions, and showed a genuine interest in their team members' lives — seeing them for the multitudes they hold, not just for the work they were responsible for.

While most folks strive for the latter, there are common barriers and traps that managers can fall into that pull us out of a liberatory mindset with our teams. Here are the barriers that came up most during this year's cohort.

Barrier 1: Avoiding regular feedback.

When we asked the cohort, "What feels like your biggest challenge when it comes to feedback as a supervisor?" several themes emerged. Folks expressed a fear of being disliked or seeming too perfectionist or "uncool." They don't want to sound too harsh, hurt people's feelings, or damage the relationship. They expressed nervousness around defensive reactions. And some admitted to simply being overly nice and positive all the time — which, while it comes from a caring place, can actually do a disservice to the people we lead.

The reality is that giving and receiving feedback is hard, especially when we haven't seen or experienced positive examples of feedback being normalized in the workplace. While the fear of being disliked is real, studies have shown that relationships actually deepen when authentic feedback is shared. Here are some of the antidotes we explored with the cohort:

Aim for a 4:1 feedback ratio. For every piece of constructive feedback, aim to share four moments of celebratory feedback — and think of this as a cumulative ratio over time, not a formula to apply to every single interaction. The goal is that the people you supervise never feel like they're constantly under a microscope or bracing for criticism every time you connect. So if last week's one-on-one included some tough but necessary feedback, make sure your next check-in leads with genuine celebration and appreciation. Studies have shown that this ratio helps build trust and creates the relational conditions for growth. When people feel consistently seen and valued over time, they're far more likely to receive constructive feedback without shutting down. Studies have also shown that being honest — even when that means sharing something tough to hear — actually deepens relationships.

Embrace a growth mindset — in both directions. As someone in a position of power, it's important to keep our own defensive reactions in check when we receive feedback. When those we manage build up the courage to give us feedback, we should recognize it as a gift — they're offering something to support us in being a better version of ourselves. This goes both ways: when we give constructive feedback to our supervisees, we have to genuinely believe that they have the capacity to change and grow.

Gather counsel when you need it, but make sure to close the feedback loop. When we're sitting on feedback, we sometimes feel the urge to go to another person within the organization for a different perspective on the situation. There's nothing wrong with seeking outside counsel — but sometimes the process ends there, and we never actually circle back to the person who needs to hear it. This is when resentment, frustration, and unspoken tension can quietly build. Remember: those loops have to be closed.

“Clear is kind.” Gotta credit Brené Brown here for this quote from Dare to Lead. This one is simple and an easy one to forget. Vague feedback, softened to the point of being unrecognizable (or thrown into a feedback sandwich), doesn't protect people — it leaves them without the information they need to succeed (and often leaves them confused). Feedback delivered with care and clarity is one of the most generous things a supervisor can offer. Being direct doesn’t equate to being mean, especially when we’re sticking to the 4:1 ratio.

Barrier 2: Executive leadership who are not open to changing the way things are done, and the sometimes impossible position of being middle management

During one of our peer coaching sessions, several participants spoke to a struggle that many supervisors in nonprofits know all too well: wanting to create a more liberatory work environment while having executive leadership who act out of alignment with those values. One participant shared, "The team I supervise is asking to engage in liberatory practices like participatory budgeting, but I'm having pushback from my ED." This is real, and it's painful.

Many leaders can be hesitant to shift from "power over" to "power with." Sometimes there are understandable reasons behind that hesitancy — resource constraints, risk aversion, pressures from the board of directors. And at the same time, this hesitancy can sometimes be unknowingly rooted in fear and power hoarding. Either way, middle managers often find themselves caught in the middle, trying to protect and empower their teams while navigating pressure from above. It's a genuinely difficult position, and it deserves to be named as such.

Here are some antidotes the cohort explored:

Find your leadership allies. You don't have to navigate this alone. Identify who else in your organization shares your values — peers, other managers, senior leaders who are more aligned — and build relationships with them. Change inside institutions rarely happens through one person pushing alone. It happens through coalitions.

Practice managing up — within what feels manageable for you. Managing up means finding strategic, thoughtful ways to advocate for your team's needs and values with those who have more institutional power. This might look like bringing data, framing requests in terms of organizational impact, or finding entry points where leadership is more open to experimentation. Know your limits here — managing up requires energy and political capital, and only you can assess what feels sustainable and safe in your specific context.

Embrace fractals. This is one of my favorite frameworks, drawn from adrienne maree brown's work in Emergent Strategy. The idea is that the patterns we practice at the smallest scale can shape and reflect the larger whole. Even if you can't change the whole organization right now, you can practice liberatory leadership within your sphere of influence — with your team, in your one-on-ones, in how you run meetings, and make decisions together. Those small patterns matter. They are not just preparation for the change you want to see. They are the change. And these changes have the potential to ripple outward, inspiring other members of your organization to do things differently.

Barrier 3: Falling into the white supremacy cultural characteristics of perfectionism and individualism

During one of our peer coaching sessions, a participant shared something that resonated with many of us: "I've been struggling to ask for help because I expect to do everything perfectly and alone."

So many of us know this feeling. When we step into leadership positions, we often don't take the time to examine the dominant narratives our society perpetuates about what a "good leader" looks like: I can't make mistakes. A good leader can handle it all. Leaders don't show doubt or emotion. These narratives are deeply embedded in white supremacy culture, and they often do enormous harm to the people we lead and to ourselves.

Perfectionism tells us that mistakes are failures rather than information. Individualism tells us that needing support is a weakness rather than a sign of wisdom. Together, they create isolated, burned-out managers who model the very patterns they're trying to move away from.

The antidote to this isn't lowering standards, it's interrogating where those standards came from and who they serve. It means practicing vulnerability with your team, normalizing mistakes as part of growth, and actively modeling the behavior of asking for help. It means building a supervision culture where people don't have to perform invulnerability to be seen as competent. When we, as supervisors, do our own work to unpack these internalized narratives and model vulnerability, we give the people we lead permission to do the same.

Barrier 4: Setting your team up for success in a more liberatory setup

Shifting to a more liberatory leadership style requires time and intentional execution. One of the things we see supervisors sometimes underestimate is that team members who have only ever worked in top-down environments will need time and support to adjust to having more autonomy and decision-making power in their roles. More freedom can initially feel disorienting, even anxiety-inducing, for people who have been conditioned to wait for direction. That adjustment is normal, and it's part of the process.

Here are some practices that can help smooth that transition:

Invest in role clarity. Liberatory leadership doesn't mean ambiguous leadership or the absence of a leader. If anything, liberatory leadership helps to create more leaderful teams, but that means we need to be clear about where role boundaries lie. People thrive with autonomy when they have a clear understanding of their responsibilities, their scope, and what success looks like in their role. Take time to co-create role clarity with your team members rather than handing it down from above; this process in and of itself is a liberatory practice.

Be explicit about decision-making. One of the most common sources of confusion and frustration in teams is unclear decision-making authority. Who gets to decide what? When does something need to go up the chain, and when can a team member act independently? Making these structures explicit — and revisiting them regularly creates the conditions for people to step into their power without fear of overstepping. Maybe this means you need to revisit or create a new decision-making matrix (like MOCHA, RACI, DARCI, etc.) so that the new way of making decisions is crystal clear.

Be mindful of the burden of participation. Giving staff more power and agency is a core value of liberatory leadership, but it has to be done with care. Participatory processes — collaborative decision-making, shared planning, peer accountability structures — take time and energy. If these are added on top of already full workloads without corresponding relief elsewhere, they can quickly become another form of extraction. As you expand your team's agency, keep asking: Are we asking people to take on more without giving them more in return? Consent, compensation, time, and recognition all matter here.

Closing Thoughts

Liberatory supervision is not a destination. It's an ongoing practice, full of tension, learning, and imperfect attempts to do better. The barriers above aren't signs that someone isn't cut out for this work. They are reminders that we’re humans who have been shaped by the same systems we're trying to transform.

What gives me hope is watching supervisors in our cohort show up with humility, curiosity, and genuine care for the people they lead. That willingness — to examine habits, sit with discomfort, and keep reaching toward something better — is the foundation for a more liberatory culture.