If you’ve ever tried to roll out new technology or a new workflow in an insurance or benefits environment, you already know that change doesn’t break your organization, it reveals its strengths. Every obstacle that shows up is simply the system doing what the system does best: surfacing where people are confused, overwhelmed, unsure or trying very hard not to disappoint anyone. (Insurance may be a risk business, but we attract a remarkable number of us that rely on the “avoid” tactic of risk management.)
At CalNonprofits Insurance Services (CNIS), we often describe ourselves as both academics and practitioners. We appreciate a good framework, and we’re also the ones scratching our heads on a Thursday, realizing that the “simple rollout” somehow now involves 17 stakeholders, three follow‑up meetings and someone suggesting, “Maybe we circle back.”
When Connections asked for an article about obstacles to change, we didn’t want to treat the topic like symptoms to eliminate or problems to push through. We wanted to talk about what those obstacles do for us, how they challenge humans to practice new behaviors, strengthen decision‑making and develop healthier ways of working together. Because the truth is, obstacles aren’t interruptions to change. They are the change.
Open the Door to Different Points of View
People‑pleasing is usually the first obstacle to appear, and it’s a familiar one in our industry. You’ve seen it: the enthusiastic nodding in the meeting, followed by a quiet side conversation later that starts with, “I didn’t want to say anything, but …” People‑pleasing is a survival strategy in hierarchical systems where questioning the plan once carried risk. In change work, though, it’s like taking the batteries out of the smoke detector because you don’t like the sound.
In practice, this means leaders walk out of meetings thinking alignment has been achieved while their team members carry unspoken concerns out of the meeting that will eventually surface as resistance. Leading for potential change looks deceptively simple. It’s the leader who pauses and says, “What am I not hearing yet that I really need to know?” It’s the leader who explicitly invites dissent and makes it safe for others to offer a different point of view before the plan hardens. Very often, the most important data arrives the moment people realize it’s welcome.
Invite Healthy Discussion
Closely related, and equally disruptive, is conflict avoidance. We’ve normalized it by calling it “being nice,” but avoiding conflict is rarely kind. It’s how confusion lingers, resentment grows quietly and rework multiplies. You see it when two teams disagree about who owns a step in a new process, but no one wants to make it awkward. So, everyone waits, productivity slows and frustration rises.
In practice, healthy leadership means naming the issue plainly and calmly: “We have a roles and responsibilities gap, and it’s creating confusion. Let’s clarify this now.” Ten minutes, a whiteboard and a conversation later, the fog lifts. Trust increases not because conflict was avoided, but because it was handled directly and respectfully. No buzzwords required, just facilitation.
Set Specific Thresholds for Clarity
Ambiguity is another obstacle that reliably appears during change, particularly in highly regulated environments where getting things right matters deeply. Many people believe they need full clarity before acting. In complex systems, that level of certainty rarely arrives on schedule. Waiting for perfect information quietly stalls progress.
What this looks like in practice is a leader redefining the threshold for movement. Instead of asking for certainty, they define what enough clarity looks like. “If you can move this forward without risking compliance, harming the client or creating confusion, take the next step. If not, bring the question forward.” People don’t need absolute certainty, they need boundaries, permission and trust.
Provide Support Based on Individual Emotional Readiness
One of the most overlooked obstacles is the simple fact that humans are often in different emotional and psychological starting points when change arrives. One person may be energized, another overwhelmed, another skeptical and another quietly irritated that they weren’t consulted earlier. This isn’t dysfunction; it’s reality.
Leading for potential means noticing those differences and adjusting accordingly. It means offering encouragement to the person who’s anxious, stretch opportunities to those who are ready, boundaries where avoidance shows up and clarity where confusion lingers. Instead of imposing a single structure on everyone, leaders fine tune support to what helps people thrive now and prepares them to thrive next.
Give Permission to Perform
Then there’s hierarchy, or more accurately, the residue of hierarchy. Even in modern, collaborative organizations, many people still hesitate, asking whether they need permission because, historically, that’s how safety was maintained. You hear it in questions like, “Should I run this by you first?”
In practice, leaders make empowerment explicit. “You don’t need approval for this. I trust your judgment.” And then they reinforce it by resisting the urge to step in the moment things aren’t perfect. Allowing people to make decisions and learn from them is what builds capability rather than dependence.
Author Malcolm Gladwell talks about the “tipping point” as the moment when accumulated small changes suddenly become visible as transformation. In organizational change, that moment often arrives right after things feel hardest. It’s the phase where leaders are practicing better questions, clearer facilitation, stronger boundaries and more adaptive support. Teams are learning how to navigate discomfort, take ownership and adjust together. It doesn’t always look elegant in the moment, but it’s where capacity is built.
Obstacles aren’t signals that change is failing. They’re evidence that learning is happening. They show leaders what their teams need, reveal where habits no longer serve and create opportunities to practice new ways of working. When leaders stop treating obstacles as problems to eliminate and start treating them as feedback, the entire process shifts. The work becomes more human, more effective and even fun.
We’re not observing this work from a distance. We’re in the middle of it, experimenting, adjusting and learning alongside our teams. And while change will always come with friction, it turns out that friction is often where the real growth thrives.