Why power makes allyship harder than it should be

It’s a strange thing—how the more power you hold in a room, the harder it feels to use it for someone else. I used to think that once I had influence—when I became the founder, or at least someone people looked to for direction—it would get easier to speak up. To call out bias. To stand next to someone who was being sidelined. To be a better ally.

But it didn’t get easier. If anything, it got harder. The fear didn’t disappear. It just changed shape. It wasn’t about being punished or overruled anymore. It became about being misread, misunderstood, or called out for doing it wrong. It became about losing credibility, or making someone else uncomfortable, or appearing performative.

And so I stayed quiet more often than I’d like to admit. This is the paradox no one talks about: the higher up you go, the more you can afford to speak up—and the more afraid you become of doing it.

The fear of allyship doesn’t show up as a dramatic meltdown or a moral crisis. It slips in quietly. It whispers questions like:

“What if I say the wrong thing?”
“What if I overstep?”
“What if they think I’m doing this to look good?”

These fears are subtle. But they’re powerful enough to keep smart, decent people from acting when it matters most. And when you lead a team—when people look to you for cues—they become contagious. Your hesitation teaches others to hesitate too.

I’ve seen founders and senior managers freeze in moments when someone needed backup. Not because they didn’t care, but because they were stuck in self-consciousness. Their brains went into overdrive about optics, intentions, tone. By the time they figured out what to say, the moment had passed—and so had trust.

There’s a cost to silence. But it rarely shows up in quarterly numbers. It shows up when someone stops volunteering ideas in meetings. When a high-potential hire suddenly pulls back or opts out. When someone who once spoke up goes quiet. It shows up in resignation letters that don’t say “bias” or “hostility”—they say “not a good fit” or “looking for growth elsewhere.”

One of the best designers I ever worked with left the company six months after being publicly talked over, undermined, and ignored by a louder male peer. It happened in small ways. Subtle, plausible deniability ways. But she noticed. And so did I. I didn’t intervene.

At the time, I told myself I needed to stay neutral. That it wasn’t my fight. That I’d say something in the next one-on-one. I never did. And when she left, she didn’t call me out. She just said, “I need a place where I don’t feel like I’m always explaining why I deserve to be heard.” It still haunts me.

People don’t realize how heavy visibility can feel. When you’re the founder—or even just one of the more senior folks in the room—you know your words carry weight. People take cues from you. They remember what you say. And what you don’t. That weight can be paralyzing. Sometimes you freeze because you’re scared of making it worse. Sometimes you think maybe someone else will say something better. Sometimes you don’t even realize the moment’s passed until someone points it out later.

I used to think silence was safe. That staying quiet was better than getting it wrong.But silence, in power, is loud. It’s never neutral. It’s interpreted. It’s heard as indifference. It becomes the default tone of the company.

Allyship isn’t about heroism. It’s about discomfort. It’s about learning to move with fear, not waiting for it to disappear. And here’s what I’ve learned: the fear doesn’t mean you’re not ready. It means you understand what’s at stake.

You’re afraid because you know this matters. You’re afraid because you’ve seen what happens when people get it wrong. But if you let that fear lead, you don’t just protect yourself—you protect the status quo. That’s not leadership. That’s avoidance dressed up as professionalism. The real work of allyship starts with naming the fear and showing up anyway.

If I could go back to that meeting where my designer got shut down, here’s what I’d do:

I’d pause the conversation and say, “Let’s make space for her point—she wasn’t finished.” I’d check in with her afterward, not to smooth things over, but to ask how she wanted to handle it. To offer options, not apologies. And most importantly, I’d talk to the team—not just about that one incident, but about how we show up for each other as a norm, not an exception. What I used to think was allyship—private support, behind-the-scenes encouragement—that’s not enough. Not when the exclusion was public. Not when the silence is systemic.

Founders are control freaks. I say that with love. I am one. We want things to run smoothly. We want everyone to get along. We want to scale culture, not conflict. But inclusion doesn’t scale through comfort. It scales through clarity—and repeated discomfort. Allyship often feels like a threat to harmony. And early-stage teams are terrified of disharmony.

So what happens? We avoid naming dynamics that feel messy. We say “let’s take it offline.” We praise both sides for being “passionate” instead of unpacking power. We mean well. But in trying to avoid tension, we protect the very hierarchies we claim to reject.

Another reason people freeze in allyship moments? They think they have to fix everything. But you don’t have to be the perfect defender. You just have to interrupt the harm. Even clumsily.

You can say, “Hang on, I think we talked over them.”
Or, “Can we pause—I want to make sure we heard that fully.”
Or, “I don’t want to misstep, but that didn’t sit right with me.”

It doesn’t have to be dramatic. It just has to be present. Allyship isn’t about rescue. It’s about alignment. Are your actions aligning with your values—even when it’s awkward? Especially when it’s awkward?

That’s the work.

A lot of leaders say they care about DEI. They go to the trainings. They repost statements. They hire the consultants. But what they don’t do is change how they behave in real-time when tension enters the room. That’s where allyship fails—not in the vision, but in the moment. If you want allyship to become part of your culture, you have to practice it where it counts: in meetings, in decisions, in feedback loops. And you have to make it normal. Not noble. Not headline-worthy. Just expected.

You can normalize this by:

• Building inclusive interruptions into team norms
• Making space in meetings for people to challenge behavior safely
• Rewarding courage, not just compliance

Because allyship isn’t a campaign. It’s a muscle. You build it by using it—even when it shakes.

When early-stage founders ask me how to “build inclusive culture,” I tell them this:

Don’t focus on the poster or the pledge. Focus on the moment someone gets sidelined. That’s your test. What do you say? What does your team see you do? That one moment tells them everything. If you intervene awkwardly, but with intention—you build trust. If you say nothing—you’ve said everything. It’s not about perfection. It’s about presence. You have to be seen showing up. Even when you’re scared. Especially when you’re scared.

We often treat allyship as a sacrifice. As if it costs you something to speak up. As if using your voice means giving up your position. But the truth is, allyship is power. It’s the most honest use of influence. It’s not about being a savior. It’s about refusing to stay safe in systems that harm others. So if you’re scared—good. That means you’re awake to the weight of your words. But don’t let that fear silence you. Use it to check yourself. Then move anyway. Because the people on your team don’t need a perfect ally. They need a present one.