Leadership in the Age of Tiptoeing

When psychological safety turns into comfort and risk goes quiet

Somewhere along the way, psychological safety quietly turned into comfort. And comfort, while pleasant, has a way of hollowing out the very thing safety was supposed to protect.

I didn’t think that observation was especially radical when I first named it. It felt more like pointing to something that had already been sitting in the room for a while. Judging by the response, a lot of people had been noticing the same thing and not quite finding the words for it.

What’s stayed with me since is who this lands on the hardest.

It’s not executives. They are buffered by power, distance, and options. And it’s not individual contributors either, at least not in the same way. It’s frontline managers and directors. The people in the middle.

They’re the ones trying to draw honest input out of teams that have been trained, often over years, to keep their heads down and their dissent polite or invisible. They’re the ones saying, “I really want to hear concerns early,” while knowing experience has taught people to be careful about when and how they do that.

They’re also the ones who sometimes do hear the concerns in time, but don’t have the authority, support, or systems in place to act on them. And so the feedback dries up. The dissent disappears. Comforting calm takes its place, and you find yourself smiling nervously about how well the team is finally “gelling.”

Then you walk into meetings with senior leadership carrying all of that context. The risks. The half-formed worries. The things that don’t fit neatly on a slide.

And you can feel the pressure to perform reassurance. To show you’ve got it handled. To not be the person who always brings “problems.” To not give the impression you can’t manage your team or your work.

You get all the squeeze. None of the juice.

What makes this harder is that none of it is explicit. No one tells you not to surface bad news. No one says disagreement will follow you. It lives in patterns. In what gets rewarded. In who gets remembered for being “hard to work with.”

So people adapt. Language gets vague. Risks get softened into watch items or flagged as yellow on dashboards that get shown but never really discussed. Disagreement turns into alignment theater.

And when something finally breaks, everyone acts surprised, even though some version of it had been circling quietly for months.

This is where it stops being a culture problem and starts being a business risk. Late signals cost more. They create operational drag, increased expense, and sometimes legal or ethical consequences that could have been avoided earlier. And when trust erodes, people don’t just stop dissenting. They stop asking for help.

It feels safer to say “capacity is tight” than “I don’t know how to solve this.”

Zoom out, and this pattern starts to look familiar beyond work. We’ve lost some of our ability to sit in disagreement without either shutting down or escalating into something performative and aggressive. The middle space, where you can say “I see this differently” and still mean “I’m here in good faith,” has grown uncomfortably thin.

Psychological safety was meant to rebuild that muscle. Not by removing tension, but by making it survivable.

So what do you actually do with this, especially if you’re in the middle and don’t control the system?

I’ve found it helps to think in three directions.

First, inward.

Pay attention to your real reflexes, not the polished ones. Notice what happens in your body when someone challenges you unexpectedly, names a risk you hadn’t seen, or says out loud the thing you were hoping wouldn’t come up yet. You don’t have to be perfect. You do have to be honest with yourself about what you’re signaling in those moments.

People learn very quickly whether curiosity is real or performative.

Second, with your team.

Don’t just invite honesty. Protect it when it shows up. That’s the part people remember.

If someone raises a concern and it immediately gets reframed, smoothed over, or mentally filed away as “that person is difficult,” the lesson lands fast. Sometimes the most powerful thing you can say is, “I’m glad you said that,” followed by a pause long enough to prove you mean it.

You don’t have to resolve everything in the moment. You do have to follow up. Taking input seriously means closing the loop, not just tabling it politely.

And third, managing upward.

This is the hardest part. When you surface concerns to senior leadership, resist the urge to fully sanitize them in the name of professionalism. You don’t need drama or ideology. You do need clarity.

Name the risk plainly. Anchor it to outcomes leaders already care about. If you don’t have a fully baked solution, ask for guidance. You’re not being negative. You’re doing the job.

None of this guarantees safety. Some systems reward thoughtful dissent. Others smile politely and remember who made things uncomfortable. Pretending otherwise doesn’t help.

What does help is being intentional. Knowing what must be said. Choosing how to say it. Being honest about which lines you will cross and which ones you will not.

Psychological safety is not the absence of tension. It is the presence of trust when tension inevitably shows up.

Building that trust takes more patience, more self-awareness, and more stamina than most leadership books ever admit. Which may be why comfort is such a tempting substitute.

If this feels familiar, it’s often because you’re carrying more than just work. You’re carrying unsurfaced risk, muted disagreement, and responsibility without real authority.

I put together a short Leadership Load Check to help managers see whether what they’re experiencing is normal tension or a signal that something structural needs attention. It’s designed to offer clarity, not advice.

You can explore that here if it feels useful.