Walk into almost any underperforming organization and you’ll find two things: leadership wondering what went wrong, and employees who could tell you exactly what went wrong. And they’ve known it for months, sometimes years.

The diagnosis isn’t the problem. The access is.

Leaders routinely underestimate the institutional knowledge sitting in the seats below them. The person who processes the same broken workflow every single day has a level of operational insight that no consultant, no survey tool, and no off-site exercise can replicate.

That knowledge is an asset most organizations are failing to leverage. Not because it doesn’t exist, but because the conditions to surface it don’t.

That’s a leadership problem. And it’s entirely fixable.

Why People Stop Talking

It doesn’t start with a dramatic blowup. It starts with an idea that went nowhere. A recommendation that was ignored. A problem that was raised and quietly buried.

The person who raised it learned a lesson: putting yourself out there isn’t worth the risk.

In our assessment work, we look specifically for four organizational behaviors that signal dysfunction has taken root. Fear of personal responsibility is one of them: a cultural dynamic where individuals stop volunteering ideas, stop flagging problems, and stop taking initiative because the potential downside of being wrong outweighs any possible upside.

When that behavior becomes the norm, the organization loses access to the very intelligence it needs to improve.

The second is a sense of helplessness: the belief that nothing you say or do will actually change anything. Both are contagious. Once enough people adopt them, you end up with a team that shows up, does exactly what is asked, and keeps everything else to themselves.

Leaders often interpret this as disengagement. It is, but disengagement is a symptom.

The cause is an environment that has, over time, punished honesty or simply failed to reward it.

The Wrong Way to Ask

Here’s where most organizations make their mistake: they try to solve this with a survey.

Anonymous, multiple choice, 1-5 scale, with a section at the bottom for open-ended comments. Results get aggregated, a few themes get identified, leadership nods at the data, and the deck gets filed.

Twelve months later, same survey. Same results. Same nod.

Surveys have their place. They can tell you where the temperature is running hot. But they cannot tell you why, and they cannot surface the nuanced, specific, operationally grounded insight that drives real improvement.

They also tend to be shaped by whoever wrote the questions, which means you get answers to the questions you already had, not the ones you should have been asking.

The employees who actually have the most useful information are often the least likely to put it in a comment box.

They’ve learned that comment boxes don’t lead anywhere.

What It Takes to Actually Get the Truth

Creating an environment where people will tell you what’s really happening requires three things.

First, structure the conversation so it’s safe.

One-on-one conversations and small facilitated focus groups consistently yield more honest data than large group sessions or anonymous surveys.

People will say things in a well-facilitated small group that they would never write down, because the dynamic of the room makes honesty feel less like risk-taking and more like problem-solving. The facilitator’s job is to hold that space and keep the conversation productive.

Second, ask questions that open doors rather than confirm assumptions.

Not “Do you feel supported by leadership?” but “Walk me through a time when you ran into an obstacle doing your job. What happened?”

Not “Does the structure work?” but “What does your day look like when things are running well? What does it look like when they aren’t?”

The goal is specific, observable data, not sentiment. Sentiment tells you how people feel. Operational data tells you where the system is broken.

Third, and this is the part most leaders skip: close the loop.

If employees tell you what’s wrong and nothing changes, they’ve learned that honesty is pointless.

But if they tell you what’s wrong and something changes, even something small, even with a public acknowledgment of what they said and what you’re going to do about it, that changes the culture of disclosure.

People start believing the conversation is real. And when they believe the conversation is real, they give you everything.

What You’re Actually Looking For

The goal of this kind of assessment isn’t just to collect feedback. It’s to identify the gaps between how the organization is designed to function and how it actually functions.

Those gaps live in strategy, structure, people, and leadership.

Is there clarity from the top about where the organization is going and how each role contributes to it? Does the structure actually orient resources toward execution, or is it organized around hierarchy and habit?

Are roles and responsibilities clear enough that people know what they own and what they don’t? Are expectations being set and managed consistently, at every level?

Most employees can’t articulate the answer in those terms. But they can describe the experience of it.

“I never know who owns that decision.”

“We keep getting tasked with things that aren’t in our lane.”

“My boss says one thing and then rewards the opposite.”

Those are the raw materials of a real organizational diagnosis. A skilled assessor knows how to translate them.

The data is in the room. The question is whether you’ve built the conditions to access it.

The Leadership Accountability

There’s a harder truth underneath all of this.

When employees stop talking, when they hold their insights, their frustrations, and their operational intelligence close to the vest, it is rarely because they don’t care.

It is usually because their experience with leadership has taught them that candor is either risky or pointless.

That’s not a communication problem. It’s a leadership problem.

And the solution isn’t a new survey platform or a suggestion box in the break room.

The solution is leaders who actively work to create the conditions where telling the truth is the path of least resistance.

That means setting expectations and managing them consistently. It means following up when someone raises an issue. It means conducting assessments not to check a box, but to actually understand what’s happening in the organization and act on it.

The employees already know what’s broken. The question is whether you’re leading in a way that makes it safe, useful, and worth their time to tell you.

That’s on you.

Executive Takeaways: What Leaders Can Do Right Now

Stop Diagnosing Engagement and Start Diagnosing the Environment

Low engagement is a symptom. The cause is usually unclear expectations, broken processes, or a history of leadership ignoring input. Start there.

Replace the Survey With a Structured Conversation

One-on-one interviews and facilitated focus groups surface specific, actionable data that aggregate sentiment scores never will. Ask open-ended questions about real operational experiences, not abstract feelings.

Ask the Right Questions

“Walk me through what happens when X breaks down” will tell you more than “Do you feel supported?” every time. You want observable data, not satisfaction ratings.

Close the Loop Publicly

When someone tells you what’s broken and you act on it, say so. Name what you heard, what you’re doing about it, and why. That single behavior does more for a culture of candor than any team-building exercise ever will.

Assess the Full System

Candor gaps almost always point back to structural or strategic problems: unclear roles, untraceable objectives, and misaligned incentives.

What your employees describe as frustration is often a map to what’s actually broken in the organization.

Make This a Leadership Discipline, Not an Event

One honest conversation doesn’t rebuild trust. Consistent follow-through over time does.

Assess, act, communicate, repeat.

Mike Westman & Ed Gillcrist are former USMC helicopter pilots and co-owners and co-CEOs of Shackleton Group, Inc. For 25 years, they have helped organizations across defense, government acquisition, and commercial sectors build the strategy, structure, and leadership discipline required to achieve and sustain desired results. They have published articles in Fast Company, Training Magazine, HR Future, U.S. Naval Institute Proceedings, Training Journal, People Matters, and OD Innovator.