I didn't understand management's perspective until I became a manager. Once I did, I forgot what it was like to be an employee.

I've shared that observation with hundreds of leaders over the years. Almost universally, they recognize something in it.

The gap between how leadership sees an organization and how employees experience it is one of the most persistent and consequential dynamics I encounter in culture work. It's not a gap of intelligence or intention. It's a gap of perspective — one that develops naturally as people move into positions of greater authority and information, and that requires deliberate effort to close.

What Leaders See — and What They Miss

From a leadership vantage point, a lot of things look better than they are. People are generally more positive in your presence than they are in the hallway afterward. Problems that have been escalated to you have already been filtered. The culture you see in a town hall is not the same culture that operates when you're not in the room.

This isn't duplicity. It's rational behavior in a system where honesty has historically had costs. Employees learn, through experience, what their leaders actually want to hear — and they adjust accordingly.

The leaders I've worked with who have the clearest view of their organizations are almost always the ones who have done something to make unfiltered information feel safe to share. Not just said the door is open, but demonstrated, through their responses to difficult truths, that telling the truth doesn't cost anything.

How to Get to the Other Side of the Table

The phrase I use in facilitation work is 'getting on the same side of the table' — shifting from an adversarial or hierarchical dynamic to a genuinely collaborative one. Here are three practices that I've seen make a real difference:

  1. Listen with the intent to understand, not to respond. When a leader walks into a difficult conversation already knowing what they're going to say, they're not actually listening — they're waiting. The shift to genuine listening is more physical than intellectual: Itit requires slowing down, asking follow-up questions, and tolerating uncertainty.
  1. Share your own perspective as perspective, not as fact. One of the things that creates the most distance between leaders and employees is the experience of a senior person presenting their view of reality as if it's the only one. 'Here's how I see it — what am I missing?' is a different kind of leadership than 'Here's how it is.'
  1. Create forums where honest conversation is structurally possible. The conditions for real dialogue are rarely present in a standard all-hands or team meeting. I work with organizations to design conversationswhere the usual dynamics are temporarily suspended, and something more honest can emerge.

The culture you want — one where leadership and employees are genuinely rowing in the same direction — is built on a foundation of mutual understanding. Not agreement about everything, but a shared sense of what's actually true about where the organization is and where it's going.

That requires leaders who are willing to see what's actually there, not just what they've been shown.

When did you last hear something about your organization from an employee that genuinely surprised you? And what did you do with that information? If you’ve received feedback and are feeling stuck as to “what’s next,” our team can help. Fill out this form to get started.  

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