Every new CEO is told to do a listening tour. The standard version: meet 30 to 50 stakeholders in the first 60 days, ask them what's working and what isn't, take notes, look thoughtful, thank them for their time. Most listening tours look exactly like this. Most listening tours produce almost no useful insight.

The reason is simple. People don't tell new CEOs the truth, even when they think they're telling the truth. They tell new CEOs the version of the truth they think the new CEO wants to hear, or the version that makes them look good, or the version that's been rehearsed so many times it's no longer connected to reality. Across five CEO tenures, I've come to think of the standard listening tour as one of the most overrated rituals in executive transition.

Here's the version that works.

Stop interviewing. Start observing.

The single biggest change I'd make to the standard listening tour is to reduce the number of structured interviews and dramatically increase the number of observation hours.

Sit in the office where the membership team takes calls. Don't ask questions. Just listen for two hours. Watch the staff meeting where the events team plans the next conference. Don't speak. Just notice the dynamics. Attend the operational standup that happens every morning. Don't introduce yourself as the new CEO. Just be in the room.

You learn more about an organisation in three hours of unobtrusive observation than in three days of stakeholder interviews. People perform for interviews. They behave normally when they think nobody important is watching.

Ask the questions that don't have a good answer

The standard listening tour questions are useless: What are we doing well? What could we do better? Where do you see us in five years? Everyone has prepared answers to these. The answers are anodyne, optimistic, and roughly what the previous CEO heard.

The questions that produce real information are harder to ask and harder to answer:

  • What's the thing you've stopped raising because you're tired of raising it?
  • What would you do differently if you were CEO?
  • Who in this organisation do you think most needs to be told something difficult, and what is it?
  • What's the truth that the previous CEO didn't want to hear?
  • If you knew you couldn't be quoted, what would you tell me?

These questions are uncomfortable. That's the point. They surface the information that polite organisational conversation keeps buried. Some people will refuse to answer them, which is itself information. Most people, given permission to speak honestly, will say something they've been holding for years.

Talk to the second layer, not just the first

The standard listening tour focuses on the senior team and board chair. Those conversations are necessary, but they're also the most heavily edited. Senior people have learned to manage upwards. They will tell you what serves their interests, framed as what serves the organisation.

The unedited information lives in the second layer. Mid-level staff. People who have been in the organisation for 10+ years across multiple CEOs. The administrative officer who has watched four CEOs come and go. The membership coordinator who knows which members are quietly disengaging. The finance officer who reconciles the actual cash flow against what gets reported to the board.

These people are rarely on listening tour schedules. They should be. They know more about the actual operating reality than anyone else.

The truth about an organisation lives mostly in the people the senior team forgets to introduce you to. Make a point of finding them.

Listen for what people don't say

The most diagnostic information in a listening conversation is often the absence of information. The senior staff member who talks for 45 minutes about everything except the topic you raised. The board member who answers a different question than the one you asked. The long-tenured operations person who carefully avoids any mention of a particular colleague.

Those absences are signals. They tell you where the unspoken tensions are. They tell you which topics have been ruled out as discussable. They tell you what people are protecting and why.

Note the absences. Don't interrogate them in the moment. Come back to them across multiple conversations. If three separate people avoid talking about the membership renewal process, that's not a coincidence. There's a story there. You'll surface it eventually if you keep listening for the gap rather than the content.

Talk to people who left, not just people who stayed

The strongest single addition to a listening tour is conversations with people who recently left the organisation. Former senior staff. Former board members who served their terms. Former long-standing members who quietly didn't renew.

These people have nothing to lose and nothing to gain by being polite to you. They will tell you, with surprising directness, what they thought was wrong. They will name patterns that current insiders can't or won't name. They will give you the unedited version of what the previous five years actually felt like from inside.

Not all of what they say is true. Some will have axes to grind. Some will be telling you why their own failures were everyone else's fault. But triangulated across multiple departed people, the pattern is usually consistent and consistently revealing.

Map the network, not just the org chart

The formal org chart shows you who reports to whom. It does not show you who actually influences whom. In every organisation I've led, the influence network is materially different from the reporting structure. There are people with no formal authority who carry enormous weight. There are people with significant formal authority who are widely worked around.

The listening tour is where you map this. Ask, in every conversation: who do you go to when you need to get something done? Who's the person whose opinion changes things around here? Who do people listen to when there's a difficult decision?

Names that come up repeatedly across different conversations are the actual operating system. Some will be senior. Some won't. The senior ones who don't come up are people whose authority is positional rather than earned. Worth knowing.

What you do with all this

Listening is preparation, not performance. The point of the tour is not to demonstrate that you're a listening leader. The point is to develop, by the end of 60 days, a private working hypothesis of how this organisation actually operates — its real dynamics, its real strengths, its real fault lines, its real opportunities.

That working hypothesis becomes the foundation for every significant decision in the first year. Most new CEOs make their first 12-month strategic moves based on a model of the organisation that's wrong in important ways. The cost of that wrongness compounds. A better listening tour produces a better model, which produces better decisions.

The standard listening tour produces neither. It produces the appearance of listening. Real listening is harder, less performative, and worth significantly more.