The Possip Paradox: Why Fear Stops School Leaders from Strategic Listening

I had a conversation recently with a leader that’s sticking with me.

She was candid and able to articulate clearly what others also feel.  Her fear wasn’t that Possip wouldn’t work.  Her fear was that it would.

What if we learn too much- and then have to do something with it?

Wow.  An honest concern so clearly articulated. It highlighted the leader’s challenge. It also highlighted the reality of a lot of survey tools – they often achieve the intended outcome: performative listening.

The truth is very few organizations don’t do any surveying. The reality is very few do surveying that matters. 

The Paradox of Feedback in Education

Here’s the paradox we don’t talk about enough:

Leaders don’t avoid effective listening systems because they won’t work.
They avoid them because they will.

Traditional surveys are often “safe.” You send them out once a year, get a report, and often learn very little that requires immediate (or long-term) action.

Systematic listening doesn’t just pile more work on your desk or leave you with a longer to do list. It replaces ‘fire-fighting’ (which takes 10 hours) with ‘fire-prevention’ (which takes 10 minutes). It tells you exactly who is at risk of leaving so you can save the enrollment.”

Once leaders reach that point of action, they feel powerful and in control. But the fear before getting to that place is real.

The Irony of Avoidance

There’s an irony also that administrators face without a true listening system.  They end up overwhelmed, being in reaction mode, and it becomes a vicious cycle.  Being in triage and listening mode is overwhelming, leaving little capacity or desire to be proactive in listening.  

Avoiding listening doesn’t reduce the work.  It just concentrates it into moments of stress and urgency.

Applying Jim Collins’ 'Flywheel' to District Strategy

This is where Jim Collins’ work came to mind- specifically Good to Great and Great by Choice.

Collins talks about the Flywheel: the idea that progress comes from building disciplined systems that feel heavy at first, but create momentum over time. He contrasts this with the Doom Loop, where organizations lurch from issue to issue, always reacting, always exhausted. Possip acts as the motor for that Flywheel. We automate the ‘Ask’ and the ‘Analysis’ so your team isn’t doing the heavy lifting- they are just steering.

He also describes the 20-Mile March: committing to steady, consistent progress to reduce chaos and risk.

Listening systems operate the same way. See Possip in Action.

They can feel scarier upfront because they ask for discipline. Consistency. Follow-through. But over time, they actually reduce volatility, lower stress, and prevent costly surprises.

Over time, instead of adding stress and responsibility, listening systems distribute responsibility over time- when it’s easier to manage.

Reaction feels easier in the short term because it delays accountability. But in the long term, it’s far more expensive- emotionally, operationally, and financially.

Moving from Reactive to Proactive School Leadership

The irony of avoidance is that avoiding listening doesn’t reduce the work. It just concentrates it into moments of crisis- an angry board meeting, a drop in enrollment, or a wave of teacher resignations.

This is where Jim Collins’ concept of the Flywheel is critical. Many districts are in the “Doom Loop”- lurching from issue to issue, always exhausted.

Listening systems build the Flywheel. At first, leaders fear that asking for feedback will add weight to the wheel. But here is the secret regarding Possip: We do the heavy pushing for you.

  • We Ask. (Automated routine).
  • They Reply. (Frictionless).
  • You Act. (We sort the data so you only see what matters).

The shift isn’t about having more information to drown in. It’s about having the right intelligence to lead.

If you are ready to move from “Reaction Mode” to “Prediction Mode,” we’d love to talk. Let’s help you get your listening flywheel going.