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Let’s Make Socrates Our Retrospective Facilitator

Philip Rogers
A Path Less Taken
Published in
3 min readSep 19, 2019

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Introduction

History tells us that Socrates, upon being confronted with a choice between exile or death, chose death. He is famously quoted as saying, during the course of his trial, “the unexamined life is not worth living.” Given this general context, it would not be a stretch to say that for Socrates, being able to live a life where he could continue to seek his truth was his “prime directive.” That is, he was simply unwilling to accept a condition where he could not live life to the fullest.

Now, let it not be said that it’s my intention to push teams into an existential crisis during a retrospective — certainly not! What I am suggesting is that there are some things we can learn from the Greek philosophers, which can potentially be useful to us in a team construct.

The Thought Process

One of the things that we can potentially learn from the Socratic dialogues is that what Socrates would frequently observe, both about himself and about others, is that we tend to spend a great deal of time thinking and acting in ways that are based on erroneous assumptions and thought processes.To help us recognize our errors, he would use what has come to be called the Socratic Method.

To keep this simple, let’s boil the Socratic Method down to two primary stages:

  • Deconstruction
  • Remediation

Deconstruction

During this initial part of the conversation, Socrates would ask questions that were intended to help his interlocutor recognize various contradictions and shortcomings in his own opinions.

Eventually, the conversation would turn, after many questions, where it would reach a point such that the person is willing to say the simple phrase “I don’t know.” And it is at this point that the person in the dialogue — and indeed any one of us — can now learn something.

Remediation

The second stage of the conversation is where Socrates would seek, through dialogue with the person, to arrive at a point where the person’s opinions were based on a more solid epistemological foundation.

Without going too far down into the weeds, during remediation, Socrates would ask questions and seek to build incrementally on fundamental assertions like these:

  • There is a thing called truth
  • Truth is something that is knowable
  • Truth is something that can be discovered
  • Truth is part of a larger symphony of facts based on reality

Applying the Thought Process to a Retrospective

Sadly, it’s unlikely that Socrates will show up at our retrospective, so how might we apply the Socratic Method (or something like it) in a retrospective context?

Much of the Socratic Method is driven by asking and answering questions, so let’s pose some questions below that could be helpful.

The Deconstruction Phase of a Retrospective

Sample questions:

  • Based on what we know now, what might we have done differently?
  • What assumptions drove our decisions to proceed with <the thing we now think we would have done differently>?
  • Is there someone we could have turned to who could have helped us avoid <the thing we now think we would have done differently>?
  • Are there any general flaws in our thought process, and if so, what impact are they having?
  • Which tools or techniques did we try that helped, or that did not help?

The Remediation Phase of a Retrospective

Sample questions:

  • What have we learned?
  • What areas of uncertainty might still exist, and what can we do to shed light on those areas?
  • How do we plan to adjust our approach going forward, so that we don’t potentially repeat the same mistakes?
  • Which changes could we make to how we work that could potentially have the greatest positive impact on how we work?
  • Is there any potential for us to share what we have learned with other individuals or teams, so they don’t make the same mistake that we did?

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Philip Rogers
A Path Less Taken

I have worn many hats while working for organizations of all kinds, including those in the private, public, and non-profit sectors.