Cornerstones of the Retrospective
Thinking about world retrospective day …
I found out from a colleague recently that in the new year, on February 6th it will be world retrospective day ( http://worldretroday.com/ ), who’d have thought such a thing existed? The cynical me immediately thought of all the other labeled days we have and following a brief google discovered that I’m writing this on both “national pastry day” and “weary willie day” ( https://nationaldaycalendar.com/december-overview/) I remain somewhat unconvinced by the latter. However a brief conversation on the value and heritage of the retrospective set the synapses firing and reminded me of the true value of this practice.

The retrospective as we know it today is synonymous with Scrum (and post-it notes). Its also arguably one of the least understood and most beneficial aspects of what is fundamentally a continuous improvement process born out of the need to learn from and adapt to change in a complex environment. It provides practitioners the opportunity to find out if what they have been doing is working and answers the questions that were set out at the beginning of each sprint.
Codified Scrum doesn’t particularly focus on hypotheses, that thinking tends to emerge further down the line but as there is no certainty in software development whether we choose to perceive a backlog item, a user story as an hypothesised test makes little difference. It will either succeed or fail within the framing available and the retrospective will be an opportunity to assess and learn from that. Lessons born out of failure are by far the most impactful and long lived.
The ideal of maintaining an open minded posture and learning from failure is a steel-thread that can be chased back to the cornerstones of modern civilisation and is a trait that correlates and causes success to emerge in both organisations and individuals.
In the book Managing Flow Ikujiro Nonaka talks about the knowledge creation philosophy of Seven-eleven and although presented within the context of the Seci process the need to socialise, externalise, combine and internalise knowledge is enshrined in their egoless, emotionally intelligent method of learning. For them success is born from failure and unlike the dogged determination seen in the monolithic enterprise failing to fail for Seven-eleven would be seen as missing an opportunity to improve themselves and their organisation on behalf of their customers; something we tend to lose at an age when we stop asking why.
“each store-staff is required to think and act based on his or her own subjective insights about the local market, accumulated though daily interaction with customers. These subjective insights are verified objectively through hypothesis building and testing… staff at Seven-Eleven stores are encouraged to think as customers, instead of thinking for customers” (1).
It is their willingness to be vulnerable to the truth that allows them to progress and flourish, commercially this translates to growth and cashflow. The retrospective here happens at the end of every test and only through delineation and recognition of ego can this practice embed throughout every echelon of the organisation.
Japan of course is fertile hunting ground for considered practice, there are a multitude of other examples that could be discussed within the same rough window of time, be that the Deming “plan, do, act, check” cycle or the improvement kata made famous by Toyota. All born from a need and understanding that the present can only be partially understood in the past and that we will always know and need to learn more now from events occurring on the journey between our original plans and our point of inflection with the current moment. As life is change we need to update our perceptions and mental models continuously if we wish stay in tune with a more holistic consensus.
In other spaces within a similar time we come across the same thinking applied to different contexts. The OODA loop (observation, orientation, decision, action) was a military process conceived by Colonel John Boyd, majorly born out of retrospecting on failed dogfights with Soviet era Migs during the Korean war. Boyd concluded that agility rather than absolute speed had the greater propensity for success, responsiveness over strength.
Boyd posited that the OODA loop could be applied to any situation in which it was necessary to keep the initiative.
“Because human beings must cope with a constantly changing reality, it was therefore necessary to challenge rigidities in thought. Then these new thoughts would rigidify in their time and so would need dissolving in turn” (2).
Learning cycles allow the alignment of individual perceptions to a collective reality and present the opportunity for correlating thought to a future vision, one which can be revisited and realigned a priori to the divergence again of those very perceptions as progress is made.
Open minded learning however wasn’t born in the skies of the Korean war. Rather we can slide further back along the lines of the retrospective steel-thread and closer to the origins of its pedigree.
The earliest example of a retrospective i’ve come across are in the Golden Verses of Pythagoras, 3rd Century BC, it is at this point we touch upon its true origins. In themselves the verses are for want of a better term a set of ethical aphorisms to reflect on nightly in order to continuously improve the practitioners ethical interactions with the world.
“In what have I done wrong? What have I done? What have I omitted that I ought to have done?” (3).
The similarities to todays Scrum retrospective are so lucid its hard not to see the Ctrl-C and Ctrl-V in their creation, a backlog of stories versus ones own stories of the day.
The ability to discern ethical actions and the practice of continuously improving our ethical interactions with the world is otherwise known as phronesis and seems to me to be the very cornerstone of the continuous improvement processes of our time. Hellenistic philosophies in general focussed on how to achieve human flourishing (eudaimonia to them), arguably Stoicism provided the most process oriented and effective means of any of the schools of that time.
Stoics nightly would review the day gone by both against goals they had set themselves in the morning but also against their own ethics, assessing progress or improvement in values such as courage, justice, temperance and practical wisdom.
“When the lamp has been removed from my sight, and my wife, no stranger now to my habit, has fallen silent, I examine the whole of my day and retrace my actions and words; I hide nothing from myself, pass over nothing. For why should I be afraid of any of my mistakes, when I can say: ‘Beware of doing that again, and this time I pardon you” (4).
Writing above Seneca would frame the complexity of life in the turbulent times of the Roman empire by wrapping each day in a retrospective and much like the Pythagoreans look to asses his own progress daily. By framing life’s complexity in this way leaders throughout time have not only been able to ensure consistency in their behaviours but also build the necessary resilience to thrive in uncertainty.
Indeed Seneca’s framing was so absolute that he would see each day as its own iteration.
“Begin at once to live, and count each separate day as a separate life.” (5)
The boundaries of phronesis have these days been blurred, the line between self-efficacy, valued living and the values of the corporation have been conflated and confused by the rhetoric of Ted talks in particular by sophists looking to ask questions neither religion nor philosophy have been able to answer for millennia and leaving a chasm in those looking to find answers that the corporation will never be able to provide. Thats at one polar extreme, at the other is the organisation that broadcasts values through a hierarchy but offers no explanation as to the context, application or point of those values and how one is able to guide themselves through uncertainty with principled decision making.
Phronetic leadership provides a middle ground between those two extremes, the individual finds resilience and efficacy of decision making by questioning their own momentary efforts in accord with values. To continuously question why we do what we do is a means of encouraging open mindedness and helps us tackle our own bias’s and subconscious behaviours. In itself phronetic leadership looks to bring about the good in an organisation where the good is a consistent reality shared through a common perception one made real through continuous introspection, inspection and sharing of knowledge from which the synthesis of new ideas emerge.
This story of the retrospective wonders far from the anxious participants of an awkward team gathering looking to learn why their user story for calling the flakey backend service never quite made it to the definition of done. But perhaps at the next one the team may look to reflect on some of the challenges from a different perspective, how did they work with each other? What knowledge did they create and share that will help the organisation be good? Or if you’re Uber how today did we become an organisation with more integrity than yesterday?
Regardless phronetic leadership, self-efficacy and the ability to continuously learn from an egoless posture are neither the soul pursuit nor qualifying criteria achieved through age, study or position. They are opportunities open to us all and examples that can be found from the youngest to the oldest in our society.

The retrospective runs throughout time and in many different spaces, the most progressive of people have thrived through its practice applying it under different banners and in many different contexts. The major theme that persists is in listening either to yourself or others and being open to the idea that change is constant and applying learning to change is in itself the greatest opportunity for improvement of ourselves and the organisations we contribute to. The only time we truly fail is when we choose not to learn; how much time do we really have to keep treading the wrong path before we must change direction?
- Managing Flow, A Process Theory of the Knowledge-Based Firm — Ikujiro Nonaka et al.
- Strategy, A History — Lawrence Freedman
- https://en.wikipedia.org/wiki/The_golden_verses_of_Pythagoras
- Seneca, On Anger
- Seneca, Letters to Lucilius