Lessons Learned in 2020

A lot has already been written about the year 2020 and I’m confident that an awful lot more will be written about the impact on society this particular year has had. As the events of the year unfolded and various aspects of life were forced to adapt to the different challenges that were thrown up, it seemed like more and more material for academic papers, theses, policy documents, training materials, and even half decent fiction was being presented on an almost daily basis. From the technology leadership perspective I think 2020 showed that there’s work to be done around how to adapt Agile processes to remote work, but while interesting this isn’t the only area where there’s something to be learned, so in the best traditions of the internet here’s a list of things I consider among the lessons 2020 taught.


Easily the single biggest take away from 2020 is in the field of communications. Over time many of us have developed a strong preference for written communication methods like email and texts to get our messages across to the point where phones are no longer deployed on desks by default and tools like Teams or Slack have become established as the comms tool of choice. However, a bias for a particular type of media doesn’t make it the best way to communicate and during difficult times like those experienced this past year when tensions ran a little higher than usual and nerves were a little more frayed the miscommunication issues known to be associated with written messages became more frequent.

Written communications just don’t work for everyone as some people don’t write clearly and some don’t comprehend willingly, which triggered a need to adapt how to communicate in order to accommodate these differences in style. While this became more obvious this year as all those hallway conversations that normally happen in the office just didn’t take place and were instead replaced by emails, the fact is that there is a broader lesson to be learned about the tools we use to collaborate with others as well as how we respond when faced with an email that seems unfair or overly critical. Taking a beat before responding or doing away with the CYA email in favour of a clarifying phone call is something that should be taken from 2020 and re-established as normal practice.

Risk Management

Wired published a great article in June 2020 about pandemic insurance and how no one wanted to buy any in 2019 (https://www.wired.com/story/nathan-wolfe-global-economic-fallout-pandemic-insurance/) and it speaks to the obvious about how risk is really managed in businesses around the world. Organisations need to get better at risk management. Right now “risk” is too often considered like a gamble that doesn’t pay off and therefore isn’t worthy of attention. Conversations about bus factor issues in teams all the way up to business continuity in the face of global pandemics or more localised and very real risks like fire never seem to resonate the way they should until it’s too late.

2020 made a distant risk into a crushing reality which cost people their jobs as businesses were forced to close and markets became inaccessible. In IT, a lot of firms discovered the consequences of under investment when they tried to get their workforces to operate remotely and in the panic of trying to get teams working the conversations about laptops and cloud as risk mitigators were forgotten. Suddenly, the only issue with getting a laptop was finding somebody to sell you one, whereas at the start of the year the justification arguments still raged as did budget fights around moving on-prem applications to the cloud. In hindsight these fights seem silly but it’s a pity that they ever happened at all.


The value of culture in an organisation is well documented but what interests me about culture when considering 2020 is how culture manifests in the real world in terms of traditions and cultural norms expressed by a team or firm as a whole. Established traditions are a valuable way to build and reinforce culture but where tradition is helpful at a practical level is as an aid in times of crisis.

Traditions remind us of who we are and help to ground us when times get tough. Teams that are encouraged to connect to their culture (like the very strong culture around software development) and create traditions of their own are able to guide themselves through new, high pressure situations with greater ease as they can base their actions on the standards of behaviour and insights of the community of which they are a part, and of which they are reminded whenever they do something “traditional” like a daily stand-up or distribution of a new set of stickers for laptops.


The concept of agility, as in adaptability in the face of uncertainty, was strongly tested in 2020. Companies struggle with agility, not just adopting the Agile values and principles used to guide development, but in being responsive to the opportunities and challenges that come along regardless of the scale of those events. Companies strategise and lay plans and place value in adhering to those plans without enough concern for the value to be delivered as a result of those plans. This results in long backlogs that teams are tied to delivering without regard for the potential need to pivot away from the backlog at short notice.

A stronger sense of agility suggests that teams should shorten the timelines of their deliverables in accordance with Agile practices, ensuring that stories are atomic and that it is possible to drop everything and pivot to something completely different by the end of the current sprint. Beyond that specific Agile action, there is a need to build capacity into teams to allow for a disruptive event to be capitalised on.

Away from development, 2020 showed that there is a benefit for organisations to think on shorter time frames, to iterate on most activities, to report frequently so that issues can be identified early and actioned quickly.


In times of disruption, whatever the cause, reassurance can be found in the regular routines of life. Real disruption triggers ad hoc responses and these responses too quickly become normal – how many times this past year did you hear the phrase “the new normal” to describe pretty much anything that was happening? Accepting ad hoc structures as normal isn’t the most productive approach nor does it make for happy teams, as trying to work in uncertain times using uncertain methods only creates stress.

It may seem contradictory but agility thrives when there are structures in place that promote responsiveness, as long as those structures build capacity and recognise the activities that are really going on in the organisation. Regularly scheduled cadences of work that facilitate as much BAU as possible are absolutely essential as are techniques to identify what constitutes “Business As Usual” in a world where change is a constant. A good example of this that was validated by the events of 2020 is that meetings specific to a narrowly defined topic should be minimised where possible and more flexible structures be implemented in their place that can handle when things change.


It’s a truism that we learn more from hard times than from good, but it’s also too often true that we never learn. Anyone who’s worked a project in the real world knows that the “lessons learned” part of the process is frequently skipped due to time constraints, which is such a shame. 2020 was a year where a lot of people had too much time on their hands, stuck at home with nowhere to go, but even after having all that time we should still take a little more for a retrospective on what happened, how we handled the situations presented, and what we can do better as a result of having learned a little from the experience.

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