Staying up all night to get Lucky: The Importance of Retrospectives

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Retrospectives: every custom software development project should conclude with a retrospective to determine how and why luck contributed to its success or its failure.

My grandmother always said, “Better lucky than good.”

“Unless it is my money that you are spending.”

Grandmothers and many others happily share advice that interestingly promotes getting lucky over doing good. In custom software development the line between lucky and good is often quite blurry. And yet, when asked how a project succeeded, the answer is all too often, “well, I think we just got lucky!”

Is it better to be lucky or good?

It is true that often the answer depends on luck. Sometimes a well-managed project may simply encounter bad luck. Sometimes your project may suffer from bad management and yet it succeeds purely on dumb luck.

Does staying up all night to meet a deadline show dedication or is it a fool’s errand? Personally, I advocate for good over lucky. Consistent success depends upon an ability to look back and learn from your successes and from your failures.

Why conduct retrospectives? Because luck is not a strategy.

Outside of Agile development, it is rare in the quality assurance and custom software development industries, that we conduct retrospectives.

It is an even rarer event that we document the retrospectives of successful projects. When things go right we are more likely to pat ourselves on the back and move on. Often, it is only when things go wrong that we stop to take a deeper look.

Conducting retrospectives should be standard operating procedure.

I find the lack of retrospectives exceptionally shocking in the field of custom software development and quality assurance. Given that projects frequently deliver late and over budget, the keys to success seem overly taken for granted.

Everyone knows that it is generally more expensive to fix mistakes than to avoid them. And understanding where things have gone wrong in the past is an excellent way to anticipate future problems. Why then, is it not a given that every team should invest in a simple tactic that is proven to deliver continuous improvement?

Retrospectives are an opportunity, not a burden.

Retrospectives provide an opportunity to effectively record experiences and events. All too often the information exists, but only in people’s heads and if a key “head” leaves the organization then the lessons learned are lost overnight.

And even without employee turnover, once a project is completed and we move on to the next task, it is all too easy to fall into the same familiar patterns of development even if they don’t work or they are not the most efficient.

Furthermore, if we pass off our projects or our teams as simply “lucky” or “unlucky” we cannot effectively harness our capabilities. Perhaps we could be luckier. Or perhaps one day our luck will turn if we don’t understand why it exists.

Do you really want to gamble on every project?

Even when a successful custom software project can be chalked up to a fair bit of luck, we should take a careful look at how and why luck contributed in a positive manner. Maybe the actual contributing factor leads back to a particular developer or tactic and not to “pure luck.”

Or, maybe we will see that at a particular point in time we skirted disaster: if component A had been implemented, as intended, before component B, our project might have outright failed. In other words, a mistake contributed to our “good luck,” when the project really out to have failed. Can we really count on two wrongs making a right in the future?

There is high value in conducting retrospectives.

I strongly believe in the value of retrospectives. To me, the most valuable training a company can engage in is: “when and how to conduct a retrospective.” There is nothing more applicable to learn at a company than how to record and quantify experiences of the company.

A successful retrospective is one that is thoughtfully conducted and carefully documented. In this manner, the retrospective is sure to provide all stakeholders the opportunity to improve, while also providing the opportunity to learn. Retrospectives must be documented so that they can be shared widely and overtime.

The benefits of conducting retrospectives are extensive:

  • Improved communication between all stakeholders
  • Honest communication that demonstrates a commitment to transparency
  • Building a company specific repository of best practices
  • Improved ability to identify possible pain points for customers
  • Finish solutions faster and with better quality
  • More accurate development of requirements and adherence to schedule

When should we conduct a retrospective?

Retrospectives are valuable both during and at the end of a project. Conducting periodic smaller retrospectives during a project will certainly help to assess a project’s progression and make it easier to redirect or change paths before it is too late. Final retrospectives provide a valuable long-term tool and method to document lessons learned.

Periodic Retrospectives

Periodic retrospectives are a key component of Agile development, but it is a useful tactic across pretty much every domain. If you think about it, successful football coaches conduct retrospectives every time they call a timeout. And in accounting, monthly profit and loss statements provide a retrospective or a snapshot of where the company is on the last day of the month.

Periodic retrospectives may be less formal than an end of project retrospective, but they can still be extremely useful. That said, although I believe in periodic retrospectives, what I focus on this piece is the importance of the final retrospective.

Final Retrospective

Every single custom software development project, successful or not, should terminate with a complete and thoughtful retrospective.

The most valuable and necessary retrospective takes place at the end of a project. Again using the accounting analogy, an end of project retrospective is a bit like an end of year financial audit. This article focuses on the value of conducting final retrospectives.

Who benefits from a retrospective?

The IRS requires nonprofit organizations with budgets over a certain dollar value to conduct an annual financial audit. Audits are not only useful to the IRS, they are exceptionally useful to all stakeholders, from decisions makers, such as upper management and boards of directors to the employees. An audit assesses not only the financial state of the organization but how and why certain decisions or actions took place. Audits conclude with recommendations to ameliorate or improve decision making and record keeping in the future.

Retrospectives in custom software development are similarly valuable at multiple levels to audits in nonprofits. Everyone from business analysts to developers to QA testers will benefit from a retrospective. I cannot think of any viable reason that any software development team should not conduct a retrospective at the end of each and every project.

What does a retrospective look like?

Retrospectives have three key components: the people involved, the questions, and the final analysis or report. The goal of the retrospective is to review how a project has progressed from start to end, with a final assessment that includes lessons learned, and future recommendations. Ideally, all team members participate and share their answers to a set of questions.

1) The People: Who participates in the Retrospective?

Depending on the size and location of your development teams, ideally, everyone involved in a project should participate. If possible, local management should sit with each team and conduct a live assessment.

Hearing co-workers and talking together is often more productive than simply filling out a written survey. Given the opportunity to speak, members of your development and QA teams will feel that their opinion is both important and valued.

2) The Questions: What to ask during a retrospective?

(Don’t worry, it is not rocket science!)

The first three questions are fairly standard, but the final three entail an evolved process to effectively create and implement lessons learned from a retrospective.

  1. During this project, what did you feel worked well?
  2. During this project, what did you feel did not work well?
  3. In the future, what actions would you recommend taking to improve future projects?
  4. Retrospective ideas for identifying luck:
    1. Where did we get lucky?
    2. Was this really “luck” or a “lucky coincidence”?  
    3. Could we replicate this “lucky” success in the future (or avoid this failure)
  5. The final step is to work with all stakeholders to identify:
    1.  Lessons Learned
    2. Future Recommendations

3) Documentation

Without a little analysis and documentation to record the lessons learned and to make future recommendations, a retrospective quickly loses its value. Sure, giving everyone the opportunity to talk about their experience is of value. However, as we already discussed, memories are short and people move on.

To truly implement a valuable process you need to put some effort into conducting and concluding an effective retrospective. Maybe you need to bring in an outside consultant. Maybe you need to create a cohort or assign a thoughtful member of your team who writes well to type it up into a report. Whatever you do, make sure that you have a clear objective, an outline, and a process in place before you start.

Every time you conduct and document a retrospective, your team will get better at the process and the results will increase in value. Over time your lessons learned and your future recommendations will become more precise and targeted.

Retrospectives in action — an example of “where we got lucky.”

Let’s say that right as project X commences, you hire Bob to replace a retiring developer. Bob has followed his wife to a research position at the local university. Previously, Bob worked in a tech hub that also happened to be an early adopter of a new technology stack. Purely by coincidence, just as you hire Bob, another part of your team decides to implement this same technology stack (no one knows about Bob).

Your team has little to zero reasonable expectation that there will even be a “Bob” in town to hire when deciding to use the technology stack. Nor does anyone consider the possibility that you might need a “Bob.”

A few weeks in, when the new technology proves to have a few more rough edges than expected, weird crashes, flaky performance and so on, Bob is your “lucky” salvation.

How could a retrospective help avoid Bob’s situation in the future?

To start with, your team needs to identify that this is a “lesson learned.” Next time your company decides on using a new technology they should intentionally plan on securing a “Bob.” If you can’t find a Bob locally, perhaps this is an indicator that this is not an appropriate time to bring this tech to your company. Or maybe you need to set up an external recruitment plan.

Without retrospectives it doesn’t get better, it get’s real.

Over the years I’ve worked on a number projects that have fallen victim to the “Bob” scenario. To solve a problem the company adopts a piece of tech touted by a big company (aka Microsoft, Google, LinkedIn). And then only a few a months into the project we’ve found ourselves knee-deep in problems.

Each time I’ve watched a similar evolution take place. The first assumption is usually that the configuration of the technology is incorrect. Next, there is a search for bugs to be fixed in the next release. Finally, there is the decision to hire “Bob” or a team of “Bob’s” thereby disrupting operations and budgets by bringing on one or more individuals who actually know the ins and outs of this particular piece of tech.

In the end, only about two-thirds of these projects actually made it into production. Ouch. That is the reality.

Maybe it’s not the lack of retrospective, it’s the quest for new technology that is the real problem?

No, I’m not against new technology. Sometimes we need it and in the appropriate situations, new technology can work really well. Unfortunately, implementing new or custom technology is not an across the board success story.

And yet, this scenario often repeats itself within the very same companies that have already experienced a failure. This is why retrospectives are vital.

Learning from past mistakes

Companies need the ability to learn from and document past mistakes. Development teams need to have a method to memorize lessons learned and manage the turnover in both staff and technology.

The best bet for everyone is to conduct and widely share honest retrospectives. When this happens, we see what went well, what went wrong and where we got lucky. And, we can do our best to avoid, duplicate and or prepare in the future.

Successful Development is Intentional

Frankly, staying up all night to get lucky doesn’t work much on the social scene nor does it work on the professional level. What does work? Preparation. Analysis. Lessons Learned. Retrospectives.

At the end of every project, you should conduct an honest retrospective so that next time you’ll know what you can do to be prepared. Make sure that your success comes from intentional acts and not simply because “you got lucky.”

Retrospectives significantly improve the software testing process. Period.

The custom software development and software testing process is at odds with almost all other technologies. Can you imagine a caterer baking a custom order wedding cake and then testing it for flavor and attempting to go back and “fix” the flavor? Once the cake is baked, it’s done. It’s over.

Most industries test first and then build. Conducting retrospectives delivers a bit of this logic into the custom software development process and improves the software testing process. Retrospectives allow us to integrate lessons learned and avoid repeating the same or similar mistakes. Why fix it, if you can do it right the first time?

Ok. You convinced me to conduct a retrospective. Now What?

As I mentioned above, the most valuable training you can provide your team is how to conduct a retrospective. Fortunately, I am not the only one who is knowledgeable about retrospectives and many resources exist. If you would like to look in detail at what it is like to conduct a retrospective, I recommend this article: The 7 Step Agenda for an Effective Retrospective.

My last piece of advice is this: keep the environment surrounding a retrospective positive. If a retrospective turns negative, some people become defensive and afraid. Others simply tune out. Negative retrospectives lack the transparency and clear communication that are vital to constructing effective lessons learned.

Keep in mind that the purpose of a retrospective is not to critique or diminish your team or any one individual. The goal is to develop a culture of continuous improvement that benefits all stakeholders.

If you enjoyed this piece, please share and discuss!

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