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The Importance of an Annual “Year in Review”

It’s great to focus on the future as the calendar year comes to a close, but don’t forget to spend some time considering the past.

Damian Scalerandi

By Damian Scalerandi

SVP of Professional Services Damian Scalerandi leads every step of IT project delivery with multi-cutural teams to help accomplish client goals.

10 min read

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The old quote that “those who can’t remember the past are condemned to repeat it” has been heard by every history student or consumer of political oratory past their teenage years. The lesson of the quote, that the events of the past hold lessons relevant to the future, is a good one that shouldn’t be lost on technology leaders.

As the year winds down and a new year begins, most organizations’ focus is on dispensing with the past as quickly as possible. Managers are scrambling to close budgets, finish projects, and hope that year-end reporting and processes are completed successfully. Similarly, leaders are focused on closing the literal and figurative books on the past as quickly as possible so that they can begin their holiday break and focus on finishing their strategy for the following year.

A Strategy without the Past is no Strategy at all

This zeal for the future often extends to the strategic planning exercises that accompany a new calendar year. Perhaps it’s human nature to close out the past. I’ve seen many leaders gloss over whatever introductory elements of their strategic planning mention the past year’s successes, failures, and continuing efforts. 

Whether it’s a formal part of your strategic plan or an exercise that serves as an input to it, you should begin your strategic planning with a formal and diligent analysis of the past.

This review should include at least 3 elements:

  1. An analysis of the market and external environment over the last 12 months. What significant changes occurred across technology, markets, and society? Were these changes expected evolutions like a new iteration of a technology or profound and unexpected changes like the COVID pandemic?
  2. How did your portfolio of strategic projects fare over the past year? Which projects were successful and which failed or were abandoned? What were the primary causes of the successes and failures? Were they due to an internally-driven reason like budget or an external factor that you articulated in your analysis of the external environment?
  3. Are there any thematic elements to your analysis? For example, were you highly successful in some projects due to a new or existing partnership? Did you place a “big bet” on a program that assumed certain market conditions that later changed? Were you missing key capabilities that made it impossible to execute some projects?

Let’s examine each of these elements in more detail.

Reflecting on the Environment

Strategies and long-range plans can’t exist in a vacuum, a fact that has been dramatically illustrated over the past 2 years when COVID foisted lasting changes on everything from how and where we work to the reliability and design of our supply chains. Spending the time in your annual review to examine the shifts in the environment is not only a study of history but an examination of how your strategy fared against environmental elements that were both predicted and out of the left field.

Understanding environmental events both inside and outside your company also provides critical information to determine how your strategy performed when accounting for these events. For example, a strategy to roll out new technology to support in-person live events that launched in early 2020 was unlikely to be successful no matter how wonderful the technology or skillful the implementation team was.

However, it’s often too easy to point fingers at external events as the reason a strategy didn’t meet expectations. It’s also easy to miss elements of a strategy that allowed it to progress despite unfavorable external circumstances. 

By way of analogy, consider a race car driver that clocked a time 5% slower than their usual average. This might cause concern unless one considered that the race took place on a rainy day, the car was using a new tire compound, and the driver ultimately won the race. Without those historical references to internal and external environmental factors, the 5% performance decrease might be dismissed as substandard, rather than a positive result and proof point for the new tire technology.

Analyzing Your Portfolio Performance

Most organizations already have tools and methods for tracking the performance of their strategic portfolio but fail to look much beyond financial and delivery time metrics. Ask yourself if particular types of projects tended to perform differently than others, or if you are grouping your portfolio correctly.

Groupings based on the organizational structure, such as lumping all projects for the marketing department together, might make organizational sense, but probably miss other critical variances. For example, most of your cloud migration efforts could be struggling, but grouping them by organizational unit obscures that fact

Try viewing your portfolio performance from different angles like organizational unit, core technologies deployed, or risk levels. Ultimately, you’re looking for a grouping factor that indicates an area where you’ve created internal “best practices” that can be scaled to other parts of the portfolio, or areas that are struggling and could be improved through common mitigations.

Look for Themes

With the time-consuming efforts of the previous 2 steps complete, search for themes. You might find that particular elements of your portfolio performed well, even if the internal or external environment changed dramatically. See if there’s a common technology that helped accelerate delivery or if new management methodologies like Agile are delivering on their promises.

Even one or two key themes can provide critical information that will inform your emerging strategy for the coming year. These themes can also serve to identify capabilities that are deficient, missing, or perhaps emerging assets that should play a role in your next strategic plan

This retrospective isn’t meant to serve as a “witch hunt” to find flaws and punish those associated with them, but as a means to learn from the past. This learning ultimately allows your organization to improve its ability to deliver in the future. Like an athlete that regularly reviews both their training history and current performance, searching for themes to inform their next training cycle, so too can your organization increase its performance through an annual review that turbocharges the next cycle of strategic planning.

Damian Scalerandi

By Damian Scalerandi

Damian Scalerandi is SVP of Professional Services at BairesDev. Damian leads every step of IT projects from design through project delivery. His 10+ years of experience in the tech field helps him lead globally diverse teams on large-scale tech projects.

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