Introduction.  Best-In-Class Strategic Planning Perspectives.

CIO Executive Editorial published an article by Stephanie Overby in 2017 which presented recommendations for best practice strategic IT planning from CIOs of some of the world’s best technology companies.  Their insights are summarized below into three primary ideas which can help both executives and implementers realize their strategic goals with more pragmatic solutions.


  1. There is no separate IT Strategy.

“The line between business strategy and technology strategy has disappeared. They are one and the same.”

– Chris Bedi, CTO at ServiceNow

“The best IT plan is no longer simply a rundown of the financial investment required or a list of technologies to implement. Rather, it is an assessment of the changes demanded to achieve business goals. “While the financials are still important, the starting point needs to be the business strategy.”

– Brad Strock, CIO of PayPal

While these comments may seem intuitive or redundant, IT has too long isolated itself from strategy and focused on tactical goals.  Part of this was a lack of cross-training between high-tech and business groups and another cause can be a trend in modern Western industry to over-emphasis cost-reducing goals. Productivity doesn’t always align to neat timelines and sometimes higher costs are necessary before a stable state is reached.  However, while the transition to viewing IT as a “service” – for example, IT Service Management (ITSM) – likely helped efficiency on a local level by using IT technicians to cater to other functions throughout the organization, it did not bring in IT professionals necessarily to the senior decision-making ‘table’ and therefore marginalized its overall value.

Therefore, there is value in the modern CIO trend of tying IT operations and planning to strategy.  For a long time, it’s been lacking.  In many modern technology-based companies, IT and operations are literally the same.  A transition to increased automation and remote-control applications increases this trend across industries traditionally marginalizing IT, such as manufacturing or logistics.  By training IT planners in business processes and strategy goals, we reduce unneeded requirements for re-engineering and limit the risk that proposed solutions will miss their mark completely.


  1. Best-practice planning is incremental with inherent flexibility.

Leaders should “match planning frequency to the cadence of the business….Long-term roadmaps still have their place, but they have largely fallen out of favor, given today’s era of rapid technology and business shifts. While IT leaders must ensure that their choices are flexible … the IT strategic plan should largely focus on the mid-term horizon, typically 12 to 18 months ahead.”

– Stephanie Overby, Author at CIO Executive Editorial

Applying flexible and reactive planning techniques, such as Agile, to traditionally stoic processes such as architecture is profound.  This a fusion which can enable – if done right – strategic plans to be implemented with incredible flexibility.  Some of the most common complaints I’ve seen – “we don’t have a plan” or on the other side, “we’re too inflexible”.  What if you could minimize both those risks by maximizing the benefits of each?

Iterative “Agile Sprints” allows designers to quickly gain feedback before continuing their project; giving them an indicator whether the end-product will be well-received.  While this high-frequency feedback mechanism has limitations – not all product development is appreciated immediately, and Agile Sprints may miss more long-term trends – in the right industry and application, iterative planning can be a fixing solution for instability or volatile markets.


  1. Implementation Requires Key Performance Indicators (KPIs) – aka Performance Measures.

The best IT strategic plans include measures of success that will serve as mile-markers for progress over time. In today’s technology-driven marketplace… metrics should focus less on the inputs or outputs … and more on actual business outcomes.

– Stephanie Overby, Author at CIO Executive Editorial

Without defined measurable goals and measurement against them, a strategy can quickly become a pretty set of charts that get looked at once and filed away. I think measurement along the way is critical.”

– Chris Bedi, CTO at ServiceNow

For many organizations and individuals, the idea of using tangible performance metrics is intrinsic. Manufacturers, line managers, and other tangible producers (mining, refining, etc.) have used performance metrics to measure not only their products, but the quality their careers.  But tangible performance metrics are sometimes foreign to strategic planners and more specifically enterprise and IT architects.  Metrics historically included basic outputs like ‘did we successfully model the business/architecture to the desired level or detail’, or ‘how many models (‘artifacts’) did we create over the time period’.  Success strategy, because of its long-term approach, is hard to measure.  Because many strategic goals are not concrete but rather related to purpose and meaning rather than raw profit, it’s difficult to measure strategy in the short term.  Many successful long-term strategies were difficult and assumed failures in the beginning.  Strategic planners and the executives they support can mitigate some of the risk of strategic investment by setting SMART goals and KPIs along the way.



Overby, S. (2017, October 27). Anatomy of an IT Strategic Plan in the Era of Digital Disruption. CIO Executive Editorial. Retrieved November 26, 2022, from


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