Thinking Strategically on Technology

The most serious mistakes are not being made as a result of wrong answers. The truly dangerous thing is asking the wrong questions.

PETER DRUCKER

It is September 2019 and you are asked to pick the fake news story from 2020. Here are your headlines choices:

1. US Population Quarantined for Much of 2020
2. Tom Brady Becomes QB for Tampa Bay
3. TikTok Upends Donald Trump’s Campaign Strategy
4. Bill Belichick is Subway’s Newest Pitchman

A tough choice in which all the options seem equally ridiculous and far-fetched. Brady leaving New England or a nationwide lockdown would have seemed far more plausible than the near humorless Patriots coach selling footling subs. Was TikTok even a blip on the radar screen this time last year?

Isn’t this meant to be an essay on testing your technology strategy?

Of course it is. But proper etiquette requires paying homage to the Bizarro World absurdity known as 2020. An intelligent treatise on technology strategy will be posited, but not before presenting evidence that my business writing style has evolved to reflect my virtual teaching style used with my twin boys. Regrettably, there are no winners. Sorry. 

How is a “Fake News Game” a metaphor for the role of CTO?

CTOs have a tough job. They are tasked with maintaining a technology strategy that will stand the test of time and be adaptable in unpredictable circumstances. And 2020 has over-delivered in the category “unpredictability”. Just like the 4 farcical options posed in the fake news game, CTOs have felt the pressure of 2020’s volatile environment and the immense challenges brought about by the impact of COVID-19.

What is a technology strategy test?

In 2020, we have seen production lines shuttered, supply chains upended, transportation options narrowed, economic recession, workforce displacement from offices to homes, unpredictable consumer demand, unemployment, and an economic recession. CTOs, if your company’s technology has made it without so much as a hiccup in 2020, in lieu of reading this article, take the next 15 minutes off to watch TikTok video tips on improving your golf short game. You’ve earned it and TikTok’s overlords have big plans for you once they learn that your flop shot is your Achilles heel.

A technology strategy test is an analysis to determine whether your company has the resources, plans, and resource agility in place to effectively execute your technology strategy. In a worst-case scenario a company should not be learning for the first time where their technology strategy weaknesses are in the middle of a major crisis.

Bear in mind, this is a test of your technology strategy and it is not meant to replace technology infrastructure testing. The goal of a technology strategy test is to look for weaknesses and gaps at a strategic level that could cause your company not to effectively execute their overall strategy.

How does one conduct a technology strategy test?

If you don’t have a technology strategy, you should start by creating one that supports your company’s strategy. These questions will even be of use in constructing a technology strategy.

The process can be as simple as reviewing your technology strategy against a series of simple questions. Here are the questions and some thoughts to consider with each one:

1)   Will our technology strategy keep us ahead of trends in technology?

Technology should be able to play a key role in helping companies establish a competitive advantage. Look at your company’s competition and learn what you can about their technology. If your company is in the middle of the pack, look to the technology of the leader and determine what can be done to emulate their success. If you are the leader amongst your peers, find ways to further differentiate your technology from the competition to further increase your lead within the market. Also, look to what is keeping you at the head of the pack and determine which technologies could be vulnerable and allow your advantage to be eroded.  

2)   Will our technology strategy be able to embrace uncertainty?

Your strategy requires that you make decisions that will be optimal both in the short and long term. However, the situation in business is not always likely to remain constant. Consider within your technology strategy the ability to adapt to a range of circumstances. Think of this â€œrange” as a continuum of uncertainty – at the low end, uncertainty may be a small range of what could change. At the extreme end, that uncertainty may be so extreme that predicting the possible conclusion needs to account for a wider range of outcomes. Does your strategy take into consideration the ability to deal effectively with a high degree of disruption?

3)   Have we taken measures to avoid bias within our technology strategy?

A common cause for bias is often something along the lines that “we are too close to the work” – and that can be an influential factor in evaluating a technology strategy. Consider as a starting point the various manifestations of cognitive bias – systematic ways in which the context and framing of information can influence individuals' judgment and decision-making. Cognitive bias is not always bad – our thinking, evaluation, and make decision-making processes can be more expedient as a result of cognitive-bias. However, be considerate of the manifestations of bias – overconfidence bias (inflated sense of skill, talent, or self-belief), self-serving bias (positive outcomes attributed to skill, negative outcomes attributed to luck), herd mentality (copying what others are doing), and confirmation bias (seeking-out data that confirm pre-existing ideas / beliefs) are just a few examples of cognitive bias.

4)   Do we have alignment amongst key stakeholders and team members and agreement to execute on our technology strategy?

Just because you have a strategy doesn’t mean that you have buy-in from stakeholders and team members. It is vital to ensure that key individuals are well-versed in the strategy, the business drivers that it serves, and that they are taking the appropriate measures to execute the strategy.

5)   Have we translated our technology strategy into high-level action plans?

Doing so will not only ensure that the goals of the strategy are being executed, but, it also is a great way to validate that key stakeholders understand and support the strategy. The action plan contents should be a proof-point of both alignment and the commitment to executing the strategy.

When to Conduct a Technology Strategy Test?

Testing your company’s technology strategy should be at least an annual exercise. Many companies would have been far better positioned to manage the challenges faced in 2020 had their technology strategy been tuned-up based on these five simple questions detailed below.

While many technology leaders are still dealing with 2020’s challenges, this exercise should not be delayed. Just because your company weathered 2020 is not a reason to forgo a test of your company’s technology strategy.

How does this help my organization with next month’s robot lizard uprising?

None of this advice will help at all. Once the robot lizards have become sentient, it is too late to prepare. Your engineering school likely did not cover robot lizard behavior. Too bad. MIT is offering a certificate / executive education course on the topic. Cost: $17,500 for the online course. Alternatively, you could hire my kids – they covered the topic earlier this month in virtual school. They are eagerly awaiting the coming battle and have told me to “bring on the android reptiles…”

Any last insights related to testing your technology strategy?

Why not... Let me echo the words of the legendary corporate philosopher:

The most serious mistakes are not being made as a result of wrong answers. The truly dangerous thing is asking the wrong questions.

PETER DRUCKER

Timeless advice from an inspired gentleman who impacted multiple generations of corporate leaders. And yet he failed to achieve the career pinnacle of being a pitchman for Subway.

About David Tossell

David Tossell is a 25+ year IT industry veteran – much of that in travel marketing & distribution technology. Today, David is a IT solutions and strategy senior executive for DataArt. His areas of focus include travel/hospitality, healthcare/life sciences, finance, retail/distribution, and media/entertainment. David is based in Dallas.

Contact David at dtossell@dataart.com.

Any opinions expressed are David's personal point of view.