Tag Archives: leadership

Trapped by Technology Fallacies

After a working in tech at several large companies over a couple of decades, I’ve observed some of the worst fallacies that cause damage to organizations. They don’t arise from malice, but from a scarcity of professional reflection in our field. Technologists often jump to problem solving before spending sufficient time on problem setting, which leads to the creation of inappropriate and brittle solutions. Donald A. Schön discusses this disconnect in his seminal work, The Reflective Practitioner,

…with this emphasis on problem solving, we ignore problem setting, the process by which we define the decision to be made, the ends to be achieved, the means which may be chosen.

Problem solving relies on selecting from a menu of previously established formulas. While many of these tactics can be effective, let’s examine some of the dysfunctional approaches used by technologists that lead to pain for their organizations.
  • Fallacy #1 – Hammer-Nail: Technologists often assume that all problems can be beaten into submission with a technology hammer.  It’s like the bride’s father in My Big Fat Greek Wedding, who believes that Windex can be used to cure any ill. Similarly, technologists think that every challenge is just missing a certain type of technology to resolve it.  This, even though we generally speak about maturity models in terms of people, process, technology, and culture. I can’t tell you how often I’ve seen someone design and implement a seemingly elegant solution only to have it rejected because it was developed without understanding the context of the problem.
  • Fallacy #2 – Best in Class. I’ve heard this so many times in my career that I just want to stand on a chair and shake my fist in the middle of a Gartner conference. Most organizations don’t need “best in class,” they need “good enough.” The business needs fast and frugal solutions to keep them productive and efficient, but technologists are often too busy navel gazing to listen.
  • Fallacy #3 – Information Technology is the center of the business universe. I once worked for a well-known bank that had an informal motto, “We’re a technology company that happens to be a bank.” The idea was that because they were so reliant on technology, it transformed them into a cool tech company. I used to respond with, “We also use a lot of electricity, does that make us a utility company?” Maybe a little hyperbolic, but I was trying to make the point that IT Doesn’t Matter. When Nicholas Carr used that phrase as the title of his Harvard Business Review article in 2003, he was considering technology in the historical context of other advances such as electricity and telephones, “When a resource becomes essential to competition but inconsequential to strategy, the risks it creates become more important than the advantages it provides.” In the early days of tech, it gave you an edge. Today, when a core system fails, it could sink your business. The best solutions are often invisible to the organization so it can focus on its core competencies.
While technology can be very effective at solving technical problems, most organizational issues are adaptive challenges. In The Practice of Adaptive Leadership, the authors identify this failure to differentiate between the two as the root cause of business difficulties,

The most common cause of failure in leadership is produced by treating adaptive challenges as if they were technical problems. What’s the difference? While technical problems may be very complex and critically important (like replacing a faulty heart valve during cardiac surgery), they have known solutions that can be implemented by current know-how. They can be resolved through the application of authoritative expertise and through the organization’s current structures, procedures, and ways of doing things. Adaptive challenges can only be addressed through changes in people’s priorities, beliefs, habits, and loyalties. Making progress requires going beyond any authoritative expertise to mobilize discovery, shedding certain entrenched ways, tolerating losses, and generating the new capacity to thrive anew.

The end goals that we’re trying to reach can’t be clearly established if we don’t sufficiently reflect on the problem. When we jump to problem solving over problem setting, we’re assuming a level of confidence that hasn’t been earned. We’ve made assumptions in the way systems should work, without thoroughly investigating how they are actually functioning. When Postmodern critic Michel Foucault speaks of “an insurrection of subjugated knowledges,” he’s questioning the certainty of our perceptions when we’ve disqualified information that might be important in gaining a broader perspective. Technologists are more effective when they recognize the inherent expertise of the non-technologists in the businesses they serve and operate as trusted partners who understand change leadership. Instead of serving the “religion of tech,” we should focus on delivering what organizations really need.
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The Five Stages of Cloud Grief

Over the last five years as a security architect, I’ve been at organizations in various phases of cloud adoption. During that time, I’ve noticed that the most significant barrier isn’t technical. In many cases, public cloud is actually a step up from an organization’s on-premise technical debt.

One of the main obstacles to migration is emotional and can derail a cloud strategy faster than any technical roadblock. This is because our organizations are still filled with carbon units that have messy emotions who can quietly sabotage the initiative.

The emotional trajectory of an organization attempting to move to the public cloud can be illustrated through the Five Stages of Cloud Grief, which I’ve based on the Kubler-Ross Grief Cycle.

  1. Denial – Senior Leadership tells the IT organization they’re spending too much money and that they need to move everything to the cloud, because it’s cheaper. The CIO curls into fetal position under his desk. Infrastructure staff eventually hear about the new strategy and run screaming to the data center, grabbing onto random servers and switches. Other staff hug each other and cry tears of joy hoping that they can finally get new services deployed before they retire.
  2. Anger – IT staff shows up at all-hands meeting with torches and pitchforks calling for the CIO’s blood and demanding to know if there will be layoffs. The security team predicts a compliance apocalypse. Administrative staff distracts them with free donuts and pizza.
  3. Depression – CISO tells everyone cloud isn’t secure and violates all policies. Quietly packs a “go” bag and stocks bomb shelter with supplies. Infrastructure staff are forced to take cloud training, but continue to miss project timeline milestones while they refresh their resumes and LinkedIn pages.
  4. Bargaining – After senior leadership sets a final “drop dead” date for cloud migration, IT staff complain that they don’t have enough resources. New “cloud ready” staff is hired and enter the IT Sanctum Sanctorum like the Visigoths invading Rome. Information Security team presents threat intelligence report that shows $THREAT_ACTOR_DU_JOUR has pwned public cloud.
  5. Acceptance – 75% of cloud migration goal is met, but since there wasn’t a technical strategy or design, the Opex is higher and senior leadership starts wearing diapers in preparation for the monthly bill. Most of the “cloud ready” staff has moved on to the next job out of frustration and the only people left don’t actually understand how anything works.

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Mindful Security

Recently, I was invited to participate in a podcast on the topic of mindfulness. A friend and former editor of mine thought it would be helpful to discuss how the practice could potentially help stressed-out and oversubscribed IT professionals. I’ve actually had a meditation practice on and off for the last eight years and sometimes it seems like it’s the only thing keeping me sane. Especially in the high-pressure realm of information security. While I’m not an expert on meditation, I’ve spent a considerable amount of time studying and trying to understand its impact. Hopefully, people will find the information useful as an alternative method of reducing the inevitable stress and anxiety we’re all feeling in this industry lately.

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