Posts by Bob McCallister

For most of us, alerts are a constant in our working day. We get reminders about meetings, notifications from dozens of apps, and other signals regarding activity we should act upon right now. For the technology leader, however, cyber alerts take priority over all others. But knowing about a security breach is pointless unless you know how to properly react in context. You may quickly be able to resolve certain technical questions. After that comes…  MORE

Every time a CIO makes a major decision, they’re simultaneously not making an alternate decision. These are trade-offs. You favor innovation over stability. Speed over security. Transformation over cost reduction. Whatever the trade-off, the final decision depends on long-term goals, priorities, budget, and market conditions. The challenge is that you can usually make a rational and sound argument for every potential option. What’s a tech leader to do? Consider the decision to invest in the…  MORE

Any history of technology must include discussion of the unintended consequences of innovation. The so-called paperless office increased paper consumption. Email and texting caused employees to work more hours. Social media exposed us to privacy and security issues. Inside IT departments, a different flavor of unintended consequences has reared its head: Adopting AI to increase efficiency and cut costs may eventually leave them without capable IT leadership in the pipeline. By replacing junior and entry-level…  MORE

Ever since the dawn of the “Digital Transformation” concept, IT leaders have perceived the initiative as a point A-to-point B type of project. Specifically, at a high level, that means integrating digital technology into every aspect of the enterprise. But the cultural and business context for digital transformation has changed – in fact, it constantly changes, especially with the introduction of emerging technologies like AI. Transformation, in itself, is no longer the sole objective. You…  MORE

Among their key responsibilities, CEOs must assure that their organizations keep up with the latest technical innovations. Falling behind, or being too slow to implement the new solution, can put them in a competitive hole that’s difficult to climb out of. This is why CEOs often want to make technology transitions as soon as possible – seemingly starting tomorrow. But for CIOs, the challenge is bringing the company leader down to earth and distinguishing for…  MORE

Here in 2026, every organization – no matter what they sell or provide – is essentially a technology organization. Efficiency, sales, and profits depend on the quality of software, systems, and the people who oversee them. But in many cases, the IT department has become similar to the quarterback on the football team: They get all the credit when the team wins and all the blame for a loss. That’s not fair, of course, but…  MORE

There’s an old adage that the quality of one’s relationships is determined by the quality of one’s communication. From a tech leader’s perspective, that sentiment is more important than ever. Organizations today have massive technology budgets. Those dollar allocations bring serious expectations in terms of what the investment will produce. But CIOs often can’t articulate the real-world business value they deliver. That needs to change. Because of the convergence of business and technology, the perception…  MORE

Productivity and efficiency are the two pillars of measuring IT performance. Leaders want their teams to get the most accomplished in the least amount of time. When the results fall short of expectations, the default conclusion is that there must be a flaw in the process or workflows. After all, what else is to blame for missed deadlines and results that don’t quite align with project plans? But in many cases leaders need to extend…  MORE