CIO Advice 2020

As the pace of technology innovation remains high, the role of the CIO continues to bear the pressure that comes with that pace. Gone are the days when the CIO could get by simply by keeping the IT infrastructure running. Today’s CIO must add real value to the organization and adapt the CIO role to meet the ever-evolving challenges that come with progress.

Here are 5 of the top challenges we see CIOs facing in 2020 and beyond.

1. Leveraging Data into Actionable Information

We’ve all been hearing about the importance of data for years now, but data in and of itself isn’t always valuable. First, CIOs face a complex challenge of leading their organizations not just to collect data, but to collect the right data. Dispense with the noise, and focus intensely on the data that will move your organization forward.

Even still, it’s not enough even to have the right data. The challenge facing the modern CIO is leveraging the right data into actionable information. It’s all too common for organizations to become lost in their data rather than learning from it.

The CIOs that can find ways to cut through the trove of data and gain real insights from it are the ones whose companies will succeed in 2020 and beyond.

2. Driving Agile Innovation

Companies that don’t innovate die. That’s the world CIOs face today, and tomorrow doesn’t look any different. CIOs, then, need to drive their organizations to become agile businesses that prize and encourage regular innovation. This is a far cry from the notion that CIOs must simply keep equipment and infrastructure reasonably up to date.

No, the modern CIO must do more than that. Regularly and publicly solicit new, outside-the-box ideas from your direct reports, and encourage them to do the same. We know: not every idea will be a good one. Still, companies must create cultures where employees feel free to innovate, and even to fail. The CIO should drive the culture shift that’s necessary to get there.

3. Maintaining Security—Without Alienating Users

Security is, of course, a serious ongoing challenge for CIOs. News of major breaches hits near weekly, and many CIOs lie awake at night fretting that their business will be next. Having a robust security protocol in place is a necessity.

It’d be simple enough to end this point here, but there’s another element that bears discussing.

Digital security efforts are essential, but CIOs must balance their security efforts with user experience. There are at least two reasons this balance is important. First, your people need to remain agile. If people who need data can’t get to it (or can’t get to it quickly), your organization will suffer. Yes, the lost efficiency is less visible than a massive data breach, but the damage is real nonetheless.

Second, the more frustrating it is to do things right, the more likely users are to skirt the rules or game the system. People usually aren’t trying to circumvent your security measures for nefarious purposes. They’re just frustrated in trying to do their work and looking for a more user-friendly approach.

The challenge for CIOs in 2020 and beyond is to find strong ways to secure their systems that don’t slow people down or block them from the data they need.

4. Getting All the Right Skills

It’s always tough to land the most qualified, most skilled people, in any field and any industry. Throw in a tight labor market and it gets even tougher. To compound the problem, tech and IT continue to invent new job categories and specializations at lightning speed.

Getting all the right people will all the right skills and certifications has been a CIO challenge for some time, and it will likely be an even greater one for CIOs in 2020 and beyond. Some research firms including Gartner report on a skills gap: companies need more workers with certain skills than exist. Gartner estimates 75% of companies will face noticeable disruptions by 2020 because of the skills gap. The CIO’s challenges are to find the right hires and to stay ahead of the curve in recognizing what roles will be needed in the near future.

5. Knowing When to Upgrade

Another challenge facing CIOs is knowing the right time to upgrade legacy systems. Newer, shinier systems are available, but will they integrate with legacy systems? Your old systems are stable, and the new ones are unproven. Wait too long to upgrade, though, and a competitor could get an edge on you.


If you haven’t sensed them already, be assured: these challenges are coming. If you could use help navigating these or others, visit our Toronto IT support website at