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What to do when your boss is clueless about digital transformation

Today’s businesses can face all kinds of problems if their upper management isn’t sufficiently tech-savvy. If the boss of your company is clueless about modern technology, this can seriously impact those of us who are in charge of charting and navigating the digital transformation of our organization. This was made clear to me recently when I talked with Matt Mead, the chief technology officer (CTO) of digital tech consultancy firm SPR. Matt has a contagious passion for technology and has more than 25 years of experience designing and delivering secure, sophisticated solutions using a broad range of technologies. The following is an excerpt from my discussion with him on how businesses can deal with this problem of technology disconnect at the leadership level by attacking it from both the top and the bottom of your organization.

MITCH: Having worked in IT myself and known many IT professionals who work in companies of various sizes, I’ve often seen what looks like a disconnect between upper management and IT. CxOs and other upper-level managers are sometimes not very tech-savvy, or rather their knowledge of digital transformation technologies is shallow and limited. IT pros, on the other hand, tend to be down and dirty with all things technical when it comes to the software and services they work with. This disconnect can often cause problems for the companies involved in digital transformation, right? Can you describe a few examples from your experience?

MATT: Frequently, I see instances where high-level technology leaders, primarily the CIO, seeks an offshore, outsourced IT partner with a goal to reduce costs. And in most cases, the offshore IT partner is unable to provide the properly skilled resources at the right time. In these situations, the lower-level IT staff, who are responsible for executing the IT projects and for the project’s success, struggle to produce quality deliverables on time because their predetermined offshore provider is not able to provide the right skilled resources at the right time.

I’ve also seen instances where high-level technology leaders select a particular software or hardware and mandate its use on IT projects. While there are certainly instances where this sort of product selection is advantageous, all too often the use of the software and hardware is not well understood by the technology leader, and there ends up being pressure to use the tech in situations where it is not appropriate.

I’ve specifically seen this happen with an enterprise messaging platform. Because of the cost of the product, there was tremendous pressure coming from senior IT leaders to misuse the software by integrating it where simple intra-application technologies — which had no additional licensing costs — would be better suited. This misuse, over many years, led the IT team to build an array of new solutions that were over-engineered, not user-friendly, and ultimately very expensive and time-consuming to operate. The misuse of the platform was like shooting mosquitoes with a cannon: It works, but it was overkill and not efficient.

MITCH: What can IT do from their end to help resolve the kinds of difficulties that can occur when their company’s bosses aren’t up to snuff technically with the trendy new technologies such as digital transformation they want to introduce for their companies? Should they try and make the effort or should they just keep their heads down, nose to the grindstone, and obey orders even if they know they’re not going to produce effective results?

MATT: IT should definitely make the case for having at least some control over hiring and leveraging employees on their teams. Or, at a minimum, IT should have the ability to hire consultants of their choice if they are ultimately responsible for delivering IT solutions.

IT teams can make a case against misusing predefined product selections by pointing out the total cost of ownership. If you can reasonably demonstrate that predefined product use will actually cost more upfront, for licensing, or based on long-term maintenance, then it may be easier to get executives on your side.

IT should definitely make the case for having at least some control over hiring and leveraging employees on their teams. Or, at a minimum, IT should have the ability to hire consultants of their choice.

MITCH: How can organizations deal with this problem from the other end? Can you educate upper-management types about technology? It’s said to be hard to teach an old dog new tricks — what’s the best way of trying to do this?

MATT: Continuous learning is so important. I would hope that all upper-management types would be eager and open to learning more about technology given its importance in today’s business climate. I recommend that IT translates its message into contexts that matter to upper-management, such as short-term or long-term cost, employee happiness, customer happiness, market impact, speed and ability to change as the market evolves, rather than speaking directly from a sole IT perspective.

MITCH: Soft-skills sometimes get a bad rap by businesses because they’re seen as a cost center rather than a profit-enabler. Aren’t communication skills fundamental, though, for any kind of success? Boss-to-employee and vice-versa, company-to-customer and vice versa — it’s all about communicating effectively, isn’t it? How can one improve the culture of communication in these value chains?

MATT: I cannot think of an environment I’ve encountered where communication and soft-skills were not valued. From a software development perspective, we tend to use a lot of automation on modern agile development teams, which results in fewer human errors.

As a result of this automation, we’re seeing traditional “off-by-one” developer errors decline. But this automation has not helped reduce the bugs related to misunderstandings and/or misinterpretations in human-to-human interaction and exchange of information. Agile helps reduce this second category of bugs by having a greater emphasis on face-to-face communication whenever possible. Ultimately, it is only better communication that can combat this second set of bugs. As a result, I’d argue that soft skills and written and oral communication skills are critical for all IT team members.

I’d encourage senior leaders to consider creating cross-functional teams that help IT and the business collaborate as one cohesive team.

MITCH: Anything else you would like to add on this topic?

MATT: I see modern organizations that are thriving by embracing technology and IT, rather than viewing it as a necessary evil and cost center. I’d encourage senior leaders to consider creating cross-functional teams that help IT and the business collaborate as one cohesive team. Additionally, it’s important to gather feedback from the business on how IT could be more effective and ask IT for feedback on how they could be more efficient working with the business.

MITCH: Matt, thanks for taking the time to discuss technology and digital transformation with us.

MATT: You’re welcome.

Featured image: Shutterstock

Mitch Tulloch

Mitch Tulloch is Senior Editor of both WServerNews and FitITproNews and is a widely recognized expert on Windows Server and cloud technologies. He has written more than a thousand articles and has authored or been series editor for over 50 books for Microsoft Press and other publishers. Mitch has also been a twelve-time recipient of the Microsoft Most Valuable Professional (MVP) award in the technical category of Cloud and Datacenter Management. He currently runs an IT content development business in Winnipeg, Canada.

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