Four Types of Business Leaders Relative to their Interaction with IT

Over the course of my career, I’ve worked with executives of every kind. I’ve noticed that business leaders tend to fall into certain categories based upon two factors—their understanding of technology and their approach to working with IT. Like a Gartner Magic Quadrant, let’s map these two characteristics on a basic four box diagram.

The first trait – understanding of technology – is the vertical axis. The more tech-savvy the business leader is, the higher they are on the axis. This also includes their understanding of the role technology plays within their business and its potential impact on driving business growth and transformation. Business leaders on the upper end of the axis are always looking for opportunities to leverage technology to increase efficiency, improve the customer experience, and create new revenue streams, while those on the bottom of the axis are resistant to change and skeptical of new technology.

The second trait, mapped on the horizontal axis, indicates how the business leader interacts with the IT department. Those on the far right of the axis are the most collaborative and view IT as a partner in achieving the company’s objectives. They naturally have a high degree of trust in their colleagues. Those on the left end of the axis have a competitive relationship with the IT department. They may view them as a threat, especially when vying for budget allocation and competing for resources. They are cynical and do not extend trust easily.

The four business leader types are: The Agitator, The Underdog, The Showboat and The Champion, as shown in the diagram. Let’s look closer at each one.

The Agitators

The most challenging business partners to work with fall in the bottom left quadrant. I call them “Agitators” because they often find fault and criticize the efforts of the IT department, with little to no constructive quality to their feedback. They genuinely believe that much of the software and technology tools in use at their organization are unnecessary and make their jobs harder. I’m not talking about the people who are always complaining about network speed, system performance or application functionality with an interest in making things better and faster. Those individuals want the technology to do a better job supporting them. Agitators generally want the technology to go away.

There is a subset of the Agitator group near the middle line of the vertical axis who do see some value in certain technologies, but they want to keep it within their control. These are your biggest shadow IT proliferators. They may want better tools for their team to do their jobs, but they don’t want IT to be involved in the decision making, implementation or ongoing support and administration. The tools they want are tightly limited in scope and they are not interested in integration with other systems or data sets. They lack the foundational understanding of the value that integrated technology can bring to their business.

How can technology leaders work more effectively with the Agitators? One option is to strategically redirect every conversation with them to talk about their hobbies and favorite vacation destinations, thereby subliminally hastening their retirement. If waiting them out does not seem like a realistic option, then you have some work to do.

The first step is to understand why Agitators feel the way they do about technology. Most of the time, they have developed an animosity towards IT departments over years and years of bad experiences. At some point in their career, they were likely involved in a large technology implementation project that was an abject failure and a huge waste of time and money. Knowing that three quarters of IT projects fail, statistical probability says that most business leaders have participated in one, and some carry more scar tissue and emotional trauma from those experiences than others.

If that’s the case, you must start by not taking their comments and behaviors personally. You might begin building the bridge by asking them about their prior experiences with IT – whether it was at a prior company or with your own team. Allow them to vent, listen more than you talk, show empathy and understanding of the frustration they’ve experienced, and avoid the temptation to defend, justify and explain.

Then, you must embark on the most formidable task: rebuilding their trust. This will take time and can only be done by showing results. It may take years to do, but it can be done, one good experience at a time.

The Underdogs

Leaders of this type start every conversation with their IT staff by saying “I don’t know anything about technology.” They walk into the room apologizing for not being tech-savvy. But, their saving grace is that they respect and appreciate the IT department and trust that you are doing the right things for the business. These folks feel the need to communicate publicly that they are intimidated by technology. IT leaders, please understand, they may be trying to tell you that they are intimidated by you.

Leaders like this can be problematic if their understanding of technology is truly so limited that they fail to see the potential value it can bring to the organization. They are easily dissuaded from approving complex and costly technology initiatives they don’t fully understand. These are the business leaders who may reject process automations because “the way we’ve always done it is working just fine”.

Business leaders, did you read the description above and sheepishly think, “Ouch. That’s me. Yeah, I do that all the time.” You need to stop advertising how “un-technical” you are. Most likely, you’re not actually as clueless about technology as you think you are. There are some things you don’t understand, but you absolutely can learn and understand what you need to know. You didn’t get to where you are in your career without the ability to acquire new knowledge and understand complex concepts.

If you are a business leader in this era, you need to have a rudimentary understanding of technology and how it supports your business. You don’t need to know how to write computer code or how to harden a server or configure a managed switch, but you should know the difference between a switch and a server. You should understand the line of business applications that run your business, how they are developed and supported, and where the data is stored. You need to know enough about technology to know what questions to ask of your IT leader to ascertain whether or not the technology is serving you well.

IT leaders, I saw you rolling your eyes as you read through the last several paragraphs. But, you need these people. It takes all kinds of skills and personalities to make a strong team, and these leaders are an important part of your team. You must learn how to appreciate and work with them.

The first thing we need to do is stop intimidating them. Chill with the technical jargon and three letter acronyms. Slow down and take the time to explain technical concepts in layman’s terms. Educate them along the way. As a technology leader, that is just as much a part of your job description as any technical skill you might possess. 

Next, involve them. They are often fantastic subject matter experts. Get them on a steering committee. Interview them during a project requirements gathering phase. You’ll be leveraging their knowledge, and they will be learning through the process as well.

The Showboats

This type of leader is the exact opposite of the Underdog. They profess to know all about technology. They created a custom website for their fantasy football league. They use some obscure browser because they did the research and figured out that it is the most secure. They buy every technology gadget as soon as it is released. And they absolutely know what tools you should be using for backing up and archiving the company’s data.

These people drive IT leaders crazy.

Like a character from a Dilbert comic strip, they walk in with a ridiculous solution in search of a problem. Or, they recognize a problem, and can’t believe you haven’t solved it already. After all, they single-handedly solved that problem at their last company by signing up for a SaaS application that took care of it easily.

Business leaders, did that description sound familiar at all? Of course not! That’s not you. You don’t do that. You’re only trying to be helpful. And you really do have some valid experience to share if only the IT department would listen to you. Hello, Showboat! The good news is that you don’t have to radically change who you are. Just tone it down a little. Your contributions are valuable, but you need to understand a couple things.

First, your IT leader probably knows what they’re doing. He or she may have earned a degree in their field and has several years of experience. They have probably been with the organization long enough to know the limitations and constraints. Trust them.

Second, good IT management involves following sound processes to select new technologies, evaluate vendors, manage changes and implement solutions. These processes are in place to avoid minor service disruptions and devastating catastrophes. Allow the process to work. 

IT leaders, you need these people, too. They will push you outside of your comfort zone. They’ll keep you from becoming complacent. They’ll nip at your heels and keep you on your toes. They will stress test your policies and teach you how to effectively deal with conflict.

Leverage these types of leaders to help improve your processes and the technologies you support and implement. Include them on steering committees and advisory panels. Go to lunch with them regularly to hear their ideas.

There is also trust-building work to be done with the Showboats, but fortunately it is focused on one dimension. You don’t need to overcome a lack of trust in technology itself, as with Agitators. Showboats already know the value technology brings to them personally and the potential it has to drive growth for the business. They may not trust you and your team to deliver that technology effectively, possibly due to unrealistic expectations.

The Champions

These leaders are the unicorns. They are few and far between, and exactly the kind of leader every IT person wants to partner with. They know the basics of technology, and have a strong understanding of the value it brings to the business. And, they trust their IT leaders to make decisions and recommendations to realize that value. They have the patience to listen to the proposals and status updates, asking relevant follow up questions, and then make informed decisions. I call them “champions” because they are truly champions of technology within their organization.

But they are rare. And even the Champions don’t get it right all the time. The further a business leader is from the ideal of a Champion, the more difficulty they will have connecting with and relating to their technology team, making it difficult to achieve true alignment between IT services and business strategy.

Every business leader can benefit from understanding the thought processes and behaviors that will help them improve the relationship with their IT team. That is why I have written The Technology Doesn’t Matter to the dual audience of both IT leaders and business leaders.

Roughly half the content of the book is directed toward the business leader who is genuinely interested in learning what they can do to increase technology alignment in their business. Part of my goal is to demystify technology management, giving business leaders the confidence to interact effectively with their IT leader. I also share some of the biggest frustrations and pet peeves that can destroy trust between the business leader and their IT team. In short, my book is designed to help every business leader become a champion.

The other half of the book is directed toward the IT leader who wants to elevate the role of IT within their business. It includes guidance for managing the people side of technology, including your boss, your employees, your peers, and your self – as well as the key processes involved in achieving IT business alignment.