by Minda Zetlin

5 unpopular decisions every IT leader must make

Jun 07, 2021
Business IT AlignmentIT Leadership

Having to make difficult decisions may be the most challenging part of a CIO’s job. But from an organizational and career perspective, tough choices can be the most rewarding.

path businessman confused decision technology data binary plotted points
Credit: francescoch / ivanastar / Getty Images

Mike Anderson spent a lot of time this spring having difficult conversations about Salesforce.

“Salesforce was functionally owned by sales operations,” explains the CIO and chief digital officer of cloud security provider Netskope. “And people had no governance around the system. You add a field here, add a field there — salespeople love it when you can add more fields in a system like that.”

That was fine for a while. But in February, Anderson and his team discovered there were 499 fields in the Salesforce Opportunity object. The maximum number is 500.

Anderson knew he had to take action, and that whatever he chose to do would likely be unwelcome news for his business colleagues. It was one of the many times when a CIO has to make an unpopular decision for the good of the company, to preserve security, get the greatest business benefit from available IT resources, or — as in this case — ensure that essential systems keep working.

Tough decisions may be the most hazardous part of a CIO’s job, but handled well, they need not derail your career. In fact, your ability to make difficult decisions will likely define it.

Here are some of the most common unpopular decisions CIOs have to make, and how best to manage them.

1. Imposing governance where there was none before

This is what Anderson had to do to solve Netskope’s Salesforce problem. In a lot of companies, especially rapidly growing ones, applications are managed by the functional departments that use them, he says. “Sales has their tools, marketing has their tools, and customer service has their tools. But there are intersection points where, if you don’t get things right, you can burn everyone else’s house down,” he says. “That’s kind of the situation we were in.”

Mike Anderson, CIO and chief digital officer, Netskope Netskope

Mike Anderson, CIO and chief digital officer, Netskope

That led to another unpopular decision. “I had to tell our support organization, which was trying to migrate to a Salesforce tool, ‘I know you already paid for the licenses and it’s costing us money, but you need to hold on. We have to fix the foundation before we throw more things in,’” he says.

He knew that was bad news, but the alternative was worse, he explained. “You can either rush, and we can end up not being able to sell effectively and not be able to support our customers, or we can do it in the right sequence and have these licenses be shelfware for a little while,” he told them. “I know that can be painful, but it’s a lot less painful than having customers we can’t support.”

With the support deployment on hold, Anderson began having conversations with everyone who would be affected to determine which fields were really necessary and which could go. “I’ve had 70 conversations so far, two a day on average, asking people, ‘What are your priorities? What are you working on?’”

Based on their answers, Anderson’s team was able to remove 80 fields from the Opportunity object, putting them comfortably below the 500 maximum. Under a Salesforce lead in IT, the team is now working to create some new custom objects where some of the current fields can live.

2. Saying no to new technology

Most of the time, IT leaders love deploying new technology. But there are times when “no” is the best answer to a new technology request. This could be because the desired technology is not secure enough or robust enough for your organization, or because it would not integrate well with existing systems. It could be that the technology’s benefits aren’t worth the IT resources it would require. Or it could be a great idea, but a lower priority than other, more urgent initiatives.

Chris Conry, CIO, Fuze Fuze

Chris Conry, CIO, Fuze

“That’s the most common kind of tough conversation between myself and other functional leaders in the business,” says Chris Conry, CIO at collaboration software company Fuze.

“Sometimes a business functional peer has something they perceive is very important, and it doesn’t meet the priorities you already have in the pipeline. You already have your resources aligned to those priorities. Therefore, you have to break it to your functional peers that their priority isn’t quite at the top of the list and either needs to wait or perhaps be outsourced.”

How does Conry handle these difficult conversations? “First off, be extremely empathetic to their needs. Make sure they know you’re listening and you understand why it’s important to them. At the same time, be straight with them.” And, he says, “The more you have the potential for tension, the more appropriate it is to take that discussion offline into a one-on-one meeting or virtual meeting.”

Cathy Southwick, CIO, Pure Storage Pure Storage

Cathy Southwick, CIO, Pure Storage

Saying no can be especially hard when the person making the request is a senior executive. That once happened to Cathy Southwick, CIO at data storage company Pure Storage. “When you bring in videochat technology, the last thing you want to do is customize it,” she says. But one high-level executive wanted to do just that, so that the software would start up immediately whenever someone walked into a conference room. While this was technically possible, Southwick knew that the IT resources it would take to create and maintain this customization weren’t worth it.

So she explained it exactly that way. “I said if I have a dollar to spend, I want to invest it in something that will enhance our business or customer experience,” she recalls. “When I explained it in their words, and how they think about the investments we make on the product side, the answer was, ‘Oh, that makes sense.’”

3. Spending money on something with no obvious benefits

Business executives get psyched about deploying hot new digital technology that will give sales better insights or give customers new capabilities. No one gets excited about investing millions of dollars in a project when the end result, from a user’s point of view, will be no change at all.

And yet, IT regularly must make investments just like that, either to update or protect infrastructure. Or sometimes, IT has to spend money to pay down technology debt.

“People ask for X but what they really want is X plus Y plus Z,” Netskope’s Anderson says. “So teams rush to put all those capabilities together and what inevitably happens is they cut corners to get those features out the door.”

That means they have to go back and fix things later on. “If people haven’t been paying down that debt as they go, you get to the point where you’re forced to say, ‘We’re not going to build any new capabilities for two months, and we’re going to continue to pay the team and spend the same amount of money. We basically have to fix all the shortcuts we made over the past two years,’” he says.

That’s usually unpopular with IT employees, who would prefer to build something, as well as users, who are eager for new features. To avoid this, Anderson says, “It’s important from the beginning to say, ‘We’re going to reserve a certain percentage of our capacity to pay our debt down along the way so we don’t have it become a problem that will take months to fix.”

Tina Nunno, distinguished vice president, Gartner Gartner

Tina Nunno, distinguished vice president, Gartner

How can you best explain the need to invest in something with no obvious user benefits? “I encourage clients to do it through analogy,” says Tina Nunno, distinguished vice president at Gartner. For example, one CIO who’d been on the job for a few months was invited to tell the board about his plans for the company’s technology. “He just showed them one slide. It was a picture of a house on stilts on the beach,” she says. “He said, ‘That’s what our technology is like. We have a house and it functions, but it’s built on nothing because we haven’t invested in infrastructure. So if a big wave or a big wind comes along, it’s going to come crashing down. My plan is, for the next couple of years, I’m going to build your foundation.’”

It worked. Not only did the board approve the investment, but, Nunno says, they were still talking about that slide years later. “They said, ‘That’s what we were, but we’re not that anymore.’”

Another effective approach is to find and then highlight the business benefits of an infrastructure or maintenance project, says Rich Penkoski, deputy CEO at Deloitte Consulting. For example, he says, a financial firm needed to replace its core financial system. It was “about as basic an infrastructure project as one might imagine.” The new infrastructure would create a safe environment in which to pilot some AI technology, so he highlighted that to the company’s business leaders. “All of a sudden, the project was known more for those pilots, not for the core infrastructure,” Penkoski says. “They actually chose to stay the course as opposed to doing something that was a little more glamorous because they wanted to see this AI concept at scale.”

Every project, even an infrastructure project, has strategic value, he adds — otherwise you shouldn’t do it. You need to be able to say what that value is. “I think CIOs sometimes fall short when they cannot clearly articulate how what they’re doing is enhancing corporate strategy.”

4. Asking for more money

This is a decision almost every CIO struggles with at some point. “Do I ask for more money? When do I ask? How much do I ask for? Do I ask when I know people don’t want to spend it?” Nunno says.

Rich Penkoski, deputy CEO, Deloitte Consulting Deloitte Consulting

Rich Penkoski, deputy CEO, Deloitte Consulting

For CIOs who decide to ask for more, the best approach is to make it a choice, she says. One CIO she worked with was told to keep her budget flat to the previous year. Rather than simply comply, she went to the board. “The way she did it was kind of brilliant,” Nunno says. “She said, ‘Here’s what’s possible with our budget flat from last year.’ And then she presented an itemized menu where she said, ‘If you want this, this, that, or that, it will cost this much.’ And she left it up to them.” Sure enough, the board approved two of the items she offered.

For Southwick, the key to getting more money is giving top executives the full picture of where IT is headed and what it will cost. “Part of it is forecasting out what you’re going to need and when,” she says. “When you’re telling the story to the CFO or to your business partners, you start with the big picture so they understand. Here’s what we have today, here’s what we’re going to need. And give them an opportunity to help craft where you go.”

5. Pushing an organization to change more quickly

Technology changes at a rapid pace, but not all organizations are ready, willing, or able to absorb change that quickly. “This is a tough decision, I think, for a lot of CIOs who would love to push their organizations a little bit harder to do more strategic technology,” Nunno says. “How much change will really benefit the enterprise and not stress them beyond a reasonable level?”

The best way to persuade an organization to change with the times is by using proof, not data, she adds. Try out the new technology by running it as an experiment for a small group of employees or customers. Once executives and users have seen the technology work on a small scale, they may be inclined to try it at a larger scale.

Sometimes it’s worthwhile pushing for change, even if you may not like the consequences. Nunno recalls a transformational CIO who went to work for a company that badly needed its technology modernized. The CIO began by getting the organization to commit to doubling IT’s budget over the next two years. This meant, in effect, that no other department of the company could have a budget increase during that time.

The result? “The organization was more successful,” Nunno says. “And the CIO left because that’s what transformational CIOs do. They make a lot of change. They make tons of unpopular decisions because that’s what they’re there for. They clean up all kinds of messes. And after they do that, they leave.”

For one thing, she says, transformational CIOs don’t typically want to run an IT organization that’s running smoothly. They usually prefer to go somewhere else that needs an overhaul. But even if they did want to stay, it might not be that easy. “Think about it,” she says. “Even if the organization appreciates what they did, it will never forgive them for doing it.”