Our world is spinning so fast that getting off course from intended outcomes can happen quickly. And it isn’t just technology that’s catalyzing change. The business climate, economic conditions, rules of engagement, and even people’s belief systems and behaviors are rapidly shifting to the point that trying to keep up is like chasing a cheetah on roller skates.
To lead in this climate, you have to hone your ability to pivot, pull the plug, or pounce on a new opportunity with little lead time. You can’t make a decision, install a system, or set a team to work on a project, then move on, even as you might have done a few short years ago. You have to be able to change your mind, admit you no longer stand behind a decision, aren’t confident in a particular project and set a new course toward a better destination.
Having an agile mind and a flexible worldview is vital to IT leadership today. But how do you achieve that?
I spoke to IT experts and leaders who have struggled with and mastered this skill. Here are the agility tricks they employ to stay flexible.
Keep asking questions
“Historically, CIOs come into an organization, assess, then try to add value,” says Sathish Muthukrishnan, chief information, data, and digital officer at Ally Financial. “That could take a year. Then they spend another six months developing strategy. From year three onwards, they might implement strategy. That was the traditional playbook.”
So, the current pace of change is, in itself, an enormous pivot for a role so complex, Muthukrishnan says.
The first step to becoming an agile leader then is to accept that the old playbook won’t work. The second step, he says, is to keep asking questions.
“I ask questions so I can deepen my understanding, orient myself,” he says. “Has the context changed? Has technology changed? Have people changed? If so, why are we doing what we were doing three, four, or five months ago?”
There are some things that have not changed, he says. Learning is the same, though what you learn and the way you apply it is different. And the need for your leadership has only increased.
“The human qualities that set you apart as a leader are becoming even more relevant in an AI-first world,” he says. “It’s no longer, ‘I’m the expert. I know. I’ve done this, I’ve seen this,’ that sets you apart. The thing that sets you apart is having the courage to say I am not tied to my previous beliefs. I’m changing them because of this reason. I’m making a pivot because of these reasons. Courage and conviction go together.”
Trust the navigation — and your teams
“You have to lead with purpose and clarity. That’s important for the organization. But you need a lot of flexibility when it comes to the execution,” says Manny Rivelo, CEO of ConnectWise.
Like a ship on a wild sea, you have a destination in mind. Getting there, though, requires navigating through a lot of tumult.
“You have to be able to respond quickly to change,” Rivelo says. “It can be anything from a market shift, the technology, or internal organizational challenges. You don’t want to lose sight of that long-term strategy, but you may have to pivot along the way. It’s not only about moving with speed, but with flexibility.”
Just like that ship navigating rough seas, you have to get accurate readings and trust your navigators to know how to steer through the chaos.
“How you collect information is important,” he says. “I look at it as a signal-to-noise ratio. What is the signal that’s driving you to go someplace, and what is just noise? How do you remove the noise so you can focus on what the signal is telling you.”
Rivelo believes in facts and data. But you also need to be able to test your own assumptions and, to do that, you have to trust your team, he says.
“You have to build diverse teams that are willing to challenge your thinking,” he advises. “In my experience, you can’t train for that. You have to hire for it.”
Rivelo digs deep when hiring to find people who have a history of being opinionated and, especially, curious.
“Curiosity is one of the greatest gifts you can have as a leader. You need to be curious enough to disrupt yourself and not assume that, because we are doing things a certain way, we have to continue. The best idea should win — wherever it comes from,” he says.
Empty your cup
According to one Zen parable, you have to empty your cup before you can fill it. To learn, you have to accept that you don’t already know.
“For me, being agile means seeing the truth and not making assumptions,” says Dr. Akvile Ignotaite, founder and data scientist at System Akvile. “I go into new projects thinking, ‘Let’s see what we can learn.’ And I learn from the data.”
It sounds simple. But when you have achieved a leadership role, you likely got there because of your expertise. You have become accustomed to people expecting you to know what to do. Letting go of that expert role is, Ignotaite admits, a process.
“I try to keep a very open mind,” she says. “I make assumptions, then measure those assumptions against real user data and behavior. I can’t know everything. The speed we live in is too fast.”
Use the ‘hot-shot rule’
Every day is full of decisions and responsibilities. It’s easy to get caught up in that and keep navigating toward a goal without stopping to check whether you are headed in the right direction. To stay flexible, Ingrid Curtis, CEO at Sparq, likes to test wind direction frequently with what she calls the “hot-shot rule.”
“This is not a concept I created,” she says. It is a mental exercise that helps people to let go of a decision, path, or progress that is no longer serving their purposes.
“Imagine you’ve been fired,” she says. “Who’s the hot shot that’s coming in to take over. What do you think they will do that you aren’t doing?”
The hot shot can be fictional or a real-life leader from the tech or business world.
“There are plenty of big, wild entrepreneurs to choose from,” she says. “They come with this huge persona. And we’ve seen that it has gotten some of them — the WeWork founder, Elizabeth Holmes, and others — in serious trouble. But there is also admiration for this flagrant, ‘I’m willing to do whatever it takes’ kind of leadership.”
It’s surprising, she says, how much this game allows people to disconnect from minutia and look at their job with fresh perspective. It’s fascinating to watch it unlock ideas.
“We all allow ourselves to be hamstrung,” she says. “Yet you imagine someone else would disregard those self-imposed restrictions and be able to get the thing done. Suddenly, with that perspective, you are able to do that, too.”
Rethink your approach to decision-making
“Everyone frames agility as a personality trait — be flexible, stay curious, embrace change,” says Nik Kale, principal engineer at Cisco Systems. “All of that is fine, but personality does not scale.”
Agility, he says, is less about mindset and more about structure.
“Adaptable leaders aren’t the ones with the most flexible temperament,” he says. “They’re the ones who build decision-making systems to absorb change without breaking.”
One big part of this structure, he says, is sorting decisions by weight. Some decisions are reversable. Others are not. Therefore, those two types of decisions should be sorted into different piles. Slow down and ponder non-reversable decisions. Decide fast and iterate on those that are reversible.
“Many leaders do the opposite,” he says. “They agonize over things that don’t matter and rush through things that do.”
For reversible decisions, schedule a point where you will stop to reevaluate them.
“I put reassessment dates on the calendar,” he says. That way changing your mind is part of the process. “It won’t hurt anybody’s ego if we planned to reevaluate that decision.”
This structure, he believes, overcomes the risk decision-makers face when they change their mind.
“Admitting you were wrong, in most corporate cultures, is expensive — reputationally, career-wise, politically. People double down on failing strategies because the cost of admitting they were wrong feels higher than the cost of failure,” Kale says. “Courage shouldn’t be a prerequisite for good decisions.”
Factor in the fact that permanence is a thing of the past
According to Ram Palaniappan, CTO at TEKsystems Global Services, when the software you use every day changes almost that often, clinging to the idea that anything you decide today won’t change tomorrow is holding on to a world that no longer exists.
This is especially true when working with AI, he says. When you make a decision about something repeatable, and offload the work to AI, verifying the results is essential because an AI will amplify mistakes. This also helps you learn to trust the AI.
This kind of mental agility, he says — making decisions that you are willing to unmake if the output doesn’t match expectations — requires that people to stay alert and keep learning. That goes not just for leaders but entire teams, he adds.
“We ask our teams to spend a percentage of time upskilling,” he says. “We set goals. We provide a learning path. Then we allow them to apply what they learn in a lab facility.”
The idea is, he says, to learn to let go of the way it was.
“Tech companies change their products, sometimes daily,” he says. “We all have to be able to move like that.”
Let go of the idea that anything you decide is permanent. Decide quickly. Then check how that decision is doing.
Exercise your emotional muscles
According to Sarah Noll Wilson, founder of The Noll Wilson Group and author of Don’t Feed the Elephants, many technical leaders believe that emotion has nothing to do with their decisions. But that can make you blind to the power emotion has over them.
“When you build your emotional skillset, it gives you access to a higher level of self-awareness and intellectual humility,” she says.
Curiosity is one emotional skill. “Instead of making you fear discovering a bad decision, curiosity can make it fun to wonder — with interest and even excitement — where you might be wrong,” she explains.
Another emotional skill is to let go of the idea that it is your expertise that’s needed.
“Some problems are technical,” she says. “Those are clear and typically solved with expertise. But some are adaptive challenges. In that case, the problem might not be clear and solving it requires learning, not expertise.”
Fear is another emotion that drives resistance to change. People don’t fear change, they fear loss, she says. “Ask yourself, ‘What am I losing?’ or ‘What am I afraid I’m going to lose?’”
One of the practices her team uses to increase emotional self-awareness, she says, is a courageous audit. This is a process where leaders examine what they want to be — an agile leader, for example — and interrogate behaviors that conflict with that goal.
“A question you can ask is, ‘What do I do or not do that’s in conflict with being an agile leader?” she says. “Do I protect my ideas or my team’s ideas? Do I dismiss ideas from people who aren’t in my field or ‘in’ group? Who gets to submit ideas? Who doesn’t?”
These exercises are designed to raise your awareness of the emotional reactions that affect your decisions and to help you develop the ability to be comfortable with uncertainty.
Change how you measure and build
According to Shahrzad Rafati, founder and CEO of RHEI, keeping a plastic viewpoint requires you to fundamentally change how you build technology and measure success.
“When you spend two years building an enterprise tool, your ego becomes tied to its deployment. You lose agility because you are financially and emotionally invested in the solution, rather than the problem,” she says.
“Instead of measuring success with metrics like uptime or deployment milestones, measure workforce elevation. When your metric is ‘Did it elevate human output and strategic thinking?’ you won’t hesitate to kill a failing project.”
The second step, she says, is to find a way to experiment quickly and cheaply. “We no longer live in a world where prototyping costs millions of dollars. You can ‘vibe code’ an idea, stand up a specialized agent, and test its capabilities almost instantly.”
“Use this to your advantage,” she says, “by lowering the stakes of your experiments. If testing a hypothesis costs nothing, your willingness to abandon a bad idea and admit you were wrong goes up exponentially.”
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