The art of delegating: 6 tips for IT leaders

For some leaders, delegating is difficult. There’s a voice in your head that says, “I’ll do it myself. It will be faster. It will be right.” That voice helped you get into your current role. But it will be, eventually, your undoing.

According to David Giannetto, CEO of WorkWave, this voice is often loud in the minds of leaders because you know you can wrap your head around the details, see what needs to happen next, and get it done. “But as your role gets bigger, you will hit a point where that’s not possible anymore,” he says. “You’ll get overwhelmed. And when that happens, you need to have people around you that you can trust. You need to surround yourself with people who have earned your confidence.”

And that is the challenge. If you don’t delegate, you won’t have those people around you. Either they will have left to another employer who can give them the growth opportunities you were unable to let go of, or you haven’t empowered your staff to demonstrate that you can trust them to grow.

Delegating is a vital skill all IT leaders must learn. It’s the only way you will survive, build an excellent team, and grow your department or company. But that doesn’t make it easy.

Here are some tips, from IT leaders who have learned how to delegate even the most challenging tasks on a CIO’s plate.

Imagine you are on vacation

Though it can feel like a people problem, delegating struggles often reside within an IT leader’s own mind. The good news? You don’t need anyone to help you change your attitude toward delegation. Many IT leaders use mental tricks to help them achieve a mindset that makes delegating easier.

“A lot of leaders find it hard to trust others to do tasks they did before,” says Mike Anderson, global CIO at Netskope. “There is always this feeling of, ‘I can do it faster.’ But if your people are waiting for you to do it, to have the answer, or to tell them what to do next, you can never go on vacation.”

So, he reminds himself that, if he doesn’t delegate, he can never go on vacation without fielding emergencies or having to stay near an internet connection.

“What helps me delegate is remembering that writing code means having to maintain the code,” says Tim Panagos, CTO and co-founder of Philadelphia-based Microshare. “So, I think of delegating today’s tasks as if it were really delegating future tasks. It helps me feel good about giving up some of the present work.”

If this seems impossible, you might have some work to do. But you can get there. And delegating works.

“I go every year to a cottage in northern Michigan with my family,” explains Anderson. “There’s no cell signal or internet access, just an old landline phone that we call the bat phone. My team knows to call the bat phone only when there’s an emergency. If I answer that phone — and need to get on the internet — I have to drive into town. I have never had the bat phone ring.”

Prepare your people

There will come a time when you want to go on vacation, too. Or you might get sick, have an emergency, or become too busy working on a next-level concern to keep doing tasks you know you should delegate. But if you haven’t planned for it, you will not be able to delegate when that time comes. “And the people that don’t delegate, burn out,” says Anderson.

Delegation takes preparation. Before you can delegate, you need people to delegate to. If you feel that you don’t have those people, the first step is to determine why that is, WorkWave’s Giannetto says. “Assess first whether you don’t trust your people because you don’t have anyone competent at the level you need them to be,” he says. “If that’s true, you don’t have the right team and you need new people.”

But this might also be a mental trap disguised as a people problem. Leaders can be leery of giving staff the chance to prove they’re trustworthy, especially if a prior delegating experience didn’t go well, confirming, in your mind, that you don’t have the right people. It might be worth revisiting this. “To delegate is to accept that failure may occur,” Giannetto says. “If you don’t give somebody the freedom to fail, you’re not empowering them enough to be in charge of this task.”

That “failure” you witnessed may have been part of a learning process. “The reality, as you know if you are accustomed to doing complex things, is that you will fail ten times and succeed once,” says Microshare’s Panagos. “You likely see this path of failure to success as part of your process. But when you’re looking at somebody else’s process, you might view these as true failures.”

And after witnessing this failure, you might have decided you need to hire people who are experienced and skilled at these tasks before you can hand off anything on your plate.

“Everyone wants to hire the person with ten years’ experience using some tool or technology because they feel that’s the best person to get this job done,” Netskope’s Anderson says. “But everybody else is also looking for that person. I tell people to, instead, look for the soft skills or foundational hard skills someone needs to be able to learn that new technology or take on that task.”

You might already have that person on your team. Is there someone who has the pulse of the team or the customer, a technical skill, or a problem-solving mind that could — with some guidance and direction — be very good at the thing you are hesitating to delegate?

Start with a problem statement

When you identify that person, how you handle delegation can have a huge impact on the success of this venture. And that starts with the tasks you choose to offload. “Make sure you don’t withhold all the things you want to work on and delegate only the stuff you don’t,” Anderson says. “I see leaders delegate only the monotonous tasks no one wants to do.” That will not build your team’s abilities or help you trust them.

“I’m a firm believer that you need to delegate decision-making to the person closest to the problem,” Anderson says. “Because they’re the ones that have the most relevant information for solving the problem.”

But don’t just hand off the decision and hope for the best. There is a trick to getting the outcome you want.

“Start with a problem statement,” says Anderson. “Start by telling people, ‘Here’s the problem we need to solve and here are the guardrails within which you need to solve it.’ Then trust them to do it by asking them to come back with some solutions so you can decide together which is the right way to go.”

This gives the person handling the task the autonomy and control necessary for them to own it and apply their own creative problem solving to it. It also protects the outcome by allowing you to weigh in and guide the discussion over the decision. This process will help this person gain your trust, learn to make decisions, and become, eventually, a team member you can trust to operate more autonomously and with larger decisions.

“There is a wrong way to do this, too,” says Anderson. “That is to say, ‘I want you to use this solution, implement it this way, and get it done in this timeframe.’ That’s not delegation. That’s command and control. It might feel like delegating because you put it on someone else’s task list. But you haven’t empowered them to solve a problem.”

Let people fail to learn

Because learning often involves failing a few times, you might need to work up to delegating the tasks you hold as most important. Start by passing down things you might be more comfortable letting go of or that aren’t a crisis if they go wrong. And then resist the urge to step in and save the day when you see failure as imminent.

“They say the best salesperson does not make the best sales manager,” says Anderson. “That person enjoys the art of the close too much and can’t tolerate losing a deal. So, they always jump in and save the rep.”

That’s not delegating.

“When you do that, people will learn that it doesn’t matter what they do because you are going to swoop in and save them,” says Anderson, adding that they will also become afraid of failing.

There is also a big upside to letting your team members learn by failing: When they do figure it out, they might solve the problem in a way that’s different, maybe better, from the way you have always done it.

“This is how diversity of thought gets into organizations,” says Anderson. “You can give three people the same problem and they’ll come back with three different — often great — solutions. Then you can compare those three solutions and come up with one that brings together the best of all three.”

But you can only get to here by living with the uncomfortable, often time-consuming process of watching someone learn through trial and error.

“You’re investing in your people and allowing them to stretch,” says Panagos. “Most people in IT like to be problem solvers. They value respect, maybe more than money. Delegating is both a way of giving people hard problems and showing them that you respect them enough to allow them to try to solve them.”

It turned out, for Panagos, that, through delegating, he could also learn from his team. “I discovered they had a phrase for things I would do,” he says. “They called it ‘MITing it’ because that was my alma mater. They would say, ‘Tim is MITing this one!’ Once I realized that they had a word for the way I overcomplicate things, it gave me the introspection to ask myself, ‘Am I over designing?’ Could I do this simpler, faster, and more expediently?”

Consider delegating twice

When building a team you trust enough to delegate important tasks to, redundancy is smart. It seems costly up front, but it can lead to better outcomes — and better team building — to delegate the same task to more than one person.

“Spread your risks a little bit,” says Panagos. “Especially if you have an outsized task that will be hard to do but you feel that, ultimately, it would be better if other people knew how to do it. The first time you delegate it, give it to more than one person.”

This might seem wasteful. But it’s an investment in creating the ability to delegate, which is ultimately worth it. It will make your team see you are investing in growing their role. It will also free up a big bottleneck that could be holding your productivity back.

“The leader’s time is the thing that is most scarce,” he says. “It’s not the only scarce thing but it is often a limiter, particularly if you are a leader in the habit of keeping everything to yourself. Delegating the task to two people is probably a better use of time, organizationally, than to single-thread everything through one person.”

Crowdsource complex tasks and training

Sometimes you are faced with a task that seems, at first glance, too important to delegate. But, as you get more comfortable delegating, you might see the power in crowdsourcing.

“As a leader, you might be given a cost savings target,” says Anderson, as an example. “You’re told, I need you to hit a cost-saving, restructuring plan. Many leaders will decide to own that chore because it impacts people’s livelihoods. But what I did was to go to my leaders and say, ‘Here’s our challenge. I want each of you to come back with some options.’”

At the very least you will be presented with a plethora of ideas, many of which you might not have come up with on your own.

This strategy can even work with the task of delegating. Maybe you have someone with a skillset on your team. Instead of depending on that one person for everything involving that skill set, delegate the task of spreading that knowledge around.

“For example, IT leaders don’t always have great financial acumen, but I had a person on my team that had strong P&L skills. I could delegate anything financial to them,” Anderson says. “But I wanted all my leaders to think about running their part of the organization as a business. So, I asked that leader to grow that expertise in the team.”

Delegating is like most complex things. The more you do it, and the more you fail at it, the better you will get. “The more you exercise that muscle, the stronger it gets, and the less painful it becomes,” says Panagos. “Once you’ve got the instinct a little bit down, it comes more naturally.”

IT Leadership, Staff Management