The rise of project management software has made it easier for managers to delegate tasks and communicate with employees, but that doesn’t necessarily mean they’re delegating well.

Many supervisors continue to micromanage, miscommunicate and stress out their employees with the help of modern technology. Follow the advice of these 16 managers to learn how to delegate effectively with project management software.

Evaluate What Needs to Be Delegated

Whether the task is going to a remote freelancer or in-house employee, managers need to be careful deciding what assignments go to which employees.

“When matching individuals or teams to projects, take into consideration their ability, skills, experience and goals,” says business etiquette expert Jacqueline Whitmore. “Some tasks are more mundane than others. In this case, find someone who thrives on routine tasks. For the more intricate projects, find someone who likes a challenge and knows to tackle the manageable parts of the job before diving into the more complicated aspects.”

Speaking of mundane tasks, start by reviewing your own workload and questioning where your time goes. You might be able to eliminate redundant tasks and save both you and your employees time.  

Alyssa Gregory, founder of the Small Business Bonfire, has seen small business owners struggle to let go of their tasks and daily activities. When you’ve been doing it on your own for so long, it can be challenging to let go of the reigns.

“If you kept track of everything you do during your workday, I bet you’d be surprised to see where your time is going and what qualifies as your biggest time drains. This alone can be a powerful tool for identifying potential tasks to delegate, and even tasks to eliminate from your business.”

Once you know what you want to delegate, it’s time make sure the training and onboarding process runs smoothly.


Take Time to Onboard New Hires to Your Tasks

If you’re hiring someone to take work off your plate, you can’t expect them to learn everything immediately. It’s the role of the delegating manager to take a step back and make sure their employees are balancing their responsibilities well.

“New hires need to not only prepare themselves mentally with knowledge, but they need to be emotionally prepared as well,” says Sarah Landrum, writing for Undercover Recruiter. “Throwing them too much at one time can overwhelm them and make them feel as though they won’t be able to succeed.

“The best way to handle this is to set milestones and provide small batches of training material at a time. Once the employee has completed a batch, he/she should receive another one, and so on and so forth.”

Rodolfo Schildknecht, co-founder of Uassist.ME, emphasizes the importance of detailed onboarding for all employees, especially virtual ones.

“A virtual employee’s onboarding only consists of formal onboarding meetings, and misses out on valuable hallway chatter and impromptu meetings. For this reason, it’s important to make those initial onboarding sessions as valuable as possible. Spending this time upfront can help your virtual employee produce higher quality work from the get-go, without coming back and forth to you with questions.”

While it might be easy for an in-house employee to ask a one-off question, remote employees have a harder time contacting and explaining their problems or concerns.

Create Assignments That Will Challenge and Inspire Employees

Along with offloading time-consuming tasks, managers also want to delegate projects that will help employees grow. After all, they’re proteges, not secretaries.

Merge Gupta-Sunderji, leadership development consultant, explains that employees don’t like receiving busy work or tasks with no end result. To prevent this, provide context to why you’re asking them to do something.

“If you want to increase the likelihood of getting the end-result you desire from your employees, tell them why what you’re trying to communicate matters. In the workplace, we’re dealing with adults. Chances are you didn’t buy your parents saying ‘Because I said so’ when you were a child, so why would it be true for the adults you employ?”

Jeff Weber, SVP at Instructure, Inc., recommends assigning “stretch assignments,” or a project that challenges employees to grow outside of their normal duties.

“One way to do this is to meet with employees individually and ask them what types of projects they’d like to work on or what skills they’d like to develop, and then use that information to assign them to a project you wouldn’t normally have tapped them to complete before you knew their interests.”

These assignments give employees a sense of purpose, while giving them a new challenge to master at work.

Even if you’re not providing stretch assignments, simply highlighting the benefits of completion can ease the onboarding process of delegation.

Tim Sieck, principal partner with On Target Talent, was inspired by Adrian Gostick’s “WIIFM” philosophy, or “What’s in it for me?” which assigns a reason for doing something that benefits the employee, along with a task.

“Frankly, it doesn’t matter why you want the job done. If your employee can’t find a reason to want to do it, he or she may say no. So, if the employee has expressed an interest in being promoted, discuss how this project will prove valuable in achieving that goal.”

Other motivational incentives include networking, skill-building and long-term ease of workload.


Give Employees the Freedom to Grow and Learn

Now that your team is armed with stretch assignments and tasks, you can take a step back and let them work.

“If you are a new manager, you need to recognize that your job is now managing people, not tasks,” says Joan Cheverie at Educause.

“This is the point where you stop telling your staff how to do their job and, instead, set the strategic direction, deadlines, and benchmarks and then allow them to determine how to accomplish the job.”

This fulfills your employees’ need for choice and an ability to make decisions of their own volition.

“Effective delegation is when you give a task to someone who knows both what they have to do and how to do it how to get it done on time,” explains business systems strategist Tony Brown. “It is giving a task to someone who can take responsibility for that task if it changes. Ineffective delegation is when you give a task to someone else and it doesn’t save you any time or money.”

This means managers who spend just as much time assigning, reviewing and tracking the progress of a task are failing to delegate effectively, as it’s causing them just as much stress as if they did it themselves.

In the same way you’re reviewing your employees whom you delegate to, you should review yourself as a manager. Baron Schwartz, founder and CEO of Vivid Cortex, discovered he was micromanaging when he became part of the problem.

“Employees might put it delicately (which can make it easy to miss), but if they communicate that you’re the cause of a delay, you’re probably in too deep. … Try to take a step back and ask whether it’s a decision you should be making in the first place. Can one or more of your team members make that call just as well on their own?”

On the employee side, communicating any problems or issues up front can save time and frustration down the road.

Certified career coach Hallie Crawford found being proactive was an important step for employees on the receiving end of micromanaging behaviors.

“If you notice that it happens at a certain time of day, provide your boss with an update an hour in advance of that time. When it occurs before or after a specific meeting, help prepare your manager in advance of that meeting for whatever he needs to report on.”

Some managers actually hope to inspire employees to reach this level of proactivity as a sign they can be left alone.

video call conference chatting communication concept

Choose the Right Time to Assign Tasks

Another important aspect of digital project management is knowing when to assign tasks to employees. Even if you’re just sending comments or assigning tasks before you forget them, you could cause undue stress within the team.

Maura Nevel Thomas of Regain Your Time wrote an article for the Harvard Business Review about communicating with employees in their off-hours:

“If the boss is emailing late at night or on weekends, most employees think a late night response is required — or that they’ll impress you if they respond immediately. Even if just a couple of your employees share this belief, it could spread through your whole team. … After all, everyone is looking for an edge in their career.”

In fact, researchers at the University of Illinois have coined the term “telepressure,” or the urge to immediately respond to work communication.

Mandy Oaklander, health editor at TIME magazine, found telepressure has long-term psychological effects on employees, including lost sleep, higher levels of burnout and health-related absences. Furthermore, she found that few employees are exempt from the pressure to respond immediately to their managers.

“Individual differences are only weakly associated — telepressure is a workplace problem, not a worker problem. We learn how to respond to email through our colleagues’ behavior … and it’s a consequence of the social dynamics within a work environment.”

As a manager, it’s your job to set the tone of the workplace and let employees know that it’s OK to disengage.

Matt Krumrie, writing for Flexjobs, offers advice to managers trying to communicate with remote teams. With the rise of chat windows through Gmail, Slack and Skype, it’s easy to track your employees’ availability throughout the day. However, this can be misleading.

“If your remote worker forgets to turn on IM in the morning, or leaves status at ‘away’ for what seems like hours, don’t hover at that status, wondering where they are or if they are working. Sometimes, when things get busy, remote workers may step away, update their status, and come back and forget to update that status. … Trust them to do the job. Lead them to succeed.”

This can be difficult for remote workers in different time zones, but this respect and behavior will result in happier employees in the long run.

Make Sure Your Instructions are Clear and Detailed

There is a whole art to assigning new tasks to employees. Make sure you are giving the proper instructions for them to complete those tasks. Offering the right information can make the difference between successful or frustrated employees.

Sabina Hitchen, co-founder of Tin Shingle, was inspired by her mom — a professional chef — who taught her how to give effective directions to her staff. One key ingredient is face time.

“Set specific times of the day or week to stop everything else you’re doing and go through the directions and expectations for a new project. This also lets them prepare any question about said project and bring the to the meeting.”

This is also important for remote employees, who should be able to call into address any questions or concerns.

KerryAnn Rockquemore, speaker on faculty development and leadership, has found the same principles apply to a virtual team as in-house staff.

“If you know how to designate tasks, establish benchmarks and bring out the best out in people, you can find an awesome virtual team to support you.”

She also encourages managers to keep the lines of communication open and provide detailed feedback on performance early on.

“When you work with people virtually, they will have questions and need feedback. (They don’t just magically do perfect work without any guidance.) It’s far better to answer questions and over communicate up front than to be disappointed later on by an unsatisfactory outcome.”

Virtual success through project management software relies on many of the same principles as in-house work. Managers that respect their employees and communicate well will have an easier time than those who provide limited directions but continue to micromanage their staff.


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