How to Build Delegation into your 2020 Plan

business project management strategic planning strategy Jan 24, 2020

Getting ready to delegate means not just looking at the tasks you’d like to pass on but also at the way delegation works.  There are ways to prepare yourself for delegating though so when you’re ready to outsource it’s not a change that requires you to rebuild your business.

We’re protective of our work. 


Here are 7 strategic considerations about delegating that will have the most impact on your business. You can start these right now, even if you’re not ready to outsource...yet.


Let it go

This sounds like the easiest step but it can often be the hardest. We’ve built our businesses with much of our heart, soul, blood, sweat, and tears in them. We perhaps don’t trust our team members’ capabilities. Maybe we just love doing a certain task or type of task. This step requires you to adjust how you see yourself in your business, the role you play. 


You can do this step long before you ever look at your first candidate. Starting now look at the role you want to play in your business. What does it include and exclude? From there, don’t think of those things as yours any longer. You’re doing them until you find the right person to hand them off.


Hire your own DNA

When you started your business and did all the research about your Why, your Mission and Vision, you established your company DNA. These are the values that ensure what you’re providing is what you promised. 


Revisit your early business development work from the perspective of a worker. What specific behaviors does that DNA look like when you do the work? Next, the perspective of a manager. What would they see? Are the behaviors different or do they have crossovers? Knowing how it looks from both perspectives will help you recruit the right people by communicating what’s important to you.


Establish a firm priority system

Communication is the absolute key when delegating.  Developing this will go a long way in soothing your concerns about quality, deadlines, and responsiveness. An existing priority system greatly reduces the chances of missed deadlines and misunderstood instructions. Because there are tasks you’re no longer thinking of as your own, you’re just holding them, start applying the priority system yourself. The same way you’d assign them to your VA, OBM, or consultant. Bonus: You’ll be less stressed and more productive as well.

This is a fantastic upmind exercise. Remember, this is your business. It’s your responsibility to build a structure the worker fits into, not the other way around. Start approaching your business as the Visionary, not the Legwork.


Provide clear instructions

Misunderstandings happen. But we can mitigate that risk by providing the best possible instructions when we delegate. Depending where you are in your steps to outsourcing, there are a couple different things you can do to prepare.


From the start, keep simplicity in mind when you’re building and refining your processes.  Especially if it’s on the list of tasks you’ve identified to give away. How long would it take you to really explain to someone how to do it? Look for places where misunderstandings could happen.  Can that be simplified? If not, be prepared to address it in the instructions.

If you’re nearly ready to begin outsourcing, I recommend setting up a free Loom account. You can record step by step videos the next time you do the process. Look lets you store videos in folders so you can create your own onboarding and training resource. The only consideration is: Don’t do this step until you know your process is the way you’d like it to be. Otherwise you’ll keep having to record new videos for tiny updates. 


Be prepared to teach

I’m sure part of your DNA is being able to start quickly and not needing a great deal of hovering. Otherwise, what’s the point of outsourcing? We can’t ignore that your team will need guidance though.

Approaching team leadership from a place of education builds the strongest teams. This is part of being the Visionary instead of the Legwork. You’ve found someone made of the raw material you need to have a superstar but they’re not quite there yet. Maybe they’re missing a skill or lack experience. 

Where is your line of what you are and aren’t willing to teach? What can and can’t be taught? How will you prepare to teach your team to be a cohesive unit with the skills and drive you need?


Don’t go MIA

Building a strong team takes time. It’s not something that can be rushed, like any relationship. It has to grow. It’s built on trust. When you begin delegating that trust isn’t there yet. So you keep a close eye on them. 

As that trust grows, you’ll feel more comfortable stepping back and letting them do their thing. But that doesn’t mean it’s time to be hands-off. It’s important for ensuring quality but moreso it ensures a team member who feels included. That’s someone who will be more careful and dedicated to you. It’s always worth investing in that in a delegation relationship. Always. 


Assign a time to work together

Much like going MIA, without feedback you consultant will have no idea if they’re doing a good job. “No news is good news” doesn’t work for relationships, especially when it comes to delegation. 

Set aside time, 30 minutes or so, each week to spend time with your consultant. It can be a very simple “Keep doing this, Start doing this, Stop doing that”. Approach the time constructively; this is working with the consultant you’ve identified through a series of stages as the best person to do this work for you. Take time to recognize their wins and collaborate on the best ways to improve.

You can start doing this today. How often do you really sit down and check in with yourself on progress, snags, and solutions the way you’d check in with a consultant? Give yourself 30 minutes a week for feedback. You’ll be pleased with how much it helps and know first hand how to recognize people when you begin outsourcing.

Believing in our own abilities is important for success. But it’s impossible to do everything ourselves. We all need to delegate.

I spent full days tackling support issues. Once I hired reliable people to share the workload, I could devote my attention to other things, like improving our product and developing new strategies.

I’ve also learned that proper delegation is an art. And once you strike the right balance, the result is usually happier employees, more satisfied customers, and a healthier company overall.


When you delegate, you empower

“As we look ahead into the next century, leaders will be those who empower others.”

– Bill Gates, founder of Microsoft


Both managers and employees benefit from delegation. Initially, managers have to invest some time in training and creating systems to monitor the tasks they offload.

If you’re delegating client intake, for example, you might carve out time to walk an employee through your process. Then, once the employee starts managing intake, you could create a reminder to review their work every few days, which can happen less frequently as time goes on.

After that initial investment, managers have more time to focus on improving the business. They can redirect their attention from rote tasks to things that really move the needle for a company.

As for employees, engagement typically increases as they take on more responsibility. Professional engagement is all about continually challenging staff, and giving them opportunities to grow and advance. 

You might even find that when given the chance, your team member knocks it out of the park (and outperforms you, too).

When I assign tasks to others, they often accomplish the desired result — and improve the underlying process itself. In this case, both the employee and our company benefit from that simple act of delegation.


How to hand over the reins

First, decide which tasks you can take off your plate. If you’re not sure what’s ripe for redirecting, try delegating when:

  • Someone on your team can do it better. At JotForm, there’s almost always someone who has more knowledge or niche experience than I do — and that’s a good thing. It means we’re hiring well. If you realize that someone else can deliver stronger results in less time, don’t hesitate to delegate.
  • You can regain precious time, energy, or focus. Instead of letting your days evaporate into busywork, delegate. Then you can apply that energy to activities that make a big-picture difference for the business; the kind of work that only you can do.
  • A task is time-consuming (and doesn’t generally require your knowledge or expertise). Tasks that demand lots of initial legwork, like research or data crunching, can often be broken down and reassigned. Once the initial stage is complete, you can easily step in to review and carry the task forward.
  • Time-sensitive tasks are competing with other priorities. Often, we find ourselves with several time-sensitive projects to complete at once. Rather than falling behind on one of them, decide which can be competently finished by someone else, and focus your energy on the remaining project(s).

I recommend starting small. 

When I was ready to delegate, I hired just one customer support employee. Once that person was trained, I built out a team. 

That way, there were no customer support disruptions, even when our first employee took a vacation or a sick day. Finally, I hired someone to manage the support team, and stepped in only to provide feedback when necessary.

Once the customer support system was fully established, I focused on building a maintenance team. Eventually, I reached the point where every part of the business that could be systematized was broken into individual elements.


Habits of great delegators

“When you delegate work to a member of the team, your job is to clearly frame success and describe the objectives.” 

– Steven Sinofsky, former Microsoft executive

Delegating is most effective when managers explain why the work is being reassigned. 

When we start by offering context — how a specific task fits into overall company goals and why the employee is the right person to do it — we increase the chances of effective follow-through.

Additionally, delegation doesn’t mean passing the ball and never looking back. When managers cede responsibility and lose control of team activities, the process has gone awry.


Successful delegators regularly measure results and provide feedback. Even when I’m no longer managing a team, I check in regularly and monitor their performance. Plus, it never hurts to have an outsider, who has fresh eyes, check to see whether the processes are working optimally.

Managers who know how to delegate effectively will assign the deliverable, then let the other person figure out how to get it done. Instead of feeling micromanaged, employees will feel challenged and valued. And when given ownership of a task, most employees are motivated to prove their capabilities.

Also, just because a task doesn’t fit anyone’s job description doesn’t mean it can’t be delegated. If someone demonstrates a high level of expertise and responsibility, give them the chance to shine.


And here’s the final frontier of delegation: asking employees to participate in critical decision-making tasks, like hiring and financial reviews.

For example, you could invite key employees to attend a round of interviews, then ask for their feedback afterward. Most people feel more deeply invested when they know they’re helping to build the team.

Sharing sensitive business tasks can make us feel vulnerable, but the payoff for opening these activities to (the right) employees can also be significant. Staff will be more engaged, and you can free up your time for higher-level projects.

In preparation for my three-month paternity leave, I decided to make my COO responsible for hiring. Delegating this and other tasks that were part of my daily workload allowed me to take true paternity leave, rather than a chaotic, work-from-home sabbatical.


Be more essential, but less involved

“While it may seem difficult, elevating your impact requires you to embrace an unavoidable leadership paradox: You need to be more essential and less involved.” – Jesse Sostrin, author of The Manager’s Dilemma, Beyond the Job Description

Delegating can be challenging. As leaders and entrepreneurs, we love our businesses; that’s why we started them in the first place. 

Whether it’s coding or working with clients, we often enjoy the daily tasks that keep our companies running, too.

But if we fail to delegate, we hamper both employee and company growth. 


A chef-turned-restaurant-owner might love to cook, but in most cases, she needs to step out of the kitchen. Only then can she devote herself to big-picture goals like building a brand and elevating the business.

In the end, delegating means doing less so you can dig into the more essential parts of your company. 
It’s about enabling the most capable people to take on more responsibilities. 
It’s about building stronger teams and freeing yourself up to do the work that only you can do.

With more engaged employees and managers who are freed up to focus on the business, your entire organization will be positioned to thrive.

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