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How To Delegate Your Way to Freedom

How to Delegate with Jay Mena

“The best way to find out if you can trust somebody is to trust them.”

― Ernest Hemingway 

Many busy agency owners wear nearly all of the hats on the rack at their agency. On the busiest of days, they manage operations, staff, projects, and in some cases, even are hands-on delivering services. That makes for long strong-coffee-filled nights. Sometimes, it’s what we have to do to get things off the ground or even keep them going.

However, it is common for even seasoned agency owners and managers to hoard tasks that they should delegate to other team members at their agency. A proper delegation approach and system can change it all. It can impact your effectiveness as a manager, increase productivity agency-wide, and last but certainly not least,  get you on the road to shorter work days and some much needed sanity.

delegate tasks

Using Delegation to Cultivate a Winning Culture

A commitment to developing the skill of delegation can have a transformative effect on the culture of your agency. When you hand off a task from your plate with proper tact and positioning, it can generate a sense of pride and confidence in your team members. With the appropriate direction, delegated tasks are also opportunities to level up your team’s skills.

“Therefore, when subordinates are delegated, they may feel trusted, organizationally important, and higher status within the organization (Gardner et al., 2004; Chen and Aryee, 2007). Delegation may also boost subordinates’ self-esteem and make them believe that they are capable of performing tasks successfully and that their behavior makes a difference.” Frontiers of Psychology, 2017.

Delegation: The Secret Sauce of Top Performing CEOs

Having a delegation mindset can create shorter days, more productivity, and potentially more profit. Delegation rockstars know this full well and reap the rewards of making this a key component of their function as their companies’ leaders.

In a Gallup study performed in 2014, 143 CEOs that made the Inc.500 List had their entrepreneurial talent profiles evaluated.  Collectively, the 2014 Inc. 500 CEOs experienced a median growth rate of 1,828%.  Additionally, CEOs with a high delegator talent generated 33% greater revenue in 2013.

Delegator Talent And Business Performance Among Inc. 500 CEOs

Companies headed by CEOs with high delegator talent posted a greater growth rate, higher revenue, and a higher number of jobs created than those of CEOs with limited or low delegator talent.

Delegator Talent (Intensity in Inc. 500 Sample*)Average Three-Year Percentage GrowthAverage Revenue in 2013Average Number of Jobs Created in Three Years
High Talent (n=86)1,751%$8 million21
High Talent (n=86)1,639%$6 million17

*Gallup study of 143 Inc. 500 CEOs entrepreneurial profiles


Why Aren’t You Delegating More?

Most managers aren’t complete strangers to delegation, but many do struggle with putting it into practice and receive the help they need to manage the many hats they wear. Delegation creates opportunities for our team members to do something different, to shine, to learn, and yes, to help us move our initiatives forward as managers.

Agency owners would serve themselves well to incorporate task delegation into their planning and resourcing process. But then there are the voices in our heads. Some of the most common barriers to delegation for agency managers sound something like this:

  • “I can do it better myself.” (Not likely)
  • “My people are not capable.” (Probably mistaken)
  • “I can do it faster than I can teach it.” (You are teaching it once!)
  • “I may lose power and control of the situation.” (Good!)
  • “I may lose prestige or status.” (Oh no! 🙁 )
  • “I like to do this myself.” (what is your time worth in dollars?)
  • “I wouldn’t know where to start.” (You will now 🙂 )

At first, of course, it will require extra effort on your part; that is pretty much guaranteed. However, eliminating repetitive tasks first can give you some time back relatively quickly. Think about what your weeks will be like, a month after making this shift, three months later, a year from today.

Don’t let those voices in your head get in the way of gaining back control of your schedule, time to spend with family or to scale your agency.

How Should You Decide What to Delegate?

Prioritize Your Delegation Bucket

Task hoarding is a thing, a serious one. It reminds me of hoarding intervention TV shows where a person may painfully struggle with getting rid of garbage bags full of expired grocery coupons; everything is a collector’s item to them. It is just as detrimental to you and your business to not want to let go of tasks that anyone with instructions can complete.

Sometimes the real challenge is deciding what you should delegate, even if you are willing to. I take a counterintuitive approach to help me decide what to delegate. I put all of my tasks for the week in one bucket and named it, wait for it, Tasks to Delegate every single one starts there. I then remove the ones that I cannot delegate at this time from that list.

The idea is to consider all of your tasks delegable by default, and make a case to yourself, for why a task belongs on your to-do list and no one else’s.

Once I have sorted my tasks,  I can begin prioritizing my Tasks to Delegate list and matching tasks with the right resource for scheduling or discussions.

Recurring Tasks

Go over your Tasks To Delegate bucket, identify repetitive tasks, write instructions, or even a standard operating procedure (SOP) for these tasks. To keep things simple, you may record an instructional video and task the assignee with writing a full SOP as a subtask of the assigned task. The bottom line is, take the repetitive tasks first, prepare instructions for delegation, schedule the team member, and let go!

Here’s a checklist to help you decide what recurring tasks can be delegated:

  • Tasks where there is no thinking needed and can be completed using a template, instructions, or following an SOP.
  • Low priority tasks that do not come under your core focus area.
  • Less critical tasks that eat away at your time and energy
  • Groundwork tasks such as collecting resources, data entry, prospect research. Etc.
  • Tasks that your teammates are more skilled and experienced in and can deliver better quality, efficiency, or both.
  • Something that you want your team to learn or level up.

Growth Tasks

Handling the recurring tasks first will allow you to reallocate your time to more essential tasks as an owner or manager. This phase may take a couple of weeks or a couple of months, depending on your agency capacity and the number of tasks you have to hand over. The goal is that you make it possible for you to put more of your valuable attention and effort into growth tasks, revenue-generating activities that will allow you to grow your agency. There may be plenty of opportunity for delegation here as well, for instance:

  • You may need support to plan and execute internal projects that move your growth initiatives forward.
  • You may need assistance with research to support your vision and goals.
  • You may need a Project Manager to manage more complex initiatives and internal projects.

Avoiding Burnout Transfer to the Rest of Your Team

Reducing your workload through delegation should be done strategically and systematically. A delegation mindset must be accompanied by a process that will ensure tasks don’t fall through the cracks, requiring minimal management effort on your part.

Be mindful, however, that without the proper approach, you may temporarily reduce your stress but unwittingly create unintended pressure for your other team members, which can be avoided with proper planning.

77% of Us Professionals Have Felt The Pain of Burnout

According to a Deloitte external marketplace survey of 1,000-full-time US professionals, 77% of participants responded that they had experienced burnout at work, with more than half citing multiple occurrences.

delegating chart

Some managers don’t realize that leadership stress can be passed along to employees. A delegation from managers should feel like an opportunity for your employees.

Team Member Concerns To Consider When Delegating

There are also concerns from team members you should keep in mind so that your delegation process and handoff eases any of these concerns. A concerned teammate may sound like this:

  • I don’t have enough time to take this task on.
  • I don’t have the experience to handle this task.
  • I won’t complete this task successfully.
  • I don’t want to be responsible for this.
  • I don’t have a great relationship with my manager.

Proper handling of delegation can address all of these concerns. We can say that all of these statements are rooted in a lack of confidence, in self-doubt; not wanting to have a lousy showing with the manager. Our job as managers is to make sure we are encouraging and setting them up for success with our management approach. The right delegation mindset will produce just that.

What You Can Do to Ensure You Don’t Transfer Your Stress To Your Team

  • Verify that the teammate is a good fit for the task you are delegating. No experience with the type of task is not necessarily a deal-breaker. In fact, it may be exactly why to assign it in some cases.
  • As managers, we need to be attuned to their current capacity to avoid creating new bottlenecks in other parts of the operation.
  • Set your teammates up for a win by providing clear direction, expectations, and the resources they may need to complete the task successfully.

team together 

Where’s the Monkey Now?

The importance of delegating tasks and the impact of doing it consistently and adequately may be pretty straight forward. However, what some agency owners and managers may struggle with is delegating the responsibility along with the task, accidentally adopting the monkey, and carrying it on their own back in the process of task completion. Providing direction and setting them up to succeed is vital, but it’s their monkey to carry once that has taken place!

In the Harvard Business Review’s “10 Must-Read on Managing Yourself, “ they discuss how management time relates to employees’ interactions with their bosses, peers, and direct reports. They break time into Boss-imposed time, System/Peer-imposed time, and Self-imposed time—which can be the trickiest of the three.

Self-imposed time— they define as “things that you originate or agree to do”. A portion of Self-imposed time is time requested by subordinates, putting assigned tasks back on your plate for a decision, to answer a question, or help solve a step. In those instances, the proverbial monkey is transferred back onto your back, where you are suddenly the blocker that needs to get back to them for the task to continue.

An adequately designed delegation process should resolve this and ensure that there will not be a ping pong match played with the task after a task is delegated. Clear direction, ownership, and expectations will not only keep the pesky monkey off of your back but keep the assignee empowered to see the task through to completion.

Outsourcing Can Be an Essential Part of Your Delegation Process

You may realize that no one in your agency has the skill-set you need to handle an internal project or objective you have on your plate. You may find that you have someone with the capability required to handle your assignment but that they do not have the capacity, nor are you willing to pull your team member away from work in the pipeline to take on another project or task.

In either case, outsourcing rather than hiring more staff may shorten your curve to get things done while freeing up valuable time for you.

One approach is to take a look at tasks performed in any one of your departments and try to uncover opportunities to outsource part of the tasks in the process.

If your agency designs and develops websites, for example, a partner like GoWP can take over your page builds so your team can focus on more complex feature development. Outsourcing page-builds may allow your agency to take on more projects. It can also increase the capacity for your team, giving you the flexibility to delegate tasks and move internal projects forward.

A mix of employees and contractors may allow you to delegate different responsibilities to the person that is an ideal match for the job.

Ask yourself, “What do I need to get done? What can I delegate to my team? What should be delegated to an outsource partner to move things forward and save me time?

team table


Fundamentals of an Effective Delegation System

Picking The Right Team Member

Success in delegation hinges on your ability to select the right team members to work on your projects and tasks. Take a good look at what you have on your plate, prioritize, and decide who at your agency or an outsource service provider can be the perfect match to delegate to.

Crystal Clear Instructions

Being completely clear on what you need to be done is the most critical part of your delegation. It is worth taking the time to think things through and writing it down as instructions. These instructions should also provide context. Including the “why” for the task will provide more clarity and give the task purpose.

Never Invisible

Unless the task needs to be kept under wraps, public mention of the new task a team member is taking on can reap huge benefits and increase the odds of success; even if shared with a limited company audience.

For one, you would be publicly affirming your trust in this teammate’s ability to solve a problem or execute a task; this can be empowering and reassuring. Also, public commitment reinforces accountability.

Whose Monkey Is It?

It needs to be clear who owns the task. You may have multiple people working on an assignment. There should only be one person responsible for the project or task. Even if two people are working at the same level or role in the company, one person should be held accountable for the task’s progress and successful completion.

The Finish Line

It is vital to have a clear definition of what the completion of a task looks like. You can provide a list of criteria that will determine if the task is done. It can be a testing scenario or success checklist they have to check off prior to  submitting as complete

Communication Type

Some tasks are more complex than others, so how you handle monitoring or communicating on progress may vary. For example, if it’s a complex task or one that is time-sensitive, you may ask that they check-in at specific intervals or when a milestone is reached. It can be as simple as an update in the PM tool or Slack.

Maybe even a scheduled call if you think it is needed. For more straightforward tasks, you may want them to complete it and report once they are done. Ensure that this is communicated in your project management tool’s task instructions, or at least in your discussions regarding the task so expectations are clear.

Perfection is Not the Goal

Seeking perfection when delegating a task from your plate can lead to micromanaging and extra meetings, defeating the purpose of handing over a task. It can also frustrate your assignee. If your teammate can achieve 80-90% of what you believe you could have achieved by doing it yourself, you are on your way.

Make a note of what needs to be improved and communicate it with your teammate for correction. Next time they should be closer to your 100%. It is a process.

Tools for The Task

Provide any tools they may need to complete the task, such as any spreadsheet or documentation they may need to refer to, a video, training material, to ensure that the team member does not get stuck. The extra effort will pay off by making it possible for your teammate to tackle your task with little to no assistance from you, which is the goal.

teach others how to lead


Teach Me

Handing off more complex tasks to a team member and letting them know that they will have to teach what they learn will encourage them to understand the task more completely, and prepare to stand behind the work. Even with simpler tasks, it can cause the teammate to take full ownership and be prepared to train others in the company if needed.

Digitize Yourself

For recurring tasks, especially, putting what you know in a shared document, video recordings, audio clips, or all of the above, makes it possible to only teach once. If what we want to do is save you time, putting in the extra time to do that can shave hours off of your current schedule pretty quickly.

Empowering Feedback

According to a survey by  US psychometric testing company SHL, managers spend approximately 14% of their time correcting mistakes made by employees and redoing their tasks. Although unclear direction and expectations can be a factor, providing feedback that will help them improve performance is vital. “Great job!” is not empowering, and “You need to do a better job of discussing our value on sales calls” is not constructive. Providing more specific and actionable feedback and kudos will help your teammate improve.

Instead of saying “Great job,” something like, “The Kickoff Call with the client this morning was great. You showed you were in control by being well prepared to answer questions and you set expectations with confidence.”

Rather than saying, “You need to do a better job of highlighting the value we offer on sales calls,” I would try a more descriptive and constructive approach.

You could say, “One thing you should start adding to your sales conversations is how, besides our chops in architecting solutions, our digital strategy experience will ensure that the tech solution we develop aligns with their long-term strategy.

spread the wealth

Spread the Wealth

This last principle can be the difference between amplifying your delegation efforts or stifling them and making them ineffective. Be purposeful about sharing the rewards and the credit for a job well done. Don’t hoard the recognition from others; spread the wealth! Explicitly mention the teammates that worked with you on a task or project.

It will not only build them up but will solidify your relationship, and they will be happy to take on tasks from you in the future.

Elements of an Effective Delegated Task

If you use the elements below in every task you delegate, you should be off to a good start. Feel free to add more if you think it will help you best manage your tasks:

  • Title: Write a descriptive title that clearly states what needs to be done.
  • Details: Detailed breakdown of the task.
  • Ownership: Write the name of who is responsible for the completion of the task.
  • Due Date: Make it very clear when you want it done.
  • Purpose: Describe the “why” for the task.
  • Resources List: Share links to any resources they might need to complete the task:
  • The Finish Line: Define the criteria for the task to be considered “Done.”


Are You Ready To Start Delegating?

Are you overwhelmed at the moment? Do you want to delegate some of your tasks but there is a capability gap at your agency, or does your team lack the bandwidth to tackle additional tasks? If you have internal projects stuck or shelved altogether but need to be moved forward, then hiring out a specialist to fill that gap can be a fantastic choice.

Whether you hand off tasks to your team or whether you outsource a specialist to get things done, delegating is a critical skill that business owners should develop to achieve more, with less effort, and make it to the dinner table on time.


Jay Mena

Jay Mena

Hi there, I’m Jay. Founder of Mint Virtual, and I love working with business owners to build brands by making things run smoother, saving them a ton of time and helping them make more in the process. If you want to chat about any process challenges you may be facing, or transformations you would like to make happen this year, let’s chat!

You’ll be joining a community of highly-vetted digital agencies and web professionals with one common goal — growth! Learn more. 


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