The Ultimate Guide to Delegation

On the morning of my 18th birthday, my dad knocked on my door. 

It has been tradition for him to give me birthday presents and for this birthday, I got Robert Kiyosaki’s “Rich Dad, Poor Dad.” He chose to give this particular book to me because I’d been saying for about a year or two that I was going to start my own business.

Before reading that book, I barely had any idea on how to run a business and how to make money as a business owner. 

As I read Rich Dad, Poor Dad, I came across the Cashflow Quadrant which completely changed any of the preconceived notions and ideas I had about business.

Cashflow Quadrant

The way the quadrant was set up shows how to build a business depending on the role you wanted to play in business.

You could be:



Business Owner


The image above breaks it down pretty clearly what each quadrant/stage is.

I realised that the role I wanted to play would need me to have systems (you will hear this word a lot in this blog) and people working those systems. This was necessary so that I wouldn’t have to be chained to my desk working 16-hour days in my business. 

The DREAM is to have a business that is working on bringing in money. Isn’t that why most, if not all people start a business? But the level above that is to have a business that is working and bringing in money, but requires minimal input from you as the business owner.

The easiest way to get there?

Systems and people working for you. 

Now, if you’re fortunate enough to have a bunch of money, you can buy a business that has systems and people working for it; making you an investor. You don’t have to figure everything out yourself. 

But if you’re following the quadrant, we all have to play in those squares.

I always thought that living the dream and gaining freedom would be to have those systems and people working for me. However, that dream easily turned into a nightmare.

Be Careful What You Wish For

When I started my business a good few years after my 18th birthday, I fell into the trap of thinking and wanting more. In this case, more clients and more leads. More leads meant more money in the business. 

However, I always thought more, more, more was good, but I wasn’t thinking about the trickle down effect.

The nightmare came to life when I kept wanting more and ended in a situation where there weren’t enough hours to cater to all of my clients.

Because I was so busy, I eventually ended up in this weird marketing & fulfillment cycle. This cycle is when you are working on one or the other and when working on one, either marketing or fulfilment, you could not work on the other. This happened because I didn’t have established systems in place.

What does this mean?

If you’re not building systems, there’s always going to be a limit to the number of people that you can market to. If you haven’t got automations, it would be difficult to organize your leads and move people through the different stages of your pipeline. 

Without systems, it’s always going to feel like a feast or famine wherein you’re either going to have to choose between fulfilling or marketing. You wouldn’t be able to do both since each aspect requires a lot of input from you.

During this nightmare in the business, I was moving flats after I graduated from university. That’s when I, by some divine intervention, rediscovered Rich Dad, Poor Dad. 

The book helped me figure out the solution to the nightmare that I created in my business. 

That solution was delegation.

What Is Delegation For Me? 

Now, when you say delegation, most people think that it’s simply telling someone what to do, then they go away, do that thing, and execute it really well.

For me, that’s not delegation, that’s abdication. 

I believe that the proper way to delegate is that when I hand over a task, that person knows exactly what I want them to do and how I would like them to do it. 

The key thing here is having systems and processes in place. If you haven’t got systems and processes in place, then that means you’ll be relying on your team members to create their own systems and processes (if they are self-starters). 

You may be lucky enough that they do create their own systems or processes in place and they end up being good for you, but if you don’t have that process documented within your business and that person leaves, you’re back to square one. 

Before we go any further, it’s important for me to state that everything I’m teaching here is not from theory, but based on a good few years of experience. 

As of writing this, my team is just shy of 10 people. Each of them are responsible for different things in the business, with a couple of them having knowledge of more than one aspect of the business so that they can step in should we ever need them for whatever reason.

I’ve also helped a few clients build their virtual teams through the years. 

I say all of this not to brag, but to reassure you that all of my learnings here are not just from books, but from my own in the trenches experiences.

How has delegation helped my business?

Delegation has allowed me to build stable processes so that when work is being done, I don’t have to walk my team members through each of the steps whenever a new task is given. I can simply let them be while I focus on more important aspects of the business like sales and marketing.

It has also brought me peace of mind that things are being done by my team members in the way that I want them to be done, because of this peace of mind, I can focus on the tasks that will grow the business.

Being able to focus on marketing the business and networking with potential strategic partners has been one of the biggest benefits at the time of writing this. 

It has been particularly beneficial for me because we are currently in the middle of a growth period where I am mainly focusing on lead generation for a service that we launched a few months ago. 

If I didn’t learn how to delegate, I wouldn’t have the time to find more leads, let alone fulfil for my current clients. I probably would have been too busy with client fulfillment. 

No doubt delegation is essential in growing your business. But you may be wondering…how do you know when you’re ready to delegate? 

To answer that question, I will be elaborating the mindset that you need, based on my experience. I’ll start by sharing the five things that stopped me from delegating for a very long time.

First Obstacle: Believing You’re Always Better 

I held the belief that team members could not do the work as well as I could. That is what held me back for a long time because this made me a micromanager, which had many drawbacks. 

When I was a delegation newbie, working in my business was not fun for the people that I brought in because of how much I micromanaged. There was a very high team member churn rate. 

The solution to this was documenting all the systems and processes to act as guides for my team members. That way, they know how to complete a task the way I wanted it completed and they could then move on to the next task.

Second Obstacle: Believing You’ll Do The Job Faster 

Another belief that stopped me from delegating is believing that it takes less time for me to complete the task than if I delegated it. 

When you start delegating (depending on what you delegate), it will indeed take you less time to do the task. There is no way that your team member can learn about your business in the span of a week and start completing tasks to the level you complete tasks at.

At this point, I like to tell clients that if you think back to when you started your business, you also didn’t know everything you know now. The same is true for me. I had to make mistakes so I could learn. 

So whenever you start delegating, it’s important to bear that in mind because whoever you delegate to will make mistakes. 

Nowadays, I view mistakes as a learning and teaching opportunity for me and my team. When my team members make mistakes, I know that it’s because I haven’t explained something clearly. 

Instead of holding their feet to the fire whenever they make mistakes, I decided to create a more pleasant working environment by discussing this mistake with them and encouraging them to do better next time. 

I’ve found that this creates a more cohesive team unit, because the members of my team know that they can go and do the tasks without worrying about making mistakes. My role is to do damage control so that no mistake gets to my clients or hurts the business.

I would like to end this point by saying that your members will make mistakes. I would be lying if I said that you will be able to find somebody who would come in and not make mistakes…

…But that is NOT a reason for you not to give delegation a chance.

Third Obstacle: Lack of Trust In Your Team Members

Another thing that stopped me from delegating is a lack of trusting team members. This ties back to believing that nobody can do the work as well as I can. 

If you have systems in place and accept that mistakes will be made, then you will be able to build a nice environment of trust. 

How does that work? 

If somebody knows that they don’t have to be scared of making mistakes, they become more effective and creative. That is far better than not trusting people and not having processes in place. 

Fourth Obstacle: Wanting To ALWAYS Be Involved

Another thing that stopped me from delegating in the past is micromanaging. This was me wanting to be constantly involved and making sure that every single task is done in a particular way. 

Depending on the situation, micromanaging may be advisable when somebody new starts working with you. But as time goes on, you need to give them room to grow and flourish.

Fifth Obstacle: You Enjoy Doing The Work

The last thing that hindered me from delegating was that I genuinely enjoyed doing the work myself. As someone who is a bit of a technician and likes building and doing stuff, it became problematic for me to let someone else fulfill this technical role. 

It was difficult for me to let that aspect of the business go because I wanted to do the work myself. It becomes a problem when the work you enjoy doing is not revenue-producing work.

When is it time to delegate?

The next thing that people tend to struggle with is how do you know when it’s time to delegate or not to delegate?

There is no exact rule that will tell you when you should delegate but generally, I would say that the perfect time to start delegating is as soon as your budget allows. 

You don’t want to bring in someone else on board if it’s going to obliterate your profit margins. Naturally, you will have to take less profit because bringing someone else on board is a business expense. However, that business expense should pay you back almost tenfold.

Now, how will you know when you shouldn’t delegate? When you do not have systems or processes in place (I’m pretty sure this answer doesn’t surprise you anymore). 

How I go about delegating tasks

When it comes to delegating, one thing that stops a lot of people is that they do not know how to delegate. 

I’ll give you a quick guide on what my game is and how I go about delegating. I’ll simplify this as much as I can so that it’s not something that scares the pants off of you.

The first thing that you need when it comes to delegating is you will need a project management platform.

There are plenty of project management tools on the internet and you just need to find one that works for you. 

Within my team, we use Teamwork.

Once you have your project management platform, you will need a communications platform.

There are some project management tools that already have communication built-in, which is a win because everything is kept in one place. 

Currently, my team and I communicate through Slack.

I believe that the tool that you use is not as important as how you use the tool. Yes, there are a plethora of tools out there, but the magic is not in the tool itself, but rather how you use those tools to give tasks and manage your team.

I will give you a very quick demo of how I delegate in my business. (If there is anything that you want to know more about, please leave a comment in this blog)

Delegating: Project Management

This is currently what our Teamwork looks like.

The way that Teamwork has been set-up is that I have separated Business Management and day-to-day tasks. 

Business Management is where I work with the project managers of the team with big tasks that will drive the business forward. 

Inside of Gravitas Dashboard is a kanban system with the tasks that need to be done.

We separated regular tasks and podcast tasks simply because there was a point in time when we had too many podcast clients and it was clogging up the first column.

As the task progresses, it is moved from column to column.

One of the key reasons why we use Teamwork is because of a feature that allows you to set up task templates. These are useful if there’s something that you do repeatedly in your business, like writing a blog post or running Facebook ads.

Instead of having to write every single thing that needs to happen every time, we just create a task template to make things much easier. This is what a task template looks like:

This is what we created for our podcast clients so that whenever there’s a new episode to be worked on, the team knows what to do by going through this checklist. 

Each of these items on the checklist also have their own SOPs and documents that guide the team members on how to execute each task. 

So when I say that when you delegate, you want to be as detailed and complete as possible, this is what I mean. It’s not simply saying “go edit this podcast” or “take care of episode 4” and then leaving my team member out in the wind. 

Everybody knows what they have to do and if they get stuck, we have the SOP documents to show what they need to do. 

Another thing that we observe when delegating tasks is making sure that they are SMART.

We want to make sure the tasks are: specific, measurable, achievable, realistic and time bound. 

When creating task cards in Teamwork, let’s say to research for a blog post, I simply don’t say “research for a blog post.” That’s not specific enough. When I write the description for the task, we want to make it as specific as possible. I also make sure that I assign the task to the right member of the team. 

I indicate to the assignee what is the outcome we want to achieve. That way, I can also easily measure whether the task has been executed properly. 

That task also has to be achievable, which is something you can gauge when you know the capacity of your team members. 

In terms of being realistic, I have to make sure that any resources I provide are relevant to help the team member complete the task. I provide them with as much as they need so that they can do their job with little to no questions asked. 

We also want the task to be time bound, meaning that the deadline is reasonable and doable. 

Delegating: Communication

For communication through Slack, we have a channel dedicated to each client for client-specific updates within the team. If ever there are delays or questions regarding client tasks, these are all communicated via these channels. 

When it comes to delegating, this is where being the manager comes in. For delayed tasks, it’s important to have a conversation with the team as to why the task hasn’t been done yet. Sometimes, tasks may have already been completed but not yet ticked off on Teamwork. This is why communication is so important.

Depending on the reason given, you can then choose what happens from that point on.

Transitioning from doer to manager

This is one of the biggest things business owners worry about. 

It can be challenging finding a balance when you go from being the doer to being the manager. 

Finding this balance means tracking exactly what it is that you are doing in your business on a day-to-day basis for a certain period of time.

Once that tracking period is up, what you will then do is sit down and assess everything that you’ve done. 

This assessment comes from the point of view of asking yourself if a certain task energizes or drains you. It’s also about seeing whether that task is something that you really need to personally do for the business or if it’s something that you can hand off to somebody else.

If you do not have the systems, there’s no point trying to hand off the task until those systems are built.

Until you have the frameworks in place, it makes no sense for you to delegate because it’s going to be like the blind leading the blind. 

Once you have those systems in place and you realize that a certain task absolutely drains you, but it’s something that’s vital for the business, that’s when you can start thinking about bringing somebody else to help you. 

When you finally bring someone in and you start delegating, you can work with them to refine the systems as you go. As you do that, you naturally start to take more of a backseat and let them run with that task themselves. 

That is how you slowly go from being the doer to the manager.

Is there such a thing as perfect delegation?

This is another question I see people ask a lot.

For me, there is no such thing as perfect delegation, but there is delegation that works for you.

Everything I’ve shown you so far is just a very rough walkthrough of how I delegate and work with my team. This is what has been working for my team and business, and it may not work for you. But that’s okay.

When you create a delegation system, it makes sense to do it from a point of view of something that you’re going to use for the next 5 to 10 years. 

It’s obviously going to be an iterative process. You don’t have to force yourself to come up with something that’s perfect from the get-go. 

How do you make sure that your team members feel accountable?

This all boils down to letting them know that you trust them. 

In my case, the cherry on top is letting everybody on the team know that mistakes are not something that you get berated for. Mistakes are learning and teaching opportunities for everyone in the team.

It’s really about making sure that your team members feel responsible for the task that you give them.

Your role as the manager is to give them everything that they need to complete the task, then you step out of the way and trust that they will do a good job.

If they need help, encourage them to approach you if they can’t find the solution themselves. 

As you keep practicing this, eventually your team will start to take responsibility not just for the task, but for the entire business.

Again, this is me speaking entirely from experience. 

What skills do you need to delegate effectively?

I believe there are a few skills that you need to possess, some of them being soft skills. Some skills are those that you pick up and learn along the way.

One skill you need is critical thinking because it’s up to you to look at a task and assess how important that task is. This is something that you learn over time and eventually become really good at. 

You also need to be a good communicator. This primarily means that you know how to listen to your team members and respond in the manner that benefits your team members. 

To give you an example, one time I helped somebody hire a video editor. We had a really strong candidate until we got to the final task in our interview process. This person was taking too long to complete the task.

I reached out to the comment and said, “From your CV and your past experience, this task is not something that should take you as long.” The candidate explained to me that due to their religious beliefs, they would not be able to complete the test task that I gave them. 

So I told the candidate that this wouldn’t be a good fit and asked if there was any other way I could help him. Then there just so happened to be a guy in my network looking for a faith-based video editor. 

I made an introduction and they started working together. 

If I didn’t care about communication during the time the candidate was having issues, I would’ve just reprimanded him and stopped the whole process.

This point connects back to being able to deliver feedback in a way that isn’t harsh or a personal attack. 

Another important skill is planning and time management

This is something I personally struggle with myself, but I found that using SMART tasks and Teamwork has allowed me to better manage my time. 

The final skill that you need to effectively delegate is problem solving. I believe that in order to be a good team leader, you need to be able to think creatively about problems that arise.

When you have the courage to solve problems in interesting ways, you’ll be able to help your team more. 

Delegation is Ever-Evolving

And that’s how I’ve been able to effectively delegate and work with my team these past few years, and more importantly, how you dear reader can take baby steps and start delegating more in your business.

As time goes on, it’s important to note that the way that I delegate may also evolve, especially as the business grows. Everything I’ve elaborated here is nothing that’s set on stone and it’s not something that you have to strictly follow in your business. 

The way every business owner delegates varies from team to team. So don’t rush the process, don’t be too harsh on yourself, and learn to adapt and evolve with your team and business! 

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