How to be a CEO in the background by learning to delegate everything

The vision

A company that can operate without its founders is healthy.

A company that can grow without its founders is strong.

Founders should provide value, but their presence should never be required. A good leader can watch from a distance.

I have always wanted this for Finsweet.

Seven years ago, in the first few months of business, I realized that I could not be the only employee of Finsweet.

Designing and developing websites requires a lot of time and effort. Being a sole operator would mean that my presence is necessary for the business to operate. I knew this was not the path for me.

I want the freedom to step away from work any day, any time, for any duration, and know that Finsweet is equally as healthy and strong without me.

I do not have a goal to work fewer hours. I have a goal to create a scalable, healthy, and strong business.

It is a level of business success that I crave as an entrepreneur.

I will use the word "delegate" a lot throughout this article. This is how I understand "delegate".

Delegate — To give a task or responsibility to another person.

"Delegation = Growth" mindset

The formula:
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If I spend one minute working on Project A, I spend one less minute working on Project B.

I can delegate Project A and choose to either scale Project B or start Project C.

As I delegate tasks or even entire departments, it frees my time and mind.

I can use my available time to grow the company. I can focus on new initiatives, or create new departments, to grow Finsweet.

If I spend 20 hours per week in sales and then delegate sales to someone else, I now have 20 hours of open time.

Today I follow this mindset for all tasks, regardless of the amount of time the task takes. I will delegate tasks that take five days, five hours, or even five minutes.

My ability to delegate makes me "always available". I do not have any deadlines or time-sensitive tasks that I am responsible for. My tasks usually require less than 1 or 2 days of work, and I can do them when I want.

I can have this flexible work schedule through careful delegation.

My availability allows me to understand which initiatives we should start, who should work on them, and how to lead the team to success.

If I was spending my 20 hours per week in sales, some key Finsweet initiatives might not be alive. If they were alive, they would be dramatically different.

How do I choose which tasks to focus on? I focus on tasks that benefit significantly because of my personal input. These are usually tasks that help grow Finsweet.

Delegatable tasks

A delegatable task may have one or more of these features.

1. It can be delegated easily.
2. Someone on the team can do the task equally as well as I can — or better than I can.
3. I am not providing any special value to the task.
4. I want to give someone more responsibilities for their professional growth.
5. I don't want to do it.

How I delegate

Delegating tasks is a skill. It can be learned and it can be improved.

These are different methods I have used to delegate tasks and departments to people at Finsweet.

The "Instructional video strategy"

Show the person exactly what needs to be done via screen record tutorial video.

This strategy is best for manual tasks that can be replicated and visually communicated.

If I can give you a video tutorial on completing and managing the task, I consider it "easy to delegate" and I delegate it quickly.

This is what I do:

• Screen record of myself doing the task with a full explanation of the steps.
• Send it to someone on the team and ask them to complete the task. If it's an ongoing task, I will ask them to own the task.
• Review their first few deliveries of the task to confirm quality and accuracy.
• Release myself from the task. If all goes well, I will never have to do that task again. The new person responsible understands what needs to be done, and it's their responsibility now.

Whenever I find myself doing a task that I can delegate via screen record, I delegate it quickly.

The "Do it together strategy"

Do the task together with the person.

Creating a new process, understanding problems, and making key decisions are often challenging to communicate through a screen record video explainer.

Delegation decision-making needs more care than a one-off instructional video.

The "Do it together strategy" is where I do the task with the person before they own it. We co-work on the task together. This also applies to departments.

This strategy may take hours, days, weeks, or months. Smaller delegated tasks will take days, larger delegated tasks may take weeks, and delegated departments will take months.

After the right amount of time, the person will be ready to own the task entirely. The amount of time depends on the task and the person's abilities.

The "Do it together strategy" has been a very successful delegation strategy. It takes significantly more time and effort than other strategies, and the reward is always worth it.

It allows me to:

• Show the person how I would run the department
• Show the person how I would make decisions
• Explain why certain decisions help achieve company-wide goals
• See how the person makes their own decisions
• Make sure the person is qualified and ready for the handoff
• Have confidence and trust in delegating important decision making

After months of work together, I build a good working relationship with the person. I understand what they're good at, what areas they need more practice in, and how to give them the best path to success.

Don't micromanage

It's important to note that I do not force the person to run the department exactly like me. We co-work, we understand the best processes together, and I allow that person to be part of it.

I'm not giving the person a strict step-by-step of what they have to do. I'm showing the person how to succeed and make decisions that benefit the company.

It's up to the individual to run the position in their own way - not in the way I would prefer. While I can guide them towards the right direction, I cannot do the work for them. This is crucial for maintaining valuable employees in the long run.

The "Please help us strategy"

Ask a knowledgable person for help with the task or department.

When I don't have strong knowledge of what I'm delegating, I ask for help.

I recognize what I know and don't know.

The "Please help us strategy" is used when I don't know the skill I'm delegating.

I need [someone] to come in and help define what this task/department is.

This has happened twice with technical at Finsweet. I know the basics of technical web development, but I constantly run into knowledge roadblocks with technical as Finsweet advances. I needed help.

When I brought in technical talent, my mindset was — 

• This role and skillset is important to Finsweet
• I don't know these skills and will never be at your experience level
• I need you to help define our tasks and departments
• I can help you make decisions, but you will own the final decisions
• You will be held accountable for all wins and losses
  

"Please help us strategy" is used specifically when I don't fully understand the task or department.

Testing a working relationship with the person before delegating tasks or departments with this strategy is best. Start with a few months of small ongoing work. Give them small projects and evaluate the deliveries.

If they are a good fit, ask for help and delegate. If the deliveries are less than excellent, look for someone else. I must completely trust the person's work to use the "Please help us strategy".

How do I pick someone to delegate tasks to?

I ask myself these questions:

• Can this person do this task right now?
• Can this person do this task with training?
• Can this person grow into this task or department with more experience?

A "Yes" answer to one of these questions is required for the person to be qualified for the task. When I give someone a task, I need to feel confident that they can succeed now or in the future.

After I know they can succeed, I look at human being traits. The traits I look for depend entirely on the task or department being delegated.

• Does this person have good attention to detail?
• Does this person follow directions?
• Does this person deliver projects in the timeframe they set for themselves?
• Does this person keep promises?
• Does this person have the ability to be a leader?
• Does this person have delegation skills to grow their own team?
• Is this person polite, empathetic, and encouraging?
• Is this person a good culture fit?

These are some of the questions I ask myself each time I make an important task delegation.

Personal milestones of delegation

This is a list of key moments where I delegated work that I could not, or should not, do.

I was leading each of these roles sometime during the seven years of Finsweet existence. These are tasks that I had to do alone at some point. As we scaled, I grew out of these tasks and departments. Today I am not the lead of any of them.

After delegating each of these tasks, I "got back" a significant amount of time. This time allowed me to focus on growing other parts of the business.

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2017 - JavaScript development

• I was not able to handle client requests for JavaScript work. I was a super novice at all things JavaScript and code. It took me a long time to figure out code implementations, and it rarely worked how I wanted.
• I hired Yesse to write scripts for me whenever I needed.
• He removed all of my "why isn't this script working!?" frustrations. Instead of hours of trial and error for a required JS feature, Yesse wrote the script and explained it to me.
• This was a "Please help us strategy" delegation.

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2017 - Client project design

• I was spending too much time on design because I'm not that good at it. I was not able to get bigger and better projects because of my skill limitations.
• I hired Dan to do client web design work. Dan designed the site in Photoshop and I developed it in Webflow.
• I was able to get more leads and higher-quality projects through Dan's designs. I was able to spend more time on Webflow development, and this focus made me a pro in Webflow.

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2018 - Client project development and project management (some projects)

• I was at my maximum work hours, but more leads wanted to work with Finsweet. Sometimes I would work too much because I really wanted the project.
• I hired Duncan to help me design, develop, and manage client projects.
• I was able to sell more and develop more with Duncan taking client projects from start to finish. I was able to be more selective with the projects I took.
• Over the next two years, there was a lot of trial and error in hiring people to design and develop websites for clients.
• Onboarding the designers and developers was a combination of "Do it together strategy" and "Instructional video strategy" delegation.

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2020 - "Random personal assistant tasks"

• I didn't realize I needed this until it happened.
• Rohan sent me a message asking to work at Finsweet as my personal assistant. I respected his passion and determination, so I gave him a shot.
• He significantly reduced repeat daily work. Anything that could be communicated in an instructional video was delegated to Rohan. Rohan owned many operational tasks thatI didn't bring any special value to. This allowed me to focus on tasks that I did bring value to.
• After one year, Rohan was far more advanced in Airtable than I was, started his own initiatives, managed company-wide initiatives, and grew to a management-level position.
• This was an "Instructional video strategy" delegation.

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2020 - Client project development and project management (all projects)

• As the team grew, I reduced the number of client projects I worked on. I would have 1 or 2 active projects that I was developing. I acted as the project manager for most client projects.
• During 2020, I grew the team to the level where I did not need to develop or manage any client projects. This was a group effort over many hires and many delegations. Shoutout to all of the Finsweet developers and designers who deliver client projects.
• Delegating development and project management allowed me to work on CMS Library, the first third-party JavaScript library for Webflow. This was the start of  Finsweet product initiatives.
• This was a combination of "Do it together strategy" and "Instructional video strategy" delegation.

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2021 - Invoicing and employee payments

• Although I was not involved in design or development, I was responsible for sales, account management, client invoicing, and employee payments. However, I was overwhelmed with operational and administrative tasks in a company with 20+ employees, which resulted in me frequently forgetting to complete administrative tasks. There was a time when I missed several invoices that should have been sent months ago.
• I asked my wife to step into the business and manage our invoicing. Karla started helping me a few hours per week, which was a very important relief of tasks. Invoicing quickly grew into a full-time job. As the business scaled, the number of invoices and payments scaled with it.
• Today, Karla works at Finsweet full-time, managing all client invoicing and employee payments.
• This delegation saved me several hours weekly. It cleared many micro tasks and communications. It was equally as important that I did not have to think about these tasks anymore. Thinking about invoicing and employee payments daily takes a lot of brain power.
• This was an "Instructional video strategy" delegation.

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2021 - Sales and account management

• At this point I was still very involved with projects. I would sell the project and onboard the working team. I also acted as the account manager. If there was a big problem with the project or questions about updating the scope, I would be the contact.
• I brought on Jay Wolff to manage sales and account management at Finsweet. Now Jay is our "Head of Agency". He makes all of the decisions around Agency and manages his own team.
• This was one of the most important delegations. It freed up over 50% of my time and allowed me to continue our product exploration. Jay has successfully grown our Agency side while growing his own team of project and account managers.
• Without this hire, the Finsweet products line would still be active but look very different.
• This was a "Do it together strategy" delegation. Jay sat in on my sales calls. Then we co-ran sales calls. Then Jay had his own sales calls. After a few months, Jay was completely self-sufficient. Today, I am comfortably separated from all agency work.
• Jay came to Finsweet as a sales pro already, so I did not need to teach Jay how to sell. I taught Jay how to sell Webflow and how to ask the right questions to scope projects.

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2021 - Technical

• In Jan 2021, Finsweet was considered a very technical Webflow team, but I knew very little about technical development. We were writing complex scripts for clients and providing solutions to the community. From my understanding, we were doing well. I knew we should improve our processes and our quality level, but I didn't know what that meant.
• I brought on Alex as a technical developer. Within two weeks of working together, I wrote this article about Alex. Alex has helped us go from a quirky script company to a technical powerhouse.
• This was a clear "Please help us strategy" delegation. Alex would make suggestions for how we could improve, and sometimes I wouldn't fully understand what he was suggesting. Within one month of working together, I delegated all technical management and review to Alex. He was named the CTO and leader of anything technical that passes through Finsweet.
• This delegation gave me peace of mind. Knowing a true pro was now managing our technical work gave me a lot of confidence to continue with our technical client work and product development journey.

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2022 - HR

• I was always the unofficial "HR rep" of the company. If someone had a problem inside or outside of work, they would tell me about it. This was initially very fun for me. It was great to get to the know the team on a personal level and help them at the same time. It felt like a normal part of my workday.
• Late 2021 into 2022, we grew to the level where I was no longer able to do this. Getting into 30 to 40 employees made my initial self-management process inefficient — and ineffective. As the company grew, I was checking in less with each person and taking more time to respond to messages. Sometimes I felt like I was letting down the team.
• People at Finsweet started to ask about weekly hangouts, team building activities, and learning more about the rest of the team. We keep teams small at Finsweet, so it's possible that an employee only knows 2 or 3 other people at the company. Good for efficiency, but not good for culture building.
• We needed an HR and "People" department. We needed someone to help manage everything from onboarding to team building to personal friend. Victoria came to Finsweet at the right time. All of her experience came from HR, so this felt like a natural position for her. Within months of joining Finsweet, Victoria created and owned all of our HR processes — hiring, firing, team building, casual chatting, friending.
• This delegation gave me peace of mind as I focus on growth of the company. I know that our company's HR culture is in good hands with Victoria.

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2023 - Product website management

• When Finsweet creates a product or a tool, there is usually documentation, a landing page, and cloneables included. Each product has multiple web properties, and the amount of properties will grow as the product matures. I was the person who wrote and managed most documentation. Others helped manage it, others helped build it, but I was the center of all non-technical product initiatives. This is a time-consuming process. A lot of docs with a lot of community suggestions on how to improve them. Many time-consuming tasks go into documentation management.
• Eve has grown into our documentation lead. Eve has built and managed all of our active product documentation. If there needs to be an update to any Webflow-managed Finsweet documentation, Eve can do it.
• Today, we have grown a team around Eve to manage our product web properties. Any web properties that supplement Finsweet product initiatives will fall under Eve. This has taken many hours away from my daily tasks.
• Side note for Finsweet fans: This is separate from Wized. We're talking about Attributes, Client-First, Open Source, cloneables, etc.
• This was a "Do it together strategy" delegation.

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2023 - Content creation and community

• I was the sole creator on the YouTube channel for most of Finsweet's history. I had an obligation to make tutorials as we released new products and tools. Most legacy products had me as the only educator. Planning a video + setting up a project for a video + recording the video is very time-consuming. It takes a lot of energy to record content.
• The Finsweet Community team, led by Victoria, is working with Finsweet designers and developers to film, record, and launch 3 YouTube videos per week. These videos integrate wonderfully with our Finsweet+ community. I can completely step away from video content creation if I want to. The team is highly organized churning out content more efficiently than I can.
• This was a "Do it together strategy" delegation. I worked with the community team for the second half of 2022. We developed the 2023 content creation plan together, and now I am completely separated from the content efforts.

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Tasks to be delegated in 2023 or 2024

• Product/initiative launches. I am part of most launches. I may execute a small amount of work, but I'm mostly leading the launch. I would call myself the "coach" of launches at Finsweet. I help direct all of the deliverables and make sure each deliverable we need for the launch is assigned to someone. Although I don't lead every launch, I lead most of them. I know the team better than anyone else. I know each person's capabilities, which helps me understand who can best execute a certain task. I also have years of experience launching cloneables, products, and wild initiatives at Finsweet. I want to delegate the role of launch coach to someone.
• Content messaging / Brand voice. One of my top roles for launches is content writing or content checking. I created the brand voice nuances, so maintaining the brand voice is best done by me. I want to change that. I want to delegate the creation and management of content writing to someone. This person would help manage and maintain a unified voice across all company initiatives.

I will update this article as these tasks, and others, are successfully delegated.

Reasons delegating is challenging

Trust in decision making

Do I trust this person to make important decisions in the company?

Will this person's decisions reflect my own vision and path for the company?

What happens when this person makes a decision that I disagree with?

These questions pose a challenging barrier to pass when delegating.

It's crucial that I trust my team with decisions and let them make decisions without me. My team won't make decisions exactly like me. That's ok.

I can't expect them to make decisions like me. I have to expect them to understand the business, understand the path we're taking, and make decisions that will benefit the company.

Trust in the new decision make is crucial.

Existing decision making processes are in place

Processes must change as a businesses grows. Sometimes change is hard, but it's required to in order to delegate properly.

Since day one at Finsweet, I've been involved in every significant business decision. With a small team, this was a natural and manageable process. However, as the company grew, it became increasingly difficult to let go of workflows and decision-making processes that I had owned for years.

I found myself overwhelmed with making final decisions for numerous teams and essential deliveries. This system worked well in the early years of the business, but I eventually reached a point where I was falling behind and frequently delayed in making decisions.

This was a clear sign that change was necessary.

To ensure Finsweet's scalability, I had to alter processes so that my final "OK" was no longer required.

If I "OK" every important decision (the good part):

• I can follow my vision exactly.
• I have ultimate confidence that everything is going to be done how I want it.
• I can put my personal quality assurance check on all deliveries.

If I "OK" every important decision (the bad part):

• Slow down all company workflows and deliveries
• Make my team feel powerless with no real decision-making power
• Prevent employee growth. It's best to learn and grow from your own decisions.
• Overwork myself with too many decisions to make per day

The good part gives me peace of mind. The bad part destroys the business and the company culture.

It's clear that I have to step away from being part of decisions.

How I naturally change the decision-making process

In the past 2 years, I have carefully delegated important decision-making responsibilities to employees.

When approached with questions such as "Can we do this?" or "What should we do here?", I often avoid giving a final answer. While I may offer my perspective, I leave the decision-making power in the hands of my employees. Even if I have a clear solution in mind, I encourage them to make their own decisions and take ownership of the process.

By delegating decision-making authority, I enable my team to grow and develop their skills. Additionally, I initiate the process of change by empowering my employees to take responsibility for their decisions and actions.

Delegating tasks in my skillset

Finding the right person for a delegated task can be challenging when I have a high level of expertise in that particular skill, such as sales or Webflow development.

I have very specific requirements for these tasks and expect a high level of quality from the person completing them. However, delegating a task that I already excel at can also be challenging because of my desire to maintain quality control.

It's common to want to hold on to a task because:

• I do the task well
• I'm efficient in the task
• I like to do the task.
• I've been doing the task for three years and someone who has been working for three months won't do it as well as me.

Over time, I have come to realize that it is not necessary for the person completing the task to meet my personal level of expertise.

While a certain level of quality is required, it does not have to match my own. Accepting a slightly lower level of quality can still lead to success, as long as the person is capable of growing and improving over time.

Therefore, it is important to recognize that not all tasks need to meet my personal 10/10 quality expectations, and to be open to delegating tasks to others who may have different levels of expertise and unique perspectives.

Delegating tasks outside of my skillset

When faced with a task I'm unfamiliar with, asking for help can be challenging.

How I can introduce a new skill to the company if I lack a solid understanding of it myself? It's not always clear where to begin or what questions to ask. Understanding what qualifies as quality work can also be a challenge.

Rather than avoiding these tasks or departments altogether, I've learned the importance of hiring individuals who possess the necessary expertise to manage the departments. I try to understand the most fundamental aspects of the skill in question so that I can better understand what success looks like.

Delegating tasks outside of my own skillset can result in a time-consuming trial-and-error process.

The delegating hero-leader

The ultimate goal of a delegation hero-leader is not only to teach an individual how to complete a task but also how to delegate it effectively to others in the future.

The strongest form of leadership is guiding others to become leaders themselves. The same principle applies to task delegation.

Company culture is best when employees stay for a long time and grow within the company. Instead of hiring experienced folks, I want our amateurs to grow into experienced folks.

My goal is to foster the growth of our less experienced team members by developing their advanced skills through years of dedicated work at Finsweet. This practice is the driving force behind our strong company culture.

When I delegate a task to someone, my hope is that at some point they will have to delegate it to someone else in the future

This is a required skill for a department leader. A Finsweet department leader has to be able to delegate tasks within their team. If their department grows (success), they will face time, resource, and focus conflicts. The solution is simple: delegate.

Your delegation next steps

Keep in mind that delegating tasks is a skill that can be learned and improved over time.

It is natural to struggle with delegation when starting out, and there may be a significant amount of trial and error involved. This process can be uncomfortable at first, but it is important to remember that your time as a founder is precious and your daily decisions directly impact the business.

Don't hesitate to delegate tasks and responsibilities to others. Remember that the more you practice delegation, the more comfortable and effective you will become.

Happy delegating!