The One Task These Leading Entrepreneurs Will Not Delegate or Automate: A Quick Guide to Deciding Which Tasks NOT to Delegate or Automate (and What You Can Do Instead to Leverage Your Time.)

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"Delegation & automation" is a hot topic among business owners who are on the hunt to find ways to leverage their resources to grow their businesses without killing themselves in the process. 

The challenge is to do this process right.  Why do I know it's a challenge?  I know this because I get, frankly, underwhelming emails on daily basis as a result of doing this process all wrong.

Getting it wrong is one thing but losing opportunities by doing something else is another matter.  Might as well, don't do anything, right?

After running a quick research online, it became apparent to me that most of the tips out there are tactics-heavy (hacks) and/or lack how to frame this topic from a big picture POV.  

Also, the idea of delegating/automating what we are not good at (or what you don't want to do) seems to be the mainstream advice among so-called experts, which should be taken in with a grain of salt.

It is because this angle causes premature delegation of business tasks which I discussed in detail here.  The advice itself is not ill-intended.  What’s not clear with this particular advice is: There is the right time and place for this advice to be effective.

Here, I want to counter that idea and offer another take to lead you to a successful path.

To do this, I ran a quick experiment and asked leading entrepreneurs what they will NOT delegate or automate just to back up my take on the issue.


Here's what you will learn:

1. What not to delegate/automate according to leading entrepreneurs.

2. What can we learn from their insights?

3. What should you delegate/automate?


This post will help you take a step back to decide how to go about delegating & automating your work to free up your time in an optimal way.


What Not to Delegate/Automate According to Leading Entrepreneurs

1. Front-Facing Work

Nicole Wipp, the CEO of Wipp Enterprises (, shared her thoughts on this topic. But, before letting you in on what that is, let me explain why you need to listen to her.

Nicole works 5 hours a month to run her business. A month. Not a week. Not even a day. Mind you, her business isn't a solopreneur kind of business. 

I asked, "If you don't mind me asking, what would you NOT delegate?" 

"Sales and marketing," she continued, "Not only do I like these activities, also I know I am the best person to talk about how my business can help certain corporations, small businesses, and entrepreneurs when it comes to stacking up an effective team."

Nicole added, “…if someone feels like these activities REALLY are mentally depleting, they should find someone to help.”

Wipp Enterprises offers various programs to educate business owners as well as corporations how to spot, hire, and keep good talent.

I resonate with Nicole. While I am mindful of keeping my outreach process trainable down the road, for now, I would not delegate the tasks associated with lead gen and biz dev until I get a solid feel of the foundation being laid out. To me, these efforts can be draining at times, but it is more important for me to know the quality of output in real time.


2. IP-Driven Work & Final QC

Another thing I would not delegate or automate would be my conceptual work. It's because I'm in the knowledge business where my framework, ideas and strategies are not tactic-base. The work is more IP (intellectual property) driven. 

Naturally, this is not something I would ask other writers to write from scratch. Eventually, I can see the portion of my content creation being delegated by, for example, dictating concepts and ideas supposed by additional notes for development editors to finish up. 

Currently, my posts are edited by trusted editors only to tighten-up my writing as I am a Japanese native living in NY. That's it.

At the end of the day, though, I would not delegate the final QC (quality control) process before anything gets shipped as I see that's THE part I cannot blame on others or on any external factors but myself not to mention that's how I get paid.

Brandon Schaefer, author, speaker, and founder of which empowers CEOs and Founders of mid-size businesses seems to be on the same page with me. He stated,

"Scoping out complex implementation plans is something that's not delegated, or automated. Maybe one day it will be, but I don't see it happening in the foreseeable future. Mistakes are just way too costly."




I can't agree with him more.


3. Content Creation. Curation & Management

For strategists and expertize-focused specialists, content creation, curation & management is not something they should outsource without a solid training/communication plan in place.

Often, I see too many businesses consider social media postings, content marketing, content creation are the first ones to outsource.  I understand why.  The work is cumbersome and not so appealing to some.  So, they hand them over to their interns.

But, I will have to completely disagree with that notion because people need to see you in action on or offline for promises you are making to them, and content, in whatever format, is a great opportunity to showcase who you are and where you stand.

If you look at it this way, I bet you can no longer dismiss content creation and management to be "something to handoff to your interns."

To top it off, you can easily tell people who are outsourcing the work as their output is generally bland and lacks clear POD (Points of Difference - as opposed to POP, Points of Parity.)  Inconsistent likes, comments with no substance, choosing subpar articles to share are some of the dead giveaways.


OK, this was, by no means, close to vital-material.  Frankly, that doesn't bother me one bit.  This is an example of me to show people, whom I haven't met in person, this is the way I chose to talk and act.  I can't delegate this or program MeetEdger ( to do this.

However, I'm not saying you should never delegate/automate content creation, curation & management.  I'm not knocking on social media scheduling apps, either.  I do use a couple of scheduling apps myself.

What I'm saying instead is, until you build the foundation of your business, this is not something you should consider delegating/automating first as there are many other tasks you should be delegating/automating effectively.

When your business gets to high six-figure and above (annual gross), you can consider outsourcing these to a highly regarded agency which houses great writers and strategists with a sizable monthly fee in exchange. They will work with you to understand your goals and how not to lose the tone of your unique voice. 

Ultimately, though, it is still your responsibility to monitor the quality of content being generated and distributed.  So, technically, this is not something you “set it & forget it.”  


4. Relationship Building

Let's shift the gear a little.

"I'd say those "Sensing" / "Feeling" tasks e.g. coffee with customers to seek feedback or meeting someone from the oil & gas sector to have a direct "feel" of the market," says Dickson Tang, author and leadership expert based in Singapore (



Interior Design Consultant based in the UK, Russell Dowers shares his thoughts:


"Don’t automate what should be a human interaction, it will quickly devalue your brand/business."



The message Dickson and Russell share is this:

Don't cut corners when it comes to building and nurturing relationships thinking you are exercising an effective hack & it will generate new leads and revenues. 

It just won't.

To prove a point, here an example of what happens when you don't take this advice to heart:


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Do you think this person checked my past events in detail before reaching out to even see if this is a fit? 

I think not.

Did this person bother to offer why's and how him speaking would benefit my audience? 


Just to be fair, the sender of this email did not do anything wrong.  Actually, the person did an OK job being personable and friendly.  It’s the boss’ fault that this is not going to get anywhere.

Let me put this in a context as to why this doesn't work by sharing my honest reaction to the email:

“Wait, what? So, now I am the one who needs to look up all these links, learn about the person & figure out how this person can fit into the existing programing format I have for my events?  Then I need to get on a call to discuss further?!  Oh, hell no…”

If you want a “Yes,” put everything on a silver platter & hand it to them. Don’t make them think. Don’t give them extra work.
- Yours truly, Maiko Sakai

By the way, this is coachable. You could delegate part of the process effectively if you do it strategically by giving your aid a bullet-pointed list of pressure points, and you edit the final draft. That’s not too hard, is it?


5. Reviewing Key Metrics (KPI) & Financials

This was not brought up by anyone during my experiment. But as a growth strategist, I feel compelled to throw this one in there.

When it comes to financial management, you do not have to have an extensive experience to manage it all.  It is perfectly fine to outsource, delegate and utilize some automation to manage day-to-day financial activities. 

However, in the area of business finance, you cannot opt for being “oblivious.”  I have written an extensive post about what you can do if this is not your strong suit.

You can always start small by remembering this should not have to be a complicated subject matter. Ultimately, this is about measuring your business performance based on a few key metrics and reviewing what comes in and goes out of your business bank accounts.

This may sound oversimplified, but it is true.  That is all there is, and you need to get used to the idea of reviewing data.

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What Can We Learn from Their Insights?

When I try to analyze or assess anything, I look for patterns and trends. It's pretty easy to gather there's one thing in common surrounding this topic.

They do not delegate/automate activities that are directly tied to the quality of your business offers and growth.

Some of the activities mentioned here can be time-consuming and unscalable. The secret is, that should never be the main reason or motive you delegate/automate those tasks. 

So once again, I'm not on board with the simplified acid test of delegating things you are not good at.

Katy Cowan, the founder and editor of brings it home with her thoughts:

"Anything that stops my own personal growth. I want to be involved and valuable. It’s so important to keep pushing skills and experience. I’ll only automate or delegate if this allows me to focus more on learning."




This is a great "acid test" to determine what to delegate/automate.  Successful entrepreneurs like Katy has one thing in common: they all demonstrate a high level of commitment to investing in themselves in order to stay relevant and further develop their Zone of Genius, which leads to the growth of their businesses. 

In addition, asking ourselves, “Why do I think doing X (insert a task here) matters to my business?  What is the impact?  What is the expected outcome do I seek by doing this?” - can be a meaningful way of deciding what to delegate/automate and what not to.

Here’s a quick example:

Why should you care about increasing followers on your Instagram account? 

Your answer might be, “This is the best platform for my business to connect with my prospects while we showcase our work visually.” 

Sounds like it truly matters to grow your business.  If that’s the case, why should you hand off the management of your Instagram account to someone who may not be able to handle the weight of responsibility in the way that you can?

You get the idea. 

The process of delegating or automating anything should require on-going work.  It is easy for us to come up with a list of things we may not be good at and push them off our plate.  But, I urge you to take a moment to consider these tips before you do.


Do's & Don't's: Do Start with Internal Business Activities

To avoid making embarrassing mistakes that can set your business back, focus on delegating and automating internal operations first. 

I like to use the analogy of a fine dining kitchen.  The role of executive chef is to do QC before all dishes leave the kitchen.  He or she may not be the one doing all the prep and cooking.  Instead, he or she is the one tasting, double-checking on plating, adding final touch, and making sure each plate is smudge-free before sending them off.


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Executive Chef, in business, is YOU

Here are some examples of how to get started:

Building Professional Relationships:

Do: Get help on scheduling and maintaining your calendar, but you make yourself available to confirm them personally.

Don't: Just letting your assistant or scheduling app handle your calls and meetings. 

Unless you run appointment-heavy business, you want to ensure you leave enough room for a personal touch with people you are interacting with.


Outreach, Business Development & Marketing:

Do: Delegate backend research, and you personally do outreach tasks yourself.

Don't: Assign your assistant to do the entire outreach process to pitch your business.

Needless to say, this is a bad move. There are agencies specializing in doing outreach for you on LinkedIn and other platforms.  These agencies charge for their in-depth understanding in your style and approach and pretend to be you while they do outreach.  I am not opposed to this idea if you can commit yourself to spot-check their work regularly.  The key is for you to have a clear vision of how you would approach your outreach effort.


Crafting Conceptual Work / IP-Driven Work:

Do: Get help on prep and organization of your experimental efforts i.e. venue search, communication with participants, etc., and you conduct them yourself.

Don't: Assign your team to conduct testing and have them report back.

You have to be the one to check the temperature of participants’ feedback. Even for a large brand which outsources focus groups should have a representative from the brand to oversee the process.  If you cut corners with this work, you will not be able to develop effective offerings that people would happily pay. 


Content Creation, Curation & Management:

Do: Work on your own content, and get help on just scheduling them out, then you do the final QC before giving it a go.

Don't: Tell your assistant, intern, or VA to manage content marketing without in-detail SOP (standard operating procedure.) "Just post something 3 times a day," won't cut it and you know it.


Reviewing Key Metrics (KPI) & Financials

Do: Get help on data-entry, fact-checking and fact-finding process, and you formulate a strategy and lead on executing it.

Don't: Avoid the task altogether for a long period of time.

Also, getting support from your accountant or financial advisor regularly can make this task a habit.  Eventually, you should be the one to have the final say over what to pursue based on data you gather.  If you don’t feel right, you have to know why and must feel comfortable to say “no.”


In Sum:

"Hand over the work you aren't good at" once again is a dangerous advice. At minimum, you need to:

1.     Understand why you aren't good at doing tasks in question,

2.     How those tasks should ideally be carried out to grow your business,

3.     Own the responsibility of the outcomes by delegating/automating those tasks.

At times, the idea of “saving time” takes over our brain and forget why we are trying to get these tasks done in the first place.  If what matters to you involves building relationships, maintaining high quality of work, showcasing your business, and improving your business performance, you as the owner of your business need to be the one to be “hands-on” about the actual tasks and how they should be carried out.