Bootstrapped Giants

If your business plateaued, do this 1 thing…

Published 17 days ago • 5 min read

A few weeks ago, I asked you all to email me questions and issues that I can help with.

Two questions kept coming up:

  1. How do I get my business out of its plateau so it can grow again?
  2. How do I get out of the day-to-day operations of my company?

Believe it or not, these questions are interrelated.

Your business isn’t growing… because you suck at delegating. And you suck at delegating because you’re either micromanaging or worse, abdicating.

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Most entrepreneurs who are early in their leadership journeys either manage every detail and every person’s tasks or they hand something over and move on.

SOME entrepreneurs find a way to both micromanage and abandon, but they haven’t found the happy medium: delegation.

And when you are inconsistent or too involved in every detail, your business’s capacity is limited. You are your organization’s limit.

Your brain, your capacity to make decisions and to process information, holds it back.

So if you’re slammed, guess what? Your company stops growing. This is why working ON the business and delegating are SO important.

1. Admit why you suck at it

Ask this question and most people start talking about lacking systems, missing knowhow, or being surrounded by the wrong people. All of that is false.

The real answer is… (and this is the answer for most things when you dig enough): FEAR.

You are scared. And you like control. This business is your baby. It’s your identity! All your income comes from it.

Of course, you’re scared. What if some person screws up a task? Why hand it off when you can do it in 5 minutes?

Or have the abdication fear: What if the person views me as a micromanager? What if they leave me because I check too much?

All roads lead back to: you are afraid. Probably afraid you’ll fail. Maybe feeling impostor syndrome.

So how do you deal with it? There’s only one way: confront your fear.

Sometimes, this is easier on a micro level. Rather than the big fear “what if my company fails?” - confront the small fear: “what if this person screws this one task up?”

Plan around it. Most of the time, owning your fear to yourself and others ACTUALLY releases it.

In a previous email, my partner and CEO of Aux, Kasey, told you how I gave her feedback on her deck, rather than doing the work myself.

What she didn’t know at the time was that I felt a little afraid when I delegated the work to her. I was afraid she wouldn’t do it as well as I would.

So I thought to myself… I’ll give her feedback and then check the document in the morning. My fear allowed me to find a happy medium between micromanaging and abdication.

Take it even a step further - when you feel fear, share it with the team. “I’m handing you this task. Here’s what I feel a little nervous about.”

This feedback loop actually helps the person and ensures a strong outcome. Over time, this will build your confidence in your ability to find the happy medium of delegation: Hand the “task” off while maintaining accountability.

This blocks you and then unblocks your business.

2. Create LANGUAGE around delegation

If you don’t have language around something, you can’t really address it. The reality of running a business and accomplishing things is there are many levels at which people can operate in a workplace.

My favorite tool for this is called the “Ladder of Leadership”

This is a tool used in all my companies. It helps managers and reports meet each other where each is.

Let’s think about a couple of examples:

An entry level person or junior person needs EXPLICIT instructions for what to do. Step 1, Step 2, Step 3. They ask “Tell me what to do” and a manager says “I’ll tell you what to do.”

But could you imagine a board doing this with its CEO? No way! The dynamic at that level is all the way at the top of the ladder (and flipped), the CEO walks in and says “here’s what I’ve been doing.”

Every person in your organization is somewhere in between. More senior people jump to “I think,” or my favorite, “I recommend.”

Those are great for individual contributors turning into managers. For managers and executives, I expect it one level higher: Make a plan and tell me what you intend to do and why.

The best way to start using this in your organization is ANYTIME someone brings you a question/problem/issue, the response is always “What do you recommend?” - what happens is it forces them to think about it and actually make a suggestion.

In the beginning, you’ll agree 4/10 times… within months, you’ll agree 8/10 times and soon that person will jump up a rung on the ladder.

3. Build clarity around people’s skills

There’s a next level here. It’s called Task Relevant Maturity. A mouthful but an easy and simple concept.

How well do you know how to do the task at hand? Here’s a personal example: I have never shaved. If you gave me a razor and said, “Shave your face,” I would have no clue what to do and probably screw it up.

To be successful, I’d need step-by-step instructions and oversight. On the other hand, I’ve tied a turban thousands of times. I need no instructions. It would be strange for you to try to explain how to do this to me.

In business, I’ve sold a company but I’ve never used Photoshop. Even though one task seems HUGE, I know how to do it.

Therefore, I can be high on the leadership ladder. I can tell you what I’m up to and provide regular updates. But if you wanted me to make a simple flier in Photoshop, I’d be REALLY low on the ladder.

The point is: The ladder is not a singular thing for each person. But instead, each person is at a different place on the ladder for different skills.

If you don’t make space to bring clarity to this and talk about it, you’re bound to both be disappointed and create frustration for people. You may not give ENOUGH guidance in some tasks while over-guiding in others.

This will be unpleasant for you and the team and may lead to messed up tasks or frustrated people, which would reinforce the FEAR you felt at the start.

The biggest takeaway from both of these is to increase your level of intentionality and language multiplefold! This will lead to successful delegation.

So there you have it! Why your business isn’t growing…

  • Whenever I set goals, those goals ALWAYS include people’s time and resources. For Bootstrapped Giants for example, our goal is to have 100k email subscribers growing 5% per month with < 5 hours a week of my time and < 10 hours of the CEO’s time.
  • Sometimes, there are tasks so important and so sensitive or urgent that the CEO/Owner has to take the reins and manage everything closely. These should be few and far between and when they happen, let everyone know why and be clear about what they should expect. Most people will get on board.
  • Like any sport or skill, this takes practice from everyone. Do it early and often!

I wrote this based on email replies from people like you. Hit reply and tell me what you’d like me to write about next.


Bootstrapped Giants

Jesse Pujji

Bootstrapped to an 8 figure exit @ampush. Now building a $1B+ bootstrapped venture studio @GatewayX and sharing everything I learn along the way.

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