The Leadership Delegation Trap: Step Back Too Soon, and It All Falls Apart

Every founder will eventually need to delegate leadership, we know that.

It’s not really an if – scaling simply requires more than one brain. That’s the truth.

But that doesn’t mean that you should replace yourself from day one and retire to the Caribbean, piña colada in hand.

Actually, if you exit too early… You risk f*cking up your business completely. We don’t want that.

There are some basic elements of a company that you MUST set up properly before hiring an external manager to do all the managing for you.

And in this article, I’ll show you exactly what these elements are, how to put them in place, and when you can safely replace yourself and call it a day.

Let’s avoid this leadership delegation trap, shall we?

What Will Happen To My Business If I Step Away Too Early?

If you start to go aside too early, without putting your processes on the rails and without automating anything, you’re risking a lot.

See, your company has to be able to continue running without you. The goal is not to let it form without you.

If you haven’t built the correct systems and processes first, things will just get crazy.

Think of your business like an orchestra. 

If you immediately hire an external manager – they’ll be the main violinist.

Not you.

And by the way, it takes some time for a certain accepted atmosphere to develop… so you’d better not trust this secret ingredient into someone else’s hands. 

Ask yourself:

How should people act? What values is the company guided by? How fast/hard do you work? What are the expectations?

Culture doesn’t just magically “happen”, you know?

You have to deliberately set it in place, and no one else can do that for your company but you.

I mean, organic culture can happen too. When there’s no formal leadership figure, a leader tends to emerge anyway.

That’s not necessarily a bad thing, especially if you hired great people with the right position. But if you go down this route, be prepared for a wildly different company than you had imagined.

Should The CEO I Hire Be Similar To Me?

Before I answer that, let’s address another concern.

If you’re thinking: “Hiring a CEO??? WHAT?! It’s my company!”, relax.

Take a big breath and be honest with yourself.

Are you the BEST person to handle growth?

If the answer isn’t an immediate “hell yeah”, then it might be smart to hire an external CEO.

And that’s not a bad thing. You might be a builder or a creator. It’s okay (and smart) to admit someone else is better suited for where you’re headed.

That doesn’t make you less of a founder. You’re just smart enough to get out of your own way.

Alright, back to the original question.

If you end up hiring an external manager, know that you’ll never find your clone.

And that, my friend, is an amazing thing. Look, there are many stages to a business, and you can’t excel at all of them

Just to name a few:

We got the formation stage, product building stage, active growth stage, maturation stage, plateau stage, etcetera etcetera…

The personal qualities that are required at each stage are all very different. You’re probably not good at all of them.

(except for if you’re some kind of Superman/very mentally ill person who can change so drastically quickly)

As a rule, a person is either inclined to one of these stages. Not all of them. Every stage requires completely different psychological and professional qualities.

So no, your new director should NOT be exactly like you. They should be better in areas where you lack.

They should be a great continuation of what you set up in your company, not your replacement.

So… When Should I Look To Hire a Director?

At the beginning of the article, I told you, you needed to take care of certain basic “elements” of a company before making this hire.

Let’s get to it. Here’s the breakdown:

Culture: Set The Tone Before You Pass The Mic

Before you bring in someone to run the show, you need to define how people show up inside your company.

Are you scrappy and resourceful, or polished and corporate? Do people move fast and break things, or slow down and document everything? You have to define:

• What gets rewarded?
• What gets tolerated?
• What gets people fired?
• What is your brand like?

You need to model the behavior and then codify it. Think of it like writing the social “operating system” for the company. Directors can enforce it — but you have to build it.

Product-Market Fit: You Can’t Delegate What You Don’t Understand

If you haven’t nailed product-market fit, you have no business delegating leadership.

Why?

Because product-market fit isn’t something you can totally “outsource.” It’s a dance between what you’re offering and what the market is hungry for. Only the founder (you) has the obsessive insight and flexibility to tune that in.

Once you’re getting consistent demand, high retention, and referrals without having to bribe people or light your ad budget on fire — then you can look at handing over the reins on scaling.

Until then, stay close to the feedback loops. Talk to customers. Read every churn reason. Be the PMF bloodhound.

Processes: Build the Machine Before You Hand Over the Manual

Wow, I love making these subheadings.

Anyway…

You wouldn’t hand someone a Ferrari and say, “Just figure it out.”

Same thing here.

You need to operationalize your business before someone can “manage” it. That means building clear, repeatable processes for:

• Sales & lead gen: What’s your process to consistently bring in new business looking like?
• Customer onboarding: What happens as SOON as someone sends you money?
• Product delivery: Do you have a predictable and repeatable way to deliver your product or service?
• Internal communication: Is there some kind of schedule… or something?
• Reporting & metrics: What do you report, and how often do you report it?

If your company is running on vibes and last-minute Slack messages, you’re not ready to hire a director.

And yes, document everything. Standard operating procedure documents (SOPs) aren’t sexy, but they save lives (and profit margins).

Strategy: Set the Direction, Then Let Others Drive

Strategy is not the same as execution.

Before you bring someone in, you need to know:

• Where are we going in the next 1–2 years?
• What does success look like?
• What hills are we willing to die on?

That doesn’t mean having a 200-slide MBA deck. It means having clarity.

The director should align with your vision, not invent it. Their job is to translate the “what” into “how.” But if you haven’t decided on the “what,” they’ll fill in the blanks — and you might not like what they write.

If you read this part and at any point thought “oh cool, I still don’t have that”… I have JUST the thing for you.

In my free 8D Framework to Launch Your Business, you’ll find every step of starting a business, from idea to execution, to sales and marketing, and even legal stuff.

I highly recommend it if you still need to put some systems and processes in place (so most of you reading this):

Should I Still Delegate Tasks If I Want To Do Them?

Trust me, that is mostly a trap.

I’ve been in such situations, so I get it.

Personally, I LOVE to do certain tasks. For example, I love creating products.

I love independently tinkering with my hands, so I constantly fight the urge to make things happen with my own hands.

It’s exhausting sometimes, but I know it’s the right thing. As much as I’d love to stare at my laptop for hours and create cool products… my time is best spent managing people who will do that.

This is great because it saves me lots of time.

(If you’re a control freak and need to oversee absolutely everything anyone does, it probably won’t save YOU much time…)

But in the past, I also had businesses where I couldn’t “replace” myself, and everything that was brought from it was simply considered a salary (for my cofounder and I).

But is that the best way to operate?

Well, the problem with this “business” is that if you cannot replace yourself.

If you can’t find someone on the market with the same (or even better) qualifications as you, pay them the same money as you pay yourself, and calmly leave…

You are not doing business.

You are doing bullsh*t.

You built yourself a wonderful job, from which it is impossible to escape.

Now… if you LOVE doing the job, that’s perfectly fine too. But then, understand you are best suited as an employee, not a leader (which is totally cool, don’t let people tell you that you must be a leader or else you’re not good enough).

What If I Am a Jealous Founder?

First, understand that jealousy is a very normal feeling. It’s okay to feel that.

Watching someone else run your business is emotionally… kind of weird.

But ego is growth’s biggest enemy – think of letting go as a ‘maturity’ test.

Something that really helps is looking at your company like an external investor would. As objectively as you can. Think:

“At this stage, for example, our company has already sufficiently proven its success. The product-market fit has been found. We understand how to scale. How to just start pouring money into hiring new employees, into marketing, into expanding infrastructure — and grow, grow, grow, grow. Very quickly and very much…

… am I the right person to lead this growth? Yes or no?”

By looking at it from a third-person view, you can (at least partially) remove your emotions from this decision.

It certainly makes it easier to bear.

This is how mature and responsible decisions are made.

A very mature decision would also be to check out our Unit Economics course. Inside, you’ll find all the tools you need to mathematically scale your business.

Just tweak a couple of numbers… and watch the revenue increase. That’s what Unit Economics gives you.

If you’re at the stage to delegate, this will definitely interest you.

Takeaways

Yes, delegation is necessary if you want to scale your business. Absolutely.

However, delegating leadership TOO soon can really harm your business. There are a number of things you need to do FIRST before delegating leadership:

• The goal is to have the company continue without your direct involvement. Not to form without it.
• I mean, it can form without it, but then the company will be much different from what you imagined (which can be okay, too).
• When hiring a director, don’t expect to find another you. That’s impossible, and you actually don’t even want that.
• Business has lots of different stages, and a different personality/expertise is needed for each and every one. You can’t POSSIBLY excel at all of them.
• When you hire an external director, find a great continuation of you, not your replacement.
• Before you bring in someone to run the show, you need to define how people show up inside your company. Define the culture first.
• Find your product-market fit BEFORE delegating leadership.
• Also, build your processes and SOPs first.
• And define your long-term strategy and vision.
• If you can’t remove yourself from the business by hiring someone else to do what you do for the same money, you don’t run a business. You run a bullsh*t.
• Feeling jealous is normal and expected. Be an adult and learn to deal with it. A tip here is to look at the business as if you were an outside investor and making the decision based on that.