5 Leadership Mistakes I Made in My First Business

By Nicholas Rubright

Updated Over a Week Ago

Minute Read

Being a great leader means you don’t make the leadership mistakes I made like always saying the wrong thing or being too harsh. Being a great leader means that you work for your team. You serve them by removing barriers that prevent them from doing what‘s necessary to move things forward.

This is something I learned the hard way. When I was in college, I started a music streaming business that was meant to compete with the likes of Spotify, Apple Music, and others.

There were several flaws in the business itself, sure, but I made tons of leadership mistakes along the way. These mistakes prevented us from launching the service quickly enough to own the market.

Here are 5 of the biggest mistakes I made during the development of this business and what I learned.

Mistake #1: I Lacked Decisiveness and Vision

One of the biggest mistakes I made during the development of this company was that I lacked decisiveness and vision.

I was always changing my decisions too quickly. First, it was a mobile app. Then, it was a desktop app.

This lack of clarity also hindered my ability to raise money and get licensing deals from record companies. I’d send them multiple emails and follow-up emails with varying ideas of what I wanted to do. Eventually, they told me to leave them alone until I had a more clear idea of what I needed.

What I learned from this is that you need to be decisive and stick with your big decisions. If you change your mind frequently, you’ll never get anything done.

Construct a clear vision and plan from the beginning, and this will create visible movement forward inside your business, which will motivate your team and allow you to give them more clear instructions on what needs to happen.

Mistake #2: I Failed to Systemize Things

When it came to communicating with my team and getting them to work together, things were all over the place.

I’d send them emails and Skype messages and talk to them on Facebook about tons of different things.

My partners and employees were always very confused about where to go when they needed something. We had multiple developers and designers with no clearly defined roles.

What I learned from this is that if you build a flawed foundation, then at scale, things will start to collapse on themselves.

Systemize and organize things from the beginning. Keep all of your communication in one place by using something like Webex, where screen sharing, video conferencing, and other team collaboration features are all in the same place. This will make it easy for your team to communicate.

Mistake #3: I Failed to Enable My Workers

One of the biggest things that can prevent your employees from making progress on their work is not giving them the ability to make judgment calls.

If you hire someone to do a job, you need to trust them. If you’re paying someone to accomplish a task, you aren’t paying them to do it your way; you’re paying them to do it the best way.

In my first business, I micromanaged my staff way too hard, and that stopped things from getting done. I wanted things done my way.

What I learned, however, is that if they’re an expert, their way is most likely the best way. They’ve probably been doing their work a lot more than you have.

Rather than telling your workers how you want them to do something, give them the objective, let them tell you how they’re going to accomplish it and give them the tools they need to do things successfully. Give them the freedom to make important decisions that are related to their job.

During the development of my first business, I was incredibly impatient. I wanted things done instantly.

Mistake #4: I Hired Fast and Fired Slow

During the development of my first business, I was incredibly impatient. I wanted things done instantly.

This was reflected in my hiring practices. If I wanted a website built, I’d hire the first developer to contact me.

On top of that, when it came to getting rid of people, I had a very hard time doing so. I was afraid it would take too long to find a replacement.

Instead, I should have taken the time to vet my options before hiring. I learned that instead of hiring fast and firing slow, I should hire slow and firing fast.

Mistake #5: I Failed to Help My Workers Maintain Efficiency

Another flaw of wanting things done my way is that when it came to any type of execution, I wanted my workers to follow the exact process I put in place.

When they would come to me and suggest software that would help them do their job more efficiently, I would ignore it or put it off until later. Instead, what I learned is that I should have listened to my employees when they needed help.

If a writer needs a grammar checker to help cut down on editing time, I should get one for them.

If a salesperson wants to leverage software to automate their follow-up email sequence, I should get them a subscription.

If a developer wants to use a particular language because that’s what they’re familiar with, I should listen to them.


What I learned from the leadership mistakes I made is that by listening to the needs of your workers and addressing the problems they bring to you, things become more efficient – especially at a large scale.

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Nicholas Rubright
Nicholas Rubright
Nicholas Rubright is a digital marketing specialist for Webexe a platform designed to make team collaboration simple.
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