10 Common Leadership Mistakes New Entrepreneurs Make

By Maxim Dsouza

Updated Over a Week Ago

Minute Read

When I started my first business, I made many terrible leadership mistakes. I paid the price for it the hard way. Let’s take a look at the mistakes I made and how you can avoid them.

To start, I believed people would follow my words simply because I was the boss. And that was just one of my mistakes.

I learned the technology side of the business, like a young kid eager to learn a bicycle. But when it came to leading people the right way, it took me years to wrap my head around it. I made the mistake of assuming I had the natural ability to lead people.

If I had a chance to go back in time, here is the advice I would give myself before I started my first venture.

These same tips apply even if you are taking up a managerial position for the first time:

1. Thinking You Can Do Things With Full Authority

During my early days as a self-made boss, I assumed all employees would listen to me.

To an extent, employees will listen to the boss. Depending on where you live, people will obey authority to different degrees. In certain cultures, employees tend to follow the leader no matter what, while in some other areas of the world, team members are not afraid to question the boss.

Regardless, you cannot just boss people around. Employees will give their best if you treat them with respect. You will have a hard time if you order people around.

You still need to maintain the line where you do not operate like everyone’s best friend. But at the same time, you also need to earn respect from people rather than demanding it.

“Authority without wisdom is like a heavy ax without an edge, fitter to bruise than polish” – Anne Bradstreet

2. Micromanaging

When you become a leader for the first time, you will have transitioned from the role of an individual contributor. You come from a routine of doing all the things yourself.

The same habit carries on as a leader too, where you expect to know the little details of every single thing. If you keep asking people for updates and feel the need to approve every small decision, you will inhibit everyone’s growth.

Unless you stop micromanaging, you will annoy them to a level where they crib about you behind your back. Give people the freedom to do their work and make their own decisions. They will surprise you.

“Micro-managing creativity kills it. To encourage creative brilliance, foster an atmosphere where it can thrive and then step out of the way and let it happen.” – Stewart Stafford

3. Doing Things Faster

When I was leading a team of programmers, I would easily become frustrated when others took longer to write their code.

I had forgotten that I was expecting high-quality output from people with little experience. When I had their level of experience, my code was much worse.

As an individual contributor, you might have been a high achiever. So you tend to compare the work of others to your own to point out mistakes.

  • “Do you need an hour for that?”
  • “You missed an easy point.”
  • “Why is that so difficult to do?”

Your statements of arrogance and sarcasm do not go unnoticed. Don’t expect everyone to produce your quality of work, especially right away. Guide people on how they could do it better. And have patience until they learn.

Sure, you can do it faster today. But can you do more than five people if you spend time teaching them? No way. Unless you’re a terrible teacher.

You might want to stop wasting time now on training. But as a leader, you have to think about the long-term returns of a team. 

“If you want to do a few small things right, do them yourself. If you want to do great things and make a big impact, learn to delegate.” – John Maxwell

4. Expecting Everyone to Think and Act Like You

I had the habit of expecting people to operate as per my style. Whenever there was a problem, some people would panic, while others would hunt for a solution.

“Why can’t everyone do the same?” I wondered. I even considered those who panicked as poor performers. 

But not everyone has the same reaction to every situation. Each person has his own style. If you expect everyone to align with the way you think, your employees will leave faster than a pack of wild birds.

If you manage to hire people like you, your business will run into failure.  You are not managing a bunch of “you’s”. You need to work with a diverse set of people who have their own opinions and ideas, many of which are better than your own. Respect differences of opinion without trying to prove yourself right every time. 

“A diverse mix of voices leads to better discussions, decisions, and outcomes for everyone.” – Sundar Pichai

5. Believing Leadership is Inbuilt

If you have to learn a new skill like playing the guitar or learning a new technology like Machine Learning, how would you go about it? You read some books, take some courses, try some exercises, or attend classes.

But when it comes to leadership, people assume they already have all the arrows in their quiver. Too often, your quiver is filled with the wrong arrows or none at all.

You need to put the effort in to learn and improve at leadership, like any other skill. No one is born with leadership skills. The best leaders become so because they have the intention to learn.

 It took me many years to accept the fact that I sucked at leadership and that I must spend time working on it.

“Leadership and learning are indispensable to each other.” – John Fitzgerald Kennedy.

6. Pointing Out Mistakes But Forgetting to Be Appreciative

When employees made a mistake, I quickly showed them where they went wrong and how to correct it the next time. When someone did a good job, I took it for granted. My mind said, “He’s just doing his job.”

Uttering a few words of appreciation speaks volumes to the people around you. It makes them pump their fists and gear up to do even better next time.

Do not worry that your appreciation will lose value if you say good words too often. The more you applaud people, the more they will give in return. The more you find faults, the more Monday blues people will have. 

“A person who feels appreciated will always do more than what is expected”- Author Unknown

7. Believing People Don’t Need Guidance

I assumed all I needed to do was distribute tasks, and people would figure out the rest. It turned out that no one bothered to step up and do anything beyond the work distributed.

The most crucial role of a leader is to set the direction for the team and ensure each person understands where the whole group is headed. Set a vision and set SMART goals to help your team get there.

If you do not set a clear vision as the leader, your people will either wait for you to provide instructions or scamper around without a clue. It is like arriving at the airport as a group without knowing where to go.

No matter how smart the team members are, the leader must guide them toward a goal and make sure they do not go astray. 

 “Where there is no vision, there is no hope.” – George Washington Carver

When you show where the team needs to go and let the people figure out the path, everyone starts applying their ideas, and magic happens.

8. Thinking You’re the Smartest and Always Right

The hardest fact for a new leader to digest is that people lower down the hierarchy can be smarter than them. When an employee suggests a better idea, an arrogant leader considers that as a beating against his ego.

You must accept the fact that you are not the smartest person in the room. Just like you have your strengths, your employees will know certain areas better than you do.

Sometimes, a new hire might suggest a brilliant idea that you never thought of. As a leader, if you do not have the humility to accept better insights and smarter people, you will fail sooner or later.

You are not in your current role because you were the smartest among the lot. Your job is to guide the team toward the right goal.

“Outstanding leaders go out of their way to boost the self-esteem of their personnel. If people believe in themselves, they accomplish amazing things.” – Sam Walton

9. Failing to Delegate

 During my first tenure as a technical team leader, I had the habit of doing all the tougher jobs myself. I would spend most of my time working on tasks. As a result, people remained at the same skill level, and I had to continue working longer to get things done.

As a leader, you must spend enough time bringing the best out of people. You must:

  • Train people on areas you’re good at even if they take longer to deliver the same output
  • Talk to people to understand what motivates them.
  • Figure out the roadblocks people are facing and gather ideas to overcome them

If you focus on tasks, only your skill grows while your people suffer. If you shift your focus on people, the people will take care of the tasks for you.

“When the best leader’s work is done, the people say, ‘We did it ourselves.’” – Lao Tzu

10. Trying to Change Everything Yourself

During my first tenure in leadership, I wanted to change the whole world around as soon as possible. I made many changes in a short time without understanding the potential impact. Things went haywire and caused more damage than good.

When you take a leadership position, do not hurry to bring in drastic changes. Spend time understanding why things are the way they are before you even plan to change them.

When you begin your journey as a leader, you start with some coins in your pocket. Every time you do something right, you gain more coins. Every time you falter, you lose some. The day you lose all your coins, you are finished as a leader.

Based on that metaphor, as a new leader, if you make mistakes early, people lose trust in you. Based on the gravity of your mistake, you may not even have an opportunity to come back.

When you start fresh, focus more on avoiding mistakes than rushing to deliver exceptional results.

“Patience is not the ability to wait but the ability to keep a good attitude while waiting.” – Joyce Meyer


Leadership is a never-ending journey of lessons. When you think you got all the ropes of leadership, you will notice that you have so much more to learn.

The only way to get better at leadership is to learn, try different approaches, make mistakes and improve. You will never meet a leader who was always perfect. 

Do not have an arrogant mindset where you believe you will produce results unlike any leader has ever done before. With such pride only comes a great fall.

 Take each day of your life as something new to learn in leadership. And make no mistake; you will have something to learn every single day.

“All I know is that I know nothing.” – Aristotle

What Leadership Mistakes Do New Entrepreneurs Make?

If you have ideas about leadership mistakes that might be helpful to readers, share them in the comments section below. Thanks!

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Maxim Dsouza
Maxim Dsouza
Maxim Dsouza is a self improvement blogger. He has been a part of multiple failed start ups and learned the hard way. On his blog, Productive Club, he provides unique tips and tricks on productivity, time management and entrepreneurship from his real life experience.
  • Merci beaucoup pour cet article très clair et fondé sur les expériences vécues. Really interesting

    • Maxim Dsouza says:

      Thank you Ndremana. I am glad you found it useful.


    This is a great piece of teaching. If any willing or typical leader adopts it, that leader will make great impact , and will win the heart of his /her followers, no matter in what sphere of leadership, he may be operating.
    Bounty I Gabriel Pepple-Nigeria

    • Maxim Dsouza says:

      Thank you for your kind words, Gabriel. Though I have written this article myself, I struggle with these areas frequently. But, leadership is a journey for life.

  • Gareth van Rensburg says:

    Hi Maxin, I liked your article, your points resonated with me, never be arrogant and evaluate how much time you need to do it properly, and lastly never give up.

    Thank you.

    • Maxim Dsouza says:

      I am glad you liked the points Gareth. Humility is an important leadership quality like you rightly mentioned.

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