Preparing for your first leadership or managerial role is a big undertaking. You’re now tasked with not only your own success, but that of your employees and your team.

Along with the increase in your workload and responsibility, you may face challenges you aren’t yet prepared for as a brand new manager. Fortunately, mistakes and difficulties can serve as learning experiences and make you a better leader in the future.

Below, eight successful entrepreneurs share the biggest mistakes they made when they were new bosses -- and what they would do differently now.

Failing to set expectations up front

A leader must be able to very clearly set the right expectations up front. Andy Karuza, founder of FenSens, says this is one thing he learned the hard way.

"Confirm details like cost, timelines, tasks and other key elements up front, so you can hold people accountable to those," Karuza says. "If you don't set up expectations, then one of you is going to get burned eventually."

Micromanaging your team

Like many new leaders, Rachel Beider, CEO of PRESS Modern Massage, was scared to give up control over certain processes or jobs within the company at first.

"My fear of delegation held me back from moving forward at a better pace," Beider says. "I had to learn to hire amazing people and then truly trust them."

Beider admits that delegating tasks can feel like letting go of the steering wheel, but it's necessary for growth.

Trusting too easily

On the opposite end of the spectrum, some new leaders find that they are too trusting of their employees, without holding them accountable for results. This was the case for Kristin Kimberly Marquet, founder of Marquet Media, LLC.

"In the early days, I would trust my employees to do their work without accountability check-ins," Marquet explains. "While most team members did do their work well, I had one or two who did not meet their obligations, resulting in termination."

Today, Marquet has weekly accountability check-ins to ensure all work is completed adequately and on time.

Avoiding confrontation

When Bryce Welker, CEO of The Big 4 Accounting Firms, first became a boss, he wanted to be pleasant and get along with everybody. Unfortunately, that desire created a conflict when he had to discipline a team member who was being disruptive and harming the company.

"I took a lot longer than I should have to address this issue because I didn’t want to be overly confrontational," says Welker. "This mistake cost my business a great deal!"

Being impersonal

As a leader, there's often pressure to maintain a sense of authority because you're ultimately responsible for your team's results. However, Syed Balkhi, co-founder of WPBeginner, notes that it's a big mistake to be too impersonal and robotic.

"This doesn't build respect or communication," says Balkhi. "Talk to people around you. Share something about yourself and ask them about their lives. This can play a huge role in employee retention."

Succumbing to self-doubt

Ashley Merrill, founder and CEO of Lunya, experienced a lot of self-doubt as a new leader and always assumed that she was the problem. 

"Since I didn’t come from deep industry or leadership expertise I was accustomed to my own subject matter ignorance and was quick to assume I was wrong," Merrill says. "This mindset helped me learn, but also made it hard for me to trust myself and take quick action."

Trying to manage all employees the same way

Each of your employees is unique. Trying to manage each of them with the same leadership style is rarely the most effective strategy.

"Since employees come from all walks of life with all sorts of backgrounds, I quickly learned that I needed to adjust my management style based on the individual," says Andrew Schrage, co-owner of Money Crashers Personal Finance.

Not showing your appreciation

Solomon Thimothy, president of OneIMS, feels that he didn't show enough appreciation to his team for their contribution when he was a new boss. As he puts it, you can never be too grateful for the people that help you grow your business.

"Never forget to let your team members know that they are doing a great job," Thimothy adds. "It motivates them and keeps you grounded at the same time."

Published on: Nov 25, 2019
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