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11 Tips for Transitioning From Employee to Employer

YEC Question: What’s your best leadership advice for going from employee to boss — of yourself, and maybe others too? (name one tip)

Get Ready For The Investment

“You’re used to managing a crushing workload, difficult clients and phone on perma-ring, but when you’re the boss, you get to handle ego and emotions too. An important lesson is that managing personalities, expectations, egos and abilities is just as important as everything else on your plate. A happy, healthy, productive team is a product of time and energy spent caring for your team on a personal level.”

– Yael Cohen | Founder, President, CEO, F–Cancer

Pick Up The Boss Work

“One of the most common thing that employees do when they become the boss is they still do employee tasks.That kind of work is supposed to be done by employees and you are supposed to do boss work! When we run a business, it is our job to build systems and manage people to run these systems. If you find yourself doing the work, keep asking yourself, how can I replace myself for this task?”

– Louis Lautman | Founder, Supreme Outsourcing

Remember The Other Side

“One thing I find important as a boss is to remember what it was like on the other side, as an employee. For example, I used to hate when a boss would micromanage me. I sometimes catch myself doing that with my employees, and then stop and remember how much it bothered me, and try to stop the habit myself. You want the people working for you happy and productive, so remember what made you happy.”

– Justin Beegel | Founder, Infographic World, Inc.

Seek Perspective

“Always know where your organization is in its life cycle and where you are as its leader. Your role and the company’s needs will change at the pace of growth and you need to be steering the ship through its various phases. Regular reflection, time off and insights from outside will help you to zoom out.”

– Christopher Kelly | Co-Founder, Principal, Convene

Learn To Delegate

“The hardest part of moving up the ladder is knowing what to hand off to someone else (or even to automate). Most of us assume that as the boss, we have to do everything. The reality is that we’re responsible for everything — but who actually does the work isn’t important.”

– Thursday Bram | Consultant, Hyper Modern Consulting

Keep Up The Confidence

“Believe in yourself and your decisions and get comfortable with managing employees. Stay firm in your resolve, but not rigid and inflexible. Don’t be afraid to ask more experienced mentors for advice and to utilize the services of consulting firms. If you keep focused, stay calm, and are willing to work hard, you will find it extremely rewarding and fun!”

– Zach Cutler | Founder and CEO, Cutler Group

Maintain Transparency

“I strive to be really transparent and open with my employees. I’ve experimented with varying levels of openness, but ultimately, being more transparent and honest with everyone is the best option. If they understand me, and my drive to push them to be the absolute best they can be, we can have success both individually and as a company.”

– Justin Beck | Co-Founder and CEO, PerBlue

Create The Systems

“Focus on creating systems and getting organized. If you do not have systems in place with clear directions and checkpoints, then you’re going to struggle to manage and lead your team. Once you have systematized your business and organized your own projects and tasks, then you can lead by example.”

– Pete Kennedy | Co-Founder and Managing Partner, Main Street ROI

Start Planning Ahead

“Planning is the key to having perspective on what’s most important now and working ahead to proactively address potential challenges. If you are the boss and you don’t plan, you not only create stress for yourself, but also for your employees. Make this a daily habit so that you know how to lead best.”

– Elizabeth Saunders | Founder & CEO, Real Life E®

Discipline Makes A Difference

“When you’re an employee, you can usually rely on upper management to guide you and prod you when work needs to get done. When you’re the boss, the responsibility lies completely on you, so you need to practice discipline and focus. If you don’t, who will?”

– Steven Le Vine | CEO/President, grapevine pr

Build Your Brand

“Make sure you focus on building your professional brand. The more credibility and authority you have, the more opportunities will come your way and you will be able to lead more effectively.”

– John Hall | CEO, Influence & Co.


The Young Entrepreneur Council (YEC) is an invite-only organization comprised of the world’s most promising young entrepreneurs. In partnership with Citi, the YEC recently launched #StartupLab, a free virtual mentorship program that helps millions of entrepreneurs start and grow businesses via live video chats, an expert content library and email lessons.

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