From the day that you first decided to start a small business, you have been the lifeblood behind every activity. You've done it all – making every decision and watching over every operation. But, what happens next?


Whether you want (and need) a vacation, fall ill, want to retire or maybe just find someone to take the business to the next level, you want to know that the business will be safe and prosper. You need to have confidence in someone else who can take on the mantle.

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Trusting someone else to take over for you is a necessity, even if it's one of the toughest aspects of small business ownership.

Here are six things you can do to make sure that everything gets done to your satisfaction when you can't be there.

1. Identify likely candidates

Do you have a second in command who is always there to lend you a hand in a pinch? That person may be the logical person to take the reins, but don't ignore some candidates that are less-obvious choices.

You might be impressed by less-visible employees who consistently make suggestions on efficiency and cost savings. Others may be going to night school on their own dime to learn business management. You might notice that team members turn to one person within their ranks for leadership. So, while one person who is gunning for the job may be the perfect choice, cast a wider net to make sure that you find the right new you.

Also, look outside the business to others who have been in similar industries, have strong management styles and share common values with you and your business.

Related article: 8 Different Types of Small Business Management Styles – What’s Yours?

2. Learn what you know

Don't expect to jump immediately into the training process. You've been doing the job for a long time, so chances are you take the details of your job for granted and may forget to mention them to a CEO-in-training.

Do you have a list of people to notify when you issue a new policy? If you change the color of a product that you purchase from your primary vendor, do you have to make sure that backup vendors can also accommodate the change in a pinch? Do you know of a small glitch in the production process that affects the delivery date you promise to customers?

There's a reason why they say the devil's in the details. Make sure that you know every one of them before you try to teach anyone to step into your shoes.

3. Do some hand-offs – and coach

You're no different than every small business owner who has an overabundance of work. Wouldn't it be nice to go home at 5 pm once in a while? You can accomplish this by handing off some of your responsibilities to the candidates you selected.

Whether you hand over bookkeeping tasks, managing human resource issues or even making more decisions, don't expect speed or perfection at the outset. In fact, don't expect to get home by 5pm right away either. Since you must initially take on the role of trainer, you absolutely need to resist the temptation to say "I can do it more quickly myself."

Be prepared to teach, supervise and answer countless questions. But, your efforts will help you gain more free time eventually — while identifying which candidates have the skills and aptitude as leaders.

Click here to learn more from our small business expert Carol Roth

4. Be a true mentor

Step-by-step training alone does not create head honchos. Your protégé needs confidence that can only be created through a full mentor relationship. You need to establish a friendship that encourages honest two-way communication.

Your candidate must be comfortable to readily express concerns about anything, including taking the top leadership role. You need to start the conversation to get the ball rolling. Telling your mentee stories about your own experiences making difficult decisions or handling tough customers is better than just asking if there are any questions or concerns.


Also, communicate to other staff about why you have confidence in this person and why you believe that even if their style is different, they will be an ideal person to lead the company’s continued success.

5. Go away

You can't predict someone's abilities until you test them. While you probably shouldn't plan a six-month world tour right away, all of your mentoring efforts have certainly earned you a week on a beach sipping daiquiris. Don't be overly available for questions. If you can't leave your devices at home, at least leave them in your hotel room. Your protégé needs the opportunity to exercise decision-making muscles.

If you are bringing in an outside candidate, consider moving to an executive chairperson role so you still have some say, but the day-to-day rests firmly in the other person’s camp.

6. Don't expect a clone of yourself

The objective of replacing yourself is to ensure that your company will continue to thrive without you at the helm for a week, months or forever. Your replacement's role is to get the job done — not to get the job done your way. Every person has individual ways of reaching specific goals. If you prepare them properly, don't be surprised if you learn a few new tricks from them along the way.

About Carol Roth

Carol Roth is the creator of the Future File™ legacy planning system, “recovering” investment banker, billion-dollar dealmaker, investor, entrepreneur, national media personality and author of the New York Times bestselling book, The Entrepreneur Equation. She is a judge on the Mark Burnett-produced technology competition show, America’s Greatest Makers and TV host and contributor, including host of Microsoft’s Office Small Business Academy. She is also an advisor to companies ranging from startups to major multi-national corporations and has an action figure made in her own likeness. 

Web: or Twitter: @CarolJSRoth.

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Bank of America, N.A. engages with Carol Roth to provide informational materials for your discussion or review purposes only. Carol Roth is a registered trademark, used pursuant to license. The third parties within articles are used under license from Carol Roth. Consult your financial, legal and accounting advisors, as neither Bank of America, its affiliates, nor their employees provide legal, accounting and tax advice.

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