The Succession Readiness Scorecard

Eight questions. Count your honest yes answers. Do not count “sort of.”

  • Could the business run for a month without you?
  • Is there one person you would trust to run it today?
  • Are the key jobs written down, step by step?
  • Do your books show the real profit, without your personal costs mixed in?
  • Do your best customers know someone besides you?
  • Have you said out loud when you want to step back?
  • Have you talked to an attorney or CPA about the handoff?
  • Does your family know what you plan to do?
Seven or eight: you are ahead of most owners. Pick the path and set a date. Four to six: you have two or three years of work ahead, which is fine if you start now. Three or fewer: the business still lives in your head, and that is the first thing to fix, no matter who takes over.

Most owners score low on the first three questions. That is not a character flaw. It is what happens when you are the best at the work. The small business management guides cover how to move the work out of your head and onto paper, one job at a time.

Four Ways to Work With Dr. Paul

02

Business Plan Writing

Your successor needs a loan? Dr. Paul writes the business plan and financials a lender will want to see.

Plan writing and prices →

03

Fractional CFO/COO

Get the books clean and the systems written down over the next few years, with Dr. Paul part time.

Fractional CFO and COO →

04

Small Business Education

Free guides on management, finance, and operations for owners getting a business ready for the next owner.

Free guides →

Family, Key Employee, or Outside Buyer

There is no best answer. There is a best answer for you, and it depends on what matters most: the money, the name, or the people.

FamilyKey employeeOutside buyer
Biggest strengthKeeps the name and the legacyAlready knows the work and the customersUsually pays the most cash up front
Biggest riskAn heir who does not want it or is not readyCannot get the money to buy you outWalks if the books or systems are messy
How you get paidOften slowly, sometimes not at allLoan plus payments to you over timeCash, loan, and sometimes an earn-out
What must be readyTraining, a family agreement, estate planningA plan a lender will fundClean books and a business that runs without you
Who else you needEstate attorney, CPALender, attorney, CPALicensed broker, attorney, CPA

Notice the last row. Every path needs professionals Dr. Paul does not replace. His part is the business side: the numbers, the plan, and the training that makes the handoff stick. Pair a business consulting session with your attorney and CPA, and every decision has the facts behind it.

A Community Where the Handoff Question Comes Up Early

Sun City Center is an active-adult community in south Hillsborough County. Many of its owners serve older customers, and many owners are thinking about their own next chapter.

1961year Sun City Center was founded; it is still unincorporated
30,952people at the 2020 Census
62.4%of residents are 65 or older, per Census QuickFacts

Sources: U.S. Census Bureau, QuickFacts, Sun City Center CDP (population and age); founding year via Sun City Center, Florida (Wikipedia). Checked 10/29/2026.

Three local resources for the handoff

South Hillsborough Chamber of Commerce. Started in 1961 as the Sun City Center Area Chamber and based in Sun City Center since 1984, per the Osprey Observer. A good place to meet the next generation of local owners.

Florida SBDC at USF, Hillsborough. No-cost consulting that covers buying and selling a business, per its Hillsborough page.

Hillsborough County Tax Collector. Its business page notes that tangible personal property taxes follow the equipment, not the owner. A successor could inherit an unpaid bill, so check before the handoff. Source: Hillsborough County Tax Collector.

Unpaid taxes are one example of a loose end that is easy to fix now and painful to discover at the closing table. Dr. Paul is a Florida business consultant who works with owners statewide, and the Tampa Bay business consultant page lists all twenty growth and survival questions for the region.

Dr. Paul’s Insight: You Learned It Over Years

Dr. Paul’s Insight · From Management and Leadership for Small Businesses, Book 1, Chapter 17, “Watch Me and You Will Pick It Up: A Bee’s Apprentice” · Dr. Paul’s Fabled Forest Business School Series

“I don’t understand it,” Beatrix said to him. “I learned everything by watching. Watching my mother. Watching the old beekeepers. Nobody wrote anything down for me. I just watched and I picked it up.”

“How long did that take you?” asked Doctor Owl.

Beatrix thought. “Years,” she admitted.

“How long did you give Clementine?”

“A week.”

Dr. Paul’s take: That is most succession plans. The owner learned the business over a career, then expects the next person to pick it up in a few weeks of overlap. It does not work for a new hire, and it does not work for a son, a daughter, or a buyer either. In a community like Sun City Center, where many owners are already thinking about the next chapter, the handoff deserves the same years it took you to learn. Start by writing down how the work gets done. The guide to employee onboarding shows you how.

A Small Local Work Force Changes the Key-Employee Path

A key employee is often the best successor. In Sun City Center, the Census numbers say that person may be harder to find nearby, so the search may need to start sooner and reach wider.

27.2%of residents age 16 and up are in the civilian labor force, 2019 to 2023
248employer firms in the community, reference year 2022
$404.8Mhealth care and social assistance receipts in 2022, more than total retail sales

Source: U.S. Census Bureau, QuickFacts, Sun City Center CDP. Checked 10/29/2026.

Read together, those numbers could mean a thin local bench of future managers, a short list of local peers who might buy, and an economy that leans on health care. If your successor is not on the payroll yet, you may need to hire that person from the wider south Hillsborough area and give them years, not months, to learn the business. Real succession planning Sun City Center owners can count on starts with that search. Owners great at the trade often put this off because hiring a future owner feels like business-side work. It is, and Dr. Paul helps you plan it; he does not pick the person for you.

What to Do Five Years, Three Years, and One Year Out

Work backward from the day you want to step away. Here is what each stage looks like.

Five years out

Decide and document

Pick your path. Start writing down how every key job gets done. Separate personal costs from business costs so the books show the real profit.

Three years out

Name and train

Name the successor, or start looking for a buyer. Hand off one area at a time, and check the results instead of doing the work.

One year out

Prove it runs

Take real time away. Let the successor run the business while you watch the numbers. Get the legal and tax structure set with your attorney and CPA.

Handoff day

Step back on purpose

Introduce the successor to your best customers and vendors. Agree on how long you stay available, and then keep that promise.

This is the Plan step of Dr. Paul’s Organize-Plan-Grow™ Strategy, pointed at the end of your ownership instead of the next year.

The Book on Building a Business Someone Else Can Run

Management and Leadership for Small Businesses book cover, Dr. Paul's Fabled Forest Business School Book 1

Dr. Paul’s Fabled Forest Business School Series · Book 1

Management and Leadership for Small Businesses

Onboarding, delegation, SOPs, and the first manager, taught through one Fabled Forest owner per chapter. A succession plan is a training plan with a deadline. This book gives you the training part, with a worksheet at the end of each chapter you can use on your own business the same day.

Get Book 1 on Amazon →

Succession Questions Sun City Center Owners Ask

When should I start planning who takes over my business?
Three to five years before you want to step back. That gives you time to pick a successor, train them, clean up the books, and sort out the legal and tax side with your attorney and CPA. Owners who start late usually end up with fewer choices and a lower price.
Is it better to pass my business to family or sell it to an outsider?
It depends on what you want. Family keeps the business in the name but may not bring money or skills. A key employee knows the work but often needs financing. An outside buyer can pay more upfront but wants clean books and a business that runs without you. Dr. Paul helps you compare the three against your goals.
How can a key employee afford to buy my business?
Often through a mix of a bank or SBA loan, savings, and payments to you over time. The lender will want a business plan and financial projections. Your attorney and CPA should structure the deal, and Dr. Paul can help with the plan and the numbers behind it.
Can Dr. Paul help a Sun City Center owner without meeting in person?
Yes. Dr. Paul works with south Hillsborough owners by phone and video from Deltona. Many succession conversations start with one call about the timeline and the options, then a few working sessions on the plan.

The best succession plans start years before anyone needs them.

Dr. Paul Borosky, DBA, MBA

Business Consultant, Author & Educator | 14+ Years | 1,000+ Clients Served

DBA, National University MBA, Focus in Finance, Webster University Serving Tampa Bay from Deltona, FL

Dr. Paul Borosky, DBA, MBA is a business consultant, author, and educator, and the founder of Quality Business Plan. He works with Sun City Center and Tampa Bay owners on business planning, financial modeling, fractional CFO services, and the everyday problems of businesses that depend too much on their owners. He is the creator of Dr. Paul’s Organize-Plan-Grow™ Strategy, author of numerous published books on Amazon including Dr. Paul’s Fabled Forest Business School Series, and publisher of over 1,000 business-focused videos on YouTube. He has taught as an adjunct college instructor and teaches in Florida public schools.

14+
Years Experience
1,000+
Clients Served
$100M+
Projects Funded
1,000+
YouTube Videos

This page is for general educational purposes only. It is not legal, financial, tax, accounting, estate planning, or other professional advice. Succession involves legal and tax decisions; work with a qualified attorney and CPA. Community data is cited to its sources and changes over time. The Fabled Forest and its characters are fictional.