4 Steps to Effectively Transition or Sell Your Business
A succession plan takes commitment, but when done right, it should help you net a much better sales price for your business when the time comes.
Did you know 70% to 80% of middle-market, closely held businesses put on the market do not sell? And 83% of businesses lack a formal, written transition plan?
I’ve had many discussions with middle-market business owners about planning for the future in order to generate the most successful sale or transition of their business. In my September 2017 article, “Small-Business Owners’ Biggest Retirement Mistake,” I explained why a succession plan is critical to the future of any business, and now I’ll address how business owners can develop and implement a strategic succession plan.
While this may seem like a daunting task, it can be helpful to compare the process to the steps you would take to put your home on the market. Begin with an appraisal and home inspection to evaluate the current condition of the home and identify cosmetic and structural areas of weakness. Next, create a plan for improvement, such as fresh paint, new floor coverings and a refreshed landscape. Finally comes the most challenging part: executing the plan and following through on the necessary improvements to make your home market-ready. Making these modest improvements could make a meaningful difference in the final sale price.
From just $107.88 $24.99 for Kiplinger Personal Finance
Be a smarter, better informed investor.
Sign up for Kiplinger’s Free Newsletters
Profit and prosper with the best of expert advice on investing, taxes, retirement, personal finance and more - straight to your e-mail.
Profit and prosper with the best of expert advice - straight to your e-mail.
These same steps generally apply to the process of preparing for a transition or a sale of a business, ensuring that you are succession-ready and maximizing enterprise value along the way. Below, we outline how to effectively identify key areas of weakness in your business, develop and deploy a strategic plan and successfully transition or sell your business when the time and offer is right.
1. Assessment
This is essentially the appraisal and complete review of your business. A thorough assessment analyzes key areas of the business and identifies areas needing attention and improvement. The examination is taken from the eyes of a prospective buyer, and demonstrates to the business owner what drives value in today’s market. Proprietary software helps evaluate the current state of performance across eight major functional areas of the business:
- Planning
- Leadership
- Operations
- Marketing
- People
- Finance
- Sales
- Legal
Our approach has most often revealed poor-scoring results in three key areas: planning, leadership and people. Why? Most closely held business owners are too busy working in and managing their business with the help of a controller and have not delegated control. They are wearing too many hats. Sound familiar? Without a capable, competent and enabled management team behind them it is difficult to improve the position and value of their enterprise. Bottom line, if a business cannot operate without its owner/manager, there is considerably reduced value to a buyer.
An assessment helps to identify these pain points, so that you can develop a strategy to resolve them and maximize business value prior to a sale or other succession event.
If you move along at a productive pace, this initial assessment should take approximately 60 days.
2. Strategic Planning
Once you see what’s broken, you’re ready to design a blueprint to improve the value of your business. In partnership with certified exit planning advisers (CEPA), CPAs and attorneys, among others, it’s key to take a team-oriented approach to ensure the people who have a long-standing relationship with you will be an integral part of the planning process.
Without any significant hiccups, this stage should take four to six months.
3. Implementation
With a plan in place, it’s time to put shovels in the ground and get to work. Over the course of one to three years, the strategy needs to be deployed to get the business transition-ready, sale-ready and succession-ready. Make sure to measure the success of current initiatives, and continually re-evaluate progress and objectives established in the strategic planning phase.
Perhaps the greatest challenge business owners have is implementing the plan and following through. Once the sobering reality of all the work they need to fit into their already busy schedule comes to light, many begin to lose their initial enthusiasm. Finding a trusted consultant who will motivate you and prepare you for the inevitable roadblocks you will approach along the way is crucial to achieving the best results. The more time you put in executing your succession plan, the better the outcome.
As with most things in life, there will be challenges. While sometimes the everyday whirlwind of business will get in the way of your ability to enhance and improve your enterprise, it is critical you do not deviate from this discipline. If the business owner doesn't have the commitment, then almost certainly their employees won't — it is a group effort to become transition-ready.
4. Transition
After successfully executing your succession plan, you will now have the confidence to entertain an opportunity from a potential purchaser. Being prepared for a potential buyer, you can evaluate whether or not it’s a good offer, what the pitfalls might be, and take a closer look at the tax implications. All of these elements will lead to a sale at the highest multiple of the original value.
Whether you are just launching your business venture or are a few years away from retirement, you should always keep the future of your business in mind. But remember, you don’t have to go through this process alone. Cultivate a trusted team of employees, managers and advisers, as well as family and friends, to help make the transition to the next stage of your life as smooth as possible.
Profit and prosper with the best of Kiplinger's advice on investing, taxes, retirement, personal finance and much more. Delivered daily. Enter your email in the box and click Sign Me Up.

Nick Giacoumakis is the founder and president of New England Investment & Retirement Group Inc. (NEIRG) and a nationally recognized wealth management adviser with a passion for helping business owners achieve success throughout all stages of ownership.
-
Are You Prepared to Live Longer? MIT AgeLab Answers QuestionsA new measure of longevity readiness indicates that for many Americans, the answer is no — and suggests what is needed to get on track.
-
NordVPN’s Huge 77% Black Friday Discount Is One of the Top VPN Deals We’ve Seen This YearSave up to 77% on NordVPN with this Black Friday deal, a practical choice for improving online security and streaming access.
-
As Holiday Shopping Kicks Off, Consider Adding Some Financial Literacy to Your Child's Wish ListNow is a prime time to teach your child some financial literacy and consider focusing on experiences rather than spending hard-earned money on material gifts.
-
I'm a Wealth Adviser: Here's How to Maximize Your Generosity Before the OBBB's 2026 Cap Kicks InWith the OBBB set to dramatically change charitable tax deductions in 2026, donors might want to consolidate gifts into 2025 to lock in current tax benefits.
-
I'm a Financial Planner: Here's How to Make the Most of Your Charitable Giving on a BudgetMaximizing the charitable donations you plan to make this year can help your financial plan stay on track and help give the most to the causes you care about.
-
I'm a Wealth Planner: These 3 Steps Can See You and Your Heirs Through a Wealth TransferBoth givers and receivers need to be seriously strategic about communicating, understanding tax efficiency and leveraging smart money moves.
-
Unwrapping Your Estate Plan for Your Kids: A Gift That'll Keep Giving Long After the HolidaysThe holidays offer families a perfect opportunity to discuss important, often difficult topics like long-term care, estate plans and legacy.
-
5 Ways to Teach Your Kids About Giving Back, From a Financial PlannerTeaching kids generosity goes beyond simple rules and can involve fun, practical strategies, such as letting them lead giving, volunteering together and more.
-
I'm a Financial Planner: Here's How You Can Use AI to Improve Your FinancesApps can help with budgeting, saving and investing, financial coaching and debt management. But providing your personal information can also raise your risks.
-
When Checkout Charity Gets Uncomfortable — and Maybe Even IllegalCashiers asking customers to 'round up' their total for charity can cross an ethical line if there's no disclosure about the benefiting organization.