How to Avoid the Mess Most Businesses Make When It’s Time to Step Away
Key Takeaways
Most business owners wait too long to plan succession
You must get clarity on who’s involved and who makes decisions
Know your business’s real strengths, risks, and leadership gaps
Build a practical, flexible plan that includes leadership, ownership, and financial realities
Communicate it clearly, implement it actively, and update it regularly
Most Businesses Aren’t Ready for the Owner to Leave.
They don’t plan. They hope. Hope is not a strategy.
If you want to build something that outlives you or at least gives you and your family options, you need a real succession plan. One that works in real life, not just in your lawyer’s file.
Let’s break it down.
Identify the Right People First.
You cannot do this alone.
Succession planning starts with figuring out who has a stake and who has a say. That’s usually the owner, the leadership team, key family members, and maybe board members or advisors.
Bring them in early. Let them shape the process, not just respond to it later.
Everything awesome I’ve done in life has been because I’ve been accountable to another human.
This is one of those times.
Know the Real State of the Business.
Before you start grooming successors or shifting shares, look in the mirror.
What’s working? What’s not?
Where is the business vulnerable if you step away for 90 days? Or gone permanently?
What leadership talent is ready, and who needs development?
The best succession plans come from a place of strength, not fantasy. Assess now, fix what needs fixing, then build the plan.
Build a Succession Plan That’s Real.
Succession planning is more than just saying Joe takes over when I’m gone.
You need to outline:
Who is leading
How ownership transfers
What the financial impact is for your business and your family
What happens if you are gone tomorrow
Include legal and tax considerations. Use real deadlines. Plan for real life. Not perfect scenarios.
Tell People. Don’t Leave Them Guessing.
Once you’ve got a plan, talk about it.
Be clear with your team. Your customers. Your partners.
Uncertainty is a killer. People fill gaps with fear. Be the one who sets the tone and shows them what’s coming.
You don’t have to share every line item, but you do need to communicate the why, the what, and the when.
Put It Into Action. Then Watch Closely.
Implementation is not a checkbox. It is a season.
Start preparing successors. Begin transferring responsibilities or equity, depending on your plan.
Track progress. Course correct when needed. Review it at least once a year.
Plans that sit in drawers don’t work. The ones that evolve do.
Keep the Plan Alive.
Markets shift. People change. Life happens.
You have to keep the succession plan alive by checking it often, updating it, and making sure it still works for your future goals.
If you’ve ever said I’ll get to that next year, let me say this.
Life happens, whether we’re ready or not.
Operating from a position of strength means doing the hard work now before you’re forced to.
Bonus reference: For a rigorous take on this topic, see “The Power and Importance of Succession Planning” via Harvard Business School.
If you’re running an agency or SMB and you’re ready to stop guessing about the future of your business, I can help you build a real plan that works for your life.
Not everyone’s a fit. But if this hits home for you, reach out.