Dear Business Owner,
If you’re holding this guide, you’re already doing something most owners don’t: you’re thinking ahead.
That alone sets you apart.
Whether you’re five years from exiting or just beginning to wonder what would happen if you stepped away, you’re in the right place. Succession planning doesn’t start with spreadsheets or lawyers. It starts with clarity: about what you want for your business, your team, and your legacy.
For family-owned and founder-led businesses, those conversations are often more emotional than tactical. That’s normal. After all, this business is personal. You’ve poured your energy, your values, even your identity into it. And now you’re supposed to plan your exit?
It’s no wonder so many put it off until it’s too late.
This guide is designed to help you take the first, low-pressure step. No jargon. No pressure to make sweeping decisions today. Just a simple framework to begin thinking, asking, and preparing with intention.
If you’re a business advisor, venture partner, or investor who supports founders through transitions, feel free to share this. It’s a trusted conversation starter for clients who may not know where to begin, but who need to.
Inside, you’ll find:
- A practical readiness checklist
- Common pitfalls to avoid
- Questions to help you clarify your next chapter
- An invitation to talk, if you want help thinking it through
You don’t have to have all the answers yet. You just have to be willing to start asking the right questions. That’s where real legacy begins.
Warmly,
Sandra Lief
What Is Succession Planning—And Why Now?
Succession planning is simply the process of preparing your business for a future without you at the helm.
It’s not about naming a replacement tomorrow. It’s about putting the right pieces in place so that—when you are ready—the business, the people, and the value you’ve built are ready too.
⚠️ Why Many Business Owners Avoid It
“I’m not ready to step away.”
“My kids aren’t ready.”
“We’ll figure it out when the time comes.”
“There are too many emotions involved.”
Sound familiar? You're not alone. For many founders—especially in family-owned businesses—the idea of stepping back feels risky, emotional, or unnecessary... until it's urgent.
But the truth is, delaying succession planning doesn’t preserve stability-it just postpones uncertainty.
💡 Why Start Now?
Even if you're years from an exit, succession planning offers clear benefits today:
✅ Protects Business Value
A business with a succession plan is more resilient and far more valuable to buyers, partners, and investors.
✅ Strengthens Leadership
Succession conversations often reveal hidden gaps in skills, roles, and structure—giving you time to develop your bench strength.
✅ Reduces Family or Team Tension
Early planning creates clarity and transparency, avoiding power struggles or misunderstandings later.
✅ Builds Optionality
Whether you're planning to sell, pass the torch, or stay involved in a different way—succession planning gives you choices.
Venture partners and business advisors take note:
Founders who engage in early succession planning are more likely to achieve a successful, values-aligned exit—because they’re not rushing to make decisions in a pressure cooker.
🧭 You Don’t Have to Know the End Game
Succession planning isn’t about deciding everything right now. It’s about opening the door to smarter questions and more confident leadership.
The next page includes a Succession Readiness Checklist to help you see where you stand—and where to start.
The Succession Readiness Checklist
Where do you stand today?
Use this quick-check tool to assess how prepared your business is for a leadership transition—whether that’s five months or five years from now.
✅ Succession Readiness Checklist
|
✔️ |
Question |
|---|---|
|
☐ |
Do you have a written succession plan (even a draft)? |
|
☐ |
Have you identified potential successors—family or otherwise? |
|
☐ |
Have you talked with those successors about their interest and readiness? |
|
☐ |
Are roles, responsibilities, and decision-making authority clearly defined across leadership? |
|
☐ |
Is there a formal leadership development process in place? |
|
☐ |
Do key employees know how the business would run without you? |
|
☐ |
Have you spoken with legal and financial advisors about ownership transition? |
|
☐ |
Has your family discussed the long-term vision for the business—openly? |
|
☐ |
Is there a plan in place in the event of an unexpected exit or emergency? |
|
☐ |
Have you involved an outside advisor to help guide these conversations objectively? |
🟡 How to Use This Checklist:
- 8–10 checks: You’re ahead of the curve. Now’s the time to refine and align with your successors.
- 4–7 checks: You’ve started, but there are gaps to fill. Don’t wait for a crisis to do it.
- 0–3 checks: It’s early—but this is the perfect moment to begin.
👣 Next Step
Every checkmark here represents clarity, alignment, and peace of mind—for you, your team, and your family. If you’d like help thinking through these areas, contact us and we’ll schedule a call.
The 3 Most Common Succession Pitfalls
Even the most successful leaders can stumble when it comes to succession. These pitfalls are especially common in founder-led and family-owned businesses—where emotions, relationships, and identity are deeply entwined with the company.
❌ Pitfall #1: Waiting Until It’s Urgent
“We’ll deal with that next year.”
It’s easy to push this off—until illness, burnout, or an unexpected offer forces your hand. Without a plan in place, you’re left making critical decisions in a pressure cooker. And so is your family or team.
📌 Pro Tip: Start the conversation years before you think you need to. The earlier you begin, the more options you have.
❌ Pitfall #2: Assuming They Want It
“Of course my kids will take over.”
Maybe. Maybe not. Many family transitions derail because the successor never wanted the job—or didn’t know they were expected to take it. Or worse, multiple family members assume they’re the one.
📌 Pro Tip: Replace assumptions with conversations. Interest, readiness, and capability all matter.
❌ Pitfall #3: Doing It Alone
“This is a family matter—we’ll figure it out internally.”
Without a neutral perspective, succession discussions can quickly become emotional, political, or avoidant. Outside guidance helps keep the process objective, strategic, and on track.
📌 Pro Tip: A trusted third party—like a business valuation advisor, executive recruiter, or family business consultant—can help you navigate decisions with clarity and confidence.
🧭 Remember:
These pitfalls don’t happen because people don’t care.
They happen because succession feels overwhelming, personal, and easy to postpone.
This guide is your invitation to step forward—with clarity, not fear.
Let’s Talk Succession
You don’t have to make big decisions today.
But if this guide sparked questions, stirred some reflection, or simply reminded you that the future deserves your attention—you’re exactly where you need to be.
This Starter Kit is yours to keep, share, or revisit whenever the timing feels right. There’s no agenda here—just an invitation to begin thinking differently about what’s next.
💬 When You’re Ready, We’re Here
Whether you’re:
- Two years out from retirement or ten
- Exploring a sale, or preparing the next generation
- Or simply wondering how to begin the conversation
You don’t have to do it alone.
The right hire doesn’t just fill a role—they protect your legacy.
And that’s where we come in. When the time comes, we’re here to help you move forward with clarity, care, and confidence.
At FairchildHR, we specialize in succession planning from the talent side—helping business owners identify leadership gaps, align the right people with the right roles, and build a future-ready team.
Until then, feel free to pass this guide along to anyone in your circle who might benefit.
Warmly,
Sandra Lief
President, FairchildHR
📧 This email address is being protected from spambots. You need JavaScript enabled to view it.
🌐 www.fairchildhr.com
