Succession Coaching
You know you need a succession plan—you just do not know where to start.
Succession is not just about picking a date and drafting documents. For many business owners, it starts with something less concrete: a feeling that change is coming—but uncertainty about what that change should look like.
At Firefly Insights, we do not rush you into a decision. We coach you through it. Whether you are exploring an exit for the first time or reevaluating your original plan, we help you slow down, ask the right questions, and design a transition that works—for you, your team, and your legacy.
What is Succession Coaching?
Succession coaching is not just about preparing to leave—it is about making thoughtful decisions that shape the future of your business, your role, and your legacy. Whether you are years away from transition or already feeling the pressure to decide, we help you slow down and explore the questions that matter most.
At Firefly Insights, we help you:
Clarify what you really want—for yourself, your team, and your company
Understand what your business is worth and how to unlock that value
Identify and prepare the right successor or leadership team
Explore all your options—including employee ownership, family transfer, or third-party sale
Weigh the financial, tax, and cultural implications of each path
Move forward with confidence, knowing your plan reflects your values
You do not need to figure it all out at once. We guide you through the process so you can make the right decisions—when you are ready.
Your Transition. Your Terms.
Every business owner’s journey is different—and so is every transition. Rather than starting with a pre-set path, we start with your goals. We work alongside you to design a plan that reflects your values, supports your team, and protects what you have built.
Clarifying your visions
Are you looking for a full exit, a phased transition, or a new role in the business? We help you explore what “stepping back” really means—for you, your team, and your future.
Exploring all pathways
From family transfers and employee ownership to third-party sales, we map out the full landscape so you can make confident, informed decisions.
Preparing the business
We work with you—and your team—to ensure the company is “transition-ready,” with the right structures, people, and communications in place for a smooth handoff.
Bringing in the right partners
Whether legal, financial, or cultural, we help you bring the right advisors to the table at the right time—so every piece of your plan fits together.
Is Succession Coaching Right for You?
Succession coaching is not about making a decision today. It is about giving yourself the time, support, and perspective to make the right decision when you are ready.
You might benefit from this process if:
You are unsure whether you are ready to step away—or what stepping away even means
You thought you wanted to sell, but something about it does not sit quite right
You want to explore options like employee ownership, but do not know where to start
You are thinking about the future—not just for yourself, but for your team and community
Many of the business owners we work with know they need a succession plan, but feel unsure where to start. We help you build clarity, test your thinking, and explore what a good exit could really look like—on your terms, and in your time.
How We Work with You
Clear, collaborative, and tailored to your business.
There is no set formula for succession—because no two business owners are starting from the same place. That is why we offer a flexible, month-to-month engagement model that meets you where you are and adapts as your clarity grows.
You set the pace. We help you keep momentum.
Each month, we typically:
Meet for a structured, confidential coaching session
Clarify your goals, concerns, or decision points
Explore your options and the trade-offs behind each one
Identify next steps—whether internal conversations, leadership prep, or further exploration
Introduce trusted professionals when needed, at the right time
Whether we work together for a few months or long term, the process is designed to give you space to reflect and the support to move forward—with confidence, not pressure.
Questions You Might be Wondering
When should I start thinking about succession planning?
Ideally, the day you start your business—but practically, the sooner the better. Even if you are years away from stepping back, starting early gives you more options, smoother execution, and space to make thoughtful decisions.
What if I am not ready to step away yet?
That is completely okay. Succession coaching is not about rushing decisions—it is about creating the space to think things through and prepare for the moment you are ready, whenever that may be.
I don’t have a successor in mind. Can you still help?
Absolutely. We help you explore all your options—including identifying and preparing someone within your team, or building toward a different kind of transition.
What if I do not know what kind of transition I want yet?
That is exactly what succession coaching is for. We help you unpack your goals, test your assumptions, and explore all available paths—so you can make decisions with clarity, not pressure.
How long does the process take?
That depends on where you are starting and what you need. Some clients work with us for a few months to clarify direction; others stay engaged longer as they build out leadership capacity or prepare the business for transition. We move at your pace.
How is this different from traditional succession planning or exit advice?
We do not push a single outcome. Instead, we coach you through the thinking, help you explore your options, and support you in building a transition plan that truly fits. You lead the process—we help you navigate it.
Let's Talk
Curious about how it works—or if it’s even possible for your business? Let’s start the conversation. You’ll walk away with clarity and next steps, no pressure.