For owners who aren't done but know they have to design the future they want.

Consider a recent experience I had, one that plays out more often than you might imagine: an owner spent five decades building two businesses from nothing. Hands-on. Rarely took a vacation. Still showis up every day beacuse it's who he is and what he does.

His wife knows the origin story by heart: a fender bender, a dream, and fifty years of relentless work, in her words, building the American dream. She's his biggest cheerleader. She's also the one watching things slowly change.

He's moving slower. Certain tasks take longer. And every critical piece of operational knowledge from vendor relationships and pricing to maintenance schedules and invoicing exist in his head.

Her concern didn't arrive as a crisis. It arrives every morning when it's harder for him to get up and every night when he comes home exhausted.

If something happens to him, I wouldn't know where to start.

So she asked for help. Not to push him out. Just to document the business well enough that she wouldn't be left scrambling.

We developed and presented a thoughtful plan that required his involvement.

He respectfully said no.

He's ok with things changing when he's gone but for now he sees no need to change anything. She'll figure it out when she has to.

If you've spent even a few years building a business, you probably understand why it often feels 'too soon' for this conversation.

This Isn't Resistance. It's Identity.

It's tempting to label that moment as avoidance. But that framing misses the point.

For most long-tenured owners, their business isn't a job. It's the primary vehicle through which they've defined themselves and taken care of their families.

Perhaps you can relate.

Your business is your biggest headache and proudest acheivement. Working the way you do is deeply engrained, a familiar routine that gives your days structure and years meaning. Contracts, clients, suppliers, new products and markets, and competitors are all characters in your life story.

So when someone raises the question of what happens if you're no longer in the picture, it doesn't feel like planning. It feels like a threat.

Who am I if I'm not doing this?

That question rarely gets asked out loud. But it drives almost every response in the conversation.

Owners Feel the Shift Before They Acknowledge It

Here's what's rarely said plainly: most owners, like you, have already experienced changes in how you relate to and operate in your business.

What you had patience for in year one is grinding you down in year 10. What felt challenging in year 12 is exhausting in year 21. You can't believe you're still having some of the same conversations. Some days, you might even feel trapped by what you created.

And yet, you keep on going.

You're not in denial though you may be overly optimistic about the likelihood that things can change or your willingness to make changes happen. It's the hard you know, which is more comfortable than the unknown of what a second or third act might look like.

Figuring out what's next not only feels hard but scary. Anyway, you're not ready be done so you'll figure it out "when you have to" which usually means figuring it out too late.

What the People Around You Are Actually Trying to Do

When a spouse, child, business partner, or employee raises questions about your succession or exit plan, it's rarely a power play.

It's contingency planning driven by the very real fear of being handed the wheel without knowing where anything is or how to keep things from falling apart.

When that concern surfaces directly, it can land as pressure. You probably respond by shutting down to protect yourself. The people who care about you shut down when you react by making them feel like they're sticking their nose in or challenging you.

Without a shared framework for the conversation, families and businesses cycle through the same tension for years without resolution, speaking different languages about how they feel, what they fear, and what's at stake.

The Cost Doesn't Announce Itself

Sometimes these things sort themselves out.

More often, what happens is slower and messier. In the midst of grief, crisis, or strained relationships, successors struggle to reconstruct institutional knowledge from scratch. Decisions get made without the context that would have lead to different choices. Feeling get hurt and relationships suffer.

Sometimes it all unravels before the owner's eyes without anything they can do about it. In other situations, the owner's intent gets lost and things actually do come apart at the seams when they are gone.

That's the part no one sees coming. Or they think it won't happen to them and their family.

This Is Not an Exit. It's an Extension.

Business transitions, succession planning, exit planning, and even estate planning are almost always positioned as endings to be avoided.

Instead, they can be a continuation or an evolution that, as the business owner, you can control and design.

The shift starts when you ask yourself

These questions create options, new ways of thinking about how you show up in your business, and how you can make intentional choices that preserve and take care of the assets, legacy, and people you care about.

Your "What's Next" plan for you and your business won't be created in a single meeting or a few legal documents. And it won't be created alone. That's why it's never 'too soon' to start thinking about what you want and how to make it happen.

The Decision

Work is how most people define themselves and measure their value or self worth, so it's reasonable to expect that being a business owner may always be a huge part of your identity and personal narrative.

The deeper issue is how to separate yourself from your business enough to enjoy other parts of your life and make it feasible for other people to run your business when you no longer want or are unable to be there.

Transitions are a part of life. There was once a time when you didn't own a business or a house. Maybe a time when you didn't have kids or live near your parents. When you could water ski rather than play pickleball.

And there will be a time when you are no longer running your business. The question is, can you stop seeing that as a threat and embrace the opportunity to design your life, identity, and business in ways that transcend this moment?

When was the last time your were in love with your business?

If you're like most business owners, your business is successful enough to support your life. Growth is still possible. But the work still demands an enormous amount of time and attention.

You're tired of wearing every hat.
You're don’t want every decision running through you.
You’re starting to wonder how long you want to keep working this hard.

And a question begins to surface:

Wasn’t this supposed to get easier?

It’s a reasonable question.

But the answer usually isn’t working harder, hiring faster, or chasing the next growth strategy.

More often, the answer begins with a different kind of thinking.

It begins with exit planning.

Exit Planning Isn’t About Leaving Your Business

Many owners assume exit planning is something you start when you’re ready to sell your company.

But that assumption creates one of the biggest strategic blind spots in entrepreneurship.

Exit planning isn’t about leaving your business.
It’s about building a business that doesn’t depend entirely on you.

When you approach your business with the end in mind—thinking about how leadership might transition someday, how decisions get made, and how the company could operate without you—you begin strengthening the very things that make ownership more enjoyable today.

Exit planning becomes less about an event in the future and more about how you build the business now.

What Exit Planning Actually Means

Exit planning is the process of preparing both the business and the owner for an eventual transition of leadership or ownership.

That transition could take many forms:

Regardless of the path, the work focuses on strengthening the foundations that make a business durable and transferable:

These improvements increase business value.

But they also make the company far easier and more enjoyable to run today.

Why Exit Planning Improves the Experience of Ownership

The businesses owners describe as the most rewarding to lead tend to share a few characteristics.

In other words, they are businesses that can operate successfully without the owner at the center of everything.

Ironically, those are also the businesses that are easiest to sell or transition.

But even if an owner never intends to sell, building a business this way creates something far more valuable in the meantime.

It creates freedom.

Why Many Owners Wait Too Long

Most business owners spend years building their companies.

They focus on customers, employees, growth, and solving the next operational challenge.

Thinking about stepping away someday can feel distant—or even uncomfortable.

For some owners, it raises questions they would rather avoid.

So the conversation gets postponed.

But here’s the truth every owner eventually faces:

Every business owner will transition out of their company at some point.

The only real question is whether that transition happens by design or by default.

Building With the End in Mind

When exit planning becomes part of how you think about your business, your decisions begin to change.

You start asking different questions.

These questions don’t just prepare the business for a future transition.

They help you build a business that works better today.

The Real Goal of Exit Planning

The goal of exit planning isn’t simply preparing to leave your business someday.

The real goal is building a company that gives you options.

And when a business is built this way, something interesting happens.

It often becomes exactly the kind of business owners hoped they were building all along.

One that is profitable.
One that is resilient.
And one that is genuinely satisfying to own.

FAQs

What is exit planning for a business owner?

Exit planning is the process of preparing a business and its owner for an eventual transition of leadership or ownership by strengthening leadership teams, systems, and financial performance.

Is exit planning only for owners who want to sell their business?

No. Exit planning helps owners build businesses that can operate successfully without them, whether they plan to sell, transition leadership internally, or simply work less.

How does exit planning make a business easier to run?

Exit planning strengthens leadership teams, systems, and processes so the business no longer depends entirely on the owner for decisions and operations.

When should a business owner start exit planning?

Many advisors recommend beginning exit planning five to ten years before a potential transition so there is time to strengthen leadership, improve systems, and increase business value.

Why does exit planning increase business value?

Exit planning improves the factors buyers care most about, including predictable cash flow, leadership depth, operational systems, and reduced dependence on the owner.

More FAQs

When business owners tell me they’re doing strategic planning, it usually means they are defining next year’s revenue targets, hiring plans, and a few growth initiatives.

That’s important.

But if you’re also wondering things like:

• Can this business run without me?
• What would it actually sell for?
• Am I building something scalable — or just a demanding job?
• Should I grow, specialize, or eventually sell?

…then the kind of planning you do today matters a lot more than next year’s numbers.

Because businesses that become valuable, transferable assets are rarely built by accident.

They’re built by leaders who think about the future in four different ways, each answering a different leadership question.

The Four Types of Planning Business Owners Should Understand

Business owners thinking about growth, succession, or eventual exit should understand four distinct planning approaches:

  1. Scenario planning – explores possible futures that could impact the business
  2. Strategic planning – defines the direction and priorities of the business
  3. Business model planning – determines how the company generates revenue and creates value
  4. Contingency planning – prepares the business to respond quickly to disruptions

When used together, these approaches help business owners increase valuation, reduce owner dependence, and build a business that can operate beyond the founder.

Let’s use a Managed Service Provider (MSP) as an example.

Scenario Planning: What Could the Future Look Like?

Before choosing a direction, leadership explores possible industry shifts.

For MSPs today, those might include:

• Private equity continuing to acquire regional MSPs, accelerating consolidation
• AI dramatically reducing Level-1 helpdesk tickets through automation
• Cybersecurity becoming the primary reason clients hire MSPs
• Microsoft, AWS, and other vendors expanding managed services offerings
• Clients demanding vertical expertise rather than general IT support

The goal isn’t predicting the future.

It’s asking better questions:

Scenario planning broadens thinking about what might happen so leaders can design strategies that remain effective under different conditions.

Strategic Planning: Where Are We Going?

After examining several possible futures, the MSP defines its direction.

For example:

Become the cybersecurity and compliance partner for regulated small and mid-size businesses in our region.

Strategic initiatives might include:

• Building Managed Detection & Response (MDR) capabilities
• Developing expertise in frameworks such as HIPAA, SOC 2, or CMMC
• Partnering with cybersecurity and compliance platforms
• Expanding vCIO advisory services
• Specializing in industries like healthcare, finance, or manufacturing

Strategic planning defines where the business is going and what it will prioritize.

Business Model Planning: How Will We Create and Capture Value?

Next comes designing how the company generates revenue and delivers value within that strategy.

Examples might include:

• All-inclusive per-user managed IT and security bundles
• Recurring Managed Detection & Response subscriptions
• Compliance monitoring and reporting services
• vCIO strategic advisory retainers
• Cybersecurity incident response retainers

This is where strategy becomes predictable revenue, improved margins, and increased enterprise value.

A well-designed business model is often one of the biggest drivers of business valuation and transferability.

Contingency Planning: What Will We Do When Something Breaks?

Finally, leadership prepares for disruptions and unexpected events.

Examples for MSPs include:

• If a ransomware attack hits multiple clients, activate an incident response protocol
• If Microsoft changes licensing rules, adjust pricing and contracts quickly
• If a key engineer leaves, shift clients to documented service delivery and cross-trained staff
• If a strategic buyer approaches, understand your company’s current valuation and what a good deal would look like

Contingency planning ensures the business can respond quickly to disruption while protecting profitability and long-term value.

Why This Matters for MSP Owners

For MSP owners, these layers of planning aren’t theoretical.

They shape how your business responds to rapid changes in technology, cybersecurity threats, vendor ecosystems, and industry consolidation.

A strategy built on a single assumption about the future can become fragile quickly.

And fragile businesses are difficult to scale, difficult to transfer, and difficult to sell.

The MSPs commanding the strongest valuations today tend to look different.

They are:

• security-focused
• built around recurring revenue
• operationally documented
• supported by strong teams
• less dependent on the owner
• able to scale beyond the founder

In other words, they’re not just good service businesses.

They’re transferable assets.

Why This Matters for Every Business Owner

This idea isn’t unique to MSPs.

It applies to every industry.

Whether you run a construction company, marketing agency, manufacturer, professional services firm, or retail business, the same reality holds:

A business that depends entirely on the owner is hard to scale, hard to step away from, and hard to sell.

The businesses that create the most freedom, flexibility, and long-term wealth for their owners tend to be the ones built to operate beyond them.

In fact, roughly 80% of businesses that go to market never sell, often because they rely too heavily on the owner or lack transferable systems and leadership.

That’s why succession planning and exit planning shouldn’t be last-minute activities.

They’re strategic disciplines that help owners strengthen the very things that drive business value, resilience, and optionality.

Questions Every Business Owner Should Ask About the Future of Their Business

No matter what industry you're in, these questions can help you think more deeply about the business you're building.

• If you stepped away for two weeks with no phone or laptop, would your business keep running smoothly?
• Are clients loyal to the company, or primarily to you?
• Does your revenue model create predictable income, or constant reinvention?
• Could someone else clearly understand how the business works from your systems and documentation?
• If a buyer showed up tomorrow, what would make your business more valuable — or less?

Sometimes the most important strategic question for an owner isn’t simply:

How do we grow?

It’s:

What kind of business am I actually building?

FAQs

When should a business owner start succession or exit planning?

Ideally several years before a transition. The most successful owners treat succession and exit planning as present-tense strategic activities, integrated into annual planning and leadership development.

What makes a business transferable or valuable?

Businesses that can operate without the owner, generate predictable cash flow, and rely on documented systems and strong leadership teams tend to command higher valuations.

Can you increase the value of your business even if you never plan to sell?

Yes. The same practices that increase valuation — recurring revenue, leadership depth, documented systems, and reduced owner dependence — also make businesses easier and more enjoyable to operate.

More FAQs

Most business owners measure success using familiar metrics:

Those numbers matter.

But here’s a question many owners never ask:

Did your business become more valuable this year?

Not just busier.
Not just more profitable.

More valuable.

Because revenue pays the bills.
Profit funds your lifestyle.

But business value creates wealth and optionality.

What Does It Mean for a Business to Increase in Value?

A business increases in value when it becomes less risky and more transferable to another owner.

Buyers don’t pay for effort, loyalty, or years of hard work.
They pay for predictable, transferable cash flow with manageable risk.

That means a company’s value is influenced by factors like:

When these improve, the business becomes more attractive to buyers, lenders, and potential partners.

And its valuation increases.

Can Revenue Growth Decrease Business Value?

Surprisingly, yes.

A business can grow revenue and still become less valuable if the growth increases risk.

For example:

Growth that increases dependency or volatility can reduce what buyers are willing to pay.

That’s why focusing only on revenue or profit can be misleading.

The Real Question Behind the Question

When I ask owners how much their business increased in value this year, what I’m really asking is:

These questions reveal something financial statements alone often hide:

How transferable your business really is.

The Drivers That Determine Business Value

Buyers evaluate businesses primarily through the lens of risk and sustainability.

The most common value drivers include:

Revenue Diversification

Heavy reliance on a few customers creates risk.

Leadership Depth

Businesses dependent on the owner are harder to transfer.

Margin Consistency

Predictable profitability supports higher valuation multiples.

Documented Systems

Standard operating procedures make a business teachable and scalable.

Recurring Revenue

Contracts, subscriptions, and repeat business reduce revenue volatility.

Customer Concentration

A broad client base protects future cash flow.

Improving these drivers steadily increases the value of the business.

Why Business Owners Should Track Valuation as a KPI

Most companies track performance using:

But very few track valuation as a performance metric.

And what you don’t measure is difficult to intentionally improve.

When owners start thinking about valuation as a KPI, decisions change.

They think differently about:

They stop building a job.

And start building an asset.

Build for Value Even If You Never Sell

You don’t have to plan to sell your business to benefit from building one that is valuable.

In fact, the businesses that are easiest to sell are usually the most enjoyable to own.

Because they:

In other words, they give the owner something many entrepreneurs eventually realize they want:

Freedom.

If You Don’t Know Your Business Value

If you’re not sure what your business might be worth today—or what factors are increasing or decreasing its value—an Enterprise Value Assessment can provide a baseline.

It helps identify:

Once you understand those drivers, you can begin making decisions that improve the value of the business over time.

And when the day comes that you want to sell, transition leadership, or simply step back, you’ll have far more options.

A Simple Exercise for Business Owners

If you want to start thinking about your company’s value more intentionally, ask yourself:

  1. What would my business likely sell for today?
  2. What valuation multiple would a buyer apply and why?
  3. What are the top three risks that would reduce that multiple?
  4. What one improvement would increase value the most over the next year?

If you can’t answer those questions with confidence, you’re not alone.

Most owners have never had a structured conversation about what drives the value of their business.

Book a call to learn more.

FAQs

What determines the value of a business?

Business value is driven primarily by predictable cash flow, growth potential, and risk factors such as owner dependence, customer concentration, and operational systems.

Why do profitable businesses sometimes fail to sell?

Many businesses depend heavily on the owner or lack transferable systems and leadership depth, which increases risk for buyers.

Should business valuation be tracked as a KPI?

Yes. Tracking valuation as a KPI encourages owners to focus on factors that improve transferability, sustainability, and long-term wealth creation.

More FAQs

Design Your Future on Purpose

Complete the Owner's Compass Questionnaire

At some point, you reach a quiet crossroads as a business owner.

Your business is successful enough to meet your financial needs but it still demands tremendous amounts of your time and attention. Growth still feels possible, but you’re not sure you want to work that hard anymore. You may be thinking ‘Wasn’t this supposed to get easier?’. Selling sounds appealing, but overwhelming. Succession is something you talk about and then set aside.

So the question starts to surface:

Should you keep growing your business or should you start preparing to exit?

It’s a reasonable question.
But not a terribly useful one.

The Real Issue Isn’t Whether to Stay or Sell.

It’s Alignment.

When you frame your decision as grow versus sell, you’re oversimplifying what’s really going on.

What you’re actually wrestling with is:

Until you get clear on those things, any strategic decision - growth, succession, or exit - will feel incomplete.

Why More Information Hasn’t Solved This

When you feel stuck, your instinct may be to look for answers in:

Those are important tools—but they assume you already know what you’re optimizing for.

Without that clarity, patterns tend to emerge:

The problem isn’t a lack of options.
It’s failure to orient first before taking action. 

Introducing the Owner’s Compass 

The Owner’s Compass was designed to help you answer a more fundamental question:

Given who you are, what you want next, and what’s true about your business, what paths actually make sense for you right now?

Instead of forcing you into a single decision, the Compass helps you:

It doesn’t tell you what you should do.
It helps you understand what is and can become true for you.

What the Questionnaire Asks You to Consider

The Owner’s Compass looks at the factors that shape every owner’s options:

Together, the results place you along a continuum of viable paths, rather than pushing you into a box.

What You Learn About Yourself

Owners who complete the Owner’s Compass often begin to see whether you’re really seeking:

Once that’s clear, decisions stop feeling so heavy.

Why This Matters Now

Your energy changes. Markets shift. Life evolves.

The biggest mistake you can make isn’t choosing the “wrong” strategy - it’s committing to a path that doesn’t fit who you are or what’s actually true about your business.

Clarity doesn’t force a decision.
It creates better ones.

If you’re feeling tension between growth, transition, and exit—or if you sense that something needs to change but you’re not sure what—the Owner’s Compass is a powerful place to begin.

Schedule your free one-hour consultation to review your Owner Compass finding and make clearer strategic decisions this year.

FAQs

How do I decide whether to grow, transition, or exit my business?

The decision depends on alignment between your personal goals, your risk tolerance, and the current state of your business. Owners who understand what they want next and how dependent the business is on them can make clearer strategic decisions about growth, succession, or exit.

Is growing your business always the best strategy?

Not necessarily. Growth that increases complexity, risk, or owner dependence can reduce freedom and long-term value. The best strategy is the one aligned with your goals and the realities of your business.

When should a business owner start thinking about transition or exit planning?

Ideally, owners should start thinking about transition planning five to ten years before a potential exit. Starting early provides time to build leadership, strengthen operations, and increase the value and transferability of the business.

What is the difference between transitioning and exiting a business?

Transitioning typically means stepping back from day-to-day operations while ownership remains intact or shifts gradually. Exiting usually involves transferring ownership through a sale, succession plan, or merger.

Why do many business owners struggle with the grow vs. exit decision?

Many owners frame the decision too narrowly as grow or sell, when the real issue is whether the business still fits the life they want next. Questions about identity, risk, and personal goals often shape the decision as much as financial considerations.

Can a business grow while preparing for transition?

Yes. In fact, the strongest businesses grow while simultaneously improving leadership depth, systems, and profitability so the company can operate without relying entirely on the owner.

What is the Owner’s Compass?

The Owner’s Compass is a framework designed to help business owners evaluate their personal goals, business readiness, and strategic options so they can identify the paths that make the most sense for their future.

More FAQs

I know what you’re thinking — it’s “too soon” to think about succession and exit planning.

You’re not alone. That’s what most business owners think, whether they’re five years or three decades into their business journey. But waiting until you’re ready to sell or have to leave the business because of life circumstances means you’ll likely end up like most of your peers: part of the 80% of businesses that go to market and never sell, or among the 70% of family-owned companies that never make it to the second generation.

It doesn’t have to be that way. With advanced planning and intentional strategies, you can exponentially increase the likelihood that you’ll exit on your own terms with clarity, confidence, and control.

Below are five readiness essentials that every business owner should start working on now, no matter your industry.

This article was originally published in the September 2025 issue of Independent Dealer.

1. Solidify Your Financial Foundations

If your financials are rock-solid, great. If not, now’s the time to clean them up.

That means accurate, up-to-date profit and loss statements, balance sheets, and cash flow analyses — all prepared in a way that a potential buyer or successor can easily understand.

It might also mean evaluating whether the advisors who’ve helped you so far are the right ones to position your business for a successful transition. Transparency and professionalism in your financials boost both your credibility and your valuation.

2. Clarify and Strengthen Operational Know-How

Can your business run smoothly without you?

Start documenting everything that keeps your operations humming from how you manage vendors and customers to how you deliver your product or service.

Create clear standard operating procedures (SOPs), integrate technology where it helps, and ensure that systems and processes are teachable and transferable. The more your knowledge is embedded in the organization, the more resilient and valuable your business becomes.

3. Cultivate Your Human Capital

Your people aren’t just employees — they’re your company’s most valuable asset and the key to its continuity.

Identify those with deep customer relationships or essential skills and start preparing them for leadership now. Coaching, mentorship, and intentional development not only prepare your next generation of leaders but also make your business more attractive to buyers or successors.

A business that can thrive without being dependent on one person — especially the owner — is a business built to last.

4. Differentiate and Communicate

In a world of sameness, your differentiation is your superpower.

Too many businesses are “the best-kept secret” in their market. Strengthen your brand, clarify your message, and communicate what truly sets you apart.

Whether it’s exceptional service, specialized expertise, community impact, or innovation make sure your market (and potential buyers) know your value. A well-defined and visible brand doesn’t just attract customers it attracts opportunity.

5. Define What a “Good Exit” Looks Like for You

This one’s personal. A “good exit” isn’t just about the money. It’s about what matters most to you.

Maybe it’s keeping the business in your family. Maybe it’s rewarding loyal employees through an internal sale. Maybe it’s maximizing value and moving on to your next adventure.

Knowing your ideal outcome early shapes every decision you make from your financial preparation to who you hire and how you structure deals. Without that clarity, even good offers can create stress and second-guessing. With it, you can move forward with purpose and peace of mind.

Plan to Finish Strong

Succession and exit planning aren’t about endings; they’re about continuity. They’re about ensuring that your business, your people, and your legacy continue to thrive long after you’ve moved on to your next chapter.

The best time to start was yesterday. The second-best time is today.

When you plan with purpose, you give yourself and your business the future you both deserve.

Are you ready for the peace of mind that comes from knowing your financial house is in order, your operations can thrive without you, your people are prepared to carry the torch, and your unique value is clearly understood by the market? Then let's make it happen together!

FAQs

When should a business owner start planning their exit?

Ideally, business owners should begin exit planning five to ten years before they expect to transition or sell their company. Starting early allows time to strengthen operations, develop leadership, and increase the company’s valuation.

What makes a business easier to sell?

Businesses that are easier to sell typically have:

These factors reduce risk for buyers and increase valuation.

What is the biggest mistake owners make when preparing to exit?

One of the most common mistakes is waiting too long to start planning. Owners who delay exit preparation often discover that their business depends heavily on them or lacks the systems and leadership buyers expect.

Do I need to plan an exit if I don’t intend to sell my business?

Yes. Building a business that is exit-ready improves profitability, resilience, and leadership capability—even if you ultimately choose to keep the company or pass it to family members or employees.

How can a business owner increase the value of their company before selling?

Owners can increase business value by:

These changes improve transferability and reduce buyer risk.

What is a successful business exit?

A successful exit is not defined only by the sale price. It occurs when the transition aligns with the owner’s financial goals, personal priorities, and legacy for employees, family, and customers.

How long does it take to prepare a business for sale?

Most businesses require three to five years of preparation to maximize valuation and ensure the company can operate successfully without the owner.

More FAQs

A few months ago, Dr. Donna Marino and I decided to do a series of LinkedIn Live conversations about grief in business. It’s something we’ve both experienced personally and often find ourselves helping clients navigate.  

We started by looking at what it means to be a business owner or a sudden successor who has to keep everything going while experiencing the sudden loss of a loved one, a prolonged illness, a business partner's passing, or a personal crisis like divorce. By the end of our first conversation, Donna and I had identified ways to think about preparing for, navigating through, and managing grief in your small or family business. 

First and foremost, your main job is to take care of you, the person who is grieving, before you worry about your business. The best way to do that is to prepare for loss when you’re not actively experiencing it.

1. Before the loss: Building a business that can withstand life’s uncertainties

Having a business continuity plan in place means that when a crisis occurs, your team is prepared to support you so you can take care of yourself and your family. 

Legal and financial readiness

Many owners assume that family or team members will “step in” if something happens to them. But assumptions are not strategies which is why succession planning is so important.

Operational continuity planning

If your business depends on you to function day-to-day, it’s more vulnerable than you think.

Emotional and leadership resilience

You won’t lead well through grief if you haven’t made it a habit to practice vulnerability and self-awareness. Investing in your ability to manage and cope with stress is one of the best ways to build resilience and overcome adversity.

2. During the loss: Leading through crisis without losing yourself

When grief strikes, leadership is still expected. That doesn’t mean you have to go it alone or go at full capacity.

Communicate honestly with your team

Your people don’t expect perfection, but they do need clarity.

Redistribute and prioritize workloads

This is not the time to carry everything on your shoulders.

Protect your cognitive and emotional capacity

Grief affects your brain. Executive functioning, memory, focus, and emotional regulation all take a hit.

3. After the loss: Rebuilding with intention

Once the initial storm passes, there’s often an urge to “get back to normal.” But a wiser question is: What version of normal do I want now?

Reevaluate your leadership role and business design

Grief changes you. Use that change to create a new relationship to your business that is more aligned to your personal priorities.

Institutionalize what you’ve learned

Treat your experience as a case study in business resilience.

Shift the culture around grief

Many companies offer one or two days of bereavement leave — often only for immediate family. That doesn't reflect the reality of loss, especially in close-knit or family-run businesses.

You can be a leader and still be human

Grief is not a detour from leadership; it is leadership. How you prepare for it, how you walk through it, and how you grow from it speaks volumes about the kind of leader you are.

There is no way to avoid loss, but there are many ways to avoid chaos, burnout, and isolation when it happens. If you’re building a business that’s meant to last, grief readiness must be part of your continuity plan in anticipation of the day when it won’t be business as usual. 

Need help preparing your business for the unexpected? At Purpose First Advisors, we help business owners build value and resilience; especially for even when life throws curveballs. Let’s talk.

Most business owners track the same handful of numbers every year:

Those metrics matter. They tell you how the business is performing right now.

But they don’t answer a much more important question:

Is your business becoming more valuable?

Because revenue pays the bills.
Profit funds your lifestyle.

But business value creates wealth and optionality.

It determines whether you can sell your company, transition leadership, borrow strategically, or step back from day-to-day operations.

What Does It Mean to Treat Valuation as a KPI?

Treating valuation as a KPI means measuring and managing the factors that determine the market value of your business—such as profitability, risk, leadership depth, and revenue stability—on a regular basis.

Instead of evaluating performance only through revenue and profit, owners also track whether their decisions are increasing the company’s long-term enterprise value.

This changes how leaders think about hiring, pricing, operations, and growth.

Because every decision is evaluated through a different lens:

Will this increase the value of the business?

The Factors That Drive Business Valuation

Business value is not determined by revenue alone. Buyers evaluate companies based on risk, sustainability, and transferability.

Several core drivers influence valuation.

Profitability

Consistent and improving profitability signals operational strength and financial discipline. Businesses with stable margins typically command higher valuation multiples.

Transferability

If the business depends heavily on the owner to generate revenue or make key decisions, buyers see risk. Companies that operate successfully without the owner are significantly more valuable.

Revenue Quality

Recurring or predictable revenue increases buyer confidence. Businesses that rely on repeat customers or long-term contracts tend to receive higher valuations.

Leadership Depth

A capable management team ensures the company can continue performing after an ownership transition.

Operational Systems

Documented processes and strong systems make performance more predictable, scalable, and transferable.

Why Tracking Valuation Changes the Way Owners Lead

Most owners run their businesses using operational and financial KPIs.

They measure things like:

But very few track valuation as a performance metric.

When valuation becomes part of annual planning, the conversation shifts.

Leaders start asking different questions:

These questions align daily decisions with long-term wealth creation.

How Business Owners Can Increase Valuation Over Time

Improving valuation rarely comes from a single initiative. It results from consistent focus on the factors that reduce risk and improve performance.

Owners who want to increase the value of their business often focus on:

Even if a sale is years away, these changes make businesses more profitable, resilient, and enjoyable to own.

A Strategic Insight Worth Remembering

Revenue measures activity.
Profit measures performance.
Valuation measures wealth creation.

If owners want their businesses to create lasting financial value, valuation must become part of the conversation long before an exit is on the horizon.

Measuring What Matters

When valuation becomes part of your strategic planning process, your annual plan becomes more than a roadmap for revenue growth.

It becomes a value acceleration plan.

You gain clarity about:

From there, your strategy, KPIs, and leadership priorities can align around one question:

How do we build a business that becomes more valuable every year?

Final Thought

You don’t have to be planning to sell your company to benefit from building one that is valuable.

In fact, the businesses that are easiest to sell are usually the ones that are most enjoyable to own.

Because they:

And that’s what building a valuable business is really about.onal timeline. 

Ready to add Valuation as a KPI to your business? 

FAQs

What does it mean to treat valuation as a KPI?

Treating valuation as a KPI means regularly measuring and managing the factors that influence the value of your business—such as profitability, risk, leadership depth, and revenue stability—rather than focusing only on revenue or profit.

Why should business owners track business valuation?

Tracking valuation helps owners understand whether their company is becoming more attractive to buyers, lenders, and investors. It encourages strategic decisions that increase profitability, reduce risk, and improve transferability.

What factors influence the valuation of a business?

Business valuation is influenced by factors such as:

How often should a business valuation be updated?

Many advisors recommend reviewing valuation annually as part of strategic planning. This allows owners to identify risks, track progress, and prioritize the actions that will most improve the company’s value.

Can a company grow revenue but lose value?

Yes. Revenue growth can reduce value if it increases risk—for example, by creating customer concentration, operational complexity, or greater dependence on the owner.

What is the benefit of knowing your business value before selling?

Understanding your business value early gives owners time to address weaknesses, strengthen operations, and increase valuation before entering a transition or sale process.

Is valuation important even if I don’t plan to sell my business?

Yes. Businesses that are valuable are typically more profitable, resilient, and easier to operate because they rely on strong systems, leadership, and predictable revenue.

What KPIs increase business value?

KPIs that improve business value often include gross margin, customer concentration, recurring revenue, employee retention, and operational efficiency. These indicators help reduce risk and increase buyer confidence.

Back in February, Dr. Donna Marino and I hosted a LinkedIn Live conversation about the how myths, personal beliefs, and emotions play a significant role in family succession planning.

That conversation became the inspiration for an article we co-authored for Family Business Magazine in which we talk about the need for frequent, candid conversations and the important role trusted advisors play in helping families navigate the complex and often complicated landscape where family relationships and business continuity collide.

Whether you started the business or are helping carry it forward, the responsibility can feel both meaningful and complicated.

My family business

My personal experience with family business succession planning is one of unspoken expectations, avoidance, and a distinct lack of planning. Despite having years during a long illness to talk with me and my siblings, as well as his own brothers, about the current state of the business and what might happen when he was gone, my dad stayed silent on the matter. It wasn't until he died that we found out he left the business to one of his brothers and that my uncle was only willing to accept the bequest if we (his nieces and nephews) used my dad's life insurance to pay off the debt.

What followed was months of conversations about "this is what your father would have wanted" and coming to terms with how my uncle's feelings of entitlement and being 'owed' something collided with the reality that my dad's business was not financially viable and the things my uncle had done to help my dad 'run' the business during his illness prolonged the inevitable need to cease operations.

In hindsight, one might say that my siblings and I could've started the conversations my father wanted to avoid. I even thought that myself - that I had failed to push the issue and force the conversation. Realistically though, as I approached my 40th birthday I was still my dad's child. I knew he would shut down and shut me out if I brought up things he didn't want to talk about or deal with. I knew I couldn't force him to do anything. And I didn't want to fight with him. He wanted to avoid the reality of his illness, his mortality, and a failing business, as well as the emotions and expectations of his children and siblings, so we didn't talk about it. Frankly, no matter how many times I rehearsed my opening line and talking points, when the time came I could never bring myself to address the situation directly.

That saddens me because it meant he dealt with a lot of financial worry by himself when he didn't need to, and he left a lot for us to deal with in his absence. It also saddens me because I know our family's experience is more of the rule than the exception. But it doesn't have to be that way.

"One of the things we often miss in succession planning is that it should be gradual and thoughtful with lots of sharing of information and knowledge and perspective, so it's almost a non-event when it happens." Anne M. Mulcahy, Family Enterprise Foundation

Collaborate and communicate

To be clear, I didn't know how to start these conversations with my family and we didn't have someone like me or Donna Marino to help us figure it out. When it's you and your family, old habits, communication patterns, and decades of relationship baggage make it hard to do this work alone. In fact, it may be an unreasonable expectation. I know first-hand that it's not enough to know what you should do. You need someone who has the experience and emotional distance to initiate and facilitate some of the hardest conversations you may ever have.

Because taking care of a family business isn’t just about protecting what was built.
It’s about deciding what it needs to become.

With that in mind, I suggest the following for those who want to become more intentional about their relationship to their family business, explore what a 'good' transition might look like, and engage an advisor to help you talk about tough topics and make important decisions.

If you're the business owner:

If your the family member:

For more information about how Purpose First Advisors can help you and your family plan for the future, visit our strategic business advisors page or schedule a free consultation.

FAQs

What makes family businesses different from other businesses?

Family businesses involve overlapping roles between family relationships and business responsibilities, which can create both unique strengths and complex challenges.

Why is managing a family business often more complicated?

Decisions in family businesses are not just strategic—they are personal. Emotions, history, and relationships can influence leadership, communication, and decision-making.

How can family businesses balance relationships and business decisions?

Clear roles, open communication, and agreed-upon expectations help separate family dynamics from business decisions while maintaining trust and alignment.

When should a family business start succession planning?

Succession planning should begin well before a transition is needed. Early planning allows time to develop future leaders and align family members around the future of the business.

What are common challenges in family business transitions?

Common challenges include unclear leadership roles, differing expectations among family members, communication breakdowns, and difficulty separating personal and business decisions.

How can family businesses prepare the next generation for leadership?

Preparation includes leadership development, clear expectations, exposure to different parts of the business, and ongoing communication about roles and responsibilities.

Why is communication so important in family businesses?

Strong communication helps prevent misunderstandings, aligns expectations, and supports both the health of the business and the relationships within the family.

How can family businesses protect both the business and the relationships?

By creating clear governance structures, defining roles, and having proactive conversations about the future, family businesses can support long-term success while preserving relationships.

More FAQs

Sometimes the people who can get you to really think about what's next - how long you want to keep working, what will happen if you suddenly can't work, how much you want to work, what selling could look like - are spouses, children, and employees.

Who in your life wants to know - deserves to know - what your succession plans are?

Even if you're scared, overwhelmed, or intimidated by the prospect of things changing, might the concerns and need for clarity from people you care about be the encouragement you need to prioritize finding someone to talk with about business exits, leadership transitions, and ways to preserve your legacy?

The questions my client's employees were asking her about the future combined with her growing desire to work less got her to make the call.

“I thought I’d work forever and forever is now,” is what she said when I asked her what had changed, and why she was reaching out to talk about selling her business.

She took a sip of her coffee and said, “I’m well past retirement age, my employees want to know what my timeline looks like, and I don’t want to work this hard anymore. At the same time, I’m trying to cut back on my hours but I keep going to the office. I’m freaked out about what I’ll do when I’m not working but also tired and ready to work less.”

“This all makes sense and almost every business owner I talk to can’t imagine not working. Frankly, I’m really glad your employees have been bugging you for a plan and you’re ready to talk.”

“Yeah, it's time. I’d like to start slow, maybe with an with an emergency succession plan and go from there.”

I smiled and said, “That’s a great place to start. That process will open up your thinking about how you run your business, what you might want to keep doing while you scale back your hours, and what legal documents and internal processes you need in place to ensure business continuity in the event you become incapacitated (or fly off for an extended Tahitian vacation.)"

“Oh, I’m the only one who writes proposals, does invoicing, does the banking - there's a lot of things that no one else does,” she said.

I exclaimed, “I know! That’s why your employees want to know what the plan is and I want to help you train them to do these things so a potential buyer will be confident that the business can run profitability without you.”

She smiled, lowered her head and raised her eyes, “I get it. I’ve just never had to train anyone on the things I do and so many little details and nuances live in my head.”

“Yeah, " I said “and it means that you’ve built a $3m business with one hand tied behind your back.”

"My job is to help you think about what will make your business most attractive to potential buyers and create as many of those conditions as possible. High owner dependence makes your business less valuable. So does a lack of standard operating procedures and cross-training.”

I went on to say, “For you to work less, others need to work more or we need to hire other people to take on different roles. You need to train them and let them practice doing new things. You need to teach them all the things you do instinctively that make this business successful.”

She leaned forward and said, “I do have one person I’ve been showing how to do some things and she might even be interested in buying the business.” she said. “It’s important to me to help her do that when we’re both ready.”

I smiled and said, “That’s so good to know. What a wonderful thing to work toward!

I made a note and explained, “that means it’s also important for you to start making financial decisions based on demonstrating consistent, reliable cash flow. If your employee eventually needs a bank loan to make this deal work the bank will want to see the numbers that tell them the business can service the debt.”

“Fortunately, we have time to document, train on, and delegate your responsibilities before we go to market. And we have time to get your financial documents in order in anticipation of due diligence and an underwriting process.”

With a sigh and a smile she said, "It's a good thing I’m not ready to be ‘done, done’ tomorrow. This sounds like a lot of work!”

“It is.” I put down my pen and said, “which is why it's always best to run your business to be exit ready and transferrable regardless of whether you are ready to or interested in selling. Now the most important thing is to get started and make these changes."

“Let’s get focused. I’m ready to do it,” she said, sitting up a little straighter in her chair.

Getting focused helped this owner increase revenue 34% and profit 137% YOY, update her estate plan, review her wealth management strategies, create an emergency succession plan, identify a prospective buyer, and set an asking price 40% higher than initially anticipated.

Even if you think you’re going to work forever, you might change your mind. Let’s talk about integrating succession planning and value acceleration strategies into your annual growth plan to position your business to be as appealing as possible to potential heirs or buyers. That gives you more business exit and transition choices whenever you decide to change your role in the business or sell.

FAQs

Why do employees start asking business owners about succession plans?

Employees often begin asking about succession when they notice signs that the owner may eventually step back—such as changes in workload, age, or business direction. These questions usually reflect concern about stability, leadership continuity, and their own future within the company.

When should a business owner start talking about succession plans?

Ideally, owners begin discussing succession and transition plans five to ten years before a leadership change. Early conversations allow time to develop leaders, strengthen systems, and create a thoughtful transition strategy.

Why do many business owners avoid succession planning conversations?

Succession planning can raise difficult questions about identity, retirement, leadership readiness, and the future of the business. Because these topics are both strategic and emotional, many owners delay the conversation even when they know it’s important.

What are the risks of avoiding conversations about the future of a business?

When succession planning is avoided, uncertainty can grow among employees, family members, and leadership teams. This uncertainty can lead to confusion about decision-making, reduced confidence in long-term stability, and missed opportunities to prepare the business for transition.

How can business owners start conversations about the future of the company?

Owners can begin by sharing their general thinking about the future of the business, asking key team members about their goals, and exploring what a successful transition might look like for everyone involved.

Who should be involved in succession planning conversations?

Succession planning often involves a mix of stakeholders including the owner, potential successors, senior leadership, family members (if applicable), and trusted advisors who can help guide the process.

Why do early succession conversations strengthen a business?

Early conversations allow organizations to identify leadership talent, clarify expectations, and strengthen systems so the company can continue operating successfully through future transitions.

More FAQs

maroon quotation marks
  • I have said many times to colleagues, “I wish I had hired Christy Maxfield a few years ago.” Even with a 27-year-old company, I have learned so much from her. Christy has been an invaluable partner helping me operate my company more strategically, i.e. strengthening financial reporting, guiding succession planning, navigating complex people decisions, and increasing the overall value of my business. Christy brings insight, clarity, and genuine care to her work. Her disciplined approach and guidance has made me a more confident and effective business owner and positioned my company for its next phase of long-term success.
    Laurna Godwin
    Owner, Vector Communications
  • Christy’s coaching has has been instrumental in elevating my business to new heights. Her ability to facilitate strategic conversations has been transformative, helping me identify opportunities, overcome obstacles, and refine my business strategies for optimal results.
    Paya Sample
    Owner, Peak Leaders Collective
  • Christy took the time to assess my business model, understand my goals, and identify areas for improvement. What impressed me most was her ability to provide tailored strategies that were practical and immediately implementable.
    Sue Bailey
    Owner, Celebrating Life Cakes
linkedin facebook pinterest youtube rss twitter instagram facebook-blank rss-blank linkedin-blank pinterest youtube twitter instagram