And what it’s quietly costing your growth, your joy, your team, and your future exit options

If it feels like every decision still runs through you, it’s not a coincidence.

It’s a design.

Not one you chose intentionally—but one you reinforced over time.

And now it’s limiting how far your business can go.

The Real Problem Isn’t Your Team

Most owners don’t start here.

Instead, the frustration sounds like:

But here’s the uncomfortable truth:

If everyone still comes to you, it’s because the business has learned to rely on you.

Not because your team is incapable.

Because of the system you (unintentionally) created.

How This Pattern Gets Built

This doesn’t happen overnight.

It’s usually the result of success.

You were:

So people came to you.

And you responded. Again and again.

Over time, a pattern formed:

You decide → things move → results happen

So the behavior gets reinforced.

Or

They decide → you second guess their decision → they learn not to try and instead run everything through you.

Until one day, you realize - you hate this. They hate this. This can't continue. And you don't know how to change it.

Why This Becomes a Growth Ceiling

At a certain stage, what once made you effective starts working against you.

Because every decision flowing through you creates friction:

And most importantly…

It limits your ability to increase revenue, profitability, and value. Not to mention transferability.

A business that depends on you to function is harder to grow, harder to lead, and harder to sell.

Buyers don’t pay for owner effort. They pay for systems that work without you.

The Hidden Cost: Value and Freedom

This isn’t just an operational issue.

It’s a value issue.

When your business relies on you:

High owner dependence is one of the most common reasons businesses fail to reach their full value potential.

And it's deeper than that because beyond financial valuation, a business that depends on you has real, measureable costs for you right now:

Your time and peace of mind.

Your energy.

Your ability to step back without things breaking.

Your willingness to stay engaged and lead your team to be and do their best.

Why Letting Go Feels So Hard

If the solution were simple delegation, you would’ve done it already.

But this isn’t just about process.

It’s about identity.

When you’ve built the business by being the one who solves everything, stepping back creates tension:

This is where most owners get stuck.

Not because they don’t know what to do. Because they’re not ready to change how they lead.

What Actually Has to Change

You don’t fix this by telling your team to “take more ownership.”

You fix it by redesigning how decisions happen.

That means:

1. Clarifying decision rights
Who decides what and how, without you.

2. Building capability, not just delegation
Training people to think, not just execute.

3. Allowing for imperfect execution
You've made mistakes and they will too. Autonomy and accountabilty come with the responibility for making and dealing with the outcome of the decisions you make both good and bad.

4. Changing what you measure
From “Did it get done right?” to “Are the right people doing the right things at the right time?”

This is how a business becomes more enjoyable to own whiler also becoming more valuable and transferable.

Better Questions to Ask Yourself

Instead of asking:

“Why does everyone come to me?”

Ask:

“Where have I made it easier for people to rely on me than to think for themselves?”

"How can I change that?"

With each new choice you make you take control of how your business is designed so that it best serve you.

FAQs

Why does my team rely on me for decisions?
Because your business has been conditioned to route decisions through you, often unintentionally through speed, habit, and past success.

Is this a leadership issue or a systems issue?
Both. Leadership behavior creates the system, and the system reinforces the behavior.

How do I stop being the bottleneck?
By clarifying decision ownership, developing your team’s decision-making capability, and redesigning workflows so progress doesn’t depend on you.

Does this impact business valuation?
Yes. High owner dependence increases risk and lowers transferability, which directly impacts valuation and exit options.

The Bottom Line

You can’t be the glue that holds everything together and build a business that runs without you.

At some point, you have to choose:

If you’re starting to see where this shows up in your business but aren’t sure how to unwind it without creating chaos that’s exactly when we can help.

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.

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.

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  • 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.
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    Owner, Vector Communications
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