By: Steve Messina AI can feel like the ghost in the machine, everywhere, unpredictable, and impossible to ignore. In the workplace, it’s equal parts fascination and fear. But let’s be honest: every major leap in innovation, from the internet to automation, started with a healthy dose of panic. Good news: HR doesn’t need to exorcise these fears; it needs to lead through them . You’re the guide through the fog, the steady hand on the flashlight. So, let’s step into the dark corners of AI anxiety, and uncover how HR can turn each one into a moment of courage, clarity, and strategy. The Ghost: Hidden legal hurdles Few things send chills down an HR leader’s spine like potential compliance issues that haunt you. The legal maze around AI, bias, privacy, transparency, is vast and shifting. With every new regulation or class-action headline, that maze grows a little darker. How to face your fear: Don’t get lost in the fog. Build a cross-functional task force with your legal and IT partners to craft evolving, airtight AI policies and ethical standards. Keep them alive, review and refresh them regularly as laws evolve. Most importantly, be transparent . When candidates and employees understand how AI supports fairness rather than replaces it, trust takes root and fear fades. The Vampire: Cold, hard algorithms This creature thrives on data alone, no heart, no intuition, no nuance. The fear? That AI will drain the “human” out of human resources. Algorithms can crunch performance metrics, but they can’t detect an employee’s unspoken burnout or sense of belonging. How to face your fear: Don’t hand over the keys to the castle. Train managers to use AI as an assistant, not an oracle. Encourage them to pair insights with empathy, metrics with meaning. When HR champions ethical, emotionally intelligent use of AI, the vampire loses its bite, and humanity wins. The Divisive Devil: Uneven AI expectations AI can be the ultimate workplace Rorschach test: one person sees opportunity; another sees apocalypse. Some employees dive in headfirst, while others hesitate, worrying about job loss, bias, or even the carbon footprint of the tech itself. Left unchecked, this divide can fracture your culture faster than any software bug. How to face your fear: Shine a light on the unknown. Host open Q&A sessions or “AI town halls” where people can voice their concerns and learn together; and host it with the CEO . Position HR as the bridge between executive push for AI and actual human readiness. Offer upskilling paths and small wins to build confidence . The more people feel included in the journey, the less room there is for fear to fester. The Data Zombie: Breaches of privacy and trust Imagine a hungry horde of data leaks and privacy breaches, chomping through your company’s reputation. The risk is real: employees can unknowingly feed sensitive information into AI tools that aren’t as secure as they seem. How to face your fear: Arm your people with knowledge and your systems with armor. Set strict data standards for every AI tool, and offer training that’s memorable, not dry policy slides, but real-world examples of what to share (and what not to). Make it clear that protecting data isn’t just IT’s job, it’s everyone’s defense against the zombie apocalypse. The Monster: Job security jitters AI might as well be the monster under the bed for many employees. As automation creeps into every department, fear of being replaced or rejected can eat away at confidence and morale. When learning opportunities don’t keep pace with AI’s evolution, even your best talent can start to feel like they’re falling behind. Facing your fear: Exorcise the monster with transparency and training. Be candid about where AI will change roles , and where it will elevate them. Invest in continuous learning that helps employees offload tedious tasks and flex their creativity instead. When people see AI as a sidekick, not a saboteur, they don’t just feel safer, they feel unstoppable. HR: The magician that turns fear into progress AI doesn’t spell the end of human work, it demands a redefinition of it. HR is the magician in this story, blending data with empathy, strategy with storytelling, and innovation with inclusion. There are HR fears about AI adoption, but that’s okay. Your potion for progress? A mix of policy, education, data, and transparent dialogue. Stir in a culture of trust, and you’ve got the secret sauce for turning AI anxiety into alignment. With HR leading the charge, AI becomes more than a disruptive force, it becomes a partner , helping people do their most meaningful work. 

By: Sam Reese As CEOs plan for 2026, uncertainty and rapid change can make it easy to get stuck in incremental thinking. From persistent economic volatility to shifting workforce expectations and the acceleration of AI adoption, many business leaders are defaulting to caution. CEOs tend to play it safe and can be hesitant to make big moves. Caution is understandable; the past few years have been unpredictable. However, that mindset can be dangerous. Incremental progress might feel secure, but it rarely leads to real growth. Now is the time to think big — to revisit the long-term vision and ensure every part of the strategy supports it. Below are 5 strategic planning priorities for best-in-class leaders as they map out 2026 and beyond: 1. Think Big, Not Incremental Right now, many leaders are frozen by uncertainty. They’re so focused on surviving the next quarter that they’ve lost sight of the bigger picture. Hitting a few short-term targets might feel like progress, but focusing solely on the short term could come at the expense of long-term success. Incremental thinking can quietly stall growth. When leaders lower their expectations or assume the next year will be a “reset” period, they stop challenging their teams to innovate. Employees pick up on that mindset immediately. If leaders tell their team it’s going to be a tough year, they’ll take that as permission to play it safe. The best leaders keep their long-term vision front and center, even in uncertain times. These long-term goals drive every decision. 2. Integrate External Trends Strategically One of the biggest mistakes I see leaders make is tinkering with trends without a clear strategy. Take AI, for example. Some companies are experimenting with tools and calling it a strategy. But the most successful CEOs develop a clear plan for how AI fits into their business, enhances their operations, and strengthens their value proposition. Otherwise, AI becomes a distraction rather than a driver of growth. The same principle applies to workforce strategy. Hybrid and flexible work arrangements are here to stay. According to our recent Vistage research, CEOs are increasingly settling into stable workplace models: 43% report a hybrid workforce, 45% are fully onsite, and 8% are fully remote. Retention now depends on giving workers choice and autonomy. In many industries, leaders are adapting how they communicate, manage, and engage teams to make flexibility work without sacrificing alignment or culture. Supply chains and geopolitics are another critical area where leaders can’t afford to be reactive. Businesses with connections to global supply chains are proactively planning to manage tariffs, regulations, and potential disruptions. Waiting until a problem hits is too late. Strategic leaders anticipate these risks and build their plans around them, rather than hoping for their preferred outcome. 3. Communicate Mission, Vision, and Values Relentlessly Leaders may assume their teams understand their organization’s mission, vision, and values because they shared them at a past employee meeting. In reality, people forget. They get caught up in day-to-day tasks and lose sight of why the work matters. Especially in hybrid or decentralized work environments, effective communication is constant, clear, and specific. And, great leadership isn’t just about talking. It’s about listening and empowering others. The people closest to the frontline often have the best ideas. Great leaders encourage them to speak up, take ownership, and contribute solutions. 4. Balance Growth Ambitions with Focused Investment Ambition is essential, but so is focus. Great leaders filter every decision and new initiative through the lens of their core business purpose. They ask: “Does this move us closer to being the very best at what we do?” If the answer is no, then it’s a distraction. Focused investment may mean saying “no” as often as “yes.” Growth doesn’t come from piling on more initiatives. It comes from concentrating energy, resources, and attention on the few things that truly drive value. 5. Prioritize the Metrics That Truly Matter One common pitfall in strategic planning is focusing on too many metrics. When everything feels important, nothing really is. Successful leaders identify the single key success metric that drives their business forward. This metric helps track whether a company is fulfilling its purpose and moving the organization in the right direction. Once that metric is defined, dashboards, reports, and meetings are simplified. Too often, teams get bogged down in secondary metrics that create noise but don’t drive impact. In effective organizations, every initiative, KPI, and project supports the primary goal. If there’s one piece of advice I would give CEOs planning for 2026, it’s this: Lead the strategic planning process. Great leaders don’t delegate strategy to someone else or treat it like a box to check. They know they need to be in the room, asking the tough questions, shaping the direction, and ensuring the team is aligned with the vision. And they are disciplined about where they invest their time, energy, and resources. The companies that succeed will be the ones that combine bold vision with relentless focus, clear priorities, and leadership that actively guides the path forward. This story first appeared in Entrepreneur . 

Most owners assume growth is the goal. More customers. More revenue. More staff. And they’re right. Buyers do reward growth. But they pay a premium for companies that grow while keeping a positive cash flow cycle. More than 80,000 business owners have completed their Value Builder Score Report , offering a window into how they think about money inside their companies. One of the questions on the intake questionnaire asks owners to “Select the statement that best describes your cash needs,” with four options: 1. We regularly or occasionally raise or borrow money. 2. We keep excess cash as a rainy-day fund. 3. We distribute excess cash to shareholders. 4. Unsure. The results reveal something telling; Owners who maintain excess cash receive acquisition offers that are, on average, 25% higher than those who don’t. It’s a reminder that cash creates confidence and buyers pay a premium for businesses that show it. That’s a lesson Stan Markuze learned when he co-founded Joyride Auto, a marketplace for impounded vehicles. Before Joyride, buying auctioned cars was painfully outdated. Every other Wednesday, a few local dealers would gather in a parking lot to bid on abandoned cars. Stan and his partners moved the process online and, more importantly, re-engineered how the money flowed. Each car sold for about $1,000. Joyride added a 15% buyer’s fee, charged up front. The tow yard got paid later, when the buyer collected the car. Joyride got its cut immediately. No inventory. No receivables. No waiting. Within two years, the company was generating millions in revenue with fewer than twenty employees. When a private equity firm acquired Joyride, they paid roughly seven times annual revenue — thanks to its positive cash flow cycle. By collecting before delivering, Stan was able to fund growth from profits instead of investors, keeping more of his equity until the exit. Why Buyers Love Positive Cash Flow A business with a positive cash flow cycle collects money before it spends it. That means faster cash conversion, less capital at risk, and the freedom to grow without taking on debt or dilution. Buyers prize these businesses because they can scale without sucking up cash. The faster a company turns sales into money in the bank, the higher its valuation.

By Trent Lee, Compass Leadership Advisors One of the most common frustrations I hear from CEOs is this: “I want my people to make decisions without running everything through me… but I don’t want them making decisions that violate our core values or take us off strategy.” It’s the leadership paradox. You want ownership—without drift. Autonomy—without chaos. Initiative—without misalignment. And here’s the truth most CEOs don’t see: Misalignment isn’t a people problem. It’s a clarity problem. In almost every organization I step into, each layer of the company is operating from a slightly different version of the truth. The CEO has one interpretation of the vision. The executive team has another. Mid-managers filter it again. Frontline employees receive whatever finally trickles down. Those “slight differences” compound into big issues: Employees hesitate because they’re unsure. Managers firefight instead of leading. Executives question whether the team is ready for autonomy. And the CEO—hoping to delegate—slides right back into the role of chief problem-solver. The real issue isn’t capability. It’s the breakdown of what I call the Clarity Cascade™ . High-performing teams nail four things: 1. Vision Clarity Not slogans. Not posters. But a shared, lived understanding of where the company is heading and why. 2. Strategic Priorities Three to five true priorities that drive value— not a laundry list of “everything we hope happens this year.” 3. Decision Filters Values translated into behaviors. This is how employees learn to make decisions the CEO would make even when no one is watching. 4. Communication Rhythm Repeating the same message across all levels until it feels almost “too obvious.” Because alignment thrives on repetition, not novelty. When these four elements are in sync, something powerful happens: People make consistent, independent, aligned decisions. When they’re not, CEOs get one of two things: Surprises… or silence. Leadership Question for the Week: If every employee made decisions tomorrow exactly as you would, what would they need to understand more clearly? If alignment is something you’re wrestling with right now, you’re not alone. I’m helping several CEOs implement the Clarity Cascade™ inside their organizations through my Vistage groups, Value Builder work, and leadership advisory. If you'd like the framework or the worksheet I use with leadership teams, reply “ALIGN” and I’ll send it over. ] 

By: Steve Messina AI is transforming how organizations attract and hire talent. But there’s a growing disconnect between innovation and trust: 66% of U.S. adults say they wouldn’t apply for a job if AI helped make the hiring decision. For HR leaders, that’s the challenge and the opportunity. AI isn’t going away, but how you use it will define your credibility. The real question is simple: Can you explain the decisions your technology makes? Because candidates, employees, and regulators already expect you to. When algorithms take the wheel In 2014, Amazon built an AI hiring system that quickly learned to favor men because it was trained on resumes from mostly male candidates. It penalized words like “women’s” and downgraded graduates of women’s colleges. The project was abandoned, but the message was clear: letting machines make hiring decisions comes with consequences. This trend, combined with the negative sentiment from candidates regarding AI in hiring, points to a significant and growing lack of trust. Employers who rely too heavily on AI for selection face an increasing perception problem. The illusion of smart hiring tools This trust gap reveals more than hesitation. It highlights how candidates see AI-driven hiring as impersonal and opaque, setting the stage for serious risks HR leaders can’t afford to ignore. These systems don’t “solve” bias; they amplify it. And when that happens, HR leaders are the ones on the hook. The EEOC now considers AI bias in hiring a civil-rights issue . “ We must work to ensure that these new technologies do not become a high-tech pathway to discrimination.” -EEOC Chair Charlotte A. Burrows A science-backed solution Behavioral science doesn’t leave room for guessing and bias. It measures observable traits that predict how people think, act, and perform at work. At PI, we have decades of data showing that behavioral fit drives measurable outcomes like improved performance, engagement, and retention. From a quantitative standpoint, PI’s behavioral assessments demonstrate strong predictive validity , meaning the traits measured are statistically linked to job success across industries. On the qualitative side, PI clients consistently report higher hiring confidence, stronger culture alignment, and more meaningful conversations with candidates. It’s always been our position that assessments don’t replace human decision-making – they inform it. Tools can provide behavioral data as a single input in a hiring process, keeping final decisions where they belong: with people. Behavioral science earns HR trust points- where AI hurts. And the data backs this up. According to our HR Playbook for the AI Era , HR professionals who ground talent strategies in behavioral data are better positioned to lead AI adoption with confidence and fairness. When HR integrates behavioral science, employees are more likely to trust the process, building the transparency and psychological safety that AI often lacks. Nearly 70% of employees said more training opportunities would make them feel more secure in their role, and those opportunities are most effective when built on behavioral insight rather than technical promises. Behavioral data doesn’t just improve hiring, it enhances culture. The same research found that 67% of employees believe AI has the potential to strengthen company culture , but only when guided by people-first leadership and data-driven behavioral understanding. This shows that behavioral science isn’t a counterpoint to AI; it’s the foundation that ensures AI adoption strengthens, not undermines, your culture. Behavioral science isn’t a counterpoint to AI; it’s the foundation that ensures AI adoption strengthens, not undermines, your culture. AI isn’t the enemy, but it’s not the only answer Will AI replace HR managers? No, but it will reshape how HR works. The goal isn’t to reject AI ; it’s to use it responsibly. AI can automate admin tasks, summarize notes, and identify trends in engagement data. But the decisions about people, the human calls, should rest on science HR leaders can defend. If you want to know how to implement AI in hiring without losing control, start with a behavioral framework . Use AI for scale and support, but let behavioral data guide your judgment when it comes to people, and make that clear to your candidates and your employees. That’s how you improve employee experience and maintain trust- and now you have a talent strategy that’s both modern and human-first. PI’s tools are designed as one data point among many in your decision-making process, never as a replacement for human judgment. This ensures meaningful human involvement at every stage. So the next time you evaluate a hiring tool, ask: Does this make my decisions clearer or just faster? If it’s the latter, it’s time to rethink who’s really doing the hiring and whether your process stands on solid ground.  *PI’s behavioral assessments align with an increase in regulation around AI for decision-making like California’s new AI hiring regulations by design. Our tools inform decisions rather than make them. As required under California’s ADT regulations, meaningful human judgment remains central to the hiring process when using PI’s solutions.

By: Marc Emmer In this year’s trend series, we reflect on a business cycle shaping a new set of challenges for Vistage members. Small and midsize businesses (SMBs) wrestle with tariff uncertainty, higher input costs, the no-hire/no-fire job market, and accelerating technological disruption. 2026 will test our resilience, discipline, and adaptability. The trend series illuminates 5 converging forces: 1. A cooling economy with persistent inflationary pressure. 2. A shrinking and disengaged workforce. 3. An explosion of technological capability and complexity. 4. The mainstreaming of artificial intelligence into every business function. 5. The widening gap between companies that adapt and those that don’t. The opportunity is to lead the transformation now while competitors are mired in the mud. The Economic Picture Growth next year will remain modest, hovering near 1–2% amid escalating costs for materials, logistics, and labor. The true impact of tariffs will become more evident in the next 6 months. Inflation is no longer a blip; it’s a semi-permanent condition that will keep pressure on margins. Interest rates may ease slightly, but not enough to restore the cheap-capital environment of the 2010s. This means companies must pivot from a growth to a profitability mindset. Expect to see more scrutiny from lenders and investors, slower payback periods for capital projects, and a premium on operational excellence — powered by AI. M&A will continue, but deal logic will shift from scale and market share to synergy and resilience. The winners will be those with clean balance sheets, stable margins, and credible plans to automate and optimize. Owners of healthy companies should put themselves in a position to exit between 2027 and 2030, before the bottom falls out of the market. Workforce & Social Shifts The war for talent is not a metaphor; it’s a math problem. With lower birth rates, an aging workforce, and restricted immigration, there simply aren’t enough workers to go around. Meanwhile, employee expectations continue to evolve toward flexibility, purpose, and growth. Engagement is the hidden crisis. Fewer than 1 in 3 employees are fully engaged, and disengagement directly suppresses productivity and innovation. The new social contract will require employers to deliver not just pay, but meaning, development, and belonging. For SMBs, this means leadership quality becomes a competitive advantage. Retention will depend less on perks and more on culture, autonomy, and communication . Technology Trends Technology is now a strategic infrastructure. What used to be “IT” is now the backbone of every decision, transaction, and customer experience. For smaller firms, the democratization of tech means you can now access the same cloud, automation, and analytics power that Fortune 500s use — but only if you deploy it intentionally. In 2026, the focus will be on integration, data governance, and cybersecurity. The new digital divide isn’t who has tech; it’s who uses it with purpose. We strongly recommend that Vistage members benchmark their competition’s IT spend and outspend them by 1-2%. AI as a Lever Artificial intelligence has moved from experimentation to execution. The coming year will see agentic AI — systems that can reason, plan, and act autonomously — entering business operations in sales, logistics, HR, and finance. AI will not replace managers, but managers who use AI will replace those who don’t. Top 10 Takeaways for CEOs 1. Expect slower growth — Plan for a 1–2% economy and persistent cost pressure. 2. Protect margins ruthlessly — Every dollar of inefficiency will be magnified. 3. Talent scarcity is structural — Build retention and engagement strategies now. 4. Productivity is the new profit lever — Focus on tech and process redesign, not just headcount. 5. Digital transformation is mandatory — Integration and cybersecurity are table stakes. 6. AI will redefine competitiveness — Early adopters will achieve 20-40% efficiency gains. 7. Culture drives performance — Leadership quality, trust, and development matter more than pay. 8. Customers are shifting behavior — They’re frugal, digital, and value experience over volume. 9. Global risk is rising — Tariffs, supply-chain disruptions, and geopolitical tension will persist. 10. Adaptability is the new moat — The ability to learn, iterate, and pivot will define success. Plan your exit in the next 5 years. The Member Imperative 2026 will reward leaders who balance optimism with realism. The next two years will not be about predicting the economy — they’ll be about controlling what’s controllable: cost structure, culture, and capability. SMBs that build lean operations, modern technology foundations, and high-trust cultures will not only survive this transition, but they’ll also emerge as more valuable companies capable of sustaining competitive advantage. 

By Trent Lee — The CEO’s Sage Let’s be honest: strategy gets all the glory. It’s fun to talk about vision. It’s exciting to reimagine your market position or draw the next org chart on a whiteboard. But execution? That’s the grind. And it’s where most companies fall short—not because they’re lazy, but because they’re misaligned. Over the past few months, I’ve been walking through what I call the Six Pillars of Execution —the foundational elements that determine whether a company actually delivers on its strategic intent. If you missed any of the deep dives, here’s the short version—and why they all matter together. 1. Strategic Understanding If your team can’t articulate where the company is going and why it matters, they’re not aligned—they’re just compliant. Execution begins with clarity: mission, vision, values, and strategic intent need to be more than wall art. They need to live in conversation, decision-making, and role design. 📌 Ask yourself: Can every leader explain the strategy in 1–2 sentences? Can every employee connect their work to it? 2. Leadership Execution follows leadership. And real leadership means credibility, communication, and change navigation. If your leaders don’t model the strategy, reinforce it consistently, and lead through uncertainty, execution will stall—no matter how smart your plan is. 📌 Strong leaders communicate often, show up consistently, and turn strategy into action through behavior—not just PowerPoint. 3. Balanced Metrics What gets measured gets managed—but only if it’s the right thing. Most organizations lean too heavily on lagging indicators (like revenue and profit) and ignore the leading indicators (like behaviors, customer input, or pipeline velocity) that predict success. 📌 A balanced scorecard connects financial, customer, operational, and people metrics to strategic goals. Otherwise, you’re just watching the scoreboard instead of playing the game. 4. Activities & Structure Structure eats strategy for breakfast. If your workflows, roles, and reporting lines don’t match your strategic priorities, execution gets bogged down in friction and confusion. 📌 Design your org chart around your vision—not your current team. Use accountability charts, review them quarterly, and ensure clarity on who owns what. 5. Human Capital Every business problem is a people problem—and most people problems come from misalignment. Great execution starts with hiring the right people, onboarding them with purpose, and investing in their growth. 📌 Hire with the head (behavioral fit), the heart (values), and the briefcase (skills). Then keep developing them—or risk outgrowing your best people. 6. Market Alignment If your internal operations don’t match your external positioning, you’re building a house on sand. You need to pick a go-to-market lane—cost, innovation, or service—and align everything around it. 📌 Are you structured to deliver what your brand promises? Are you clear on how you win in your market—and does your team know it too? Final Thought: Execution Isn’t One Thing. It’s Everything Working Together. You can’t “fix” execution with a new metric. Or a new hire. Or a one-time strategy session. Execution is a system —and it requires constant alignment across people, processes, structure, leadership, and priorities. When one pillar is off, the others wobble. But when they’re in sync? That’s when momentum builds, silos dissolve, and strategy becomes results. So, here’s your challenge:  Don’t just plan better— execute smarter. Start with alignment. Start with clarity. Start by strengthening your foundation—pillar by pillar. — Trent Lee helps growth-minded CEOs turn strategy into execution by aligning leadership, structure, and systems that scale. Want to know how your team scores across the Six Pillars? Let’s talk. Connect at www.compassleadershipadvisors.com or LinkedIn .

When an acquirer evaluates your business, they’re looking beyond what you’ve built. As successful as your company may be, buyers need to see how much larger it can grow to generate a return on their investment. That’s where Total Addressable Market (TAM) comes in. TAM is the total revenue opportunity available if you captured 100% of demand for your product or service. If your TAM is small—meaning the market for what you sell is limited—your growth prospects look capped. And if your market looks capped, so will your valuation multiple. That’s the challenge Tad Fallows faced when he built iLab, a SaaS platform serving research labs at universities and hospitals. The product worked, customers were sticky, and margins were strong. But at first glance, iLab’s TAM looked limited, only a few hundred U.S. institutions fit the profile. Early acquisition offers reflected that ceiling, coming in at about 3x revenue. Instead of taking the deal, Tad and his team went to work proving their TAM was larger. The Tactic: Prove TAM, Don’t Just Pitch It  Buyers discount hypothetical growth stories. It’s not enough to say “we could sell internationally” or “we could upsell modules.” You need evidence. Here’s how Tad did it: Go global (even in small steps). Signing just a handful of international customers proved iLab wasn’t limited to the U.S. market. Even a small share of revenue abroad reframed the company as a global solution. Show new use cases. By launching add-on modules and getting paying customers, iLab demonstrated that existing clients would buy more. That turned one revenue stream into many. These moves transformed iLab’s perceived TAM. Instead of being seen as a small, capped niche, they were able to show a pathway to a much larger market with far more upside. The Payoff With a larger, proven TAM, iLab’s valuation multiple doubled. What started as a 3x revenue offer turned into a 6x exit. That’s millions of dollars in difference, driven not by short-term sales tactics, but by reshaping how big acquirers thought the company could become. And Tad’s story isn’t an outlier. According to Value Builder Analytics, companies that can easily expand into new geographies receive an average offer that’s 18% higher. In a study of 3,380 businesses, those that said it was “fairly easy” or “very easy” to replicate their business in another region received an average multiple of 4.1x EBITDA. Those that found it difficult averaged just 3.5x. What This Means for You Your company’s value is tied to its future potential. The bigger your TAM, the bigger the story but only if you can prove it. Start small: Land even one or two international customers. Launch a pilot add-on to show appetite for more. Do that, and you’ll raise the ceiling on your company’s value long before you think about selling.

By Trent Lee — The CEO’s Sage If you own a business, there’s a truth you may not want to hear: you will exit someday . Whether it’s voluntary, involuntary, or somewhere in between, every owner eventually steps away. The question is: Will you be ready? Will the business be ready? Or will the business you built become a burden, a fire sale, or a family conflict waiting to happen? I spend my days working with owners across the country—from 10-employee shops to 200-employee powerhouses—and they all share the same pressures. They’re juggling growth, cash flow, hiring, customers, operations, and a hundred other things. And almost all of them have the same fear: “What happens to my business if something happens to me?” Or maybe it sounds like this: “I don’t know when I want out… but I know I can’t keep doing this forever.” “Everything is in my head. If I step back, the wheels fall off.” “My business is valuable… but I have no idea what it’s actually worth.” “I think I need X million to retire… but I’m just guessing.” If that’s you, you’re normal. But you don’t have to stay there. Exit Planning Isn’t About Exiting It’s about creating a business that doesn’t fall apart when you loosen your grip. Most owners think exit planning is something you do in the final lap—two years before retirement, when you’re finally ready to hand over the keys. But the truth is, exit planning is just good business . The same fundamentals that prepare a company for sale are the same fundamentals that make it easier to run, more profitable, and less dependent on you. I simplify it using a flywheel with four core components: 1. Strategic Intent – Why are you here? Where are you going? What are you trying to build beyond a job? 2. Growth – A business with no customers dies. Growth solves problems. 3. People – You can’t scale if you’re the only adult in the room. 4. Process – Consistency creates value. Chaos destroys it. And right in the middle of that flywheel sits the Endgame —your eventual transition. The First 90 Days: Getting Owners Out of the Fog When I start with a new client, we focus on clarity—because unclear owners make reactive decisions. 1. Timeline Clarity You may not know when you want to exit, but we can map your involvement, ownership, and financial dependency over time. This is where owners usually have their first “aha.” 2. Financial Reality (Not Guessing) Most owners wildly overestimate or underestimate what they need. We build a one-page wealth and cash flow projection (with your financial advisor) that answers: How much do you actually need? When do you need it? And will your business get you there? 3. What Is Your Business Worth? We run the Value Builder 60-question assessment to find the real valuation drivers. This reveals not just what the business is worth today, but how to increase it. 4. Succession & Exit Scenarios Internal sale? Kids? Key employees? Outside buyer? We model the options so your exit doesn’t destroy the business—or your people. 5. Partnership Protection Buy-sell agreements prevent disaster when partners disagree, divorce, get sick, or die. They are the prenuptial agreements of the business world—and most owners don’t think about them until it’s too late. A Ready Business Is a Valuable Business Exit planning is not about timing your exit. It’s about building a company that protects your family, supports your retirement, creates options, and gives you peace of mind. If you're a business owner feeling the weight of the future—even if the future feels far off—this is your sign: Start now. Your future self, your family, and your employees will thank you. Trent Lee helps CEOs build transferable businesses that run smoothly today and exit profitably tomorrow. Connect on LinkedIn or learn more at www.compassleadershipadvisors.com .