3 Essential Questions To Ask Before Selling Your Business
What if a business buyer showed up tomorrow with a serious offer to buy your business?
Would you be ready or would you panic?
Most small business owners say they'll sell 'someday.' But someday has a funny way of becoming urgent. A burnout. A life shift. A market dip. Or an unexpected email from a serious buyer. The truth is, big exits don't wait for perfection, they reward preparation.
If you're a freedom-focused business owner with even a whisper of a future exit in mind, the time to get clarity is now. And it doesn't start with business brokers or complex spreadsheets. It starts by asking yourself the right questions. Below are three of the most important ones, designed to bring you out of fuzzy thinking and into powerful action.
Question 1. How Much Time Do You Really Have To Prepare For Your Exit?
This is the question most small business owners skip until it's too late. They assume they'll sell in a few years, maybe after they hit a revenue milestone or launch that one last project. But life doesn't wait. Burnout creeps in. Health issues show up. Or the opportunity of a lifetime knocks earlier than expected.
It shapes what you can still fix, how confident you'll feel when selling your business, and the kinds of offers you'll be able to attract and negotiate.
So instead of drifting toward an exit someday, anchor your thinking today:
Why this matters:
Many owners think they have years, but urgency often shows up fast. Buyers don't wait while you clean up your books, document systems, or finally delegate sales.
The sooner you define your timeline, the more control you gain over the process.
Question 2. What Is Your Business Worth Today And What Do You Want To Sell It For?
Ask 10 owners what their business is worth, and you'll get 10 guesses. None backed by real data. Ask what they want to sell it for, and the answer is often a gut number tied to pride, how hard they worked or retirement goals.
This is where the 'value gap' lives: the space between what you think your business is worth and what a buyer would actually pay.
Here's how to bring clarity to your numbers:
Why this matters:
Knowing your business's value isn't just about the final price tag. It's a mirror reflecting how your business performs, how de-risked it is, and how attractive it is to outsiders.
Your revenue doesn't define your value. Your systems, structure, and owner-independence do. So if your dream number feels far away, that's not a reason to quit. It's a reason to start optimizing now.
Question 3. How Exit-Ready Is Your Business Right Now?
Many founders focus on growth and profitability, but skip over sellability.
They assume a high-revenue, well-known business will sell easily. But business buyers look for different things. They care less about your genius, and more about your systems. They want to know: can this business thrive without you?
Valuable doesn't always mean sellable. That distinction is what separates an impressive business from a big exit.
To assess your real exit readiness, ask:
Why this matters:
Buyers aren't just looking at how much money you make. They're evaluating how risky it would be to take over. The more your business runs without you, the more attractive—and valuable—it becomes.
Exit readiness is a spectrum, not a yes-or-no question. Every improvement you make adds leverage, even if you're years away from selling.
Final Reflection: If a Buyer Showed Up Tomorrow, Would You Be Ready?
Let's imagine this scenario: You get an email from someone who wants to acquire your business. They're serious. They ask for your numbers, team structure, contracts, churn rate, and delivery process. Do you freeze, or flow?
This one reflection cuts through the fluff faster than any spreadsheet:
If a buyer showed up tomorrow, how ready would you truly feel to share your numbers, answer their questions, and let go?
This isn't about being perfect. It's about being prepared. Because big exits don't just happen when you want them to. They happen when you've made them possible.
Whether your ideal exit is two years out or ten, the time to start preparing is now. Not in a reactive scramble when you're tired or out of options, but from a place of clarity, leverage, and choice.
If this article sparked something, don't let it end here. Use your answers to these questions as a roadmap. Turn insight into action, one small improvement at a time. Because you don't just deserve to sell your business, you deserve to sell it on your terms.
Hashtags
Try Our AI Features
Explore what Daily8 AI can do for you:
Comments
No comments yet...
Related Articles
Entrepreneur
9 hours ago
- Entrepreneur
Annual Workforce Plans Are Costing You Millions — Fix It With This Shift
By taking a continuous approach to workforce planning, companies can match their people with business goals and changing economic conditions. Opinions expressed by Entrepreneur contributors are their own. For companies, workforce planning isn't about to get any easier. Just ask Intel, which is laying off up to 20% of employees from its chip-making division, after slashing 15% of its workforce last summer. Tens of thousands of roles were eliminated in a matter of months. This kind of dramatic shift is increasingly the rule, not the exception. AI is a key culprit, causing headcounts to plummet in some areas and surge in others. Geopolitics and tariffs are also increasingly a factor. My company works with an exercise equipment manufacturer whose prices spiked 40% overnight, turning its workforce plans upside down. All of these points point to a stark conclusion: The way most companies approach workforce planning is no longer viable. Any business that still relies on a rigid annual plan is asking for trouble. In fact, businesses are expected to suffer a staggering $8.5 trillion in unrealized annual revenue by 2030, partly thanks to poor workforce planning. It doesn't have to be that way. By taking a much more dynamic approach to workforce planning, companies can match their people with business goals and changing economic conditions in real time. And as it turns out, AI is a key part of the solution. Here's why sticking with the status quo is so risky, and how businesses can break free. Join top CEOs, founders and operators at the Level Up conference to unlock strategies for scaling your business, boosting revenue and building sustainable success. The high cost of an outdated workforce planning If you work at a company where workforce planning is a yearly exercise, you're far from alone. Traditionally, that's how businesses have anticipated their workforce needs. Managers identify sales and revenue goals, then work backward to set budgets and headcounts across different departments. Because yearly planning is a guessing game, it isn't very effective. I know this firsthand from coming up through the software industry, where workforce plans often morph as quickly as they're written. This kind of episodic approach to workforce planning has a number of serious drawbacks: The typical cadence of workforce planning is ill-adapted to the pace of modern work. Almost 40% of companies create 12-month plans. But digital transformation has already compressed business cycles, and AI is now accelerating change at an even faster pace. Plans made last month may already be obsolete. People planning tends to be rudimentary and superficial. Only about one-third of HR leaders say their organization is good at using data for workforce planning, while more than two-thirds said their workforce planning is limited to headcount alone, with no analysis of underlying capacity. More than half of companies lack a clear picture of their employees' current skills and the roles that are likely to face disruption. Planners are still thinking strictly in terms of butts in seats versus a more nuanced assessment of discrete skills needed. What is the consequence of all that? Companies often end up with way too many people, or way too few. This translates either to bloated payrolls or, even worse, inability to serve surging demand. When we surveyed leaders, three-quarters said talent shortfalls left them unable to meet business objectives. Domino effects of poor planning include diminished productivity, burnout and diminished morale, and loss of business to the competition. Related: Why Workforce Efficiency Isn't Just Code for Layoffs How companies can embrace continuous planning Imagine a nationwide bank in the throes of an AI makeover. That's exactly what's happening at JPMorgan Chase, which plans to use AI to shrink its workforce by 10%. With more than 300,000 employees, how can JPMorgan plan and adapt on the fly? Here's where continuous workforce planning comes in. A marked departure from annual exercises, this approach incorporates real-time data to create a flexible plan that can be reconfigured in response to changing conditions. Surging demand? Challenges with retention? A spike in costs? Continuous workforce planning adapts instead of waiting to catch up. The key to that flexibility? Gaining insights into how people drive business results in real-time. Historically, accessing and understanding the information needed to make that happen has been an obstacle. People analytics platforms change everything by breaking down silos between departments, unlocking data previously trapped in spreadsheets and hard drives. Plus, AI can now connect the dots to business outcomes, while making those insights instantly accessible in plain language. For companies looking to embrace continuous workforce planning, there are three important steps: Know who your people are and where they work. People data, which covers things like headcount, seniority, engagement, training and pay, is often surprisingly hard to access. Start by leveraging the latest people analytics tools to weave together data from disparate human capital management systems, as well as email, chat, calendar and other employee apps — providing a clearer picture of your team. People data, which covers things like headcount, seniority, engagement, training and pay, is often surprisingly hard to access. Start by leveraging the latest people analytics tools to weave together data from disparate human capital management systems, as well as email, chat, calendar and other employee apps — providing a clearer picture of your team. Know how your people work. The next step is to connect that people data with business data, which includes metrics like revenue, profitability and customer satisfaction. Which sales teams generate the most revenue? What's our least profitable division? What kind of training translates to improved customer retention? This shows how employees are contributing to actual business goals. New platforms enable connecting the dots between people and business results, providing a clearer picture of overall productivity. The next step is to connect that people data with business data, which includes metrics like revenue, profitability and customer satisfaction. Which sales teams generate the most revenue? What's our least profitable division? What kind of training translates to improved customer retention? This shows how employees are contributing to actual business goals. New platforms enable connecting the dots between people and business results, providing a clearer picture of overall productivity. Harness those insights to build a dynamic workforce plan. AI-powered workforce planning tools enable companies to continuously model scenarios and adjust resources based on shifting demands. To hit next year's financial targets, what workforce mix do we need? Given the impact of tariffs on the bottom line, how should we adjust our headcount? What's the most cost-effective way to fill current talent gaps? New platforms use real-time data and predictive capacity to guide companies toward the best plan. Related: Here's What Leaders Need to Try Before Resorting to Layoffs Continuous workforce planning in action Done right, continuous workforce planning can be a game-changer for companies: One of our clients, a financial services firm with 50,000 employees, needed a plan to navigate changing customer expectations and volatile markets. It was also juggling a mix of in-house employees, remote workers and contractors. Breaking workforce planning out of its silos, the company adopted a more dynamic model that gave it a holistic picture, aligned with business goals and enabled it to react to market fluctuations. Another customer is a healthcare provider that used our workforce planning tool to forecast job vacancies accurately. By proactively hiring some 2,000 caregivers with the right skills at the right time, it ultimately saved more than $3 million. Getting the most out of continuous workforce planning When it comes to continuous workforce planning, I've seen so many companies struggle to get over a few critical obstacles. Here are some key tips to bear in mind: Continuous planning isn't possible until you overcome siloed thinking, too. Whether it's finance, marketing or HR, executives are often stuck in their own departments. The question they should ask: How can I get a holistic view of understanding people and how they work?} Whether it's finance, marketing or HR, executives are often stuck in their own departments. The question they should ask: How can I get a holistic view of understanding people and how they work?} Not all businesses can turn on a dime. Ability to change course varies by industry, with manufacturing moving much slower than, say, software. For example, Donald Trump might want Apple to build iPhones in the US, but moving only 10% of its supply chain stateside could take three years. Ability to change course varies by industry, with manufacturing moving much slower than, say, software. For example, Donald Trump might want Apple to build iPhones in the US, but moving only 10% of its supply chain stateside could take three years. It's important not to confuse plans with reality. As helpful as workforce plans are, they do have limits. So resist the temptation to over-plan and get into the weeds. The best plans are a continually evolving model, not an exact picture of conditions on the ground. In a time of AI and economic uncertainty, agility is the only option. By shifting from static to continuous workforce planning, businesses can improve their odds of not just surviving but also thriving in turbulent times.
Yahoo
11 hours ago
- Yahoo
Potential Multi-Year Growth for Saia (SAIA) If Freight Industry Rebounds
The London Company, an investment management company, released 'The London Company SMID Cap Strategy' second quarter 2025 investor letter. A copy of the letter can be downloaded here. Following a downturn in Q1, U.S. stocks experienced a double-digit gain in Q2, amid volatility stemming from tariff news. A risk-on rally followed due to a temporary pause in tariff escalations, widespread optimism around enterprise AI, and a healthy earnings outlook. Against this backdrop, the portfolio fell 0.6% (-0.8% net) during the second quarter vs. an 8.6% increase in the Russell 2500 Index. Sector allocation contributed to the fund's performance in the quarter, while stock selection detracted. Please review the fund's top 5 holdings to gain insight into their key selections for 2025. In its second quarter 2025 investor letter, The London Company SMID Cap Strategy highlighted stocks such as Saia, Inc. (NASDAQ:SAIA). Saia, Inc. (NASDAQ:SAIA) is a North America-based transportation company. The one-month return of Saia, Inc. (NASDAQ:SAIA) was 9.19%, and its shares lost 23.58% of their value over the last 52 weeks. On July 28, 2025, Saia, Inc. (NASDAQ:SAIA) stock closed at $323.23 per share, with a market capitalization of $8.61 billion. The London Company SMID Cap Strategy stated the following regarding Saia, Inc. (NASDAQ:SAIA) in its second quarter 2025 investor letter: "Saia, Inc. (NASDAQ:SAIA) – SAIA remained weak this quarter as the lingering 'freight recession' drags on for almost its third year. We remain convicted in our ownership of SAIA due to its solid balance sheet and strong network growth plan. We believe the company could be a multi-year compounder, assuming the freight industry returns to normal demand patterns. A long line of trucks transporting goods across the open road, symbolizing the long-distance transportation services of the company. Saia, Inc. (NASDAQ:SAIA) is not on our list of 30 Most Popular Stocks Among Hedge Funds. As per our database, 35 hedge fund portfolios held Saia, Inc. (NASDAQ:SAIA) at the end of the first quarter, compared to 31 in the previous quarter. In the second quarter of 2025, Saia, Inc. (NASDAQ:SAIA) announced revenue of $817 million, marking a 0.7% decrease compared to the same quarter last year. While we acknowledge the potential of Saia, Inc. (NASDAQ:SAIA) as an investment, we believe certain AI stocks offer greater upside potential and carry less downside risk. If you're looking for an extremely undervalued AI stock that also stands to benefit significantly from Trump-era tariffs and the onshoring trend, see our free report on the best short-term AI stock. In another article, we covered Saia, Inc. (NASDAQ:SAIA) and shared Polen US SMID Company Growth Strategy's views on the company in the previous quarter. In addition, please check out our hedge fund investor letters Q2 2025 page for more investor letters from hedge funds and other leading investors. READ NEXT: The Best and Worst Dow Stocks for the Next 12 Months and 10 Unstoppable Stocks That Could Double Your Money. Disclosure: None. This article is originally published at Insider Monkey.
Entrepreneur
13 hours ago
- Entrepreneur
You've Earned a Break (And 10 Bottles of Wine)
Choose every bottle and get them shipped to your door for less than $9 apiece. Disclosure: Our goal is to feature products and services that we think you'll find interesting and useful. If you purchase them, Entrepreneur may get a small share of the revenue from the sale from our commerce partners. You've handled back-to-back meetings, client curveballs, and a never-ending Slack thread—and it's still not the weekend. If "I could use a drink" is basically your internal monologue, this choose-your-own wine bundle might be the most rewarding thing you've done for yourself all month. You know a good deal when you see one, so how does this sound? For less than $9 each with shipping, you can hand-select every bottle from choices like reds, whites, rosés, dry, sweet, domestic, or international, and have them shipped right to your door. No subscription required. Redemption is so simple Start by buying your wine deal here, heading to Swirl Wine Shop's website, and selecting your 10 bottles. Maybe some cabernet from Chile, a red blend from France, or rosé from Italy? Don't worry about how much each individual bottle costs, because this voucher will make your total come to $59 no matter what. Then, head to checkout, enter your voucher code, and pay the $29.95 shipping fee. We know, this sounds kind of like a lot, but each bottle still comes out to less than $9. Musician Tom Petty said it best with, "The waiting is the hardest part," as you anticipate the delivery. Make sure you or someone 21 years of age or older will be around to sign for the delivery. Celebrating Friday nights, landing new clients, or getting through Q4 will be an even bigger treat when you don't have to overspend on a bottle. Get wine delivery including 10 bottles for just $59 and $29.95 shipping (reg. $200). Choose Your Own 10 Premium Wines for Just $59 – Up to $200 value! (Shipping Not Included) See Deal StackSocial prices subject to change.
