Are You Really Ready to Sell? The 21-Point Seller Self-Assessment Quiz (Tampa Bay Edition)

Thinking about selling your Tampa Bay business? Hold up.

Before you start dreaming about that exit check or reaching out to brokers, let's get brutally honest about where you actually stand. Most business owners think they're "ready to sell" when they're really just tired of working. There's a massive difference between wanting out and being positioned for a profitable exit.

Here's the unfiltered truth: Less than 20% of advertised businesses actually sell. Why? Because most owners jump into the market unprepared, overpriced, or with businesses that aren't truly sellable.

Don't let that be you.

This 21-point quiz will give you the real picture of your seller readiness. No sugar-coating. No false hope. Just honest assessment across three critical areas that determine whether you'll walk away with life-changing money or become another failed listing statistic.

Ready? Let's dive in.

How This Quiz Works

Each question scores from 0 to 3 points:

• 0 = No/I Don't Know (Not ready)
• 1 = Somewhat/Getting There (Needs work)
• 2 = Mostly/Almost There (Good progress)
• 3 = Yes/Absolutely (Market ready)

Be brutally honest. Your future self will thank you.

SECTION 1: The Mind Game - Emotional & Subconscious Readiness

(7 Questions - 21 Points Possible)

The first hurdle isn't your P&L statements or operational systems. It's what's happening between your ears. Let's see if you're mentally ready for what comes next.

Question 1: Do you find yourself constantly daydreaming about life after selling your business?

• 0 = Never really think about it
• 1 = Occasionally wonder what it would be like
• 2 = Think about it several times a week
• 3 = I have detailed visions of my post-sale life and what I'll do with my time

Question 2: Are you genuinely burnt out and tired of dealing with daily business operations?

• 0 = I still love the day-to-day grind
• 1 = Some days are harder than others
• 2 = I'm definitely feeling worn down more often
• 3 = I'm completely exhausted and ready for someone else to take over

Question 3: Do you feel like you've been running this business "forever" and it's time for something new?

• 0 = Still feels fresh and exciting to me
• 1 = Starting to feel a bit repetitive
• 2 = Definitely getting stale after all these years
• 3 = I could run this business in my sleep - it's time for a new challenge

Question 4: Are employee issues, customer complaints, and daily fires draining your energy?

• 0 = I handle these issues easily and they don't bother me
• 1 = They're manageable but sometimes frustrating
• 2 = These problems are becoming increasingly exhausting
• 3 = I'm so tired of dealing with people problems - I want out

Question 5: Have you started thinking seriously about retirement or your next life chapter?

• 0 = Retirement feels like a distant concept
• 1 = I've had some casual thoughts about eventual retirement
• 2 = I'm actively planning for retirement in the next 5 years
• 3 = I'm ready to retire now or pursue a completely different path

Question 6: Do you feel emotionally detached from the business you once loved?

• 0 = I'm still passionate and emotionally invested
• 1 = Some of the passion has faded but I still care
• 2 = I often feel like I'm just going through the motions
• 3 = I feel completely disconnected - it's just a paycheck now

Question 7: When you imagine selling, do you feel excited rather than anxious or sad?

• 0 = The thought of selling makes me anxious or sad
• 1 = Mixed emotions - some excitement, some worry
• 2 = More excited than worried about selling
• 3 = I'm genuinely excited about selling and moving on to what's next

Section 1 Score: _____ / 21

SECTION 2: Business Health Check - Operations & Preparedness

(7 Questions - 21 Points Possible)

Now let's talk about the meat and potatoes. Is your business actually sellable, or are you trying to sell a job that only you can do?

Question 8: Are your financial books and records professionally maintained and up-to-date?

• 0 = My records are messy, incomplete, or I handle them myself poorly
• 1 = Records exist but need cleanup and organization
• 2 = Good records with minor gaps that could be easily addressed
• 3 = Professionally maintained, clean books ready for due diligence

Question 9: Does your business have documented systems and processes that don't depend on your personal knowledge?

• 0 = Everything is in my head - no documented processes
• 1 = Some basic procedures written down but mostly informal
• 2 = Most key processes documented with room for improvement
• 3 = Comprehensive operations manual with detailed procedures

Question 10: Can your business operate successfully for 2+ weeks without you being physically present?

• 0 = Business would stop functioning without me there daily
• 1 = Could handle a few days but would struggle beyond that
• 2 = Could manage 1-2 weeks with some remote check-ins
• 3 = Business runs smoothly whether I'm there or not

Question 11: Do you have trained, reliable staff who could continue operations under new ownership?

• 0 = No staff or untrained/unreliable employees
• 1 = Some good people but training and systems need work
• 2 = Solid team with most key roles covered adequately
• 3 = Strong, well-trained team that buyers would be excited to inherit

Question 12: Is your business facility clean, organized, and presentable to potential buyers?

• 0 = Place needs major cleanup and organization
• 1 = Decent but could use some sprucing up
• 2 = Pretty good shape with minor improvements needed
• 3 = Immaculate and ready to impress buyers today

Question 13: Are your business contracts, leases, and legal documents organized and transferable?

• 0 = Documents are scattered, outdated, or problematic for transfer
• 1 = Most documents exist but need review and organization
• 2 = Generally good shape with minor issues to address
• 3 = All legal docs organized, current, and easily transferable

Question 14: Does your business have consistent, predictable cash flow that doesn't rely solely on your personal relationships?

• 0 = Revenue is unpredictable and heavily dependent on my personal connections
• 1 = Some consistency but still quite dependent on me personally
• 2 = Fairly predictable with some diversified revenue sources
• 3 = Stable, recurring revenue that would continue under new ownership

Section 2 Score: _____ / 21

SECTION 3: Market Intelligence - Actionable Steps & Knowledge

(7 Questions - 21 Points Possible)

Here's where we separate the dreamers from the serious sellers. Have you done your homework?

Question 15: Have you had a professional business valuation completed by a qualified appraiser or broker?

• 0 = Never had any formal valuation done
• 1 = Looked into it but haven't pulled the trigger yet
• 2 = Had a basic valuation but it might need updating
• 3 = Current, professional valuation from a qualified expert

Question 16: Have you researched what similar businesses in Tampa Bay are selling for?

• 0 = No idea what businesses like mine sell for
• 1 = Heard some general numbers but no real research
• 2 = Done some basic research on business sale prices
• 3 = Thoroughly researched recent comparable sales in my industry/area

Question 17: Have you browsed business-for-sale websites (BizBuySell, LoopNet, etc.) to understand the current market?

• 0 = Never looked at business sale listings
• 1 = Briefly browsed but not systematically
• 2 = Spent some time looking at current listings
• 3 = Regularly monitor the market and understand current trends

Question 18: Do you understand why less than 20% of listed businesses actually sell?

• 0 = Had no idea the success rate was so low
• 1 = Heard it was tough but don't know why
• 2 = Understand some of the common pitfalls
• 3 = Fully aware of why deals fail and how to avoid those mistakes

Question 19: Have you spoken with a professional business broker about your potential exit?

• 0 = Never talked to a broker
• 1 = Considered it but haven't made contact yet
• 2 = Had initial conversations with one or more brokers
• 3 = Developed relationships with qualified brokers who understand my business

Question 20: Have you attempted to sell your business before?

• 0 = This would be my first time trying to sell
• 1 = Thought about it seriously but never listed
• 2 = Listed before but didn't complete a sale
• 3 = Either completed a successful sale before or learned valuable lessons from a previous attempt

Question 21: Do you have a clear timeline and backup plan if the sale takes longer than expected?

• 0 = Haven't thought about timing or backup plans
• 1 = Have a general sense of when I'd like to sell
• 2 = Rough timeline with some flexibility built in
• 3 = Detailed timeline with multiple scenarios and backup plans

Section 3 Score: _____ / 21

Your Total Score & What It Means

Add up all three sections for your total score out of 63 possible points.

🔴 0-21 Points: Not Ready to Sell

You're in the early stages of thinking about selling, but there's significant work to be done. Don't panic - this is actually good news. Better to know now than waste time and money on a failed listing. Focus on the areas where you scored lowest and start making improvements.

🟡 22-42 Points: Getting There (But Don't List Yet)

You're making progress but still have important gaps to address before going to market. The good news? You're not starting from zero. Identify your weakest areas and tackle them systematically. Give yourself 6-12 months to shore up these areas before seriously considering listing.

🟢 43-63 Points: Market Ready (Let's Talk Strategy)

Congratulations - you're in rare air. Most business owners never reach this level of readiness. You've done the emotional work, built a sellable business, and educated yourself about the process. You're positioned for a successful sale that maximizes value.

The Next Step That Changes Everything

Here's what I tell every Tampa Bay business owner who's serious about selling:

Your first step is never listing your business. It's having a confidential conversation with someone who's been through this process hundreds of times.

At Lobo Business Sales LLC, we've helped Tampa Bay business owners navigate exits that change their lives forever. Whether you scored 15 or 55 on this quiz, we can show you exactly what needs to happen next.

Ready to get serious about your exit strategy?

Schedule your free, confidential consultation today - no obligations, just honest advice about your specific situation.

Don't wait until you're desperate to sell. The best exits are planned, not forced.

Questions? Text or call Dave Britton directly: [Contact info]

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