The Owner's Conversation
Please answer each question as honestly and thoughtfully as you can. There are no right or wrong answers. Your responses are confidential and will help guide our conversation.
1-If someone made you a fair offer for your business tomorrow, what would you do?
I'd accept it.
I'd seriously consider it.
I'd probably say no.
I'm honestly not sure.
2-Do you know what your business is worth?
No idea — I've never looked into it.
I have a rough guess based on general industry rules of thumb.
I have a reasonable estimate based on recent financial performance or past conversations.
Yes — I have a clear, credible valuation or formal market estimate
3-If you sold tomorrow, what would you do on Monday morning?
I have no idea — my business is my entire daily routine.
I have a vague idea, but nothing concrete that excites me yet.
I have a few specific projects, pursuits, or hobbies I'd jump into.
I know exactly what my next chapter looks like and I'm eager to begin.
4-If you disappeared for 30 days, what would your business look like when you came back?
No — I've never formally thought through or documented my transition vision.
I've thought about it in my head, but nothing is written down.
I have a rough written outline of my personal priorities and timeline.
Yes — I have clearly defined and documented what a successful transition means for me.
5-Would a buyer see systems, or dependency on you?
Heavy dependency — almost every major decision and key relationship runs through me.
Some processes exist, but the business still relies heavily on my daily direction.
Core operations run on established systems, though I'm still needed for key strategic decisions.
The business operates through established systems and a capable team; I am primarily involved in major strategic direction.
6-If you couldn't be involved in the business for 30 days, what would it look like when you came back?
It would struggle — major decisions and work would stall without me.
It would survive, but key decisions and growth initiatives would be on hold until my return.
It would run smoothly on daily tasks, with only minor items waiting for my review.
It would continue operating effectively, including handling most decisions and customer needs without me.
7-If you stepped away from the business for six months, who could actually lead it?
No one — there isn't currently a person or leadership team that could take overall responsibility.
Several people could cover pieces of operations, but leadership would be fragmented.
One person or leadership group could run most of the business, with some important strategic gaps.
A capable leader or leadership team could run the business effectively without relying on me day to day.
8-If an unexpected emergency prevented you from returning to the business, is there a clear plan for what happens next?
No — I'm honestly not sure what would happen.
There's a general informal understanding, but nothing clearly organized or documented.
We've addressed most of it, although some important operational or decision-making pieces remain unclear.
Yes — the key people involved know what happens next and the essential arrangements are in place.
9-How dependent is your business on a small number of customers?
Very dependent — losing one major customer could materially disrupt the business.
Somewhat dependent — a few key customers represent a meaningful share of our revenue.
Fairly diversified — losing one customer would hurt, but the business could absorb it.
Well diversified — no single customer or small group materially determines the business's stability.
10-How much confidence do you have in where next year's revenue will come from?
Very little — most revenue has to be won again from scratch each year.
Some — we have repeat customers, but future revenue is difficult to predict with confidence.
Good visibility — a meaningful portion comes from established repeat relationships, contracts, or steady backlog.
Strong visibility — much of our future revenue is supported by durable recurring, contracted, or highly predictable business.
11-If your CPA, attorney, and financial advisor met today, would they all describe the same plan?
No — they each know different pieces, but there isn't really one coordinated plan.
They know about each other, but most of the planning still happens separately.
I'm planning for retirement.
They've communicated on important issues and are generally working in the same direction.
Yes — they understand the overall plan, their respective roles, and how the pieces fit together.
12 — What decision about your business have you been postponing the longest?
13-Who is carrying the stress of your business besides you?
No one — I mostly carry it myself.
One person knows some of what I'm dealing with.
I have one or two people I regularly talk things through with.
I have several people I trust and can lean on.
14-If your spouse or partner answered these questions, would their answers match yours?
Probably not — we see the future of the business quite differently.
Some answers would match, but there are important things we haven't really worked through together.
Most would match — we're generally aligned, although a few areas still need discussion.
Yes — we've talked about these issues and have a shared understanding of what we want.
Not applicable / no spouse or partner
15-Apart from the business, have you figured out what you'd actually need to feel secure afterward?
No — I really haven't figured that out yet.
I have a rough sense, but I've never put a real number around it.
I have a fairly clear idea of what I would need.
Yes — I've worked through it carefully and know what I would need.
16-If the business sold today, plus everything else you own, would that be enough to fund the life you want afterward?
No — it wouldn't be enough.
I'm not sure — it might be close, but I haven't really worked it through.
Probably — based on what I know today, I believe it would be enough.
Yes — I've worked through the numbers and I'm confident it would support the life I want.
17-What part of your identity exists outside your business?
I'm not really sure — the business has been such a large part of who I am.
I have interests and relationships outside the business, but I haven't thought much about who I'd be without it.
Mostly the same.
I have a strong sense of who I am and what matters to me beyond the business.
18-What are you excited about doing after your transition?
Honestly, I don't know yet.
I have a few ideas, but nothing feels particularly clear or compelling.
There are several things I'm genuinely looking forward to.
I have a clear next chapter I'm excited to begin.
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