Questions for Reflection

01

What are you actually walking towards - not away from?

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Most owners know what they want to leave behind. Far fewer have a clear picture of what they're moving toward. The answer to this question shapes every decision that follows.

04

What does your knowing-doing gap look like?

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What do you already know you should be doing - that you haven't started? The gap between knowing and doing is rarely about information. It's almost always about something else. What is it, for you?

02

Who are you without this business?

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Not what you'll do, who you'll be. Your title, your routine, your sense of purpose have all been built around this. It's worth asking honestly what's underneath it before the question answers itself.

05

What would it feel like to have done this well?

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Not finished - done well. On your terms, at your pace, with clarity and without regret. Hold that picture. It will tell you what you're actually aiming for, which is not always what you think.

03

Are you selling because you want to, or because you feel you have to?

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Urgency and readiness are not the same thing. The trigger that brought you here - burnout, an offer, a health scare - shapes how clearly you can see your options. It's worth naming it.

06



What are you carrying that you haven't named yet?

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Fear of getting it wrong. Worry about what happens to the team. Uncertainty about your own value outside this role. These don't disappear when you ignore them, they tend to show up in decisions instead.

07

If you were out for six weeks tomorrow, what would happen?

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This is the single most honest diagnostic question for transition readiness. Not what would you like to think, what would actually happen? The gap between those two answers is where the work begins.

10

Can you tell the story of your business in numbers, month by month, for five years?

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A buyer isn't buying your past. They're buying the future, and they'll judge it based on your numbers. If you couldn't produce five years of clean, detailed financials in 24 hours, that's the conversation to start now.

08

Do your clients have a relationship with you, or with the business?

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If they would follow you out the door, that's a dependency, not a strength. A buyer is not buying your personal relationships. They're buying what stays when you leave. What stays?

11

Does your culture survive when you're not in the room?

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Values that live in one person's behaviour aren't embedded, they're borrowed. If the team doesn't hold the standard without you, a new owner will be starting from scratch. That affects value, timeline, and trust.

09

Which decisions still only go through you?

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Make the list. Every item on it is something the business cannot do without you. That's not leadership. it's a bottleneck. The question isn't whether the list exists, it's what you're prepared to do about it.

12



What would you flag upfront and are you prepared to?

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Every business has two or three things the owner hopes won't come up in due diligence. Declaring them yourself, before they're found, is the single most trust-building thing you can do. What would yours be?

13

How much of your time do you want to give your business’ new owner?

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Zero months? Six? Twelve? Twenty-four? This is your decision but only if you plan for it. Left unaddressed, the buyer sets the terms. And the answer shapes how many years of preparation you actually need.

16

What would change if you had no urgency at all?

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Sellers with no urgency negotiate from a position of power. They set the terms, filter the buyers, and walk away from anything that doesn't work. Urgency is the thing that changes that. Do you have it and does it have to be there?

14

When do you actually need to start, not when you plan to?

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Work it backwards. How long post-signing? How long for the sale? How long to fix what needs fixing first? Most owners get to this question and find they should have started two years ago. The next best time is now.

17

Who else is affected by this decision and have you thought about them?

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Your team. Your family. A co-founder who wants something different. A loyal client who doesn't know yet. Transition decisions rarely affect just one person. Getting clear on who's in the room, even if they're not in the room, changes the process.

15

Is this definitely a sale, or is it something else?

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A merger, a phased handover, an internal succession, a change of role, all require the same personal preparation, but the strategy looks very different. Have you genuinely explored the options, or defaulted to the obvious one?

18



What question do you need to ask before any of the ones you came in with?

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Most owners start with "how do I sell my business?" The more important questions usually come before that one. You don't have to answer everything today. But if there's one question sitting beneath all the others, it's worth naming it.

N E W S L E T T E R

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Every issue brings you case studies and articles on the real work of change: what it takes to commit, what gets in the way, and how to build something that actually holds.