52 Questions for Your Strategy Offsite

Which assumption in our current plan is oldest — and when did we last test it against the market?

If our biggest channel stopped working next quarter, what revenue survives, and who owns that answer?

What is the market growing into that we are not organised to capture?

Which competitor move in the last 12 months did we notice late — and why did we notice late?

What do our best customers buy around our product that we could credibly own?

Where are we competing on habit rather than on a deliberate choice?

What evidence would make us abandon our current biggest bet — and do we collect it?

Which segment finds us without marketing, and what does that tell us?

What has changed in how our buyers discover, evaluate and purchase in the last two years?

If we had to grow 30% with no new customers, whose wallet would it come from?

What regulation, platform rule or input cost could rewrite our economics in 24 months?

Which of our markets would we not enter if we were deciding today?

What does the number two player in our category do better than us, specifically?

What is the exact moment a customer realises they need us — and who owns being present there?

Which customer complaint have we normalised?

What do customers say we do better than anyone — and have we verified it this year?

Who is the customer we should politely refuse, and do we?

What percentage of last year's customers came back — and does anyone review that monthly?

What is the most common reason we lose a deal we wanted, evidenced not assumed?

If our price rose 15% tomorrow, which customers stay instantly, and what does that prove?

What do our customers' customers want that changes what our customers need from us?

Which part of our offer do customers value most — and is it the part we talk about most?

What would a customer say is the risk of choosing us, and how do we answer it before they ask?

Who influences the buying decision that we never meet?

What did our ten best customers have in common twelve months before they bought?

If we disappeared next month, what would our customers genuinely miss?

Where exactly does a rupee of revenue leak between list price and contribution?

Which product, channel or customer would we discontinue if we ranked everything by contribution?

What is our pocket price by channel — and who has seen that number this quarter?

How much discount did we give last year that nobody consciously approved?

What is the true cost of acquiring a customer, including everything, by channel?

If revenue doubled with current systems, what breaks first: cash, supply, or people?

Which fixed cost has never been challenged since it was first approved?

What return did our biggest marketing investment actually produce, and how do we know?

How many days of cash sit in receivables and inventory that a decision could release?

What would we do differently if we measured success on contribution per customer, not revenue?

Which revenue in the plan is assumed rather than evidenced?

What is the cheapest source of our next crore — retention, price, or acquisition — and do we fund it accordingly?

If we had half the budget, what would we protect — and why is it not clearly protected today?

Which decision took too long last quarter, and what would have made it fast?

What are the three metrics this leadership team should never meet without reviewing?

Who can say no to a discount — and does the organisation know?

Which recurring meeting produces no decision, and why does it still exist?

What capability must exist in-house in two years that we rent today?

If our best salesperson left, what knowledge leaves with them?

What did we decide at the last offsite that actually changed behaviour on Monday?

Which role in the commercial team would we not refill if it became vacant?

What do we measure that nobody acts on — and what do we act on that nobody measures?

Where does a deal or order wait longest inside our own organisation?

What would our frontline sales team say leadership misunderstands about the market?

Which of our processes exists to protect us from a mistake we made once, years ago?

If each of us could only keep three priorities this year, which three survive — and are they the same three?