Ten quick wins
Ask these first. Low effort, fast to act on, and most businesses have room in at least half of them.
- When did you last review your top ten vendor contracts for price and terms?
- What percentage of your costs is fixed versus variable, and where's the softest spot on the variable side?
- Which recurring expense would surprise you most if you totaled it for the year?
- If you cut this cost, does anything else — quality, speed, morale — take the hit, and can you live with that?
- When did you last raise prices, and what happened to volume when you did?
- How do your prices compare to the two or three competitors your customers actually mention?
- Which segment of your customer base is least price-sensitive, and could a price move start there first?
- Is there a version of this offer, priced 15–20% higher, that a subset of your current customers would still buy?
- Out of 100 qualified leads today, how many actually become paying customers?
- Where in the pipeline do most prospects go quiet — first call, proposal, or negotiation?
- What does your best salesperson do differently from the rest of the team?
- Do you have a documented, repeatable sales process, or does it live in people's heads?
- What's your churn rate today, and is it trending up or down?
- When a customer leaves, do you know why — or are you guessing?
- What happens in a customer's first 30, 60, and 90 days that might be setting up an early exit?
- Is there one segment of customers with meaningfully higher churn than the rest?
- What percentage of customers buy only one product or service from you?
- Is there a natural "next purchase" you rarely offer at the moment someone's already buying?
- Does your team have a specific prompt, script, or trigger for suggesting an upgrade?
- What's stopped you from formalizing this into a repeatable offer?
- Which two or three items do customers already tend to buy together?
- Have you tested a bundled price against the sum of the parts sold separately?
- Would bundling simplify a decision your customers currently find confusing?
- What margin are you willing to trade for a larger average transaction?
- What happens today when a prospect says your main offer is too expensive?
- Is there a smaller, cheaper version of what you sell that still delivers real value?
- How many "no's" this year might have become a smaller "yes"?
- Would a downsell cannibalize your core offer, or catch buyers you're currently losing outright?
- What percentage of new business already comes from referrals, without you asking for them?
- Do you have a specific, repeatable moment when you ask a happy customer for a referral?
- Is there an incentive — for the referrer, the referred, or both — that would make this easy to ask for?
- Who are your three most vocal advocates, and when did you last ask them for a formal introduction?
- How many customers have gone quiet in the last 12–24 months without formally churning?
- Do you have their contact information and purchase history readily accessible?
- What would bring them back — a new offer, a check-in, or just being remembered?
- Has anyone actually reached out to them, or have they just faded from view?
- Where do most of your leads come from today, and how concentrated is that source?
- What's your current cost to acquire one qualified lead?
- Is there a channel your competitors use that you haven't tested?
- If your best lead source disappeared tomorrow, what would you do?
- If a prospect compared you to your top competitor in one sentence, what would they say?
- What do you do that's genuinely hard for a competitor to copy?
- Are you competing on price because you haven't given customers another reason to choose you?
- What would it take to become the default answer in your category rather than one of several options?
- What specific outcome does a customer actually buy from you — not the feature, the result?
- When was the last time you rewrote your core offer from scratch instead of tweaking it?
- What objection comes up most often right before someone decides not to buy?
- If you could only keep one part of your current offer, which part is doing all the work?
- What's the next problem existing customers ask you to solve that you currently say no to?
- Could an adjacent product or service reuse your existing relationships and delivery capability?
- Is there a version of what you sell for a slightly different segment you already reach?
- What would you build if you assumed your best customers would buy it on day one?
- Do you currently offer one option, or a genuine good / better / best structure?
- What percentage of customers pick your lowest-priced option because nothing else was offered?
- Is there a premium tier that would let your best customers pay more for more?
- Would adding a decoy or anchor option change what people choose?
- What percentage of revenue today is one-time versus recurring?
- Is there a version of what you sell that could be delivered as an ongoing subscription or retainer?
- What would it take for customers to prefer a subscription over a repeat one-off purchase?
- How would predictable monthly revenue change what you could plan or invest in?
- Which digital channel has the best return today, and how much more could you put behind it?
- Do you know your cost per lead and cost per customer by channel?
- What's untested — a channel, an audience, or a message — that a competitor is already using?
- Is your website or landing page actually built to convert, or just to inform?
- What happens to a lead who isn't ready to buy today — do they hear from you again, and when?
- How many touches, on average, does it take before a lead converts?
- Is there a simple email or content sequence that could run without manual effort?
- Which leads went cold that a consistent follow-up cadence might have saved?
- Who already has a relationship with your ideal customer that you don't compete with?
- What could you offer a partner that costs you little but helps them a lot?
- Have you approached anyone about a formal referral or co-marketing arrangement, or has it stayed informal?
- Is there an existing vendor or supplier relationship that could become a two-way channel?
- Where do your customers already shop or search that you're not present?
- What would it take to sell through a marketplace, distributor, or reseller instead of only direct?
- Is there a channel conflict risk, and how would you manage it?
- What's the smallest test of a new channel you could run in the next 90 days?
- Is there a nearby region or segment with the same problem you already solve well?
- What's different about that market — regulation, language, buying behavior — that you'd need to account for?
- Could you serve a new market with your existing team, or does it require new hires or partners?
- What's the cheapest way to test demand before committing real investment?
- How long does it take, on average, from first contact to closed deal?
- Where does the process stall — waiting on you, or waiting on the customer?
- What information do prospects always ask for that you could provide upfront?
- Is there an approval step or internal handoff that adds delay without adding value?
- What does a new customer experience in their first week with you?
- Is there a point early on where customers commonly get confused, stuck, or go quiet?
- Do you know your churn rate in the first 90 days specifically, versus churn overall?
- What would make someone feel like they made the right decision within the first few days?
- How often does your average customer buy from you in a year?
- Is there a reward, status, or recognition that would make a repeat customer feel valued?
- What's stopping your best customers from buying more often than they already do?
- Would a structured program change behavior, or would people keep buying the same way regardless?
- Which vendor relationships have been on autopilot for more than two years?
- Do you know what a competitor would charge for the same service or supply?
- Is there volume, timing, or loyalty you could use as leverage in a renegotiation?
- What's the cost of switching versus the savings of staying and asking for a better deal?
- What task does someone on your team do repeatedly that a tool could do instead?
- How many hours a week go into work that doesn't require judgment, only consistency?
- Have you priced out the tools that exist for this, or assumed it's not worth it?
- What would that person do with the time back if the task disappeared?
- Do you track loss — inventory, materials, time — closely enough to know where it's happening?
- Is there a process step where things regularly go wrong or get redone?
- What would you find if you audited one month of waste line by line?
- Who on the team would notice first if shrinkage started creeping up?
- What task takes disproportionate time relative to how much it matters to your core business?
- Is there a function you keep in-house out of habit rather than necessity?
- What would it cost to outsource this versus what it currently costs in salary, tools, and management time?
- What's the risk if this went to an outside provider, and is it actually as high as it feels?
- What's your turnover rate today, and what does replacing one person actually cost you?
- When someone leaves, do you know the real reason, or just the reason they gave you?
- What would your best people say is the one thing that would make them stay longer?
- Is there a pattern in who leaves — tenure, role, manager — worth paying attention to?
- What skill gap shows up most often when work doesn't go as planned?
- Is there training that would let your current team do more without adding headcount?
- How much of your team's time is spent on tasks they've never been properly trained for?
- What would change in output if your average performer worked like your best performer?
- What does your compensation or bonus structure actually reward today?
- Is there a mismatch between what you pay people to do and what actually grows profit?
- Would your team make different decisions if they could see the profit impact of their choices?
- What behavior would change tomorrow if incentives shifted to match this?