Beyond the sales pitch
Good vendors want to solve problems; the great ones want to understand your business first. The difference is obvious when you move the conversation away from data sheets and into how they think. These five questions expose motives, priorities, and whether their success criteria align with yours.
What don’t you sell that might solve this better?
This separates sales teams from trusted advisors immediately. A vendor who can only talk about their own catalogue has not understood your problem.
Positive signals
- “Your current platform could handle this if we configure it differently.”
- “For your size, a lighter approach would land faster—here is what that looks like.”
- “We should confirm if this is a process issue before buying technology.”
Red flags
- “Let me compare our features to the competition.”
- “Sign this quarter and we can discount it heavily.”
- “We have already solved this for hundreds of companies just like you.”
How will you measure success in our environment?
If a supplier cannot explain how impact will be tracked, they are planning to declare victory once the product is installed. You need metrics, owners, and a review cadence.
Positive signals
- “We will baseline your current performance and model improvement with your data.”
- “Here is the risk register we manage throughout deployment.”
- “We agree the exit criteria up-front with stakeholders.”
Red flags
- “We deliver projects with 100% success.”
- “Our software is so intuitive it barely needs adoption support.”
- “Our team takes care of everything, you will not need to be involved.”
What happens if the numbers don’t stack up?
Great vendors lean into commercial transparency. They can model business benefit and will walk away if the ROI is not there.
Positive signals
- “We build the business case with you and we are comfortable being measured against it.”
- “This investment only works if you unlock the productivity change—let’s design for that.”
- “Here is how we would recommend you present the ROI to finance.”
Red flags
- “It depends which modules you choose.”
- “Our marketing team produced an ROI calculator we can share.”
- “It is difficult to be specific until you start using it.”
Who owns risk, adoption, and integration?
Technology succeeds or fails in the operational handover. Look for a supplier who is honest about where work needs to happen and how they will partner with your team.
Positive signals
- “We pinpoint the internal owners for change management and knowledge transfer.”
- “Our support model is transparent: here is what is included, here is what is not.”
- “We stage the rollout to prove value before scaling spend.”
Red flags
- “Support will take care of anything you need.”
- “Training won’t be an issue, it is all self-serve.”
- “We can commit to any SLA you need.”
What have you learned from projects that went wrong?
Every credible supplier has battle scars. If they cannot describe what they learned, they either have not delivered many projects or they refuse to reflect on them.
Positive signals
- “We run post-implementation reviews and adjust our playbooks.”
- “Clients tell us when onboarding fails—here is what we changed as a result.”
- “We stay involved after go-live to measure the outcomes we promised.”
Red flags
- “Nothing major has ever gone wrong.”
- “Once it is deployed, customers rarely need help.”
- “That is confidential.”
Interpreting the answers
The specific words matter less than how candid, structured, and commercially aware the responses are. Look for signals that the vendor thinks like a partner rather than a quota carrier.
They think strategically
They engage with commercial objectives, not just technical requirements.
They learn in public
They have stories, metrics, and scars from previous deployments—and they share them.
They accept accountability
They are prepared to be measured on business impact, not only uptime.
They educate their clients
They want you to understand the trade-offs so you can make the right call.
Vendors who answer thoughtfully are the ones willing to be accountable for business outcomes, even when that means a smaller initial contract. Keep them close.
Want a second opinion before you sign?
We review vendor recommendations for leadership teams who need an independent voice in the room. Together we quantify the risk, cost, and upside so every signature is backed by evidence.