10 questions every IT leader should ask before choosing a vendor

Ten tough questions every IT leader should ask before choosing a vendor—practical, research-backed, and designed to help you avoid costly mistakes.

1. How does this directly advance our organization’s long-term goals and strategy?

Getting swept up in shiny features or the latest “must-have” tool is easy. The smarter move is to step back and ask if this project moves the needle for the business or just adds another layer of technical noise. This question is the anchor: it forces leadership to connect the dots between IT spend and the bigger picture.

Why ask it?

• Misaligned IT projects are a slow leak in the budget. McKinsey found that 70% of tech leaders point to poor strategic alignment as the main culprit behind wasted investments.

• A project that does not map to core business goals will never be more than a patch, no matter how slick the demo looks.

What to do next:

• Pull out the strategic roadmap and check if this project actually fits.

• Use OKRs or a similar framework to tie the initiative to tangible business outcomes.

• Bring in both business and tech decision-makers to challenge assumptions. If the case is weak, do not be afraid to press pause or send it back for a rethink.

How this helps with vendor selection:

Vendors are experts at selling sizzle. This question keeps the conversation focused on steak. When everyone is clear on what matters to the business, it is a lot easier to filter out distractions and zero in on solutions that actually deliver. It also gives you the upper hand in negotiations—if a vendor cannot show how they drive long-term value, they are not worth your time.

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2. How will we verify that the vendor’s promises match their real-world support and incident response track record?

It is one thing for a vendor to promise gold-star support and lightning-fast response times during the sales cycle. It is another to see those claims hold up under real pressure. This question cuts through the marketing gloss and asks, “How do we know you actually deliver when things break?” Because in IT, it is not if something will go wrong, but when.

Why ask it?

• Nearly half of organizations have dealt with serious vendor-related security incidents in the last two years, according to SecurityWeek.

• Slick sales decks cannot fix production outages, security breaches, or a support desk that goes dark when you need them most.

• Overpromising and underdelivering is one of the oldest tricks in the book. The cost lands on your team and your reputation.

What to do next:

• Ask for hard evidence: independent audit results, incident response logs, and customer references that match your industry and scale.

• Press for real-world SLAs, not just generic ones. What was their average response time during the last major incident? How often do they hit their targets?

• Speak with current customers—not just the ones on their reference list. Look for patterns in reviews, forums, and peer groups.

How this helps with vendor selection:

This question weeds out the pretenders from the real partners. It forces vendors to back up their promises with facts, not just pitches. The vendors who come prepared with proof are the ones who will have your back when things go sideways. The rest are just hoping you will not look under the hood.

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3. How will the vendor help us drive user adoption and change management, not just technical deployment?

Getting a new system up and running is only half the battle. The real challenge is getting people to actually use it—and use it well. Too many IT projects stall out because the deployment was treated as the finish line, not the starting pistol. This question shifts the focus from tech specs to real-world impact. If the vendor is not thinking about how users will adapt, the rollout is already at risk.

Why ask it?

• Up to 70% of digital transformation efforts fail, and user resistance is almost always to blame, according to McKinsey.

• Even the best solutions become shelfware if they do not fit how people work or if training is an afterthought.

• Change always meets friction. The vendors worth your time will have a plan for smoothing the path, not just plugging in hardware or software.

What to do next:

• Ask for specifics: What does the vendor’s adoption and training program look like? Do they have real-world case studies or metrics on user uptake?

• Look for resources beyond basic onboarding—think change champions, ongoing support, and tailored communication plans.

• Insist on clear post-launch engagement and support, not just a handoff at go-live.

How this helps with vendor selection:

Vendors who take user adoption seriously are invested in your long-term success, not just the sale. They will offer practical change management strategies and stick around to make sure the solution delivers value. The rest will disappear once the invoice is paid, leaving you to battle frustration and low adoption alone.

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4. How does this solution integrate with our existing technology ecosystem and future roadmap?

Every IT leader knows the pain of a tool that “almost fits.” Integration headaches are legendary—one incompatible system can drag down productivity, frustrate teams, and quietly rack up hidden costs. This question zeroes in on whether the shiny new solution will actually play well with what’s already running and what’s coming next. It is not about ticking boxes—it is about making sure today’s investment does not become tomorrow’s roadblock.

Why ask it?

• Over half of IT project failures trace back to poor integration with legacy systems, according to Deloitte.

• A solution that cannot connect cleanly to your core infrastructure or future plans will create silos, manual workarounds, and security gaps.

• The cost of a bad fit is not just technical debt—it is lost agility, stalled projects, and missed business opportunities.

What to do next:

• Map out all critical integrations up front: APIs, data flows, authentication, compliance, and reporting.

• Demand a detailed integration plan from vendors, not just a vague “it’s compatible.”

• Have both IT architects and business stakeholders review the plan. If it does not align with your technology roadmap, reconsider.

How this helps with vendor selection:

This question quickly separates vendors with real engineering chops from those selling a black box. Vendors who offer clear, tested integration strategies are thinking about your whole environment, not just their own product. The rest are hoping you will accept “it should work” as an answer—which is a recipe for headaches down the line.

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5. What is the full lifecycle cost, including hidden costs (integration, training, maintenance, switching)?

Sticker price is just the tip of the iceberg. Every seasoned IT leader knows that the real price tag reveals itself over time—in integration headaches, user training, ongoing maintenance, and the not-so-small matter of switching costs down the road. This question demands a clear-eyed view of what the organization is signing up for, long after the initial invoice is paid.

Why ask it?

• Only about a quarter of organizations accurately predict the total cost of ownership for IT investments, according to Deloitte’s latest industry outlook.

• Hidden costs can erode ROI, derail budgets, and leave IT teams firefighting surprise expenses when priorities shift.

• Focusing only on upfront costs is a classic rookie mistake that seasoned leaders avoid.

What to do next:

• Itemize costs beyond the purchase: integration, migration, custom development, user training, annual support, upgrades, and eventual exit or migration fees.

• Push vendors for transparent pricing models and real-world customer examples, not just ballpark estimates.

• Factor in the cost of lost productivity and potential downtime during implementation or future transitions.

How this helps with vendor selection:

This question cuts through the optimism that often colors vendor proposals. Vendors who are upfront and specific about the total lifecycle cost are the ones you want in your corner—they help avoid ugly surprises and support smarter, long-term decisions. The rest are gambling you won’t ask the tough questions until it’s too late.

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6. What are our “no-regret” dealbreakers, and what red flags would halt the process?

Every IT leader has a war story about the project that should have been stopped before it started. This question is about defining the line in the sand—the non-negotiables that, if crossed, mean the conversation ends right there. Dealbreakers are not just about gut feeling. They are the result of hard-won experience, lessons from past failures, and a clear understanding of risk tolerance.

Why ask it?

• Major incidents almost always follow ignored warning signs. Zero-tolerance red flags, especially around security, data ownership, and compliance, should never be up for debate.

• The IT Vendor Evaluation Checklist highlights that overlooking these can turn a promising project into an expensive liability.

• Being explicit about dealbreakers protects both the organization and its leadership from avoidable fallout.

What to do next:

• Define and document non-negotiables before discussions begin: examples include lack of transparency, unclear data controls, or poor compliance history.

• Share these standards early and demand written commitments from vendors.

• Create a process for surfacing and acting on red flags—do not let wishful thinking override hard evidence.

How this helps with vendor selection:

This question keeps the evaluation process honest and focused. Vendors who respect your boundaries and respond with clarity are worth considering. The rest will try to talk around the issue—making it easy to walk away before any damage is done.

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7. What should be the primary SLAs and deliverables to measure the effectiveness and ROI of working with a vendor?

It is easy to get caught up in promises and buzzwords, but if there is no clear way to measure success, disappointment is almost guaranteed. This question is about setting the rules of the game upfront—what will the vendor deliver, how will it be measured, and what happens if they miss the mark? Without well-defined SLAs and deliverables, even the best partnerships can turn into finger-pointing contests when things go sideways.

Why ask it?

• Fewer than one in three organizations have concrete, actionable metrics for vendor performance, according to Kodiak Hub’s industry research.

• SLAs that are vague, generic, or purely technical make it almost impossible to hold anyone accountable or track ROI.

• The right deliverables keep both sides honest and drive continuous value, not just a one-and-done project.

What to do next:

• Define outcome-based SLAs that tie directly to business impact—think uptime, security response, support resolution, and user adoption.

• Push vendors for historical performance data and references that show they consistently meet or exceed these targets.

• Build regular review checkpoints and escalation paths into the contract so issues get addressed early, not after the damage is done.

How this helps with vendor selection:

Vendors who are comfortable with specific, transparent SLAs are signaling confidence and reliability. They are ready to be measured and held accountable for results. Anyone who shies away from the details is waving a red flag you cannot afford to ignore.

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8. Who will own the implementation, and how will we ensure the least disruptions to ongoing processes?

Getting a deal signed is only half the job. The real work starts when someone has to turn a plan into a working reality. This question cuts straight to the heart of accountability: Who is actually steering the ship, and how will the rest of the business keep running smoothly while the change rolls out? Without clear ownership and a disruption-minimizing plan, even the best solutions can unravel fast.

Why ask it?

• Forty-one percent of IT project failures are pinned on unclear ownership and poor cross-functional coordination, according to NIGP research.

• Teams already stretched thin cannot afford project chaos or sudden slowdowns in business-critical operations.

• When everyone assumes “someone else has it,” details slip and deadlines get missed.

What to do next:

• Assign a single owner or executive sponsor with real decision-making power—ambiguity is the enemy.

• Map out responsibilities for both IT and business stakeholders, and make sure everyone knows who to go to when issues crop up.

• Build a rollout plan that anticipates business-as-usual needs, scheduling deployments to avoid peak times and planning for temporary workarounds.

How this helps with vendor selection:

Vendors who offer structured implementation support, with clear roles and escalation paths, are much more likely to deliver a smooth transition. The rest will leave you to play project manager, firefighter, and therapist all at once—which is a surefire way to burn out your team and stall your momentum.

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9. What are the “unknown unknowns”—what risks or hidden costs have bitten us in past projects, and how can we surface them early?

Every seasoned IT leader has scars from surprises that were never on the radar. This question is about learning from history instead of repeating it. “Unknown unknowns” are the risks you never saw coming—unexpected integration issues, hidden licensing fees, vendor roadblocks, or sudden regulatory headaches. If these lurking pitfalls aren’t surfaced early, they can sink even the most promising projects.

Why ask it?

• Top-performing organizations bake risk reviews and scenario planning into the vendor selection process for a reason. Gartner and other industry leaders emphasize that pre-mortems—thinking through what could go wrong—consistently catch costly blind spots.

• Ignoring this question means relying on luck instead of experience. That rarely ends well.

What to do next:

• Run a pre-mortem: Gather your project team and brainstorm all the ways the initiative could fail.

• Review post-mortems from previous projects. What tripped you up last time? Which costs or risks were underestimated or missed entirely?

• Push vendors for transparency on their own “gotchas”—ask for real-world case studies where things went sideways and how they responded.

How this helps with vendor selection:

Vendors who address potential risks head-on and share lessons learned are the ones you want on your side. They help you avoid old mistakes and see around corners. Vendors who dodge tough questions or gloss over past failures are betting you will not dig too deep—until it is too late.

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10. If the contract or relationship with a vendor fails, what is our business continuity plan?

No one likes to plan for disaster, but ignoring the possibility is a gamble few IT leaders can afford. This question is about being brutally honest: What happens if the vendor relationship sours or the contract gets axed? Whether it is a breach, a business collapse, or a plain old mismatch, the fallout can cripple operations if a backup plan is not in place.

Why ask it?

• Only 39 percent of IT leaders feel prepared to switch vendors or recover quickly from a failed vendor relationship, according to recent Forbes analysis.

• Vendor lock-in is real. Losing access to critical systems or support can cause widespread disruption, lost revenue, and reputational damage.

• A good continuity plan is not just about risk mitigation—it is about protecting the business and maintaining leverage in negotiations.

What to do next:

• Identify which systems, data, and processes are vendor-dependent and map out alternatives.

• Build transition plans and exit clauses into contracts from day one. Know exactly how you will retrieve your data and what the handover process looks like.

• Test backup processes and document responsibilities in case of emergency. Do not wait for a crisis to find out who is on the hook.

How this helps with vendor selection:

Vendors who are transparent about exit strategies and support smooth transitions show they value partnership over lock-in. The rest hope you never ask the tough questions—until you are handcuffed to their ecosystem. The ability to walk away clean is the mark of a mature IT operation.