It will fail because you picked the wrong partner to implement it.
In the age of digital transformation, technology is no longer just a back-office function—it’s the backbone of business strategy. Whether you’re implementing an ERP, revamping your CRM, or launching a full-scale HCM upgrade, success hinges on one critical decision: choosing the right tech vendor.
Yet, this is where many organizations falter.
Time and again, I’ve seen most companies rush through vendor selection, swayed by flashy demos, big-brand logos, or the lowest quote. Months later, they’re stuck with a project that’s off-track, over budget, and under-delivering. The common denominator? They didn’t ask the right questions before signing the contract.
So, how do you avoid becoming another cautionary tale?
Start with this list of 10 must-ask questions that will give you deeper insight into your prospective partner’s capability, culture, and credibility.
- Can you provide examples of similar projects you’ve successfully delivered in our industry? A vendor with real-world experience in your domain won’t just understand your business—they’ll anticipate challenges and propose smarter solutions. Ask for case studies, Previous Letter of Intent without valuation and reference contacts. Specifics matter.
- What is your historical success rate with projects of similar size and scope? Past performance is the best predictor of delivery discipline. Look for data: on-time delivery, budget adherence, business impact.
- How do you manage SLAs, and what do your real-world SLA metrics look like? Anyone can promise service levels. Few can prove consistency. Request real SLA performance reports from current or past clients.
- What are your average response and resolution times during critical incidents? Uptime is non-negotiable. Delays during outages cost revenue—and trust. Ask them to walk you through a real incident response timeline.
- What’s your financial position? How do you ensure continuity during market volatility? You’re not just buying a service. You’re entering a long-term relationship. You need a stable partner. Review financials. Ask about contingency planning.
- How involved is your executive leadership when critical projects hit roadblocks? You want more than a vendor. You want accountability at the top. Ask to meet the leadership team during due diligence.
- Can we speak directly to 2–3 clients from similar industries? Reference checks are your best safety net. Prepare your own reference call questions. Don’t rely only on scripted success stories.
- What’s your roadmap over the next 1–3 years, and how will it evolve with our business? A capable vendor doesn’t just solve for today—they scale with you. Look for direction in AI, integration, automation, and vertical-specific innovations.
- How do you manage data privacy, compliance, and cybersecurity? This is no longer a checkbox—it’s a board-level concern. Look for ISO certifications, clear governance frameworks, and strong security leadership.
- How do you define “partnership”? Are you a vendor, an advisor, or a collaborator? Cultural alignment matters more than you think. Are they delivering a project—or co-owning an outcome? The best vendors sound like internal stakeholders.
Final Word
A tech vendor can either be your biggest asset or your most expensive lesson.
Choose one that understands your business, not just your brief.
Someone who shows up when things go wrong.
Who solves alongside you—not just bills you.
Because the questions you ask today will determine the outcomes you see a year from now.
📥 Want a downloadable checklist version of these 10 questions for your next vendor evaluation? Just say the word—I’ve got you covered.