The Power of Questions
We’ve all heard stories of costly business decisions—like the company that locked into a five-year contract for software that became obsolete in two. Or the organization that switched vendors to save money, only to find hidden fees and unreliable service down the road. These situations don’t happen because leaders aren’t paying attention. They happen because the right questions weren’t asked before the commitment was made.
Contracts aren’t just about terms and conditions—they shape the future of your business. The best leaders know that signing on the dotted line isn’t just about what you’re agreeing to, but who you’re partnering with and how it aligns with your vision.
That’s why before committing to any agreement, whether it’s a technology solution, a strategic partnership, or major investment, smart leaders take a step back and ask the tough questions. Questions that uncover potential risks, ensure long-term value, and prevent costly missteps.
Smart decisions start with the right questions. Before signing on the dotted line, here are five key questions every leader should ask.
1. Does This Align with Our Long-Term Vision?
It’s easy to get excited about a new solution that promises immediate improvements. Maybe it’s a cutting-edge software platform or a service that will streamline operations overnight. But fast-forward a year, and suddenly, it no longer fits your company’s evolving needs. What seemed like the perfect fit then is now holding you back.
Questions to Ask:
- Will this investment still serve us in five years?
- Does it align with our company’s strategic goals?
- How will it scale as our needs evolve?
2. What Problems Are We Actually Solving?
When something isn’t working, the natural instinct is to fix it… fast. A business frustrated by slow response times might rush to switch vendors, believing speed is the issue. But speed isn’t always the real issue. Sometimes, what they really need is a proactive partner who can prevent problems before they happen. Without addressing the root cause, you may just be trading one issue for another.
Questions to Ask:
- What pain points led us here?
- Does this solve the root cause or just a symptom?
- How will we measure success?
3. Are We Choosing a Vendor or a Partner?
On paper, two providers might look identical—similar pricing, comparable offerings, strong reputations. But when things go wrong, the difference becomes obvious. Some vendors do the bare minimum—delivering what’s promised, but nothing beyond that. Others step up, anticipate challenges, and help your business adapt. The real question isn’t just who can provide this service? It’s who will stand by us when we need them most?
Questions to Ask:
- Will this provider be there when challenges arise?
- Are they invested in our success beyond the sale?
- Do they offer ongoing support and insights?
4. What Are the Risks, and How Will We Mitigate Them?
Every decision carries some level of risk, whether it’s financial, operational, or regulatory. The biggest mistakes happen when leaders assume everything will go smoothly. Compliance requirements shift, hidden fees emerge, and unexpected roadblocks appear. The best way to avoid costly surprises is to identify risks before they turn into real problems.
Questions to Ask:
- What’s the worst-case scenario?
- Are there hidden costs or limitations?
- How will this impact our operations, compliance, and security?
5. What Happens If We Need to Pivot?
No matter how much planning goes into a decision, the future is unpredictable. A company might commit to a long-term service contract, only to find that their needs shift as the business grows. Or they might invest in a tool that works perfectly now but struggles to keep up with evolving technology and industry demands. In today’s world, flexibility isn’t a perk—it’s a requirement. The question isn’t if your needs will change, but when.
Questions to Ask:
- How flexible is the contract?
- What are the exit or adjustment options?
- Does this partner adapt with industry and evolving needs?
The Right Questions Lead to the Best Decisions
Smart leaders don’t make decisions based on flashy sales pitches or short-term convenience—they ask the tough questions. They think beyond today, challenge assumptions, and ensure every commitment aligns with their long-term vision. Because signing on the dotted line isn’t just about what you’re agreeing to, it’s about who you’re partnering with and how that decision will impact your future.
At Applied Innovation, we believe great partnerships aren’t just about transactions—they’re about long-term impact. Whether you’re exploring new technology, automation, or process improvements, let’s have a conversation. Because the best leaders don’t just sign contracts—they make decisions to shape the future.