If you're leading client meetings diving straight into the technical weeds, you're probably losing deals to competitors who barely mentioned technology at all, says Cory Kirkendoll, CEO of 5K Technical Services. The best MSPs treat discovery like building a business relationship, not a technical pitch. That means gathering intelligence about prospects before you ever sit down with them and using that knowledge to position yourself as a strategic partner who understands their financial realities and business pressures.
Listen More, Talk Way Less
You can use AI tools to track your speaking ratio in discovery calls. If you're talking more than 50% of the time, you're doing it wrong, says Kirkendoll. The goal is to get prospects discussing their business challenges while you listen and take notes. Kirkendoll calls this the hardest discipline to master for technical professionals, who typically love to demonstrate expertise by explaining solutions.
Resist that urge. The more you dominate the conversation, the less you understand what the prospect actually needs. More importantly, you miss critical financial and business context that would help you understand whether this prospect can afford your services, whether they're a good long-term fit and how to structure an engagement that actually supports their growth.
Can you help them grow revenue? Reduce risk? Enable their strategic initiatives? You'll never uncover the financial drivers behind these goals if you're too busy explaining your tech stack.
What to Research and What to Ask
Before you walk into any prospect meeting, you need a systematic approach to gathering intelligence and guiding conversations. Kirkendoll recommends building a “prospect profile” that captures both business and financial intelligence, transforming you from a vendor into a consultant who understands their world. Capture these elements in your CRM for every prospect before your first real conversation:
Prospect Profile
Company Demographics and Financial Scale: Number of employees, locations, organizational structure and primary revenue sources help you understand their scale and financial complexity. Are they growing or contracting? How many locations are they supporting?
Ownership Structure: Check their Secretary of State website for ownership details. Publicly traded companies operate differently than family businesses or private equity-backed firms. This tells you who controls spending decisions and what financial pressures they face.
Industry Financial Health: What sector are they in? What are the growth possibilities, competitive pressures and economic trends affecting their space? Understanding their industry's financial trajectory helps you anticipate their challenges and proactively explore solutions.
Customer Base and Revenue Patterns: Check their website testimonials to see who they serve. This reveals their revenue stability, because they'll face the same budget cycles and funding challenges their clients do.
Leadership Backgrounds and Stability: Research senior executives on LinkedIn. If they bounce between companies every two or three years, the person you start with probably won't be the person you finish with. Leadership turnover could signal financial instability or strategic uncertainty. And Kirkendoll warns that leadership changes create transition headaches where you suddenly have to prove your value to someone new who might bring their own IT contacts.
Organizational Values and Financial Priorities: Look at website messaging and company culture signals and do business with clients whose values align with yours. But also pay attention to what they prioritize financially. Do they invest in growth? Cut costs aggressively? Value long-term partnerships or chase the lowest price?
You don't need expensive databases to gather this intelligence. Kirkendoll recommends these starting points:
• Secretary of State business filings
• Public court records (including recent hires and fires)
• Company websites and social media
• LinkedIn profiles for leadership team
• Local library databases
• Online rating sites and review platforms
• Industry publications and trade media
The key is doing this work before you walk in the door. Kirkendoll's research extends to checking public records for personnel changes and understanding client companies well enough to predict their financial challenges.
Financial Benchmarking
Once you're in the room, these open-ended questions shift the discussion from technical specifications to business and financial partnership:
• Where do you see yourself in five years?
• What does your business need to grow?
• What keeps you up at night?
• What are your biggest business challenges right now?
• How many IT service providers have you worked with in the last five years?
• Why are you looking for a new IT provider now?
• Have you had a chance to tell your current provider about these issues?
That last question matters more than most MSPs realize. If prospects haven't communicated their pain points to their current provider, they probably won't communicate them to you either. Kirkendoll also suggests asking directly about their IT provider history. If they've cycled through five providers in five years, that's a red flag about either their financial stability or their ability to maintain vendor relationships.
Reconfigure Your Conversations
When you finally sit down with a prospect armed with your research and questions, do something unexpected: Say nothing about tech. Instead, focus entirely on understanding what they need to make their business grow and where they see themselves in the next five years.
This approach often catches prospects off guard. They’re expecting a pitch. They're prepared for an IT provider, but suddenly you're asking about their business strategy like a consultant.
The response you're aiming for is honest dialogue about business challenges, not a list of technical requirements. When you understand their business goals and financial drivers first, you can position technology as an enabler rather than a product. If they want to grow revenue, you're not just offering cloud migration. You're offering the infrastructure that supports scaling operations without adding overhead, and the beginnings of partnership built on financial intelligence.
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