You found the right business. The financials check out on paper. You’ve negotiated an LOI that works. Now you just need to verify everything before you wire a life-changing amount of money to a stranger.
Welcome to due diligence—the phase where deals go to die slowly.
Not because anything is wrong with the business. But because getting the information you need from the seller feels like pulling teeth. Requests disappear into the void. Documents trickle in over weeks. Simple questions turn into phone tag. And the whole time, you’re wondering: is this delay a red flag, or is this just how it goes?
It doesn’t have to be this way.
Why Diligence Feels So Painful
Most of the friction in due diligence has nothing to do with what you’re asking for. It’s about how the process is structured.
The seller isn’t hiding anything—they’re just overwhelmed. You sent a 60-item diligence list. They’re still running a business. Half those documents aren’t in one place. Their CPA has some, their attorney has others, and the equipment list is “somewhere.” They’re not stonewalling you. They just don’t know where to start.
Email is a black hole. You ask for three years of tax returns. A week later, you get two years. You reply asking for the third. Another week. Now multiply that by 40 line items across multiple threads and you’ve lost the plot entirely.
Nobody knows where things stand. You’re asking your broker for updates. Your broker is asking the seller. The seller thinks they already sent that document. Everyone’s operating from a different version of reality.
The seller’s team isn’t coordinated. The CPA, the attorney, and the seller are all providing documents separately. No one can see what the others have submitted. Gaps don’t surface until you audit the whole package weeks later.
The result: what should take 30 days takes 60. Or 90. And every week that passes is another week of uncertainty, another week your SBA loan approval sits in limbo, another week the seller wonders if you’re actually going to close.
What Actually Speeds Things Up
The conventional wisdom is that buyers need to be more organized—better checklists, tighter follow-ups, more persistent nagging.
That’s backwards. You can’t out-organize a broken process.
What actually works is making it radically easier for the seller to give you what you need. That means:
Clarity over comprehensiveness. A 100-item diligence list that overwhelms the seller is worse than a focused 40-item list they can actually complete. Start with what matters most. Add items as needed. Don’t front-load complexity.
One place for everything. Every request, every document, every question, every answer—all in one workspace that both sides can see. Tools like Vetting Vault are built around this idea: when the seller uploads something, you see it immediately. When you have a question, it’s attached to the specific item, not buried in an email.
Visible progress. The seller should see exactly what’s done and what’s still needed. You should see the same thing. No one should have to ask “where are we?” because the answer is obvious at a glance.
Low friction for everyone involved. The seller’s CPA shouldn’t need to learn a complex system to upload tax returns. The attorney shouldn’t need a login and training session to provide a lease agreement. The easier you make it for the seller’s team to participate, the faster documents flow.
The Difference a Good System Makes
Here’s a scenario most buyers have lived:
You request customer concentration data. The seller says they’ll “get that over to you.” A week passes. You follow up. They say their bookkeeper is working on it. Another week. You follow up again. They send a spreadsheet that doesn’t quite answer the question. You clarify. Three more days.
Now here’s the same request when both sides are working in a platform like Vetting Vault:
You create a request for customer concentration data with a specific description of what you need. The seller sees exactly what’s being asked. They have a question—they ask it right there, you answer it within hours. They assign it to their bookkeeper, who uploads directly. You get notified. Done in three days instead of three weeks.
That’s not about having a fancier tool. It’s about removing all the back-and-forth that happens when requests are ambiguous, communication is fragmented, and no one can see the full picture.
What to Look for in a Diligence Process
Whether you’re working with a broker who manages this or setting up the process yourself, here’s what makes diligence actually work:
Request-based structure. You should be working through specific asks, not dumping documents into folders and hoping the seller figures out what goes where. Each request should be clear: what’s needed, why it matters, and where to put it.
Real-time visibility. You should never have to ask “did they send that yet?” You should be able to see instantly what’s been provided, what’s outstanding, and what’s in progress.
Centralized communication. Questions about specific requests should live with those requests. Not in email, not in text, not in a separate channel you have to cross-reference.
Seller-friendly experience. Remember: the bottleneck is almost always on the seller’s side. They’re busy, they’re not deal professionals, and they may be intimidated by the process. The easier you make it for them, the faster you get what you need.
The Mindset Shift
Here’s what experienced buyers figure out eventually: due diligence isn’t something you do to the seller. It’s something you do with them.
Your goal isn’t to catch them in a lie. It’s to verify that the business is what they represented and to understand what you’re actually buying. Most sellers want to help—they want the deal to close too. They just need a process that doesn’t make them feel like they’re drowning.
When you approach diligence as a collaborative process with clear expectations and shared visibility, everything moves faster. The seller feels supported instead of interrogated. Problems surface early instead of late. And you get to the closing table without the months of frustration that derails so many deals.
The best due diligence processes don’t feel like an adversarial document hunt. They feel like a checklist you’re working through together.