The MSP Owner’s Stuck Deal Rescue Plan

Have you ever opened your CRM on a Friday afternoon, looked at a proposal you were certain you would win, and thought: what happened?

The first meeting was great. They understood the risks, agreed something needed to change, and asked for a proposal. You sent it. Then you followed up. Then you followed up again. Nothing.

I have been there! When I ran our MSP, I used to think persistence was the answer. If I just sent another “just checking in” email, eventually I would get a response.

After enough of those emails, I learned the uncomfortable truth: “What happened?” is the wrong question. The better question is: What am I missing?

Stop Prescribing Before You Diagnose

One prospect changed how I handled stalled deals. Everything about our meeting told me they were going to become a client. I sent the proposal, and then silence. After more follow-ups went nowhere, I called the owner and asked a simple question: “I’m curious, what changed?”

They had lost a key employee. That person had been driving the project. Replacing their IT had not become less important; it had simply stopped being the most urgent thing on their desk.

That answer was not even on my list of possibilities. I thought they might have chosen another provider, decided the price was too high, or moved in a different direction. I was not losing the deal. I was misunderstanding it.

A good doctor asks questions before writing a prescription. Salespeople often do the reverse. We send another follow-up before we understand what is actually going on. That is a little like bringing a Band-Aid to a flat tire.

What Usually Changes

Once I began asking better questions, I found that stalled deals often fell into a few familiar categories. Life got in the way. The prospect was nervous about making the wrong decision. A new person entered the conversation. They were overwhelmed. Sometimes the budget had changed.

The explanation matters because the next step should fit the real issue. A prospect may need confidence, reassurance, or time. They may need you to understand what changed in their business. Another proposal or another email will not fix any of that.

I looked back at some of my old follow-up emails years later. They all sounded exactly the same: “Just checking in,” “Following up,” and “Let me know if you have any questions.” Different dates; same email. We have all done it, so no judgment here!

The day I became more curious, I became a better salesperson. It was not because I had better answers. It was because I started asking better questions and listening to the response.

Your Stuck Deal Rescue Plan

Open your CRM this week. Find one opportunity you thought you would win, or at least one you thought had a real shot. Pick up the phone, call the owner, and say: “I’m curious, what changed?” Then listen.

Your goal is not to force the deal back into motion. Your goal is to understand it. Curiosity starts conversations. It does not end them!

The MSP owners who keep growing are rarely the people with the perfect sales process. They are the ones who keep trying to understand their prospects and clients. They ask better questions, listen better, and build stronger relationships as a result.

I will leave you with this quote from Albert Einstein: “The important thing is not to stop questioning. Curiosity has its own reason for existing.”

Have a great week and weekend!