Stop Selling, Start Asking
I was talking to an MSP leader this week about a sale they were working on. The prospect was deciding between them and one other MSP provider.
This MSP was about $500 to $1,000 more per month than the competitive MSP. That's a meaningful price difference that would make any prospect pause and really consider their options.
They had made some headway reframing the decision maker, but the office manager had shown some reluctance. They wanted details about what tools our member used and some other technical details. You know how this goes — when prospects start asking for technical specs, it usually means they're looking for reasons to justify a decision they've already made.
So, our member decided to set up the next call to sit one-on-one with the office manager before meeting with the decision maker again. Now, there were some good things here. They had a next step that they controlled. That's awesome. Having control over the next meeting is always better than waiting for the prospect to get back to you.
But I asked a few more questions like: Was not knowing their tool set really the issue? What if the tools weren't actually the roadblock here?
In general, how had he felt about what you explained in terms of your approach and what he had heard from the other vendor? Assume that he had seen your tools and technology, and thought they were all fine. Then, who would he have chosen and why? This is the question that cuts through all the noise and gets to what really matters.
Our member said he didn't know because the office administrator never said. And there's the problem right there. They were having a conversation without actually having a conversation.
This is the information you need to help this prospect decide and to know where you are in the sales process. And all you have to do is just ask. The prospect wants to make the right decision, but they need your help to get there.
So many times, it's that simple. Just ask for the information you need to help the client decide. Most prospects will tell you exactly what they need if you create the space for them to do it.
Too often, business leaders and salespeople are so busy selling that they don't stop to just ask. We get caught up in our pitch and forget that selling is actually a conversation, not a presentation. There are two common mistakes: the first I call "shotgunning," or just telling the prospect countless things that are great about you and your offering, hoping that some will stick, or assuming that you know what the prospect is thinking or feeling. The second mistake is even worse. We make up stories about what the prospect is thinking instead of just finding out.
Try selling less and asking more. Your stress level will go down, and your MRR will go up. When you know where you really stand, you can focus your energy on the deals that actually have a chance to close.
I help sales teams & closers use AI to spot hidden buying triggers and close high-ticket deals faster
1wThat headline about closing more deals by asking more questions instead of presenting is spot on. So many pitches turn into monologues when the real gold comes from the questions you ask and how you listen. In my experience coaching teams, the best reps spend most of their time exploring the prospect’s world—their goals, roadblocks, and unspoken concerns—and AI call analyses can help uncover which questions spark the deepest insights. And this applies beyond sales: in leadership, coaching, even parenting, the quality of your questions determines the quality of the conversation. What’s your favorite question to get a prospect talking?
Host of MSP Insider │ 18-Year MSP Veteran │ Speaker & Author │ Co-Founder @Cyft │ Breaking Barriers with AI in MSPs
2wFunny how many reps treat sales calls like courtroom arguments, building a case, stacking evidence, waiting for a verdict. But prospects don’t want to be convinced, they want to be understood.
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2wGary Pica I ask one open question early, it uncovers true objections...I've saved deals and time.
Founder at Linkmate | Effortless LinkedIn Leads | 7x More Visitors to Your Profile
2wGary, conversations over presentations transformed my closing rate completely this year.
Well-said, Gary Legend. Closers listen more than they speak.