Why ‘Maybe’ Is The Worst Response You Can Get In Sales

why maybe is the worst answer you can get

Way back in 8th grade, I had a bit of a ballsy moment. I had my eye on this girl in class, and I needed an angle. What did I do?  I decided to toss the choice in her court.   I passed her a note, “Will you go to the dance with me?” with the following three options: 

  • Yes
  • Maybe
  • No

Now, in this situation, as a 14 year-old boy, you want the Yes.  The No is bad for your self-esteem, and the Maybe gives you hope.

We’ll get to what the girl said at the end, but for now, let’s talk about how this same situation is a problem in sales.

In short: we have too many “maybe” answers. Way too many, in fact.

This biggest challenge in B2B selling today is best explained by how every salesperson should conceptualize a pipeline. In general:

  • 33.3% of our pipeline will buy from us in the near future
  • 33.3 % of our pipeline will buy in the far future
  • 33.3% will never buy from us — even if we tried to sell them something worth $1 for 90 cents

Sometimes I call sales reps Prisoners of Hope because they don’t ask for the order.  In sales, a Prisoner of Hope is someone who continues to accept the maybe.  They spend too much time misinterpreting buying and warning signals, so sales cycles are too long — or they carry on forever and then just die out in the end.

We’ve all seen these situations, or even been in them. It always looks/feels like this:

  • “I don’t want to talk right now. But in three months, we can talk…”
  • “We need a lot of internal stakeholders to agree before we can commit…”
  • “Send me your materials and I’ll take a look…”
  • A buyer acts very interested and then goes ghost or phantom on us — and, to try and make the sale or get context, we resort to stalking, creeping, doing fly-bys on social media, or calling from unlisted numbers.

Ultimately our prospects are being nice. They feel bad about saying no, so they don’t. They string us along.

But here’s the deal: we can’t change them. The only person (people) we can change are ourselves.

Go back to these bullets right above here. See how the first three end with ellipses? It’s all people trailing off. That usually means “no” in reality, but the trail off implies some hope for the sales rep. You become a Prisoner of Hope and here’s what happens: your prospects stay in the pipeline for way too long, and they almost never close. 90 percent or more of these Prisoner of Hope situations go nowhere.

All these leads are circling Maybe on your 8th grade note pass. You’ve got hope — but you’ve got no dance card.

However you cut it, it’s not the best approach in terms of sales tactics. So we need to start working with sales reps to stop accepting maybe and start asking for the order.

But why? Why am I saying some not-yet-seasoned sales rep should be asking for the order from a potentially big client?

Because of the power of ”No.”

Here’s the deal: asking for the order is the beginning phase of getting an objection. You need the objection — the “no” — in order to move to the next step. Conflict drives everything, and that’s especially true in sales.

There’s a famous sales study from the 1970s, done by Mutual of Omaha. The set-up is this: they went to their home market (Omaha) and targeted some folks who would be good customers for them. They picked about 1,000 people and said they’d give them insurance premiums (up to $500,000) for a year, but they had to meet with Mutual’s salespeople in order to get this offer. At the same time, they told 150 sales people that there were 1,000 available leads. The whole transaction was contingent on the salespeople asking a specific closing question. Unless that question was asked, nothing was triggered. There was no close.

So, out of these 1,000 really good, vetted leads — what percentage do you think closed?

It was about 7 percent. About 70 of 1,000 people. And why? Because the salespeople weren’t asking the question. They left about 930 leads on the table because they didn’t ask. That’s amazing!

When your sales reps aren’t asking for the order, they’re not selling strong. Sending a LinkedIn message? That’s not selling strong. (I love LinkedIn. It’ll be part of my next post, but it’s not selling strong.)

So how do you move your sales reps to ask for the order? How do they ask? How do they sell strong?

Here are three quick tips:

  • Be in the moment: I like scripts and call flows as much as the next guy and I’ve trained people on scripts and working with checklists and boxes to hit. It’s all well and good. But people with purchasing authority in organizations are usually seasoned. They’ve been around the block and they know the tactics and angles too. They’re going to respond more to a real conversation with ups and downs and sidebars and small talk and commonalities than being sold from a script. The moment changes. You go in and you want to sell a season ticket package, OK? You’ve got a whole plan of sales tactics to get there. At minute 3 of this interaction, the guy wants to talk about his vacation to Moorea. You’ve never been to Moorea and have no idea where it is. So what now? You get in the moment. Listen. Maybe Google a few things about Moorea. Talk about how you want to go now too. Sounds awesome! It’s read and react. You can go in with a baseline, but what happens in the moment matters.
  • Ask good closing questions: There are a million and five studies about the power of asking good questions. If I tried to link them all here, you’d be reading this post for two weeks. (Probably a waste of your time.) The point is: there are lots of good questions. You need to get to them to make the close. In general, yes/no questions don’t get you as far. If the target is busy, yes/no can detach them from the sales process, because they’re just giving you quick, one-word answers. Make them think. They need to be talking about their pain points and what your solution is going to do for that problem. (And yes, this is different by industry.) Remember: some products are sold because they are needed, and some are sold as an opportunity.
  • Don’t be afraid to ask: We all know people like this. We’ve all hung out with guys who approach women at the bar completely sober — and we know people who need five drinks to make that first move. Confidence varies, and that’s part of the “Prisoner of Hope” problem I described above. But jump over the confidence hurdle and ask. It’s the only way to receive. What’s the worst that happens? The target says no? If he/she says no, there’s the conflict! You can drive forward from there.


This is my baseline approach to the sales strategy of the power of no, and using conflict to drive forward. We need to get to high ground and shut down the idea of artificial harmony quickly. Use conflict to drive sales forward. It scratches the surface of everything else we do at Tyson Group. If you want to learn more about that, click here.

(Oh, and by the way … because I know you are curious … the girl said: maybe.)