There is a power in words that most people never seem to pick up on. Substituting even one word in a sentence or paragraph can have a significant and meaningful impact on the tone of the writing or the response the reader has to it.

The same goes for how we speak to people.

One tiny word can make or break a conversation, a relationship, or our perceptions of the other person or a situation.

This becomes especially important when we’re asking questions. They are one of the most powerful things we have in any conversation.

There’s a lot that goes into how we ask questions, both in and outside of sales. Tonality, body language, facial expressions; all of these play a huge role in how the question will be received. But word choice, that’s probably the biggest. And sometimes, the trickiest.

I firmly believe that questions are the number one most important thing in your sales toolkit. Others might think it is marketing knowledge, product knowledge, or the ability to overcome objections. 

⇩⇩ me every time somebody talks about needing to 

“OVERCOME OBJECTIONS” after they’ve wasted time with their pitch ⇩⇩

Unfortunately, the world doesn’t necessarily share my views on selling with questions, setting up a process, and learning how to address potential objections before they becomes roadblocks after the pitch. And yes, market and product knowledge are vital, but if you don’t know how to have great sales conversations or ask the right questions, none of that matters much. 

That’s why I’m writing a whole book on this subject. But I digress…

Questions allow you and the prospect to feel at ease in the conversation. That first question, “Would it make sense to sit down and talk about my clients’ concerns to see if there is something I might be able to help you with?” is a lot more powerful than, “Can I have 15 minutes of your time to see if I can help you?” And even that is way better than “How’s your day today….let me tell you why I am here….”

But even asking questions goes wrong when you choose your words poorly.

I can tell you a couple of situations where a small change in the words I used in a question would have made ALL the difference. Seriously, I might be in a completely different place right now. (Although, I’m pretty happy where I’m at, so I guess these mistakes turned out for the best. Definitely didn’t feel like it at the time though!)

Some of these blunders were in sales conversations, and some were in other business-related situations that ended up nosediving. 

If you have listened to the Sales Throwdown podcast, you know that, about 8 years ago, I used to work for one of the other hosts on the show. I worked for Al selling medical devices for 18 months, and it was largely a complete failure. I’ve said many times that while I think I could do it better now, there is no way I would go back to that industry.

Looking back, a lot of the pressure I felt while working in that industry was self-imposed. I was driving myself crazy because I didn’t think I was doing enough to stay employed. Al, on the other hand, would have been happy to see me crush it, but he was pleased with the work I did while I was on his team.

That split in our views of my effort occurred due to one question. 

When Al and I were talking about the opportunity, we were sitting in a bar (per the norm) because we had decided to skip Kung Fu class to talk about it. I was frustrated with my upriver options in my current role, and Al had a spot on his team that he thought I’d be interested in. He told me it would be a pay cut at first, but only until I grew a book of business and went on commission only. Then the money would be rolling in.

I asked my usual barrage of questions, and I can’t lie. The answer to “how much do most reps make?” had me Scrooge McDuck style jumping into piles of money in my head.  

“Most reps get lazy at around $250K, but there is room to make more.” I could totally handle a temporary pay cut if it would turn into that! 

And then I asked the WRONG question.

“How long was it until you went off the base and onto commission?” Al responded with, “3 months.” Yep, I could definitely handle a 3-month pay cut.

But as I’m sure you predicted, it didn’t exactly happen that way.

In months 5 and 6 in my role, I was still drinking from the firehose. I was spending more time shadowing Al than prospecting and talking with doctors. Honestly, I was kind of a mess at the time. Not only was I dealing with the stress of not being where I wanted to be sales-wise, I was also working a second job at a sushi restaurant 4 shifts per week. My partner was in nursing school and hated the idea of actually becoming a nurse. And we were still learning how to parent our very small child. All this was going on AND I was waiting for the ax to fall with Al because I was past month 4 and didn’t have a single account to my name.

I was stressed, to say the least. 

Worst part was, I didn’t have to be. Not to the level I was anyway. And it was all because of one bad question.

What I should have asked him instead was, “How long does it take a new rep to build some relationships and gain enough accounts to make the shift to commission.”

The answer to that better question would’ve been 18 months.

I had built myself a special kind of hell because of essentially one word. How long did it take “you” vs how long does it take “others.” 

See, Al was already well-known in the industry. So when he started doing medical device sales, tons of doctors already liked and respected him enough to trust him with their business. He’s nowhere near a fair representation of how long it takes to build a book of business because he basically already had one from his 15 years as a chiropractor. 

Less than half a year in, there’s no way I should’ve expected myself to be swimming in money. But I didn’t know that, and I continued to not communicate well or ask the right questions, until eventually, I gave up.

This kind of miscommunication happened again when my business partner in my very next role decided it was time to move across the country and focus on bigger things. 

When he made the decision, the plan was for us to continue working on the business together, just in a long-distance capacity. Not too hard, right? People do it all the time.

But he was also starting a new business with this move. Worried about that,  I kept asking, “Are you going to be able to focus on both things?” when the better question would have been, “How are we going to work on this project together when you are launching another business?”

If we had just been able to answer that question collaboratively and agreeably, it might not have dissolved the way it did. But with the change in our working relationship and friendship, (long distance doesn’t work for everybody), and our lack of a plan on how it was going to work, it didn’t last long after he left.

Last example, and this one was a huge sale lost to bad questions:

While still selling websites, I was talking with a prospect about their motivation for a change for their website and how they believed it could help them. I thought I’d dug deep enough, so we got to the money discussion.

I asked for a range of their budget for this project, and they told me without hesitation, “$12,000.”

Since we were the “affordable guys,” our typical sales were much smaller than that. 12k, while not an enormous amount of money for some full-service website designers, was a lot for us. Needless to say, I was very excited.

This one is not a situation where I asked the wrong question, it’s one where I missed the question entirely.

I should have asked, “Why that amount?”

But I didn’t. Too excited.

We built a scope, put pricing on it, and sent it over to them. Several days after sending the scope, they said no. I asked if we could hop on a call to discuss why they were going in a different direction. (If you don’t do that, you should! Read why here.)

They told me that they had been talking with agencies who wanted 15k-50k for a website project, and while they couldn’t afford that much, they felt that their budget should get close to a full-service agency.

Which we weren’t.

If I had just asked the question, I would have been better able to put together a project that ticked their boxes of expectations and put us strongly in the running. We were not built to do everything they wanted to do, but we had partners who could help round out the gaps. We would’ve been able to make it work.

But I didn’t know all that, and after I sent the scope, they looked at it and found somebody else. Sale lost for good.

I talk all the time about how important communication is, but believe me when I say that I’m not perfect. Not only is it something I still work on daily, but it’s something I’ve spent years practicing and screwing up. Luckily, those mistakes didn’t ruin me, and I can chalk them up to lessons learned the hard way. 

Since asking the right questions isn’t going to happen every time in every situation, you can at least build questions into your sales process that (hopefully!) don’t send your proposals directly into the trash bin. 

And please, for the love of all things, ask them BEFORE you pitch!