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Asking more questions, Listening, Fear

TSE 1047: Start Asking “Stupid Questions”!

Asking more questions, Listening, FearThe more information we have about our clients, the better we’ll be able to serve them, and we can begin by asking “stupid questions.

In 2013, I was working on a speech for Toastmasters and I wanted to talk to everyday people to find out whether or not they think the American Dream is dead.

What better place to find everyday people but on the train?

I was nervous. I didn’t want anyone to yell at me or be rude to me and I certainly didn’t want to get into a political debate.

Eventually, I mustered the courage to ask the guy sitting closest to me for his thoughts. I prepared for the worst but got the exact opposite instead. He answered my question and gave me the insight I needed to put together a great speech.

In today’s episode, I will share ways to overcome the roadblocks we create in our minds so that we can get the information we need to best help our clients.

Dumb, stupid questions

We tell ourselves that our questions are dumb and stupid. When we think that way, we end up with dumb and stupid results. We need to present our questions well so that we can get the right information from our clients.

When we ask only surface-level questions, we get surface-level answers in return.

When we then use those answers to create a quote, we find that the client is not interested or ready.

It is the same situation every time. We worry and feel like we suck at our job. Other people selling the exact same product to the same type of client are performing so much better.

How does this happen?

Clear and meaningful questions

Too often, we are so focused on how we come across to others that we don’t ask the right questions. We don’t want to appear rude or pushy.

Or, we worry that we might embarrass ourselves by asking a question that everyone else already knows the answer to. We also hesitate to “bother” an executive, or challenge the way he already does business even though our suggestions could benefit his organization.

Push the norm

We are afraid to push the norm.

Many executives are surrounded by ‘yes people.’ This creates a void that, as a consultant, you could fill.

To prepare for more clear and meaningful questions, you need to first understand where the questions will lead.

As an example, the brake light on my car went out. I did everything I knew to try to fix it without success. A mechanic, on the other hand, would have the experience and the knowledge to ask me the right questions about my problem in order to isolate the best solution.

I would not assume that any of the questions he asked me were stupid even if I already knew that, of course, I should check the bulb before coming in.

He would be viewed as an expert because he would ask all the necessary questions in order to fix my problem.

The more confident you are on a topic, the less stupid the simple questions will seem in your mind. You will know and understand that people who are not as well-versed on the subject will make mistakes with the small things.

Asking clear and meaningful questions will get you clear and meaningful results.

Know the landscape

Read industry magazines and trade journals of your targeted clients. Know why they need what you are offering.

Study and prepare so that your questions are clear and meaningful. Understand the intricacies of their business. It will make you more effective in presenting your case.

You will be able to ask questions with confidence.

When you know where the questions might lead, and you won’t be afraid to ask them. You will be prepared. Keep the questions simple and clear.

Don’t ever assume that any of them are stupid.

Start Asking “Stupid Questions” episode resources

This episode is brought to you in part by our TSE Certified Sales Training Program, which teaches you to improve your sales skills, find more customers, build stronger value, and close more deals.

The next semester begins in April.

If you’re not familiar with the TSE Certified Sales Training Program, it’s a program designed to help brand new sales reps, as well as those who have been selling forever. The 12-week module offers videos you can watch at your own pace, as well as the option to join a group discussion. It’s broken into three sections: finding, building value, and closing. It’s amazing and it’s fun!

This episode is also brought to you in part by, a Chrome browser extension for Gmail that allows you to track and schedule your emails. It’s super easy, it’s helpful, and I recommend that you try it out.

You’ll receive real-time alerts anyone opens an email or clicks a link.

The episode is also brought to you by, a sales automation platform that allows you to send cold emails in a personalized manner. To find out more about how it can help you automate your sales process, go to Your prospecting will never be the same.

I hope you enjoyed the show today as much as I did. If so, please consider leaving us a rating on Apple Podcast, Google Podcast, Stitcher, or wherever you consume this content and share it with someone else who might benefit from our message. It helps others find our message and improves our visibility.

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TSE Podcast, The Sales Evangelist, Donald Kelly

TSE 855: TSE Hustler’s League-“Think About The Prospect”

TSE Podcast, The Sales Evangelist, Donald KellyWant to change the way you sell?

Think about the prospect. Seek one individual you can help every day, and it will change the way you operate.

Today on The Sales Evangelist Hustler’s League, we discuss how to empathize with your prospect and put yourself in his shoes. By doing so, you’ll add value and you’ll become the kind of seller buyers want to buy from.

I learned this paradigm shift in the book, Stop Selling & Start Leading: How to Make Extraordinary Sales Happenfrom our sponsors at Wiley. It’s a fantastic blueprint of all the things buyers say they expect from sellers and want from sellers.

I’m offering a free excerpt of the book to this community of sellers so you can check it out for yourself.

Understand your customer

Understanding your customer is such a basic concept that sometimes we overlook it.

As a man of faith, I’ve been known to pray and ask God to lead me to someone who could benefit from my services.

If I can put myself in the customer’s shoes and understand his difficulties, then I can help him solve problems. I have to listen, understand his struggles, and focus more on solving his problems than on making the sale.

I recommend you remind yourself to think about the prospect every day.

Stephen Covey, in his book, The 7 Habits of Highly Effective People, says we must seek first to understand people, and then to be understood. Far too often we try to push something to our prospects that they don’t need.

Also, though, we have to understand the hurdles they are up against.

If, for example, you’re an interior house painter, and your prospect needs his walls painted, but he doesn’t have the time to wash them first, seek to understand his situation. He has other fires to put out. He has other priorities.

Demonstrate understanding by acknowledging his dilemma. Perhaps you’ll even incorporate washing the walls into the cost of painting them and wash the walls for him.

Adopt your customer’s point of view

My own clients tell me they are trying to grow their organization, or that they don’t feel comfortable talking to prospects. Sometimes they tell me that cold calling isn’t working for them.

These are the problem I’m helping them solve. The solution, of course, is sales training, but my focus in on the problems I’m helping them solve.

View your product or service as a solution instead of a sale. Understand that you’re selling them a way to operate their business so they can continue collecting money from their customers.

Take 30 minutes today to look at your product or service from the customer’s point of view. Ask what issues you can help him solve.

Do you feel a personal obligation to help him? If you don’t, your performance will be haphazard, and you won’t enjoy your work.

Your customers are tired of sales people. They want sales leaders. They want you to think about the prospect.

“Think About The Prospect” resources

If all of this sounds great to you but you still aren’t sure how to start, check out The Sales Evangelist Hustler’s League, an online group coaching program that brings sellers of all levels and all industries together to share insights.

You can also join our Facebook group, The Sales Evangelizersto connect with sales professionals from all walks of life.

Leave us a review wherever you consume this content and share it with someone else who might benefit from our message. If you haven’t already done so, subscribe to the podcast so you won’t miss a single episode.

Audio provided by Free SFX.



Problem Finding, Discovery Meeting, Donald Kelly

TSE 632: Stop Selling and Start Finding Problems

Problem Finding, Discovery Meeting, Donald KellyStill focused on trying to get a sale? Perhaps it’s about time to change that mindset and instead direct your attention to solving your customer’s problems. Today’s episode will help you do that.

As Jeffrey Gitomer says,

“People love to buy, but they hate to be sold.”

I know we’ve been put into so many situations where we’re required to sell. Of course, that’s your goal. But how you get to that goal is not by pushing yourself. Rather, look more into identifying problems and solving them.

Be a Problem-Solver!

Regardless of what you’re selling, the client usually comes to you because they want to ask for something. But as sellers we quickly conclude with the exact problem our product or solution can solve. That’s because we’re focused on making a sale,

Identify Challenges, Provide Solutions!

Dig deeper and find out what they’re going to be using a product or solution for. Identify other solutions than what is written on black and white for your eyes. Doing this builds credibility.

“Credibility is built very strongly when you have nothing to gain but something to lose.”

If a buyer sees that, your credibility goes out of the roof. An order-taker is not going to be as credible as somebody who is a solution-provider.

Find Problems!

The next time you go into that discovery meeting or just an initial conversation with your prospect, look for ways that you can be credible as well as ways to identify problems. Sniff them out. Find them. This shows your expertise and it makes you stand out in the eyes of your prospect from your competitors.

Here are some calls-to-action for you:

  1. Write down a way you can apply this principle in your sales process.
  2. Listen to the Sales from the Street episode on Wednesday, TSE 634, and see how I applied something similar to this and how it helped me close a deal that almost over 130% from the previous agreement.

Episode Resources:

The Science of Selling by David Hoffeld

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