When I hired a sales coach over a decade ago, things didn’t just start happening in my professional life; things started happening in my personal life as well. It started with a small change in the way I interacted with my husband.

At the end of most days, he would come home, greet the dog, grab a couple of beers, and trek down the stairs to my home office. And unless I was on the phone, he would announce that it was ‘break time’. We would then share stories about our days, talk about things that ticked us off or made us laugh. He would tell me about issues at work, and I would say things like, “You should do this.” He’d get annoyed with me, tell me I had no idea what it was like there and what this guy was like, and that would never work. 

Sound like any of your end of day conversations?

During a coaching session, our sales coach told our group call that to be successful at sales, it takes practice at asking questions. Someone asked, “But what if you don’t have any leads yet?” Aren’t leads people? Do you live under a rock? Practice on the people around you!

My poor hubby, he became my first test subject. But better to practice on him then my prospects! So at the end of each day, I started asking him questions like, “Have you tried this?” or “What if you said that, how do you think they would react?” When he would say, “Hmmm, I hadn’t thought of that.” it changed our entire conversation.

For the first few weeks, he didn’t notice what I was doing. The day he did, he turned it  around on me. “Hey, can you do this for me?” I asked. His reply? “Do you want me to do that for you?” 

Damn it! He saw me. I had to get even better at asking my questions. 

It took paying attention to details, tone of voice, and timing. A lot of focus goes into it! It’s like improv. “All of life is a stage, and we are merely the actors in a play.”

For a few years now, he (and now the kids) do this to me. They take on the cool calm voice of a therapist and we try to match question with question, no periods at the end. It has become a game that we play, and the youngest is getting pretty good at it!

We even turned it into a New Year’s Eve drinking game. If you answer with a period, you have to take a shot. You either got really good at asking questions, or you had a hangover the next day. 

Why is asking questions so important in sales?

  1. Sales is about understanding someone else’s bias and mindset. In other words, what do they believe? What do they believe is their problem? Why is it a problem for them? What is the risk to them, or the opportunity? What do they think the solution is? This is a huge responsibility. Diagnosing someone else’s problem is like going to a doctor. He has to ask questions to understand what is causing the symptoms. A good doctor, and sales person, doesn’t just want to subscribe pills. To really help, you have to treat the cause, not the symptom.
  2. When people figure out things for themselves, they are more likely to believe it and follow it. If you tell someone something (with a period at the end) and give them the answer, you are robbing them of the opportunity to learn it for themselves. “Give a man a fish, you feed him for a day. Teach him how to fish, you feed him for a lifetime.”
  3. Questions control your ego and emotions. Rather than reacting, you take the step to learn more. You aren’t the smartest person in the room telling everyone how it should be done. Seeing someone else you helped be the smartest person in the room is an even better feeling.
  4. Seek first to understand, then to be understood. Building trust starts with understanding them and being other focused. Intent is the only difference between a con and a trustworthy advisor.

My secret to asking questions.

First, whenever I think I know the answer to something, I try to keep it to myself. It’s like sitting on my hands sometimes! 

Instead I visualize the answer as if it were on a map, and there are a few ways I could go to get there, but I won’t know which way is the right way, or if my assumption is even correct that is where we need to get to. At least, not until I ask questions to verify. 

Once verified, which direction will help lead my counterpart to see if they can get to the same answer themselves? Sometimes they do, sometimes we end up with a slightly different and possibly better answer (or destination). Sometimes neither of us are anywhere on the same map or want to get to the same destination, and I have to walk away. 

The secret to asking those types of questions is simple. Your choices are:

  • What?
  • Who?
  • When?
  • Where?
  • Why?
  • How?

So get out there an try a round of Questions and Periods for yourself! Good luck. 


Carole Mahoney is the founder of Unbound Growth, a scientific sales development firm that eliminates the guesswork of hiring the right salespeople and develops sales teams using a science -based data driven process to achieve 130-160% of quota in less than 6 months with a 98% annual customer retention rate.
Website: http://www.unboundgrowth.com/
Email: e@carolemahoney.com