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Walt Gerano

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5 Tips for Asking Your Prospect Better Questions

Posted by Walt Gerano on Fri, Apr 05, 2024

You don’t want to look, act, or sound like every other salesperson when asking your prospect questions. There is an art and a science to being masterful at asking your prospect better questions and building a strong, credible relationship with them. Read on to learn 5 tips for asking meaningful, exploratory, and courageous questions.

Now even though many of you think you have this skill of asking questions nailed, it would be interesting to have a microphone hooked up to you during your next sales call to find out if you really ask meaningful, exploratory, and yes, courageous questions.

Here’s the #1 tip: think ‘presidentially’ with your questions. It is probably the single most important piece of advice we can share with you when you are meeting with an executive of a company or with a head of household. Think about the things they think about and worry about.

Executives, owners, and heads of households usually think about the bigger picture, longer-term issues such as the well-being of their enterprise. So, ask them questions about that. What you sell is just a part of the overall picture. Instead of focusing on a specific loan need, investment strategy, or benefit coverage, think broader and ask questions like:

  1. What is getting in the way of reaching your revenue goals?
  2. How does this impact growth?
  3. What is the effect on turnover?
  4. If you had to find the money to cover this cost where would it come from?
  5. How does this investment affect your longer-term goals? 

You get the idea. Really seek to understand the challenges facing your prospect, not just the specific product need you might be able to solve. This separates you from the other salespeople talking and pitching product solutions. You will be solving business problems instead!

So, what about when your prospect asks you questions like: How big is your company? What kind of service guarantees do you provide? What other companies in our space do you work with?

Here’s tip #2: These questions are not their real questions. Get beneath their question by asking: "Joe, I want to make sure I address the right concern or question you have, when you ask ‘how big’, what is your concern relative to size?" The prospect will now give you a more accurate answer – for example – I want to make sure that you have the resources to take care of our entire footprint.

Questions like these will drive a much deeper conversation.

Here’s tip #3 and a rule of thumb for questions: Follow the leader (your prospect). Too often salespeople have their list of questions and are prepared to ask those questions. They want to follow the script, but the problem is the prospect doesn’t know their lines. You have to follow their lines or lead. Here is an example:

  • You ask a question – “How concerned are you that you won’t be able to come up with the cash to take advantage of the market opportunity?
  • The prospect says Very concerned”
  • You ask Tell me more about ‘very concerned’ what specifically are you concerned about?
  • The prospect says My concerns are xy & z”
  • You ask – “Why does xy and z bother you? What is the impact?”

This is how to get to the bottom of the real issues that need to be solved – not just the surface issues. 

Let’s say you have uncovered a prospect’s motivation to take action and you know that they have a real pain that is costing them. Hidden in the conversation though is another pain. The pain of change. Tip #4 – The key thing to remember is that there are two pains at work – the pain of not changing and the pain of change. The pain of not changing has to be substantially greater than the pain of change. So, with that in mind you have to ask about the pain of not changing:

Here are some examples:

  • How long has this problem been going on?
  • What happens if you don’t fix it?
  • What is the cost to you, the company, your family, or your community?
  • Who in your organization is impacted by this change and how will you handle that?

 Tip #5: Occasionally your prospect will want to transfer the pain...

“Well if we don’t do this then the company, the department, the marketing group, etc” will… Transferring the pain to someone else makes it easy for your prospect to ignore the problem. This is why you have to make it personal. When you ask the question: “What happens if you don’t fix the problem” and you get a “pain transfer” answer, you must re-ask the question. “I’m sorry Sally, what I meant to ask is this: Why is this a problem for you specifically if you don’t fix it?”

So, there are 5 tips you can use today, to get better at discovering what is really bothering your prospect. Go give them a try right now and see how they work for you.

Do You Need More Leads? –  Free Sales Prospecting eBook Download



Topics: Sales Training, asking questions, motivating sales people, asking sales questions, sales training tips

5 Critical Sales Competencies: The Will to Sell Factors

Posted by Walt Gerano on Fri, Mar 11, 2022

There are 21 critical sales competencies that salespeople must have in order to achieve great sales success.  But there are 5 Will to Sell factors that make up the foundation of that success. 


We talk to salespeople every day who tell us they want to achieve more, they are going to change their ways, and the results will follow.  If only it were that easy.

The Objective Management Group, an organization that has evaluated over 2 million salespeople, has identified the 21 sales competencies that are crucial to success for salespeople.  There are 10 Selling Competencies(skills), 6 DNA traits (behavior), and finally, 5 that fall under the category of “Will to Sell”.

Of course, they are all important but today I want to tell you why I believe that the Will to Sell competencies are the most important of all, and without them, success will be much harder.

Desire – desire measures how badly you want to achieve greater success in sales, in other words, do you “really” want it?

Commitment – the willingness to do whatever it takes (assuming ethical conduct) to achieve your success.  Commitment is not conditional; you are either in or you are out.

Motivation – there are two parts to motivation:

  1. Are you motivated?
  2. How are you motivated?

Knowing the power behind your motivation helps you plow through behaviors when you get stuck.

Outlook – how do you feel about yourself, the company you work for, the people you work with, and finally the people you call on.  When any of these are out of alignment, we struggle to do the behaviors we know we need to execute to succeed.

Responsibility – do you take responsibility when you don’t get the results you want, or do you make excuses?

Of course, all 21 sales competencies are important but when you have a strong Will to Sell then you are coachable and able to understand what behaviors need to change (DNA) and possess the desire, commitment, and motivation to change.  The same thing is true for the selling competencies, these are learned behaviors.  Without them, it is a tough road.

As the saying goes where there is a will (to sell) there is a way!

Learn More About the  21 Core Competencies!

Topics: sales skills, sales competencies, competencies required for sales

Sales Success: Declaring Independence from Your Personal Obstacles

Posted by Walt Gerano on Thu, Jul 01, 2021

As we approach the upcoming Fourth of July holiday, our own Walt Gerano shares his thoughts regarding the obstacles holding us back from experiencing the sales success we desire.


245 years ago, 13 colonies declared themselves as newly independent sovereign states and no longer a part of the British Empire. Instead, they formed a new nation—the United States of America.

Have you declared your independence from the things holding you back from experiencing the success you desire?

When you look at your business today, you might agree that you need to prospect more consistently, qualify better, and know when to move on from a prospect. But you still have opportunities in your pipeline that are stuck. The question is why and what are you going to do about that?

Why don’t you prospect more consistently

  • You don’t have enough people to call on.
    • When was the last time you asked for an introduction or spent meaningful time on LinkedIn?
  • You don’t have the time.   
    • What activity is more important to the growth and success of your sales practice than prospecting? Schedule prospecting time first.
  • You are fearful of rejection. 
    • Rejection is nothing compared to failure.

What about qualifying?

  • Do you prepare with a pre-call plan for every call to make sure you know how you will get the answer to the question; “why am I here?” (First question you should ask on a call)
  • Are you ready for the curveballs? Those are the annoying questions that you wish they didn’t ask.
  • How and when will you deal with the incumbent?

Why are “opportunities” stuck in the pipeline?

  • Does the prospect really have enough PAIN to move forward and make a change?
  • Do they have the money to fix the problem?  Did you even ask about it?
  • Are you meeting with all of the decision-makers prior to presenting your solution?
  • Have you dealt with the “return of the incumbent?”

There is nothing here that you don’t already know. It’s the middle of the year so take a few minutes and evaluate where you are and what you will do about it.

Need Help?  Check Out Our  Sales Growth Coaching Program!

Topics: Qualifying skills, How to Increase Sales, sales commitment, increase sales

4 Questions You Need to Ask Yourself When Building a Success Formula

Posted by Walt Gerano on Fri, May 07, 2021

Success Formulas help us identify certain behaviors that we need to execute week in and out to achieve our goals. But how do you know if yours is set up for greatness or failure?


Will Rogers said, “Even if you’re on the right track, you’ll get run over if you just sit there.”

Let’s talk about getting on and staying on the right track.

If you are like most of us, at the end of the year, you evaluate your results and then built a success formula for the type of year you need to have next year. My question is, are you working from a success formula that is destined for failure?

Of course, none of us start out with the intention of failing; we just never looked to see if the train was coming!

Success formulas are great because they force us to identify certain behaviors that we need to execute week in and week out to achieve our goals. But, they cannot exist in a vacuum. Things change, and when they do, we need to change as well.

I want to share a few ideas on small changes to your success formula that can make a big difference at the end of the year.

First of all, I am going to give you the benefit of the doubt that you are doing the minimum activity on the front end, so this isn’t a call more/run faster conversation.

    • Consider prospecting for an account size that is 10% above your current target.
    • What if you improved your qualifying so that you converted just one more meeting into an opportunity each month?
    • What if you made one more telephone call each day? That’s over 200 more calls per year. Even if your technique didn’t improve (but it would), how many more opportunities would that create?
    • What about skill development? Getting better at asking for introductions, your compelling reasons for someone to do business with you.

You should evaluate every month not just how you are doing (results) but what you are doing (behaviors). Every month, answer these four questions.

    1. Do I have the right metrics? In other words, am I tracking the right behaviors that support my revenue objective?
    2. Am I performing with the right frequency? This would involve enough calls, 1st base meetings, and asking for introductions.
    3. Am I performing at a high skill level? Is my message compelling? Am I asking questions that help the prospect to discover some compelling issue? Am I listening or just waiting until it’s my turn to talk? Do I prepare a pre-call plan with each prospect in mind?
    4. What do I need to stop doing? Do I confuse being busy with a sense of accomplishment? We can all find things to do in order to avoid what we must do.

Just a few of the right changes could make all the difference when you get to December.

Need Help?  Check Out Our  Sales Growth Coaching Program!

Topics: Sales Effort, sales success formula, increase sales, traits of successful people

4 Steps to Create Loyal Client Advocates

Posted by Walt Gerano on Fri, May 08, 2020

In today's blog, we discuss how your organization can go above and beyond to create loyal client advocates for your business. 

If you are looking to increase sales in 2020 and beyond,  it is important to create a consistent experience for your customers and those that chose you to work with in the first place. 

If you are not providing a superior experience, your clients might start asking "Then, who will?"


Today's question is this: “What are you doing to keep your clients coming back and telling their peers about your business?"

Is your organization providing an excellent consumer experience for your clients? 

Are you getting to know the wants, needs, and pain points of your customers each and every single day?

Are you under promising and over delivering results? 

Now, can you think of a place where you go and wait in a long line, spend a lot of money, and yet, can’t wait to tell others how great your experience was?  Well, that could describe a number of places, but the frame of reference I want to use today is the Disney experience.  

No one would argue with the success that Disney has in exceeding expectations and creating loyal advocates. When you go there your first time, it is more beautiful than you ever imagined.  You have such a magical time that you forget about how much things cost or how long the lines are for almost everything.  

In his book, Inside the Magic Kingdom, author Tom Connellan explains the seven keys to Disney’s success and how they work to create a dazzling experience for all of their guests.  As you read the book, you can only imagine what would go into building and sustaining that kind of relationship with your customers.  

In order to achieve “dazzling”, you must have a process that is consistent and predictable.  People need to know what they can depend on when they trust you with their business.  In other words, it’s not a once-in-a-while thing; it is just the way you do things.

Keep in mind that it does not have to be the same thing for all of your clients.  The way you support your top 20% needs to be different from how you support your bottom 20%.

Download "9 Tools to Increase Sales" Whitepaper

But, at the heart of it all, everyone gets the basics.  However, if you want to increase sales within your organization and stand out from the competition, your organization must be willing to impress, dazzle, and treat your advocates like members of your family.  It may sound drastic to some, but there is a reason that some companies truly stand out in a crowded market.

It's the little things that matter in business.

So, how do you create loyal advocates for your organization?

  1. You have to find out what they wantHow do you do this?  Ask!  Give them a list of things to choose from with the option to add things that might not be on the list.
  2. Next, prioritize critical areas. The key here is to find out what they won’t tell you.  How many times have you left a restaurant after you told your server everything was fine when they asked?  Some of your clients may do the same thing.
  3. Identify performance levels and find out where they are setting the bar; don’t assume you know.
  4. Negotiate expectations. Now is the time to deal with anything you are not willing to agree to. Sometimes we say “yes” because we think it’s a deal breaker; just ask and then decide.  If it is outside your process, then you are better served to move on because, unfortunately, it will always be a struggle and they will never become an advocate anyway.

The only way to exceed your customer’s expectations is to know what they actually are, not what you think they are.  Start by having that conversation first and soon you will have them coming back for more and telling their friends.

Topics: sales effectiveness training, banking sales training, professional sales training, consultative sales coaching, corporate sales training, sales training courses, online sales training, insurance sales training, handles rejection, online sales management training, sales training workshops, sales training seminars, sales training programs, sales candidate assessment, sales force performance evaluation, insurance prospecting system, assessment tools for salespeople, life insurance call script, sales team evaluation, keys to selling success, prospecting personality definition, star sales training, keys to selling, consultative sales coaching cincinnati, consultative selling cincinnati, banking sales training cincinnati, corporate sales training cincinnati, hire better people cincinnati, sales coaching cincinnati, sales management training cincinnati, sales productivity tools cincinnati, sales training programs cincinnati, sales training workshops cincinnati, train the trainer cincinnati, hiring sales people cincinnati, increase sales cincinnati, professional sales training cincinnati, sales candidate assessment cincinnati, sales effectiveness training cincinnati, sales force performance evaluation cincinnati, sales performance management cincinnati, sales training cincinnati, sales training courses cincinnati, sales training seminars cincinnati


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    Anthony Cole Training Group has been working with financial firms for close to 30 years helping them become more effective in their markets and closing their sales opportunity gap.  ACTG has mastered the art of using science-based data and finely honed coaching strategies to help build effective sales teams.  Don’t miss our weekly sales management blog insights from our team of expert contributors.


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