Tag Archives: Questioning

How to Ask Great Sales Questions

A few weeks ago, I attended a sales conference in Las Vegas that was a real eye-opener.  Not because I saw revolutionary stuff (other than an AI app that I’m continuing to research), but because what I saw was pretty retrograde.  The keynote speaker gave us the mind-blowing revelation that we should….wait for it…ASK QUESTIONS before giving a rehearsed pitch!

I’ve been saying for 25 years that, in sales, our success hinges on understanding our customers’ needs. In fact, 80% of our chances to win the sale hinge on the questions that we ask.  Yet, too often, salespeople fall into the trap of asking leading questions that serve their own agenda rather than their customers’. Honestly, I can’t blame the salespeople – many of the sales trainers that I saw in Vegas were still preaching the “don’t ask a question that you don’t know the answer to” nonsense.  This approach not only fails to uncover valuable insights but can also breed suspicion and distrust.  I don’t have to tell you that suspicion and distrust are the enemy of good selling.

The key to meaningful customer engagement lies in mastering the art of open-ended questions. And when I say “open-ended,” I mean more than just “questions that can’t be answered by yes or no.”  I mean “questions that create an open and honest forum for dialogue – even if those answers might harm my chances of making a sale.”  These queries invite customers to share their thoughts, challenges, and aspirations freely. By asking “What are your main business challenges?” instead of “Don’t you struggle with X?”, we create an opportunity for genuine discovery.  Remember – the Investigation phase of the Buyer’s Journey is all about genuinely uncovering what the customer is dissatisfied with, where they want to be, and how we can get them there.

Open-ended questions:

  1. Demonstrate genuine interest in the customer’s business – what makes them tick, why their customers buy from them, and what help they are seeking.
  2. Reveal unexpected pain points and opportunities – sometimes even the customer doesn’t know what they’re looking for until great questioning uncovers it.
  3. Build trust through active listening – which is why you should have your main questions planned out BEFORE you meet with the customer.  That’s a basic aspect of having your act together as a professional salesperson.
  4. Allow customers to feel heard and valued – which is more difficult nowadays with as much impersonal communication as we have – and it makes the idea that a genuine person is truly hearing you and valuing the words coming from your mouth all that much more important.
  5. Provide a road map for tailoring solutions – the “one size fits all” rehearsed presentation doesn’t work anymore, if it ever did.  When the sale comes down to a selling contest, the salesperson who knows their customer the best nearly always wins.  If that’s not you – then you’re probably going to lose.

So why don’t salespeople ask more open-ended questions and give their customers an open forum?  Well, a couple of reasons.  First of all, it’s perceived as risky.  When you allow your customer an open forum, rather than attempting to direct or lead them, they might say something that disqualifies them as a prospective customer for you, or you as a prospective vendor for them.  I’m 100% fine with both of those issues.  If you’re going to lose the sale, it’s better to lose early and move on to someone else.  Plus, being honest with the customer and telling them that you’re not a fit preserves your credibility for the future.  I’ve said it before and I’ll say it again – some of my best customer relationships have started with a lost sale.

The second reason is simpler.  Salespeople are in a hurry to get to their pitch, because they think that the sooner they pitch, the sooner the close happens.  That’s not always the case, as I discussed last week.

Remember, selling isn’t about pushing products—it’s about solving problems. By approaching each interaction with curiosity and a desire to learn, we position ourselves as trusted advisors rather than mere vendors.

Challenge yourself: Every week, try to come up with at least one new open-ended question to ask your customers.  It’s a great thought exercise. You’ll definitely come up with some questions that don’t work, but you’ll also come up with some that do, which makes it worth the effort. You might be surprised by what you learn—and how it builds stronger relationships with customers.

You Can’t Fake Rapport.

Last week, I made a trip to work with a client in Central California, doing a Sales Audit.  It was a great trip for many reasons, but one of the greatest was this.  That area is San Francisco 49ers country.  The Niners just lost the Super Bowl to the Chiefs (wait – should I have said “The Big Game” so the NFL doesn’t sue me?). Which meant that, for the first time in quite a while, people didn’t ask me “How about those Chiefs!” when they met me and found out that I’m from Kansas City, so I didn’t have to talk football!

Don’t get me wrong – I don’t dislike the Chiefs, nor do I dislike football. I’m a good Kansas Citian, and I’m glad they won.  I just don’t eat, sleep, and breathe it, and when people attempt to build rapport with me by starting a conversation that way, they are assuming that I do.  Most likely, they don’t care much about the Chiefs either – it’s just a fake way of building rapport.  And that’s the problem; entirely too many salespeople attempt to build rapport in a way that is inauthentic and actually hurts your potential rapport with customers and prospects.  The good news is that there’s a real way of building rapport, so let’s talk about it.

I should tell you that I’ve always felt that rapport-building is the weakest part of my sales skills.  Don’t get me wrong, I like people, but I’m not one of those guys who can be someone’s friend within 30 seconds.  I knew one of those guys in the car business, and coming from him it was the most natural thing ever.  He was great.  When I try to build rapport by doing the old “spot their interests” tactic, it comes off like Jack Lemmon in Glengarry Glen Ross.  It’s painful.

However, there’s one fact that works in my favor.  I’m curious by nature.  I like to ask questions.  And I know one simple element of human nature.  The thing that most people like to talk about is themselves.  When someone is trying to get me to talk about football (or Kansas City barbecue – the other topic that people always bring up when they find out where I’m from), they are making an assumption that those things are things I’m passionate about. I’m not passionate about football.  I am passionate about barbecue, but I’m convinced that the best Q in Kansas City comes from my own backyard smoker.  But in either case, people are trying to build rapport by attempting to tell me what my story is, rather than asking about my story.

And that’s the key that I discovered early in my sales career.  If I just showed some genuine curiosity about my customers and prospects and asked them about themselves – giving them an opportunity to tell me their story – and then just listened, I built rapport with them without having to flap my gums.  It works.  Note that I said “listen.”  To “listen” means to engage with their words and remember those words, not just plan your next phrase.

Today, it should be easier than ever to build real rapport with people, because they are already telling much of their story on social media.  The vast majority of your prospects are already laying out what’s important to them for public consumption.  All you have to do is check it out and note it down.

Even when salespeople try to build rapport by asking questions, many of them screw it up.  They ask the wrong questions.  They ask questions that are personal in nature (“Are your kids involved in sports?”) that cross boundaries, rather than questions that are “safe” for customers to answer.  As I’ve noted in a previous Webinar, people build relationships differently nowadays.  Relationships are built on a professional basis and then segue to personal, rather than the old method of becoming buddies and then moving that relationship to a sale.  This is more pronounced with each subsequent generation, from Gen-X through Millennials to Gen-Z.

So, what can you do to show curiosity and build rapport without crossing boundaries?  Here are a few of my favorite ways.

  1. Ask your customer to tell his/her professional story. One of my favorite opening questions is, “How did you come to be in this position?”  This creates an opportunity for your prospects to tell you all of their successes, foibles, and their journey, without crossing any boundaries.  In fact, your prospect may take you into some of those personal spaces as well – but it’s THEIR choice to do so, not you prying.
  2. Ask your customer to tell you his/her favorite thing about their job. Again – you’re opening the door for them to brag.  You’re also possibly getting a window into how to sell to them.  If you sell something that can enhance their favorite thing about their job, or create more time or money to do it, you have a pretty powerful motivator.
  3. Ask about something they recently posted on LinkedIn. Yep, I’m being specific to LinkedIn here.  That’s the “professional” social media, and as such, it’s fair game in a business world.  For instance, “I saw you just took an award trip to the Dominican Republic.  That’s pretty awesome!  What did you do to win that trip?”

Those are a few examples, but remember that the key is shutting up and listening while they talk.  Don’t interrupt their story (that shows that you really don’t care about it) and don’t immediately transition from a story point to a sales pitch (ditto).  If you do hear something that can lead you to a sale, make a note and ask about it later during your normal questioning.

Real rapport building is about showing genuine curiosity by asking, and genuine interest by listening.  The old “fish on the wall” method comes across as fake – even when it isn’t.  And fake rapport sets you back instead of moving you forward.  In other words, fake rapport isn’t rapport at all.  It gets you kicked out.

Just ask Shelly Levine (Jack Lemmon’s GGR character).

How to Navigate the Buyer’s Journey

For a while, I’ve been talking about how “sales processes” are outdated, and that the important issue in sales now is to understand and navigate the Buyer’s Journey.  In fact, it’s a big focal point of my Webinar that’s coming up next week, “The Top Four Sales Trends That Could Double Your Bottom Line.”  That said, I haven’t explained what the Buyer’s Journey is.  That’s the focus of today’s article.

We are living in a perfect storm in sales right now.  Several elements that are cultural, technological, and generational have empowered buyers.  I’ve said for many years that salespeople who thought they had “control” over the customer were kidding themselves, and I was right.  But today’s buyer has control.  And they damn well know it.  And YOU had better know it, too, and respect it.  If you do, you can not only survive.  You can prosper, thrive, and quite frankly, kick the asses of the (many) salespeople who will choose not to internalize this fact of their professional life.  So, without further ado, here is now to navigate the buyer’s journey:

Step One:  Motivation

Every Buyer’s Journey begins with Motivation.  Something provokes that buyer to feel dissatisfaction with his or her current situation and envision a desired future situation.  The simplest example would be a buyer thinking, “I’m hungry,” and envisioning a time when he is no longer hungry because he’s eaten something satisfying.  That’s how motivation works.  It begins from a feeling of discontent, and the buyer begins his or her journey.

So, how does motivation happen?  You might not have realized this, but most advertising is aimed at creating that feeling of dissatisfaction in its audience.  Ads for Coca-Cola, for instance, try to make you discontented because you’re not drinking a tasty, ice cold Coke right now.  Ads for cars try to make you feel discontented with the old heap you’re driving around in (even if that heap is only a year old).  And so on, and so forth.  Advertisers attempt to create a feeling of dissatisfaction in the minds of their target customers – and get them to envision a better future state in which their products or services ease the buyer’s pain.

Motivation can also be produced through sales techniques like cold calling, email prospecting, social media outreach and prospecting, and other direct outreach tactics.  Salespeople who excel at cold calling know that they must create dissatisfaction through the words that they use – for instance, a salesperson might tell a prospective customer how they have helped a similar company to solve a problem that the prospect might be facing and then use questions to draw the prospect into a conversation.  It’s important to remember that, when prospecting, you aren’t trying to sell the customer.  You are just trying to create that feeling of dissatisfaction that will motivate the prospect to embark on a buying journey.  In fact, most of the time, the salesperson is not as much creating dissatisfaction as he is highlighting and bringing a latent dissatisfaction to the surface.

Step Two: Investigation

After the buyer has become Motivated and decides to move into a buying journey, the next step is Investigation.  At this point, the buyer knows that he or she is dissatisfied with the status quo, and that there is a better future out there.  But what exactly is the source of that dissatisfaction?  Where does that dissatisfaction rank in terms of priorities?  In the Investigation phase, the buyer’s needs and wants are prioritized.  Think of it like a visit to the doctor when you aren’t feeling well.  The doctor will ask you questions about your symptoms to define the unwell feeling.  In the same way, salespeople will ask questions of the buyer and analyze data and information to help the buyer define his or her needs or wants.

The Investigation phase goes far beyond the simple, outdated process of “qualifying,” to help the buyer define a successful purchase.  We know that there is a desired future situation that the buyer is seeking – in the Investigation phase, we help the buyer define what that situation is and how to get there.  The key to a successful Investigation is comprehensive, customer-centric questioning.  Remember, the buyer is the star of this show.  Our job is to help him get to that future state.  Questioning that is limited, narrow, and leading will work against the buyer – and likely get you kicked out of the Buyer’s Journey.  You can’t navigate the Buyer’s Journey if the buyer kicks you out of it.

Make no mistake – the Investigation phase is the key to winning the sale.  If you do not correctly capture, interpret, and understand the buyer’s needs, you cannot make up for it later in the process.  We need to make the most of this time.

Step Three: Solution

Once we have correctly identified and understood the buyer’s needs (the source of their dissatisfaction with the status quo), it’s time to show them how we can solve those needs – or, if we cannot solve them, discontinue our participation in the Buyer’s Journey.  Wait, what?  Discontinue?  Yes.  If we continue to push our products and services, knowing they won’t fix the buyer’s problem, we kill our credibility. Many a future sale has been won by a salesperson who told the buyer, frankly and honestly, that they could not solve the buyer’s problem.  And, let’s face it – the buyer will figure it out anyway.

In this phase, the salesperson must present his or her plan for solving the problem, as well as showing the advantages and benefits of adopting the salesperson’s plan by buying what the salesperson has to offer.  Further, the salesperson should show why his solution is the best available solution.  In today’s information age, the buyer can easily access data like product specifications, features and benefits, etc., so the salesperson should focus on customized presentations that directly address the buyer’s definition of success, as established in the Investigation phase.

Step Four:  Evaluation

Evaluation can be thought of as the “price and terms” phase.  At this point, if your buyer has expressed genuine interest in a purchase, he’ll likely ask the classic question:  “How much?”  It’s our recommendation to make the answer to that as quick, concise, and to the point as possible.  The more you babble before telling the customer how much a solution costs, the more the customer understands that you are scared of your price.  This invariably leads to negotiation, which in turn leads to discounting.

Make no mistake – what the buyer wants from you at this point is to know what they will be asked to pay.  Answer them.  The buyer will be asking themselves three questions:

  1. Can I afford it?
  2. Are the terms acceptable?
  3. Does it represent good value?

If the customer answers all three of those questions “yes,” you probably have a win on your hands.

Step Five:  Decision

In the Decision phase the customer decides to buy or not buy.  Your job is to ask them to do so.  The key to the Decision phase is simple.  Ask yourself four questions:

  1. Is your customer motivated?  In other words, does the customer feel dissatisfaction with the status quo in such a way that a purchase would create a desired future situation?
  2. Have you assisted the customer in a complete investigation of his or her needs, helped her define success, and gotten her agreement that you have accurately captured the source of her dissatisfaction?
  3. Have you shown the customer a solution for the dissatisfaction, and gotten his agreement that this would relieve the dissatisfaction?
  4. Have you helped the customer evaluate your solution by quoting price and terms in a simple fashion?

If the answer to all four of these questions is “yes,” then you have to ask the customer to buy.  Period.

And that, in short form, is how you navigate the Buyer’s Journey.  How important is this?  It’s vital. Going forward, my sales training will be centered around this concept, because I believe in preparing salespeople for the NEXT 20 years in sales, rather than the last fifty.

Are You Asking Enough Sales Questions?

Sales Questioning Poll ResultsAre you asking enough questions?  A couple of weeks ago, I ran a poll on a very popular LinkedIn group.  The poll question was simple:  “On the average, how many discovery questions do you ask a new customer on an initial appointment?”  If you’ve read any of my work at all, you know that I believe that the root of good things in selling is asking a lot of good questions; in fact, questioning is the longest unit in my training programs.  Well, I’m starting to feel like I’m on an island with a pretty small population.

The results were shocking to me.  Spoiler alert:  37% of respondents said that they asked 1-5 questions on a first appointment; 41% asked 6-10.  In my opinion, the sweet spot for a quality discovery is 11-15 questions; only 11% of respondents were in that bracket. 12% were discovery overachievers who asked more than 15 questions.   After I pushed my lower jaw back up (it had dropped to hit the desk), I realized that within weakness in the market, there is opportunity.  And it’s YOUR opportunity.  If 77% of salespeople ask 10 or less questions, they’re not getting to know customers very well.  That’s your competition.  Want to beat them?  Ask more questions.  But what should you be asking about?  I’ll tell you.

  • Your contact’s professional history. “How did you come to be in this position?” is a great question.  People love to tell their stories, and this question gives you a great window into their viewpoints as well as being a good rapport-building question.  For instance, a plant manager who started out turning wrenches might respond to different value propositions than one who came to the plant fresh from getting an MBA.
  • The company’s past, present, and future. Yes, many companies put this info on their website.  Have you ever seen a website that was out of date?  Me too. And if you are working from obsolete or incorrect information, you might end up presenting the wrong solutions.  Ask – or, better, refer to what you read and ask for your contact’s viewpoint on it.  That way you show that you’ve done your homework AND that you’re curious.
  • Company priorities. Just because your “stuff” is the most important thing in the world to you, it doesn’t mean that it’s the most important thing to your customer.  Where does your stuff fall on the list of priorities for your company or your contact?  This will have a lot to do with the importance and urgency of your proposal.
  • Needs regarding your stuff. Notice that we are just now starting to ask about what you sell, and what their needs are regarding it.  That’s because your end of the world is a small part of the big picture in their world – and you need to know the lay of the land before you start probing what’s wrong in your part of the world.  By the way, don’t neglect asking about what’s right in your part of the world – if you don’t get the sale, this is going to be a big part of the reason why.
  • How they define success. Ultimately, all sales questions boil down to understanding how your customer defines a successful purchase, and how you can help them achieve it.  Still, at this point, you should probably ask a direct question about how they will define success.
  • Process questions. You should also understand the customer’s buying process, and how it will impact this purchase.
  • More questions. There’s more to ask – but you get the idea. Are you asking enough questions?  Here’s what you should know:  If you ask six questions, you are now better than 37% of your competitors.  If you ask 11 questions, you are now better than 78% of your competitors.  And so on.  And you should, of course, drill down on many of those questions.

Is my survey scientific?  Nope.  It was a LinkedIn survey.  This probably skews the numbers, but does so in a positive way.  Salespeople on LinkedIn groups who respond to surveys like this one are probably higher on the scale of the profession, because they’re more engaged.  So, if anything, that means that the real numbers are worse than what’s reported on my survey. In the comments, some “salespeople” expressed disdain for the very idea that comprehensive questioning is important; one even said, “If a salesperson is a dynamic opener, he doesn’t need to ask many questions and can close the sale in one call.”  I suppose there are areas of selling where that might be true, but it’s not in a highly professional sales universe.

The bottom line – when you are considering your questioning and discovery, here are some things to remember:

  • More is typically better.
  • Asking questions shows you care.
  • The worst question is the one you don’t ask.
  • From time to time, you should re-ask questions of current customers; things change.
  • Great salespeople are always working to improve their questioning skills.

That’s all for now.  If you’ll excuse me, I have to get the look of amazement off my face.