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Mastering the Marathon: Strategies for Managing Long Sales Cycles

Have you ever run a marathon?  Yeah, me neither.  But when it comes to sales, I’ve run a number of them – the long sales cycle.  In our profession, we love quick win – that satisfying moment when a prospect becomes a customer in a matter of days or weeks. But what about those industries where the sales cycle stretches into months or even years? How do we keep our sales teams motivated, strategic, and successful when the finish line seems so far away?

Long sales cycles present unique challenges. They test a salesperson’s patience, strategic thinking, and ability to maintain momentum over extended periods. They can also tempt even the most disciplined sales professionals to neglect prospecting, as the gratification of a closed deal feels perpetually out of reach.  But here’s the truth: mastering the long sales cycle is not just a skill – it’s an art form. And like any art, it requires dedication, practice, and a specific set of techniques. Let’s explore four key strategies that can help you and your team excel in the marathon of long-cycle sales.

1. Never Stop Prospecting

Imagine you’re a farmer (no, not the old, outdated “hunter/farmer” sales term). You know it takes months for your crops to grow, but you also know that if you don’t plant seeds regularly, you’ll eventually have nothing to harvest. The same principle applies to long-cycle sales.

It’s easy to fall into the trap of thinking, “Why start new conversations when I won’t close them for years?” But remember this: you can’t finish a sale unless you start one. Prospecting is the lifeblood of your sales pipeline, regardless of how long it takes to close a deal.

Make prospecting a non-negotiable part of your daily routine. Set aside dedicated time each day to reach out to new potential clients. Use a mix of cold calls, emails, social media outreach, and networking events to keep your pipeline full. Remember, the seeds you plant today are the deals you’ll close tomorrow – or next year.

2. Think Strategically, Act Consistently

Once you’ve initiated a conversation with a prospect, it’s time to shift into strategic mode. This is where the real art of long-cycle sales comes into play.

Start by estimating a realistic timeline for the deal. Is it six months? A year? Two years? This timeline becomes your roadmap, guiding your interactions and helping you set milestones along the way.

With each contact, your goal should be to move the sale forward, even if it’s just by inches. This is particularly crucial when you’re up against an incumbent vendor with an existing contract. You’re playing the long game, so every interaction should add value and strengthen your position.

Maybe it’s sharing a relevant industry report, offering a fresh perspective on a challenge they’re facing, or simply checking in to maintain the relationship. The key is consistency. Regular, value-added touchpoints keep you top of mind and position you as a trusted advisor, not just another vendor.

3. Keep Your Contacts Current

In the span of a long sales cycle, a lot can change. Decision-makers move on, new stakeholders emerge, and organizational priorities shift. Your job is to stay on top of these changes and adapt your strategy accordingly.

Make it a habit to regularly verify and update your contact information. But don’t stop there – strive to expand your network within the organization. The more contacts you have, the more resilient your opportunity becomes to personnel changes.  “High, wide, and deep” should be your watchword.  Get as high on the corporate food chain as you can.  Get as many contacts (a wide base of influence) in the target company as you can.  And make sure that they genuinely know you and the value you bring. This approach not only provides you with a more comprehensive understanding of the organization but also helps safeguard your opportunity if your main contact leaves.

4. Be Ready When the Stars Align

Here’s a fundamental truth about sales: a deal happens when need, solution, and timing intersect, and the Buyer’s Journey completes. In a long sales cycle, your job is to be ready when that moment arrives.

Think of yourself as a constant gardener, tending to the relationship, nurturing it, and watching for signs of readiness. Maybe the incumbent vendor slips up, budget suddenly becomes available, or a new initiative aligns perfectly with your offering. Your consistent presence and value-added interactions have positioned you to capitalize on these moments.

Stay alert to industry trends, organizational changes, and any shifts in your prospect’s business that might create an opening. When that window of opportunity appears, be ready to act swiftly and decisively.

Remember, managing long sales cycles is not about passive waiting – it’s about active preparation. It’s about building relationships, demonstrating value, and positioning yourself as the obvious choice when the time is right.  As Dave Ramsey likes to say, “There are no shortcuts to anyplace worth going.”

In conclusion, succeeding in long-cycle sales requires a unique blend of patience, persistence, and strategic thinking. It demands that we resist getting demoralized due to the lack of quick wins and instead focus on building lasting relationships and delivering consistent value. By maintaining a steady prospecting rhythm, thinking strategically, keeping our contacts current, and staying ready for opportunity, we can master the marathon of long sales cycles.

The road may be long, but with the right approach, the destination is well worth the journey. After all, in sales as in life, it’s often the challenges that take the longest to overcome that yield the sweetest rewards.

How to Recognize and Reinvigorate “Legacy Performers” in Sales

Nothing stays the same, and that includes sales.  After all, I’ve been writing and making videos for the past two years on how much our profession is changing.  But I get it – change is hard.  I think that the pace of change has intimidated some professionals, who find themselves clinging to past successes rather than adapting to current market demands. These individuals, whom we’ll call “Legacy Performers,” once excelled but now struggle to maintain their edge. This article will help you identify Legacy Performers and offer strategies for reinvigoration.

First, let’s define our term.  A Legacy Performer is a salesperson who once had “it” but has lost their competitive edge. They’re not novices; their past successes are real and documented. When they tell you how they used the sharp-angle close to take a guy who wanted to buy a used ’74 Maverick and sell them a brand new Lincoln, that story was REAL.  However, the traits that once drove their success have faded. It’s crucial to note that being a Legacy Performer isn’t about age – it’s about mindset and adaptability.

Spotting Legacy Performers

  1. Aversion to Prospecting: This is the uppermost characteristic of this type of salesperson. The best salespeople know that, no matter how good you are or how much you are selling, current customers will leave (sometimes through no one’s fault – perhaps they just go out of business or retire), and new prospects will show up. Legacy Performers don’t worry about that.  Prospecting is a difficult and time-consuming process (more so now than ever), so they figure they’ll “just work on referrals.”  Over time, their customer base dwindles and they never refill the sales funnel with new prospects.
  1. Resistance to Change: While not all change is positive, Legacy Performers tend to fight against any modifications to their routine. They fear increased oversight and potential exposure of their shortcomings.  This also applies to sales tech, like CRM, and other ways that salespeople must adapt to new methods and tools.
  2. Avoidance of Customer Interaction: Legacy Performers may shy away from direct customer contact, particularly with new prospects. They often find excuses to be elsewhere when fresh opportunities arise.
  3. Constant Complaints About Customers: Instead of analyzing lost sales for improvement, Legacy Performers blame customers for failures. They have an excuse for every setback rather than seeking solutions.  There’s an old saying:  If one customer tells you “no,” they might be wrong.  If 100 customers tell you “no,” you might be wrong.
  4. Living on Past Glories: Legacy Performers frequently recount stories of their former triumphs without demonstrating current value or results. A Legacy Performer is a salesperson who used to have “it,” but doesn’t have “it” anymore.  A Legacy Performer is not someone who never had “it.”  When a Legacy Performer tells you stories about former successes, don’t mistake – those stories are real and provable, and that’s what makes the L.P. so dangerous from a company’s perspective.  The track record is there.  The traits that made it happen aren’t.  I should also make it clear that being a Legacy Performer doesn’t have anything to do with age – I’ve seen salespeople in their 20s who have been Legacy Performers.  I’ve seen salespeople in their 70s with more energy than you could contain in a room.

Turning the Legacy into the Right-Now

If you recognize these traits in yourself or your team members, it’s time for action. Here are strategies to reinvigorate your sales performance:

  1. Embrace Modern Prospecting Techniques: Leverage social media, LinkedIn, and other digital platforms to connect with potential clients. Attend industry events and webinars to expand your network.
  2. Invest in Continuous Learning: Stay updated on industry trends, new sales methodologies, and technology. Consider online courses, sales workshops, or even pursuing relevant certifications.
  3. Adopt a Growth Mindset: View challenges as opportunities for growth rather than insurmountable obstacles. Celebrate small wins and learn from setbacks.
  4. Reconnect with Your Passion: Remember why you chose sales as a career. Find aspects of the job that excite you and focus on those to reignite your enthusiasm.  If you don’t love this job, as I’ve said many times before, it’s one hell of a hard way to make a living.  If you love it, well, it can still be a hell of a hard way to make a living at times, but it’s a lot more fun.
  5. Buddy Up: If you’re not getting it done, it’s likely that someone else on your team is.  Humble yourself.  Forget the old war stories, take that person out to lunch, and ask to pick his or her brain.  Good salespeople help other salespeople, and it’s perfectly OK to seek help.
  6. Embrace Technology: Utilize CRM systems, sales analytics tools, and other technologies to streamline your processes and gain valuable insights.
  7. Set New Goals: Establish clear, achievable objectives for yourself. Break these down into daily and weekly targets to maintain focus and motivation.

Adaptation is Vital.

Our profession is changing, and what worked ten years ago won’t work now.  In fact, what works now might not work in ten more years! Successful salespeople adapt their strategies to meet changing customer needs and market conditions. By recognizing the signs of stagnation and taking proactive steps to improve, Legacy Performers can transform into dynamic, results-driven professionals once again.

For sales managers and business owners, it’s crucial to identify Legacy Performers within your team. Provide them with the support and resources needed to regain their competitive edge. Sometimes, this may involve difficult conversations or decisions about role fit.

Remember, the key to long-term success in sales is to find something to love about the profession every day. Stay curious, remain open to new ideas, and never stop growing. By doing so, you’ll ensure that your sales career remains vibrant and rewarding for years to come.

An Example of AI Gone Wrong

AI is one hell of a tool. I use it a lot myself. But I’ve also talked a lot about avoiding Chat Crap in your work, because AI can sound inauthentic, and that’s where “Good AI” becomes “AI Gone Wrong.” As Amazon stated:  “Roughly 57% of all web-based text has been AI generated or translated through an AI algorithm, according to a separate study from a team of Amazon Web Services researchers published in June.” I’m not sure I completely buy that 57% number – it seems like an awfully high number, considering how short a time AI has been in play – but even if the number is half that, it’s huge.

I also think that AI can be handy for prospect research, as well as content generation.  But you have to be VERY careful. The linked article below is one great example of AI gone wrong. Here’s the opening paragraph:

Tony’s KC:  The Heart of Kansas City’s Barbecue Scene

“Tony’s Kansas City has a rich history dating back several decades in Kansas City. Tony, a BBQ aficionado with a love for crafting the ideal smoked meats, opened the restaurant and soon won over many devoted patrons. The early going was modest, with a limited menu that concentrated on honing the fundamentals. Tony’s KC grew in popularity and offers throughout time, earning a slot on the local and tourist calendar that is not to be missed.”

Sounds like a great place to eat, right? There’s only one problem. Tony’s Kansas City is NOT a restaurant. It’s a local news blog that keeps people up to date on what’s really happening in my fair city, and only every now and then does he even talk about barbecue.

Now, think about this. This piece of terrible, lazy “writing” is on the Washington Post Magazine‘s website. That’s a national outlet. With one quick fact-check – a visit to Tony’s Kansas City blog – whoever prompted the AI could have figured out that the article was junk. Nobody did.

This happens because people think that AI is magic and infallible.  They’re using AI the wrong way because they don’t understand it, and they don’t know how to treat it.  You should treat AI like the best intern you’ve ever had:  It has a higher IQ than you, it has 20 Ph.D’s, and it has absolutely no street smarts whatsoever.  My favorite platform at the moment is Claude; I did a back to back video comparison on Claude vs. ChatGPT and put it on YouTube to explain why.

The “street smarts” have to come from you.  Your job is to guide AI, edit it, and back-check it.  Apparently, the Washington Post doesn’t understand that.  Here’s what happened.  Someone – most likely a low-paid person and possibly an actual intern – was assigned to write an article. I haven’t a clue what platform they used, or how they prompted it, but I do know that they ended up with an article that was a complete fabrication with precious little relationship to the truth.  And, once they had it, they didn’t even bother clicking through to Tony’s website (his name really is Tony Botello – that’s one thing that the article got right) in order to verify that they were in the same solar system as the truth.  As of this writing, the article has been up for a week with no changes or corrections.

So, how should you use AI platforms?  Here are a few of the techniques that I use:

  1. Prompts should be several sentences in length and be fully explanatory; one-sentence prompts usually get you junk for results. What we call “AI” is also known as large language models, meaning that the real feature is the platform’s ability to understand sentences, paragraphs, and context.  The more you put in your prompt, the better your results will be, even if you’re doing prospect research.
  2. Don’t be afraid to ask your AI platform to try again. Every popular platform has a button to do so, but I recommend suggesting your own refinements.  For instance, often I’ll say something like, “That wasn’t bad, but can you try again without the buzzwords, using plainer language?”
  3. In that vein, you should always specify a tone or style in which you want the result, as well as a length (when you’re going for a written document). If you don’t specify word count, AI tends to go very long.
  4. If your work depends on the accuracy of AI’s conclusions, take a quick moment to fact-check at least the biggest issues in the result.
  5. Once you have something you’re happy with (again, for a written document), you should always refine it a bit, to add your own language and your own touches to it. I created a video on how I use AI to create written work.  For the record, I did NOT use AI in this one.

Now, here’s what is really scary.  The Post article now becomes part of the “knowledge base” on the Internet, and will at some point be referred to as source material for other articles, whether human-written or AI-written.  Expect the amount of Chat Crap to expand exponentially.  This, friends, is why AI will not replace people in too many meaningful roles.  If you use AI platforms (and to be clear, I recommend that you use them and use them well), make sure to remember that YOU are the street smarts.  Keep that in mind, and you will do fine, and you will avoid “AI Gone Wrong.”

How to Refine Your Sales Pitch

A couple of months ago, I attended a conference for sales leaders in Las Vegas, and it was like a trip back in time.  One of the main topics – both in terms of the speakers on the stage and on the lips of some of the executives, was, “How to refine your sales pitch.” Don’t get me wrong, I’m all about polishing your sales SKILLS – but in this day and age, I think that a highly rehearsed and refined “sales pitch” is about the bottom of the list for the skills to practice.

You see, a refined sales pitch is all about YOU.  You are the star of the show in the “refine your sales pitch” world, because the concept is that you’re going to dazzle the customer with your one-size-fits-all brilliance while the customer sits rapt, hanging on every well-rehearsed word.  I’m shocked that I even have to write this in 2024, but sales just doesn’t work that way anymore.  Sales today is all about helping your customers navigate the Buyer’s Journey, and the buyer is the star of that show – not the salesperson.  With that said, there are definitely sales presentation skills that you can and should polish, and we’ll dive into those skills now.

Listening:  Wait, what?  I promised that I was going to talk about sales presentation skills, and I’m opening with listening.  Presenting is about speaking, isn’t it?  Well, it is – but the content of your presentation should depend on the individual Buyer and what they have expressed as their dissatisfaction, their Motivation, and their definition of success.  If you aren’t asking the right questions, and capturing the right information from them, your presentation will miss the mark.

The best way I’ve found to help salespeople actively listen to their customers is to train them to have a prewritten list of questions that they plan to ask.  I usually start with a boilerplate list of questions, and then add to it based on my prospect research.  And yes, after 30+ years in selling, and I have no idea how many thousands of sales calls, I still have a written set of questions.  I do this because, if I have my game plan for what I’m going to ask next, my mind isn’t trying to figure that out while the customer is talking.  Instead, I can devote my mental energies to capturing what they are saying.  The biggest reason that salespeople don’t listen is that they’re trying to figure out what to say next.  Don’t be that guy or gal.  Have your game plan together before the call starts.

Correlation:  The sales skill that I refer to as “correlation” is the ability to hear a customer express a need and immediately match (or correlate) that to a product or service solution.  That’s where you truly become an expertise provider and not a peddler of products or services.  This requires mental agility, but it’s also something that can be taught.  A great sales meeting exercise is the old flash-card method.  Have each salespeople write their customers’ ten most common needs.  Then, remove the duplicates and put each need on a flash card.  One person flashes the card, and the others quickly state the solution.  This can be done one-on-one or as a group in sales meetings, but it’s a great exercise for learning how to quickly build your “mental slide deck” presentation.  The more you can present without having to go back to the bat-cave (and, your customer assumes, draw on the expertise of others), the more credible you become.

Enthusiasm:  Yes, enthusiasm is something that you should practice and employ.  There’s an old saying in sales: “If you can’t get excited about what you’re selling, your customer can’t, either.”  One reason I’m not teaching you how to refine your sales pitch is that a highly refined sales pitch works against your own enthusiasm.  I’ve been the customer in sales calls where the salesperson had obviously refined his pitch so much that he was delivering it robotically, with no excitement or enthusiasm whatsoever.  Instead, practice (with others or in front of a video camera) delivering parts of your mental slide deck with enthusiasm and passion.  Don’t feel like you have to fake enthusiasm in someone else’s language and words; instead, make it authentically you.

Sales isn’t about refined pitches now.  It was once; I’ll fully concede that.  If today’s customer wants to hear the refined boilerplate about your company and your stuff, they’ll read it on your website.  In fact, they’ve probably already done so as the part of their independent execution of their Buyer’s Journey.  They’re talking to you because you can offer something that impersonal Internet research can’t – so give it to them.  Listen to them, correlate their needs with the right solution, and do so enthusiastically, and you’ll go farther than all the salespeople who have learned how to refine their sales pitch.

How to Sell To Younger Buyers – Or, How to Close the Generation Gap in Selling

Yesterday, I was at lunch at a popular local restaurant, and I observed a classic example of how salespeople can sell to younger buyers – or, more properly, how NOT to do it.  I observed two men walking in.  One appeared to be in his sixties, the other in his late 30s, both in embroidered company polo shirts from different companies (the uniform nowadays, it seems).  They were seated directly behind me, where I couldn’t help but overhear the conversation.  Immediately, I could tell it was a sales lunch.

The older man was the seller, and the younger man was the buyer.  And I could tell that the salesman was of the old-style “Good Time Charlie” type.  After they ordered drinks, the buyer asked, “So, you have a quote for me, right?”  And the GTC salesman said, “Yeah, we’ll get to that, but how about that Bobby Witt in the Home Run Derby?”  I’m not kidding.  The buyer asked for his price and he redirected to a sports conversation.  The buyer, being nice, said, “That was pretty awesome.  So were you able to get the specs I need?”  It got worse from there.

Here’s what was happening.  The salesman was selling in a style that has probably worked for him over the years – but has gotten obsolete in the last 5-10 years.  As I discussed in my Webinar, “From Hippies to Hipsters,” the Boomer generation typically builds business relationships based on personal aspects first, and segues that relationship to business needs later.  In other words, what the salesman was doing was probably the correct approach for a customer of his generation (although I’m finding that even Boomers are more interested to get down to business these days, for reasons I’ll discuss shortly). But the salesman had no idea how to sell to younger buyers.

Millennials and Generation Z’s tend to be much more protective of their time.  When in buying roles (or selling roles, for that matter), their impulse is to get business done FIRST.  They’re looking for a salesperson who can solve their problems and make their lives easier in a very time-efficient fashion.  If a salesperson is able to do that, THEN they get the opportunity to build a personal relationship and friendship.  In other words, the relationship dynamic is flipped on its head.

Why didn’t I mention Generation X?  Well, we tend to be fence straddlers between “personal first” and “business first,” and so we’re harder to generalize.  My own personal style has been more of the “business first” style, and for that reason, I identify well with the Millennials and Z’s.

One other aspect of this that is key is the concept of “work/life balance.”  That was a phrase that didn’t even come into popularity until the Gen-X’s were firmly entrenched into the workplace and into positions of authority.  Essentially, from Generation X forward, more and more people are identifying with the idea that “we work to live, we don’t live to work.”  In sales, this manifests itself into the concept that we need to get down to business NOW, because time I waste talking about baseball is time I have to spend later on catch-up work, and therefore time I don’t get to spend with my friends and family.

That’s where the Boomers reenter the conversation.  You see, many Boomers have watched us in the X, Millennial, and Z generations spending more time outside of work enjoying our lives and thinking, “Gee, I want some of that, too.”  In order to do it, they’ve reordered their business lives to get more done during the day.  Which means that, ironically, many Boomers are mirroring their younger counterparts’ buying styles.  Those Boomers don’t have a problem understanding how to sell to younger buyers.

One other thing to put in here is an acronym called NAXALT.  It means that:  Not All “X” (where “X” is whatever generalization you’re making) Are Like That.  Hence, there are Boomers who buy like Millennials, and there are Millennials who want to talk endlessly about football before they start talking business.  Your role is to figure out where your customers are, and meet them where they are.

Now, let’s go back to my lunchtime neighbors.  Good Time Charlie next invited the customer out to play golf on Friday, and the customer just laughed and said, “Man, if my boss thought I had enough time on my hands to play golf during a work day, I’d be fired!”  The conversation kept going in that vein, through drinks, through ordering lunch, and through eating.

Wanna know the saddest part?  The buyer wanted to buy.  I could tell.  He kept redirecting the conversation back to the quote, and buyers aren’t that insistent on knowing the price unless they are genuinely interested in buying.  But Good Time Charlie couldn’t see that there was a potential deal on the table.  Yes, I wanted very badly to turn around, tell them to pause the conversation, and quickly clue ol’ Charlie in.  But I didn’t.

I don’t know how the conversation ended.  I’m protective of my time, too, and I had a Coaching client that I needed to meet with.  What I do know is that, if Charlie made the sale, he did so in spite of himself.

What makes inter-generational selling so difficult is that sometimes, salespeople must go against their own type.  The buyer was trying to clue Charlie in that he wanted a business resolution.  My guess (because I’ve seen this many times) is that, had Charlie gone ahead and presented the quote over their iced teas, that by the time the sandwiches came, they would have been having an enthusiastic conversation about the Home Run Derby.  And both parties would have had the result and experience they wanted.

And now you’re thinking, “But Troy, you already said NAXALT, what if Charlie had gone business-first and his customer had been one of those exceptions?”  I have a simple answer.  Your customers will tell you where they want to be, and where the conversation needs to go.  Tune in.  What the buyer wanted from Charlie wasn’t a well-kept secret.  He was virtually slapping Charlie across the face.

And yes, younger salespeople can run into similar issues when selling to older salespeople, just in reverse.  My advice to you, when selling across generations, is a simple three-point plan:

  1. Start your conversation with the general rules as your approach. In other words, if you’re selling to a Boomer, think “personal first.”  With X’s on down, think “business first.” (With Generation X, even though we straddle the fence, I suggest starting business-first because if you’re wrong, your course correction is easier.)
  2. Ask a couple of “flicking the jab” questions to see how your buyer reacts. For instance, if you as a personally based question and your buyer seems impatient, flip over to business-first, or vice versa.
  3. Adapt your own conversational approach to theirs. This might even mean having two separate questioning tracks prepared.  That’s okay – it’s better to have a “plan B” and not need it, than to need it and not have it.

Whether you’re a more seasoned salesperson trying to figure out how to sell to younger buyers, or a younger salesperson trying to sell to older buyers, inter-generational selling can be a challenge.  But it’s one that’s easily overcome; just remember to meet your buyers where they are.

How Salespeople Can Be Profit Centers

What if I told you that you were your own profit center? I’ve said many times before that salespeople can, and should, be a self-contained profit generation machine.  Salespeople who create profit for their employees and their customers never have to worry about their next appointment, their next sale, or even their next job – and they also don’t have to worry about being replaced by AI.

I’ll amplify – the ability to be a profit center is one of the most valuable qualities in business.  The trouble is that most salespeople don’t understand how to create profit for their customers – or worse, they’re afraid to do it.  This is because most salespeople think that they only way they can profit their customers is by the old “save them money” gimmick – which always results in chopping their price.  That’s not necessarily the case, but to take the high road requires a lot of work.  That’s okay, because we’re not afraid of work – right?  Read on.

To be able to generate profit for your customers, you have to be willing to ask some tough questions.  They’re tough for a couple of reasons:

First, these questions may require a high degree of trust from your customers, to get them to answer.

Second, the answers to the questions may reveal problems with what you’re doing.  You have to be willing to change if that’s the case.

Basically, you have to understand a few key things about your customers.  They are:

You have to understand how your customer generates profit.  The obvious answer is “They sell their products.”  But that’s no more true for them than it is for you.  You need to know what your customer considers good, profitable business.  You also need to understand how the customer produces its product or service, and the ways that it generates efficiencies.  On the flip side, you should also know how unnecessary costs get into the customer’s production/marketing/sales system.  Yes, this is scary stuff.  If you’re an “unnecessary cost,” you’d better figure out how to generate return on investment for them.  If you know how your customer generates profit, you can help them in a multitude of ways, some of which have little to do with your actual product or service.

You have to understand how your product or service fits into their overall profit picture.  Now that you know how your customer makes money, you can start working to generate return on investment for your product or service.  What would be the cost of not using you or your products?  What are the alternatives?  More importantly, are they underutilizing your product, and you can help them maximize the investment?  Don’t be afraid to get involved.

You have to understand how your contact is rewarded.  Assuming that you have a relationship with your contact (and if you don’t, get cracking and build one), it’s time to understand his/her personal and professional needs.  When your contact is rewarded based on something you’ve done, you have generated “profit” for your contact.  This is where most salespeople will drop to the old “price cutter” model, but you need not go there.  Instead, work to make sure that your product and your time is being used efficiently, and contribute your expertise as is appropriate.  If you can connect your contact with other resources that can help, do it.

It’s worth pointing out that I’ve had this philosophy of salespeople being profit centers for over 20 years – and it’s more important now than ever.  As younger buyers come into positions of power, they don’t care how much fun you are to have a beer with, or how you golf.  They care about whether or not you can help them improve their business, and their lives.  And if you aren’t prepared to do those things, you’re going to lose out to salespeople who will.

After you’ve taken action, quantify the results in a quality business review, and you’ve generated profit – and proven your worth.  By the way, if you don’t quantify the results of your work, your competitors will.  Want to guess what light you’ll be painted in?

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.

How to Close a Sale – When Timing is (Almost) Everything

I’m constantly asked, “Troy, can you teach my salespeople how to close a sale?”  My answer is, “Sure.  It can take either 10 minutes or two days, depending on what you’re looking for.”  What I mean by that is this:  While closing is a vital part of selling, it’s the culmination of the Buyer’s Journey, which is a longer process – and teaching that process is part of my two-day training class.  The “closing” unit is about 10-15 minutes of that.  More important than knowing HOW to close a sale is WHEN to close the sale.

When should you close?  One old philosophy says that you badger the customer with closing questions from the time they enter your showroom.  This old A/B/C (Always Be Closing) philosophy has done more to kill sales and irritate customers than anything else salespeople do – and yet, I still hear people who should know better pushing this approach. Today’s empowered buyers won’t stand for A/B/C and they’ll run from you.  There’s a right way, though, and let’s find it, shall we?

A/B/C is very much a 1970’s sales approach.  Today’s customers are more savvy, more educated, have more information available to them, and ultimately have been trained by years of salespeople using heavy-handed sales tactics, and are more capable than ever to resist.  This means that today’s customer responds to an approach that is more customer-friendly and respectful.

First, let’s look at what it takes for a customer to buy:

  • The customer must be motivated; e. the customer feels dissatisfaction with the status quo and is envisioning a desired future state where dissatisfaction is removed and their situation is improved.
  • The customer must have investigated that need (with or without you); the customer and the salesperson must both understand the need, and your product must solve it (and the customer must agree that your product solves it).
  • The customer must trust you.
  • The customer must believe what you say because it’s you saying it (i.e. you have credibility in the customer’s eyes).
  • The customer must respect you.
  • The customer must not dislike you (I know that conventional wisdom says the customer must like you, and certainly that’s a huge help – but I’ve found it’s better to seek respect and trust that is genuine than to seek a like and friendship that is phony).
  • You must have presented a proposal that represents good value to the customer.

The trouble with the A/B/C approach is that it interferes with several of these parts of the Buyer’s Journey.  Closing (the Decision phase) is the part of the journey where customers are most likely to put up defenses; if you are always in some phase of a close, your customers will be defending themselves too much to be able to give you the candid answers you need to be able to match your products to their needs.  We see this all the time when salespeople focus on asking leading questions designed to maneuver their customers into a corner, rather than genuine open-ended questions designed to discover information.

Closing before your customer is ready will interfere with trust and credibility, as well; the customer will perceive you as reaching for their wallet.  (Answer to the old question: Why do customers perceive salespeople as pushy?  Because too many are.)

Instead, today’s salesperson must have patience as part of navigating the customer through their Buyer’s Journey.  To assess Motivation, accurately Investigate needs, present your Solution, check customer agreement, build trust, etc. takes time.  It’s very important that you are patient enough to allow the customer to move through their Buyer’s Journey properly and get to the closing arena at the same time you do.

Once you are at this point, the close becomes a natural part of the Buyer’s Journey, and how you ask for the business matters less than simply having the willingness to ask the customer to buy.  What’s better is that, by handling this in a customer-friendly manner, you are more likely to get invited back for repeat sales opportunities!  Isn’t that better than a one-shot quick close?  Just because it worked for someone in 1976 doesn’t mean it will work for you today.  Success in today’s selling arena requires a different approach based on respect for the customer.

Success in Selling is Intentional

I had an interesting moment a few weeks ago.  I had just done a training program with a client’s sales team.  A few days later, the sales manager reached out to me because one of his sales reps had just done the exact opposite of what he was trained to do on a big issue.  I told the sales manager to ask him why he did what he did, and the rep responded as I expected:  “I dunno.”

I’m often asked what separates top-performing salespeople from the rest. People think that it’s a combination of natural charisma, an extensive network, that vague characteristic called “drive,” or just plain luck.  In my opinion, it’s none of those things. The real key to sales success lies in the cumulative impact of intentional, daily decisions. As a sales professional, every choice you make throughout your day – from how you respond to leads to how you manage your time – can significantly influence your overall performance and results.  In other words – successful salespeople are intentional about what they do throughout the day.

The Power of Intentionality in Sales

Being intentional means approaching each aspect of your sales role with purpose and deliberation. It’s about making conscious choices rather than simply reacting to situations or going through the motions. It’s about knowing why you do things, instead of saying, “Gosh, I dunno.”  This mindset is crucial in sales, where the difference between success and failure often comes down to small details and persistent effort.

Consider two salespeople: Alex and Sam. Alex starts each day with a clear plan, prioritizing high-value activities and making deliberate choices about how to approach each task. Sam, on the other hand, tends to react to whatever comes up, often getting distracted by low-priority tasks or falling into unproductive habits. Over time, the difference in their results becomes stark, with Alex consistently outperforming Sam.  I’ve managed a ton of Alexes and a ton of Sams, and over the long run, Alex always wins out.  Sam might hit a hot streak every now and then, but Alex puts up the numbers week in and week out.

Think About the Key Decision Points in a Salesperson’s Day

Let’s examine some critical moments where intentional decisions can make a significant impact:

  1. Responding to Leads: When a new lead comes in, do you immediately pick up the phone or default to sending an email? Studies show that contacting leads within the first hour increases the likelihood of qualifying that lead by seven times. Choosing to make that call, even when it feels uncomfortable, can be a game-changer.  I’ve written about this before – treating incoming leads lightly is one of the dumbest things a salesperson can do.
  2. Customer Interactions: Do you launch into your pitch at the first opportunity, or do you take the time to ask thoughtful questions and truly understand the customer’s needs? Salespeople who prioritize needs assessment over immediate pitching are 73% more successful in closing deals.  I honestly thought salespeople pretty much agreed on this, but I recently went to a national sales convention and discovered that this is still a revolutionary concept to many salespeople.
  3. Time Management: When you have a free moment, do you use it to prospect for new opportunities, or do you find yourself scrolling through social media? Dedicating just one extra hour per day to proactive prospecting can increase your sales pipeline by up to 30%.  If you are going to scroll social media, it should be LinkedIn, rather than Facebook or Instagram.

The Compounding Effect of Good Decisions

Much like compound interest in finance, the effects of these daily decisions compound over time. Each positive choice builds upon the last, creating a momentum that drives long-term success. It’s not about making one perfect decision, but rather about consistently making good choices that add up to significant results.  You’re going to make mistakes – but if you are intentional about your actions, you can do a much better job of learning from those mistakes.  The “I dunno” guys are simply going to repeat them time after time.

For instance, if choosing to make calls instead of sending emails leads to just one additional meaningful conversation per day, that could translate to 20 more quality interactions per month. Over a year, that’s 240 additional opportunities to move deals forward or uncover new prospects.  Now, put those 240 opportunities into your own funnel ratios.  How many additional wins do you get per year?

Strategies for Being Intentional

Developing an intentional approach to sales requires effort and practice. Here are some strategies to help:

  1. Set Daily Goals: Start each day by identifying your top priorities and the specific actions you’ll take to address them.  Better yet, end the previous day by doing that, so when you walk into the office, you already know the priorities.
  2. Develop Productive Routines: Create habits that support your sales goals, such as dedicating the first hour of each day to prospecting or blocking out time for follow-ups.
  3. Regular Self-Reflection: Take time each week to review your performance. What worked well? Where could you have made better choices?  I know, I know, on Friday afternoon everyone wants to start the weekend.  Take a few minutes and do a postmortem.  Then, create your goals for Monday as in #1 above.
  4. Continuous Learning: Stay updated on industry trends and sales techniques. The more knowledge you have, the more intentional you can be in your approach.  Sales training and education never stops.  I’ve been in this wonderful profession for 35 years.  I’m still learning.

Overcoming Challenges to Intentional Selling

Of course, maintaining this level of intentionality isn’t always easy. Distractions, stress, and the sheer volume of daily tasks can all derail even the best intentions. To stay on track:

  1. Minimize Distractions: Use tools and techniques to manage notifications and create focused work periods.  Let friends and family know that “between the lines,” you’re working – and you’ll be delighted to talk to them after work hours.
  2. Seek Accountability: Partner with a colleague or mentor who can help keep you focused on your intentional practices.  I spoke at a small meeting last week where two members had created a point system between themselves to compete at workouts – which helped them stay on track with their fitness goals.  You can do the same with other salespeople.
  3. Celebrate Small Wins: Recognize and reward yourself for making good decisions, even when the results aren’t immediately apparent.

The Path to Sales Success

Remember, success in selling isn’t about a single big win or stroke of luck. It’s the result of hundreds of small, intentional decisions made day after day. Each time you choose to make that extra call, ask that insightful question, or spend time improving your skills, you’re laying another brick in the foundation of your success.

As you move forward, challenge yourself to approach each day with intention. Ask yourself: “What decisions can I make today that will move me closer to my goals?” By cultivating this mindset and consistently making choices that align with your objectives, you’ll find yourself not just meeting your targets, but exceeding them.

In the world of sales, success is a choice – a choice you make with every decision, every day. So, what will you choose today?

 

Your Biggest Obstacles are Your Own Assumptions!

I’m writing this as I am attending a conference in Las Vegas.  This is a conference that has drawn a lot of coaches, consultants, and yes – sales trainers.  One of them sat down next to me yesterday and his opening line (after a quick introduction) was, “You know, you can train a good salesperson to be an engineer a lot quicker than you can teach an engineer to be a salesperson.”  Well, I had the right to remain silent, but as they say, I didn’t have the ability.  I replied, “I strongly disagree.” I’ll explain why in a bit, but suffice it to say that the conversation wasn’t a long one, and he didn’t build the rapport that he thought he would with that comment.

His problem was that he made an assumption that I would agree with him 100%.  To be fair, I’ve heard a similar sentiment from a lot of other sales trainers – but my experiences have been completely the opposite.  I see salespeople making assumptions – and failing because of those assumptions – every day.

After I told him that I disagreed with him, I did what I always teach you to do.  I asked a question.  “What got you to that conclusion about engineers?”  He explained that he had recently come from a training class with engineers for an industrial company, and he had dreaded it, and that the experience had been difficult.  It seems that the engineers challenged many of his contentions about selling, and asked a lot of drill down questions that he found difficult to answer.  “They wouldn’t just take my word for it!” he exclaimed.

Here’s why he failed.  He went into the program with the anticipation that it would be a bad experience – and it was a self-fulfilling prophecy.  He wasn’t prepared to be asked a lot of questions.  Here’s the key with engineers.  They ask a lot of questions because they love to learn and asking questions is one of their tools for learning.  Considering that I believe that 80% of your chance to win a sale is through the questions you ask, the inquisitiveness of engineers is an asset, not a liability, and had he been open minded enough to leverage that characteristic, the program would have been beneficial and fun for him and for the engineering team.

When I talk to salespeople, many times I hear that they “already know what their customers need and want, and just have to explain how we give it to them.”  Not shockingly, these are not the most successful salespeople in their industries.

In today’s world, it’s easier than ever for salespeople to make unfounded assumptions about their prospects and customers. With so much data and information available at our fingertips, it can be tempting to review a company’s website, scan their social media, and jump to conclusions about their pain points and motivations before ever engaging with them directly.  It’s even more tempting for experienced salespeople, because they have seen so much, and yes, there are bound to be commonalities amongst your customers.  But you shouldn’t.

This approach of making assumptions is ultimately misguided and can severely undermine a salesperson’s effectiveness. Each customer is a unique individual with their own specific context, challenges, and decision-making criteria. What may seem obvious from the outside rarely captures the full picture of their reality on the ground.  Keep in mind the guy that approached me – he thought he knew what I was all about because of my profession.  He didn’t.  Admittedly, I’m a bit of a contrarian in my industry, but I’m sure I’m not the only person in the room who had had great experiences training engineers.

When you start a sales call with preconceived notions, you put yourself at a disadvantage from the start. You risk missing or overlooking key pieces of information that could fundamentally alter their understanding of your prospect’s situation, because you skip asking the important questions.  After all, why ask a question when you already know their needs? Worst of all, you disregard the basic need for every customer to feel truly heard and understood as an individual.

In the modern sales environment where skeptical buyers have access to endless information (just like you do), making assumptions is one of the surest ways to kill your credibility and rapport. On the other hand, leading with curiosity and entering each engagement with an open mind demonstrates attentiveness, emotional intelligence, and a genuine desire to provide personalized value.

Rather than making assumptions, embrace the following practices:

Ask Thoughtful, Probing Questions: Whether discovery questions, situational questions, or problem questions, the best salespeople ask a high volume of insightful questions to uncover the full story behind each prospect’s reality.  As I always say, “the worst question is the one you don’t ask.”

Listen Actively and Empathetically: Beyond just hearing the words, great salespeople listen for underlying tones, implications, and the “things unsaid” to develop a complete understanding.  And if it’s “unsaid,” now it’s time to ask some great drill-down questions to turn the “unsaid” into the “said.”  One of the best tools for listening, by the way, is to pre-plan some great questions.  Yep, I’m suggesting taking a “cheat sheet” into the sales call.  If you have something to refer back to in order to stay on track, you don’t have to think about what you’re going to ask next while your customer is talking – hence, you listen.  I’ve made thousands of sales calls in my career. I’ve had a cheat sheet for most of them (including my current ones). I’ve never had a customer say, “Hey, no fair!  You have questions planned.  Get outta here!”  You won’t, either.

Suspend Pre-Judgments: Skilled salespeople hold themselves back from rushing to any conclusions until they have thoroughly explored all angles of the situation through patient, open-ended dialogue.  My new friend at the conference had pre-judged the training experience before it happened and had already decided it would be a bad one.  Honestly, this make me wonder why he accepted the engagement in the first place!

Check and Confirm Understanding: Top performers frequently confirm and re-confirm their understanding by summarizing what they’ve heard in their own words, ensuring full alignment.  Checking questions aren’t hard, but remembering to use them can be.  Successfully navigating the Buyer’s Journey requires moving through it side-by-side with your buyer, not with you ahead and pulling the buyer through it.

The truth is that we are up to our necks in information, both digital (internet, social media, etc.) and experiential (the cumulative experience you have had and the experience of those you have been exposed to). The ability to shed assumptions and fully understand each unique customer’s reality has become one of the most powerful differentiators in sales. If you embrace open curiosity, you will build deeper customer relationships and you will be richly rewarded with insight, trust and long-term business value.

And you won’t embarrass yourself by starting a conversation in a way that immediately puts yourself on the opposite side of an issue.