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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.

What If You Forgot Everything You Knew About Sales?

Last weekend, we had a run of storms in Kansas City, and the power at my house went out.  That happens.  What’s not normal is that the power stayed out for over two days – and because of that, I had to clean out my refrigerator and throw everything away.  For the first time in over 30 years, I had to fill my refrigerator from scratch.  And I discovered something very interesting.  Do you know how hard it is to make a grocery list when you are starting from scratch?  I mean – when the ketchup bottle is empty, you put it on the list.  Remembering everything I keep in the fridge was a completely different exercise, and it wasn’t easy.

Some salespeople are (or should be) feeling like that right now.  Sales is changing, and it continues to change at a rapid pace. Some of the techniques and approaches that worked even just a few years ago are becoming outdated. Buyers are more informed, have higher expectations, and less patience for traditional sales tactics.  I’m no different; I have rewritten my training program in the last year to account for these changes.

Let’s be honest; most of you don’t have to throw away everything you’ve learned and start with an empty refrigerator, so to speak.  But with the changes, many salespeople can no longer rely on the techniques and habits built up over years or decades in the profession. The skills that made you successful in the past may now be a liability – or at least, be less effective than you were before. What if you need a complete reset?

Imagine that you wake up tomorrow having forgotten everything you knew about sales. The product knowledge, the presentation skills, the tips for overcoming objections – it has all been completely erased from your mind. You are a blank slate when it comes to selling.

Daunting as that may sound, it also presents an incredible opportunity to rebuild your sales approach from the ground up, aligned with modern buyer expectations and increased sophistication.

So if you found yourself in that scenario, how would you retrain yourself on selling? Here are some steps to consider:

  1. Immerse yourself in learning about the modern Buyer’s Journey. Don’t just read the classic sales books – look for new content exploring how buying behavior and effective selling strategies have shifted in the digital age. Yes – my videos are a great place to start, as are the articles on this blog, but I’m not blind to the fact that there are other voices.  Just beware of those voices (and there are a lot of them) that are saying the same thing they’ve been saying for decades.  If an author isn’t acknowledging the fact that sales is changing, that author is obsolete.
  2. Become a student of your specific buyers and market. Research your target prospects exhaustively – their roles, their issues and problems, their informational needs, the other solutions they are considering. Build out rich and detailed buyer personas.  Become a student of your target industry – not just how it affects you, but the trends and developments within it.
  3. Invest heavily in developing skills around questioning, modern prospecting, and articulating value rather than leading with product pitches. Sales is now about guiding Buyers through their own Journey to an informed decision.
  4. Get fluent in telling compelling stories and having conversations that are tailored and contextualized based on the specific buyer and situation. One-size-fits-all scripts are relics of the past; your customers want to feel like individuals. Give them that feeling through your one-to-one presentation and storyselling techniques.
  5. Master the art of effective follow-up and maintaining an authentic personal connection throughout a sales process that may take weeks or months with multiple stakeholders involved.  Continuing to keep everyone involved and moving at a proper pace can be challenging – but it’s doable.
  6. Learn to leverage sales technology and virtual selling approaches that enable you to efficiently pursue numerous opportunities in parallel through multiple channels and touch-points.  This isn’t optional now.  It’s one thing to understand how to correctly do a video call, and how to employ proper etiquette.  It’s another thing to be able to bring as many resources to the table as possible when you’re on a video call.  Your objective should be to simulate the face-to-face selling environment as much as possible.  For instance, can you quickly and easily take someone on a video facility tour?  Practice.  Get good at this.

The sales world has been disrupted and will only continue to evolve at a furious pace.  The Four Key Trends that I identified last year aren’t going away. Instead of trying to adapt your existing skillset in a piecemeal fashion, consider this an opportunity for a total reboot. Approach selling with a beginner’s mind and be willing to rebuild your approach from scratch based on modern buyer expectations.  You’ll find that many of your past techniques still have legs – and you’ll find that some need to be discarded in favor of updated skills. Those who can successfully retrain themselves will thrive, while those who cling to outdated methods will inevitably be left behind.

In fact, I actually discovered something funny when I went to the store.  There were several items on my list that I didn’t get, because I realized that I don’t use them much (or I don’t like them as much as I thought I did).  I also picked up some new things to try out – things that I probably wouldn’t have gotten if I’d just been restocking the fridge. One of them made for a very tasty dinner last night, so sometimes, resetting can be the best thing you can do.

How to Have a Productive Video Sales Call

Full disclosure here:  I originally decided to do a demo on how to use AI to create authentic social media posts, and I had Claude create a LinkedIn post on Zoom etiquette. You can watch that sausage being made here.  After doing it, I decided that the content was good enough, and relevant enough, to expand into a full article.  When I expanded it from the original 350 word post into this 1250 word article, all of the additional work was mine – not AI.

If you’d like to have a frustrating experience, schedule a bunch of Zoom interviews for sales candidates.  If you’re like me (I just did some interviews as part of my hiring assistance program), you’ll end your day in open mouthed amazement at how many people who purport to be sales professionals still haven’t figured this technology out.  Make no mistake – mastering the tech to make video calls is mandatory to succeed in sales now and well into the future, so let’s talk about how to have a productive video sales call.

Since 2020, video sales calls have become much more common for sales meetings, client interactions, and team collaborations. Video sales calls can be a great tool – they are time efficient, and can be done at your desk – but that’s a double edged sword. Many professionals still treat Zoom calls too casually, projecting an unprofessional image that can hurt sales and business relationships. Here are some tips to be both professional and authentic, which will allow you to make a great impression in your next video meeting:

Be Technically Prepared!  This is a pet peeve of mine.  Modern salespeople must be competent in this technology – and it’s not going away.  This is the place where most Zoom calls go awry.

  • Log into the video sales call 5-10 minutes early to troubleshoot any technical issues. If you’re trying to sell to someone, they don’t want to sit there and attempt to show you how to make your microphone work, turn your video camera on, etc.  That’s just dumb.  All video technologies that I’ve used have a “test your camera and microphone” screen before you enter the meeting room.  USE THOSE TOOLS so that, at the appointed time, you’re ready to have a productive meeting.  Another reason to log on early is that these apps have a tendency to want to “download an update” at random intervals – and you don’t want to be watching an app update when your customer is waiting on you!
  • Have your video camera set up, working, and positioned properly before the meeting starts. With that said, if you’re like me, the camera is built into the top of your laptop screen, so it’s more about positioning YOU.  Bonus tip here:  When I’m doing a Zoom call with a potential client, I’ll put books under my laptop to boost it up and get the camera at eye level.  That way I don’t have “Zoom face” of looking down into the camera.
  • Close out of any unnecessary apps, browser tabs, and notifications to avoid distractions. For me, Outlook email alerts are the worst, and I have to remember to close Outlook before a Zoom call.
  • If joining from a mobile device, ensure you have a strong internet connection. Again, this is very basic stuff, but it truly amazes me how often salespeople will attempt to make a call from their car, and they’ll have bad bandwidth.

Set the Stage.

  • Find a clean, uncluttered backdrop for your camera view. Blank walls or professional virtual backgrounds work well.  HOWEVER – virtual backgrounds use bandwidth, and can be distracting.  BE VERY CAREFUL if you use them and make sure you don’t pixelate or drop. I never use virtual backgrounds for that reason – plus, there’s always that weird aura around someone’s head when they’re talking, and I find that a bit off-putting.
  • Check your lighting to avoid harsh shadows or backlighting. Natural lighting is best.
  • Minimize potential audio distractions like barking dogs or loud household members. Also, silence your phone so that it doesn’t ring or get a text alert during the call.  If it does, you will reflexively look at it, and guess what?  You’re distracted.

Mind Your Presence.

  • Dress professionally, as you would for an in-person client meeting. If you wouldn’t wear a T-shirt and shorts to a client meeting, don’t wear them on a Zoom call.  In my own experience, I’ve found that I’m more productive in my home office when I dress professionally – even if I’m not going out to any meetings that day.
  • Stay seated and avoid excessive movements that can be distracting on camera. This might be a “do as I say but not as I do” moment; I can get a bit restless on a Zoom call. But I’m aware that it can be distracting.
  • Look at the camera, not the screen, to make direct eye contact. This is both important and difficult.  It’s natural to want to look at the other person’s face when you’re speaking.  After all, that’s what we do when we’re face to face!  But when you do, they can’t make eye contact with you.  Here’s my hack:  I look at the camera when I’m talking, and at the screen (the other person’s face) when they are speaking.

Stay Engaged.

  • Don’t multitask by checking emails, messaging apps, or working on other tasks. Admittedly, this is a HUGE temptation – but you will get caught.  And you might miss something that you should have grabbed ahold of.
  • Ask questions and contribute to the discussion to show you’re actively listening. The caveat here is that, as with any “remote” technology, it’s always easy to accidentally talk over someone. Here’s a hack:  If you’re doing a video sales call as a team, have a chat set up with you and other members of your team, and coordinate (via chat) who gets to talk next.  That way the customer perceives you as a well oiled machine.
  • Avoid eating full meals during the call, which can be unsightly and create noise distractions. The spaghetti can wait. Here’s a funny thing that happened to me a few years ago:  I was doing a video presentation to a CEO group in Boston.  They were struggling with getting their monitor to show my camera, and all they had was my audio.  The problem was on their end, not mine (my camera was working fine, it was their tech that was the problem).  I could see them, but they couldn’t see me.  It was a 3 hour presentation with breaks.  So, about an hour in, we took a 15 minute break.  I got up and grabbed a protein bar.  Confident that I couldn’t be seen, I unwrapped it, took a big bite, and of course, THAT was when they got the camera to work!

I’ve put this article in the context of Zoom calls, but the techniques cross over to all technologies.  In fact, you should also be conversant and capable of operating other technologies.  Get good at Zoom, Teams, Google Meet, and Webex (those are the most common, but there are others).  It’s not that hard, nor is it particularly time consuming. But if you want to stay relevant going forward, you need to be good at it.

By being technically prepared, setting a professional stage, minding your presence, and staying engaged, you’ll project a polished virtual image and be able to have a productive video sales call. Your sales numbers and business relationships will be better for it. Even when the environment is virtual, people still want to do business with real professionals.

How Salespeople Can Become Better Writers.

A couple of days ago, I was meeting with a long time client named Scott Hanna.  He is the President of E3 XPS, a company that focuses on trade show exhibits and commercial spaces.  He said something very profound, and it inspired this article (there will be a big hat-tip to that something in a bit).  Our conversation was about writing skills – specifically, the fact that salespeople seem to be losing the ability to write well.

This is a big problem, because more of our communication is written now than ever before.  When sales was primarily conducted over the phone and in person, our verbal skills were paramount.  We had to write letters (on paper) every now and then, but mostly, we won sales with our verbal skills.  Today, at least 50% of our sales communication is done via email, social media, text, and IM – all of which is written.  And those communications are sloppier, less precise, and less professional than ever.  This is a sales killer, so let’s discuss how salespeople can become better writers.

First of all, here’s something we need to understand.  The fact that the communication is electronic does not relieve salespeople of the responsibility to communicate in a clear, precise, grammatically correct, and persuasive fashion.  I see entirely too many “sales communications” that read like a 13-year-old’s Snapchat. This is ridiculous.  And it’s not generational or age dependent; some of the worst offenders I know are in their 60s.  Imprecise sales communication not only harms your ability to make the sale – it can cause problems with customer service and fulfillment downstream.  There’s no excuse.  So, without further ado, here are six ways that salespeople can become better writers (or you can help them, if you are their leader).

  1. Lead By Example. As I noted above, this problem isn’t confined to newer entries to our profession.  I send and receive many emails daily, and I’m constantly shocked at the lack of punctuation, grammar, spelling errors, etc. by people who should know better.  And I’m not just talking about salespeople.  I have CEO’s (very competent people) who send me emails with run-on sentences, lack of punctuation, and other mistakes that make me have to decipher what they are saying.  And if they’re sending those messages to me, they’re sending them internally.  Like it or not, as a manager and leader, you are modeling behavior for your people – and if you send them communications that are not proper business communications, you’re showing them that this is acceptable and part of your culture.    Take the time to do it right, and your people will too.
  2. Read. Here’s my huge hat-tip to Scott.  When we discussed techniques for improving writing skills, he explained that he tells salespeople to read books.  Not Internet articles, not Facebook posts, but actual paper books.  His reasoning is solid as concrete. There’s a lot of crap out there now.  Internet articles (even those on supposed “news” sites) are written terribly, and are bad examples.  However, if a publisher has committed money to printing actual books, effort has likely been given to proofreading and editing, making it a good example.  You don’t have to read my book (even though you should), but reading actual books improves your writing skill because it improves your skill with words.Full disclosure:  I should have thought of that.  I think that the reason that I didn’t is that I’ve always been a voracious reader.  When I was a kid in school and they told us to read silently, I enjoyed it.  Even when I was in a sales territory, I’d carry a book with me.  I’d read it while I had lunch, or even spend 10 minutes reading a chapter from time to time during the day.  It was my mental palate cleanser.  Yeah – I’m a book nerd and proud of it.
  3. Practice. Writing is another area where practice makes perfect.  If you aren’t confident in your skills (or you’re the manager and not confident in your team’s skills), then it’s time to practice.  The next time you have to write an email to a customer, do the best job you can, then have someone else (who IS a good writer) proofread it, make suggestions, and critique.  Writing is one of those areas where practice and critique makes us better.  Why do you think they had us write all those papers in school?
  4. Use tools. Tech should make it easier to write well.  Automatic spell check and grammar check is an easy way to fix common writing problems – IF you use it.  For instance, earlier in this article, I accidentally put an extra space between two words.  Grammar check caught it with that little squiggly blue underline, and I went back and fixed it.  The trouble is that some people disregard the spell check and grammar check, and send out communication that has those errors baked in.  That’s dumb and lazy.  Another great tool is to use thesaurus.com to find synonyms for words that you might be using too often.  There are a ton of tech tools out there to improve your writing skills; why not use them?
  5. Dump the abbreviations. One of the worst aspects of “texting culture” is the pervasiveness of abbreviations that have seeped into our written communications.  A business communication should never include “Wyd,” “Lol,” “U” for “You,” and so forth.  Nor should you use emojis.  Remember – our goal in sales communication is to look credible and as a voice of expertise.  Texting culture kills your credibility.
  6. Use AI PROPERLY. One great capability of AI is that it can reframe and rewrite your communications.  I don’t think it should be used as a crutch, but I do think it can be a great tool.  One aspect of modern communication that salespeople struggle with is the need to write texts that are short, to the point, persuasive, and still grammatically correct.  This is a great way to use AI, as AI tools can do a great job of fitting messages within a character count.  So, here was my prompt to Claude, my AI tool of choice:“Hello, Claude. I’m writing an article on how salespeople can become better writers. The level of grammatical correctness and professionalism has dropped in sales communication, and I want to persuade salespeople that it’s worth the time investment to improve and to learn (or re-learn) how to write proper business communication. As an added challenge, I want to explain how to write better text messages. Can you write a text message for me, in 240 characters or less, with proper grammar and punctuation with no abbreviations, on why it’s important for salespeople to write professionally?”

    Here was Claude’s response in 239 characters:

    “Your writing represents you and your company. Unprofessional communication makes you appear careless or unqualified. By taking the time to write clearly, with correct grammar and spelling, you build trust and credibility with prospects and clients. Well-written messages demonstrate expertise and respect for your work. Elevate your professionalism through polished writing.”

    That wasn’t bad at all.  I could edit it a bit or refine my prompt, but for the purposes of this article, that works nicely.  Claude distilled down what I wanted into the proper character count (you can also use word count), and created a persuasive text message.

The bottom line is this.  I spend a lot of time talking about the changes in the selling environment and the trends that will shape our profession into the future.  A lot has changed – but one thing that hasn’t changed is that sales communication should remain professional and precise.  Salespeople can become better writers, and hopefully, these six tips will guide you in the right direction.

Which Sales Skill Should You Focus On Improving?

I’ve had some interesting conversations lately with business owners and sales leaders who know that something is wrong.  They just don’t know what.  They haven’t kept their sales teams abreast of the way that selling is changing, they haven’t retrained and developed their people, and because of this, they are feeling a little lost.  And they want to change their results – NOW.

When people feel lost and want to change results, they look for the “magic button” that, if they can just find it and press it, will fix all their problems.  So, instead of, “Can you assess my issues and perhaps retrain my salespeople to update their skills,” they ask, “Can you teach my people how to (close/prospect/present/etc.).  In other words, they’re looking for the one piece of the skillset of successful salespeople in the current environment – and if their people can learn that ONE THING, they’ll return to success.  So, I’m writing this article to help them – and you.  I’m going to tell you what the most important skill that salespeople can possess is.

The answer is – all of them (sorry).  Salespeople need to be competent to excellent in every phase of the Buyer’s Journey, and if they’re not, sales will fall away.

First of all, salespeople need to understand what the Buyer’s Journey is, and what their role is in navigating it.

Then, the salespeople must be good at Motivating their prospects to enter a Journey, because without good Motivation skills, they won’t have anyone to sell to.  We used to call this skillset “Prospecting,” but I seldom use that term anymore.  What we called “Prospecting” is now elevated, and Motivating is really a better description of the salesperson’s role in this phase of the Buyer’s Journey.

Salespeople must be skilled at helping their Buyer through the Investigation phase, where the Buyer defines his or her needs and sources of dissatisfaction, as well as the Buyer’s Desired Future State.  Only by understanding the Buyer’s needs, dissatisfaction, and definition of success, can the salesperson deliver a targeted presentation of a solution.  If you can’t master this phase, you’re spraying and praying.

Presenting the customized, tailored Solution, using your expertise, is what guides the Buyer to the success that they are seeking – that’s why they began a Buyer’s Journey in the first place.  Salespeople need great presentation skills.  Not only is the presentation of Features and Advantages important, but salespeople should be skilled at illustrating the solution through customer success stories that engage, entertain, and show the Buyer why their solution is the best.

If your Solution works for the Buyer, it’s time to navigate the buyer through the Evaluation phase by presenting your price and terms in a fashion that is both definite and easy to understand.  The more complicated your proposal, the more fear the buyer will have.  The less definite you are in your presentation of price and terms, the more you invite negotation – and move farther away from the sale.

Finally, your closing skills help the buyer with the Decision phase of the sale.  Even today’s empowered buyers still need and want to be asked to buy – and if you forget this part of the Journey, all your work to this point will likely be for naught.  Part of this phase is the ability to handle and resolve objections, and to remove the Buyer’s fear.

My point is this:  Being a “great closer” or a “great presenter” is worthless if you don’t have the other skills.  That wasn’t always true; in pre-Internet days, if you were a great closer, you could browbeat your customers, make them bleed from the ears, and close enough business to get by.  Great storytellers and rapport-builders could also get enough business.  Even the old “hunter/farmer” sales mentality is obsolete now; salespeople have to be able to both initiate and maintain relationships.  Buyers are more empowered now, and that’s changed the landscape. Today’s salespeople have to be great all-around players.

Is that a lot of work?  Yep, it is.  I didn’t promise that it would be easy.  The best professional salespeople are tuning and improving their skills on a weekly basis.  Here’s a tip for both salespeople and managers:  Focus on one skill every week, and work to improve it.  Try things out, watch to see how customers respond, and use that feedback to figure out what works and what doesn’t.  Your customers are the best focus group that ever existed!

That’s a lot to improve.  I’m not quite done yet, though.  Today’s environment requires additions to the old skill sets.  To maximize your opportunities today, you need to be skilled and ready to use communication platforms that include phone, email, text, video, social media, and IM.  Can you write a persuasive text in 240 characters or less?  If not, you’re going to lose business to salespeople who can.  This is one place where AI (something else you need to be good at) can help you.  Type in what you want to say, and ask your AI app to condense it to 240 characters.  It works.  Just beware of “Chat crap,” and refine your result to eliminate it!

If this sounds like a lot of work, it is.  Let’s be honest.  The job of being a winning salesperson is more complicated than it used to be – and it’s not going to get any less complicated in the future.  This is a moment where you really have an opportunity to differentiate yourself, if you put in the work, learn new techniques and technologies, and keep yourself not only relevant, but vital.  My opinion?  It’s one hell of a fun time to be in sales.


You Can’t Always Get What You Want…But In Sales, You’d Better Ask!

Sometimes, the key to success in selling is to get back to basics. I’ve talked a lot in the last few years about how the balance of power has shifted firmly towards empowered buyers. With more information at their fingertips than ever before, customers can research products, compare prices, and make informed decisions without relying heavily on salespeople. This has led some salespeople to become hesitant about taking an active role in guiding buyers through their Buyer’s Journey.

In fact, I’ll be frank. I worry that I’ve dissuaded some salespeople from remembering an essential truth of selling.  If you don’t ask for what you want, you won’t get it.  To not ask your empowered buyers to buy – or help them advance through their journey – is to abdicate your responsibility as a salesperson.

Don’t make this mistake. Even as buyers have become more empowered, your job is still crucial – to your company and to your buyers. Buyers may have more information, but that information can also be overwhelming – and in many cases, inaccurate or a bad fit for their situation. A skilled salesperson (and you are one of those, right?) who takes charge can cut through the clutter, ask the right questions, and help the buyer arrive at the best solution for their needs.

The key is that you have to be assertive without being pushy. Buyers don’t mind assertive salespeople – but pushy salespeople get eliminated from the Buyer’s Journey. You have to recognize that the buyer is in the driver’s seat, but you must also understand that the buyer often welcomes guidance. By actively participating in the buyer’s journey, the salesperson can help the customer navigate the process more efficiently and come to a decision with confidence. Your buyers will find themselves thinking (or saying) “so, where do we go from here?” quite a bit.  Be prepared to guide them.

Here are some ways salespeople can reassert themselves in the sales process:

  • Ask thoughtful questions. Dig deep to really understand the customer’s needs, challenges, and goals. Don’t just go through a surface-level qualification checklist. Uncover the underlying issues the buyer is trying to solve. I’ve said for many years that 80% of your chance to win the sale is through your questioning, and that hasn’t changed.
  • Provide valuable insights. Use your industry expertise to share perspectives the buyer may not have considered. Offer creative solutions they hadn’t thought of. Position yourself as a knowledgeable partner, not just a vendor. And don’t be afraid to provide expertise, even when it’s not directly tied to a sale.  Salespeople today must earn their spot in front of the buyer, and you do that by making the buyer a little better and more knowledgeable during every sales interaction.  Salespeople are the world’s best collectors of industry best practices – and some of the worst at sharing them.  Break that pattern.
  • Journeys need a guide. Don’t be afraid to take charge of the sales cycle. Suggest next steps, schedule follow-up meetings, and keep the buyer on track. This shows you’re invested in their success, not just making a quick sale.
  • Address objections head-on. When the buyer raises concerns, don’t dodge them. Acknowledge their doubts, then provide reassurance and evidence to overcome them. Demonstrate you’re listening and want to alleviate their fears.
  • Close confidently and directly. Don’t be afraid to ask for the business. If you’ve done the work to truly understand the buyer’s needs, you should be able to make a compelling case for why your solution is the right fit. End the sale decisively, not tentatively.

The most successful salespeople today don’t just react to the buyer’s lead – they proactively shape the sales conversation and Buyer’s Journey. They recognize that even the most informed, empowered buyer still values the salesperson’s expertise and guidance. By reasserting themselves as sources of expertise, these salespeople are able to navigate the buyer’s journey and close deals with confidence.

Of course, this assertiveness must be balanced with genuine curiosity and a customer-centric approach. The goal isn’t to strong-arm the buyer, but to collaborate with them in a way that meets their needs. If you can strike this balance, you will thrive in the new era of buyer empowerment.

Sales and Marketing: The Marriage Whose Time Has Come

Note:  This article is a collaboration between myself and Stephanie Smith of The Grind Marketing.  I’ve asked Stephanie to collaborate with me because I want my readers to be on the cutting edge – and these days, you can’t be on the cutting edge of Sales without incorporating Marketing.  There will be more of this content to come.

For the entire time I’ve been in sales – and probably longer – there has been a disconnect between the sales team and the marketing team at many companies (including many that we have worked for and worked with). The salespeople, who interact directly with customers, often feel that the marketing materials and campaigns don’t match up with what they’re seeing and hearing from clients in the real world. Meanwhile, the marketing folks think the sales reps don’t fully appreciate the importance of presenting a cohesive brand image and messaging.

This divide causes issues. The messaging can be mismatched, lead generation suffers, and the overall experience for the customer gets jumbled up. When sales and marketing aren’t working together, it becomes really difficult to create a smooth, consistent experience for customers across all the different touchpoints they have with the company. This can damage trust and loyalty over time.  This is more pronounced now, since customers have more access to marketing messages through technology.

The key is getting sales and marketing on the same page through open communication and collaboration. They need to understand each other’s roles and perspectives.   Instead of working at odds, Sales and Marketing need to be viewed as one team with different, and complementary, roles.  Here are five good ways to get started:

1. Work-alongs:  We were tempted to call this “ride-alongs,” since the idea began with marketing people should periodically ride along with salespeople to see sales interactions in the field – but the concept works both ways.  Salespeople should be part of the creative process in Marketing.  In fact, the teams should have regular meetings to share customer insights, align their strategies, and get on the same page with positioning and messaging.  The marketers can take the customer pain points and challenges that the sales reps are hearing about and use that to shape more relevant marketing campaigns. And the sales team can apply the marketers’ skills around branding, messaging, and buyer psychology to have more impactful conversations.

2. Use Tech:  Sharing data and technology is also critical. You should be using a good CRM that both Sales and Marketing work with. When Sales and Marketing are using the same systems for tracking leads, analyzing customer behavior, and sharing data, both teams can make smarter decisions and create more seamless, personalized outreach.

3. Define Lead Scoring Together: Historically there has always been tension between Sales and Marketing when it comes to defining a “good lead.” When markets are hot and the buying power is in your favor, the definition surrounding what constitutes a qualified sales lead doesn’t matter as much, because the opportunities inbound are plentiful. However, when markets are down, the definition matters more. Without definition, Marketing will continue to contest; “what do you mean sales are down? We sent you 800 leads last month.” Determining how to score leads requires both teams to clearly understand the buyer persona and what makes the perfect prospect. Assigning real-time lead scoring based on an agreed-upon set of criteria reduces the blame game and allows both teams to focus on optimizing lead-generation tactics. This type of clarity also provides the flexibility for both teams to adjust mid-campaign. If the results aren’t where the team forecasted that they should be based on known customer behaviors and market conditions, the team can reposition messaging and establish retargeting tactics to fuel the funnel appropriately.

One note here – if the sales department doesn’t respond to leads quickly, they don’t have a leg to stand on in this conversation.  As I’ve demonstrated before in this space, leads get cold quickly.

4. Think Holistically About The Stages in Your Buyer’s Journey Map: Formally known as a Sales Funnel, this approach takes similar concepts in defining what stage a customer is within the sales cycle and understanding the amount of nurturing it will take to close the initial deal. With so many new ways a customer can enter the pipeline and equally as many new ways to nurture a customer without ever even having to meet with them face-to-face, this is where a sales and marketing collaboration can truly shine to deliver consistent messaging throughout multiple touchpoints required to prompt conversion. Through this tactical approach,  it is important for marketing teams to share real-time behavioral insights with the sales teams. Again, by leveraging a comprehensive CRM platform, this important customer data can help both teams understand exactly where a customer is at in the funnel before the initial call is ever made. Not only does this create a better customer experience, it also reduces the sales cycle and enhances the time-line to close.

5. Create a Service Level Agreement Between Departments: Okay, that sounds more formal than what it needs to be, but honestly developing a written agreement on deliverables and clearly defining expectations for both teams is one of the most effective ways to maximize productivity. This can be as simple as assigning mutually agreed upon goals that benefit both teams. For example, marketing will provide X number of qualified leads required to help support overall sales quotas and the sales team will aim to close X number of deals from lead generation tactics to meet specific revenue targets. All Leads that are not “sales-ready” (i.e. Motivated and ready to begin a Buyer’s Journey) will be marked as such by the sales team and sent to marketing to be enrolled in automated lead nurturing campaigns through the CRM.

In the B2B world especially, where you’re dealing with long sales cycles and multiple decision makers, having this united sales-marketing strategy is make-or-break. Your customers don’t want to have to choose between brand messages and figure out which one is the “right” one.  Presenting a unified front throughout the entire customer journey builds credibility and trust, ultimately leading to more sales.

The old silos have to come down. When sales and marketing get in sync through transparency, cooperation, and shared goals, the whole company can deliver a much tighter, more compelling experience that resonates with customers and drives better results.

Can Sales and Marketing work together seamlessly? Sure.  This article is an example; Troy Harrison is the Sales Navigator, and Stephanie Smith is a marketing expert, and we coauthored it.  In fact, we will be doing much more collaboration on this concept in the coming months.

About Stephanie Smith:

Passionate about transforming ideas into impactful stories, Stephanie Smith brings extensive experience in strategy development, marketing, content creation, branding, and digital tactics.

Results-driven with a history of leveraging new technologies and market trends to develop collaborative sales and marketing strategies that consistently generate new revenue growth. Her strategic insights and ability to navigate the challenges of blue-collar industries have led to her being approached by B2B family-owned businesses seeking to enhance their go-to-market strategies. Under Stephanie’s guidance, these businesses have seen significant growth, with some experiencing a 300% increase in year-over-year sales performance while earning industry recognition for their impactful campaigns.

With over 15 years of experience in the ever-evolving marketing landscape, Stephanie has led cross-functional teams to align with overall business goals. Her adaptability shines through in fast-paced environments, where she manages multiple projects seamlessly. This experience and Stephanie’s passion for supporting blue-collar workers and their businesses led her to a pivotal point in her career to launch a startup marketing community. Dedicated to delivering go-to-market strategies specifically crafted for small to mid-sized business structures in these industries this community helps companies thrive in today’s business landscapes.

As the Founder of The Grind Marketing Collective, Stephanie leads a team of talented professionals responsible for developing and executing innovative and impactful marketing campaigns that drive brand awareness, customer engagement, and revenue growth for the companies they serve. Leveraging their experience in marketing communications, social networking, and B2B marketing strategies that showcase the value and quality of their clients’ products and services.

Stephanie is always open to connecting! To contact Stephanie visit thegrindmarketingcollective.com or email her at stephanie@thegrindmarketingcollective.com