Congratulations! You’ve landed your first professional sales job. You’re excited, motivated, and ready to crush it. You’re also probably terrified because you have no idea what you’re doing. Welcome to the club. Every successful salesperson started exactly where you are right now – staring at a phone, a CRM system, and a quota, wondering how any of this is supposed to work.  I know I did (well, there wasn’t a CRM system).

Here’s the uncomfortable truth: A lot of companies hired you with the best intentions but haven’t built the infrastructure to properly develop you. They might not have documented processes, structured training programs, or clear guidelines for what your first ninety days should look like. That’s not an excuse to fail. That’s an opportunity to take control of your own development. Here’s what you need to do, starting today.

Embrace the Fact That You Don’t Know What You Don’t Know

The biggest mistake new salespeople make is pretending they understand things they don’t. You’re not fooling anyone, and you’re making your learning curve steeper. Your manager knows you’re new. Your colleagues know you’re new. Your prospects will figure it out pretty quickly. Stop trying to hide it and start using it as an asset.

Ask questions. Lots of them. “Can you explain how that works?” “What’s the typical timeline for this?” “How do you handle it when a customer says that?” The window where asking basic questions is acceptable is narrow – probably your first three to six months. After that, you’re expected to know. Use this window aggressively.

Find Your Go-To Person

If your company has assigned you a mentor or buddy, great. Use them relentlessly. If they haven’t, find someone anyway. Look for an experienced salesperson who seems willing to help and doesn’t treat you like an interruption. Buy them coffee. Ask if you can shadow their calls. Debrief with them after your meetings.

Most successful salespeople remember what it was like to be new, and they’re more willing to help than you think. But you have to ask. The key is having one designated person you can go to with the constant stream of questions that will come up. Don’t spread your questions across ten different people – you’ll annoy everyone and get inconsistent answers.

Create Your Own Structure

Your company might not have given you a documented sales process or a weekly routine. Build your own. Start by observing what the successful salespeople in your organization do. How do they spend their days? What does their prospecting look like? How do they prepare for calls?

Then create a basic weekly framework for yourself:

• How many prospecting calls will you make each day?
• How much time will you spend on LinkedIn engagement?
• When will you do your research and prep work?
• What does a productive day look like in concrete activities?

Write it down. Follow it. Adjust as you learn what works. The discipline of having a routine will set you apart from other new salespeople who are just reacting to whatever seems urgent at the moment.

Build Your Own Knowledge Base

Your company might not have quick-reference guides for products, objections, or common questions. Make your own. Every time you learn something new about your product, write it down. Every time you hear a great answer to an objection, document it. Every time you discover a useful resource or process, add it to your notes.

Use a simple document, a notebook, or a notes app – whatever works for you. The act of writing things down helps you remember them, and you’re building a reference you can review before calls. This becomes especially valuable when you’re on a call and a question comes up. Having your own notes to reference gives you confidence and helps you avoid the dreaded “Let me get back to you on that.”

Shadow, Shadow, Shadow

If your company allows it, get on as many calls with experienced salespeople as possible. Listen to how they open conversations. Watch how they handle objections. Notice what questions they ask and when. After each call, debrief. “Why did you ask that question?” “How did you know they were ready to talk about price?” “What were you thinking when they said that?”

This is how you acquire tribal knowledge – the unwritten wisdom that exists in every sales organization but rarely gets documented or formally taught.

Invest in Your Own Education

Don’t wait for your company to send you to training. Start learning on your own. Read books on professional selling. Watch videos on YouTube.  Listen to sales podcasts during your commute. Follow experienced sales professionals on LinkedIn and pay attention to what they’re sharing.

Most importantly, learn about the Buyer’s Journey – how customers actually make buying decisions and what role you play in helping them navigate that process. Understanding the five steps (Motivation, Investigation, Solution, Evaluation, and Decision) will give you a framework for every sales interaction.

This isn’t about becoming a sales guru overnight. It’s about building foundational knowledge that will make everything else easier.

Get Real-World Experience Fast

If you’re selling trade show exhibits, find a trade show and walk the floor. If you’re selling manufacturing solutions, visit a factory. If you’re selling software, attend a user conference. You can’t sell with conviction when you’ve never experienced the environment your prospects operate in. This experiential learning will accelerate your development more than any training manual.

Don’t wait for your company to send you. Find local events on your own. Most industry events will let you register as a vendor or visitor. Make it happen.

Accept That You’re Going to Struggle

Here’s what nobody tells new salespeople: The first six months are going to be hard. Really hard. You’re going to make calls that go nowhere. You’re going to stumble through presentations. You’re going to lose deals you thought you had won. You’re going to feel incompetent more often than you feel confident.

This is normal. Every successful salesperson went through it (even if they won’t admit it). The difference between those who made it and those who didn’t isn’t talent – it’s persistence. The struggling is part of the process. It means you’re learning. Embrace it instead of running from it.

The Bottom Line

Your company might not have built the perfect onboarding program for you. That’s okay. You can build your own development plan. Be proactive about finding mentors. Create your own structure and routines. Document what you’re learning. Shadow experienced salespeople. Invest in your own education. Get real-world experience.

Most importantly, embrace being new. Ask questions while you can. Admit what you don’t know. Use your fresh perspective as an asset instead of hiding it. The sales profession needs people like you – enthusiastic, coachable, and willing to learn. The companies that don’t provide proper structure and training are making a mistake, but that mistake doesn’t have to define your career.

Take control of your own development. The first ninety days set the trajectory for your entire sales career. Make them count.

There’s a religion spreading through the B2B sales world, and like most religions, it’s built on faith rather than evidence.  I’m hearing this preached more and more:  “Buyers don’t want to talk to salespeople. Get out of their way. Let them self-serve. Be there when they’re ready.”

And, at first glance, you might think that the data supports it. According to Sopro’s 2025 research, 75% of B2B buyers say they prefer a “rep-free” sales experience Sopro. Well, that’s all she wrote, right? Salespeople are obsolete. The future is self-service. Time to update your resume.  And time for me to find a new career.  Except….there’s more to the story.

Here’s what the same research reveals: Self-service digital purchases are significantly more likely to result in purchase regret. If you don’t believe me, go to a place where they accept Amazon returns.  You’ll find a line out the door.  Let that sink in. Buyers say they want to be left alone, then regret the decisions they make when they are.

The Numbers Tell a Miserable Story

Some of my counterparts in the B2B sales world have spent a decade preaching “buyer empowerment” and “frictionless self-service,” and the results are in. They’re terrible.  I mean – BAD.  Nearly 86% of B2B purchases stall during the buying process, and 81% of buyers are dissatisfied with their chosen provider, according to Sopro’s research.

Read those numbers again. Nine out of ten deals get stuck. Eight out of ten buyers are unhappy with what they bought. This is what “self-serve” buying looks like. Sales cycles are getting longer – 63% of B2B leads now take at least three months to decide, and 20% wait over a year. Win rates are declining. Buyer satisfaction is tanking. But sure, let’s keep getting out of the buyer’s way.

I also think that the “self-serve” attitude has led to salespeople who have decided to be reactive, rather than proactive. Make no mistake – our job is to be proactive, independent business generation machines.  That’s how we add value to our companies – but we need to add value to our customers, too.

What Buyers Say They Want vs. What They Actually Want

Wanna know the truth?  It’s shown in the numbers above: Buyers don’t actually want to be left alone. They want salespeople who don’t waste their time, head space, and money.  There’s a massive difference between those two things, but the sales world has conflated them.

When buyers say they prefer a “rep-free experience,” they’re not saying they don’t need help. They’re saying they’re tired of salespeople who show up unprepared, ask basic questions they should already know the answers to, and pitch products without understanding their situation.  They’re also saying that when they tell salespeople what they need, salespeople should, you know, listen and act on what they say.

They’re rejecting bad selling, not selling itself. The proof is in the same research. 88% of B2B buyers want to hear from vendors when researching and evaluating their options. Nine out of ten buyers want vendor input during their buying process. That’s not exactly a ringing endorsement of “leave me alone.”

The Problem with Self-Service Buying

Here’s what happens when buyers try to navigate complex B2B purchases on their own: They do extensive research. Over 80% of buyers know what product they want before starting their research, and 70% buy their initially preferred solution.

Sounds great, right? Buyers are informed and decisive.  Except they’re making overconfident but poorly-informed decisions. All that research doesn’t mean they’ve correctly identified their problem or understand which solution actually fits their needs.

Remember my principle: 80% of your chance to win or lose the sale is determined by the time you ask your last question. That happens in the Investigation phase of the Buyer’s Journey – when you’re helping the buyer define their needs correctly.

If buyers have already “done their research” and decided what they want before you’re involved, you’ve missed the most critical part of the process. You’re not helping them make a successful buying decision – you’re just taking an order for something they may regret.  That means that you need to get ahead of their Investigation phase.

The Role Salespeople Actually Need to Play

When I talk about navigating the Buyer’s Journey, the first step is Motivation – helping buyers recognize dissatisfaction with their status quo and envision a better future state.  If you’re sitting and waiting on the phone to ring, you’re missing this step – and probably a big part of the next one.  And that puts you on the back foot.

The second step – Investigation – is where most of the sale is won or lost. This is where you ask comprehensive, customer-centric questions to help buyers define their needs and priorities correctly.

You can’t do either of these things if you’re “staying out of the buyer’s way.”

Buyers who self-serve through the entire process skip right to Solution and Evaluation. They never get proper Investigation. They never benefit from someone who’s seen this situation hundreds of times before helping them think through implications they haven’t considered. The result is the misery we’re seeing in the data. Stalled purchases. Buyer’s remorse. Dissatisfaction.

When You End the Call, How Is the Customer Better?

I’ve written before about the critical question every salesperson should ask after every interaction: When you end that call, how is the customer better? This isn’t about being liked. It’s not about being friendly. As I’ve said before, the “Good Time Charlie” salesperson is obsolete. It’s about providing expertise, perspective, and insights that customers can’t get from a Google search or a product comparison chart.

Buyers can research products online. They can compare prices. They can read reviews. They don’t need you for any of that.

What they need is someone who can help them:

• Understand if they’ve correctly diagnosed their problem
• See implications and consequences they haven’t considered
• Navigate the gap between their current state and their desired future state
• Make a decision they won’t regret

But only if that salesperson has done their homework, asks intelligent questions, and provides genuine value.

Yep, I’m Going to Talk About The Generational Factor Again

Here’s what makes this even more complicated: Millennials and Gen Z now account for 71% of B2B buyers. Younger buyers have grown up with instant access to information. They’re comfortable with self-service. They’re skeptical of traditional sales approaches.

But that doesn’t mean they don’t need help. It means they’re even less tolerant of salespeople who waste their time with information they could have found themselves. Gen-Z’s and Millennials like adults in the room – IF the adults add value. The bar for adding value has gone up, not disappeared.

Putting This Into Action

The “rep-free sales experience” isn’t making buyers happier or more successful. It’s creating a landscape where deals stall, buyers are dissatisfied, and everyone loses. Buyers don’t need less interaction with salespeople. They need better interaction with salespeople.

Stop apologizing for being a salesperson. Stop trying to “get out of the buyer’s way.” Instead, become the kind of salesperson buyers actually need:

• Do your research before the call (Claude or Perplexity rocks this).
• Ask questions that help buyers think through their situation more thoroughly than they would on their own.
• Provide insights and perspectives they can’t get from self-service research.
• Help them define their needs correctly before they make a decision they’ll regret.

When you end that sales call, the customer should be better informed, better prepared, and more confident about making a successful buying decision – whether they buy from you or not. That’s not getting in the buyer’s way. That’s adding value.

And despite what the “rep-free” evangelists preach, that’s exactly what buyers need.

I was reviewing a salesperson’s weekly activity report recently, and something caught my eye. He’d logged eight customer meetings for the week. Impressive number, right? So I asked him what he’d accomplished in those meetings.

His answer? “Well, I touched base with everyone and we had good conversations.” That’s code for “I wasted eight opportunities this week.”

Purposeless Sales Calls are Cancer

Here’s a problem that’s costing salespeople and their companies millions: Too many salespeople go into sales calls without knowing what they want to achieve, and then they’re surprised when they achieve nothing. They schedule the meeting. They show up. They have a nice chat. They leave. And nothing moves forward. No progress in the Buyer’s Journey. No new information. No commitment. Nothing. This isn’t a sales call. It’s a social visit that happens to occur during business hours.

What “Another Meeting” Really Means

One of the worst objectives I hear salespeople cite is “schedule another meeting.” Unless that next meeting involves different people, addresses a different topic, or represents the next step in the Buyer’s Journey, “another meeting” is meaningless. It’s a way to feel productive without actually being productive. It’s activity without achievement. It’s the sales equivalent of running in place and calling it a marathon.

If your objective for today’s meeting is to schedule another meeting just like this one with the same people talking about the same things, you don’t have an objective. You have a stalling tactic. And you’re the one stalling, not the customer.

“Just Checking In” Is a Waste of Time

“I’m just checking in” might be the four most useless words in sales. Checking in on what? For what purpose? To what end? When you “just check in,” you’re essentially saying, “I have nothing valuable to offer you today, but I wanted to use some of your time anyway.”

Your prospects are busy. Their time is valuable. If the best you can do is “check in,” you’re training them that meetings with you are optional at best and wasteful at worst.  And I get the “checking in” impulse – I have it myself sometimes.  But instead of “just checking in,” think of two or three meaningful questions to ask.  What is it that you really want to “check in” on?  Figure it out and ask.

What a Real Objective Looks Like

Before every sales call, you should be able to answer this question clearly: What do I want to accomplish in this meeting? Real objectives sound like this:

“I want to complete discovery on their decision-making process and timeline.”

“I want to schedule a plant tour so I can see their operation firsthand.”

“I want to get agreement on the key problems we’ve identified and earn the right to propose a solution.”

“I want to present our proposal and ask for the business.”

“I want to introduce our implementation team and confirm the go-live date.”

Notice what all of these have in common? They’re specific. They represent progress. They move the Buyer’s Journey forward. These are objectives worth scheduling a meeting for.

You Have to Ask For What You Want

Here’s the part that too many salespeople miss: Once you know what you want to achieve, you need to ask for it before the meeting is over. If you want a plant tour, ask for it: “Based on what we’ve discussed, I think it would be valuable for me to see your operation firsthand. Can we schedule a time for me to tour your facility?”

If you want to move to proposal stage, ask for it: “It sounds like we’ve identified the key issues. I’d like to put together a proposal that addresses what we’ve discussed. Does that make sense as a next step?”

If you want the business, ask for it: “When would you like to get started?”

Will you always get what you ask for? No. Sometimes the answer is “not yet” or even “no.” But if you don’t ask, you’re guaranteeing a meaningless sales call. You’re leaving with nothing when you could have left with clarity – even if that clarity is “they’re not ready yet” or “this isn’t going to happen.”

When “No Progress” Is Actually Progress

Does this mean you discontinue the relationship if you don’t get what you ask for? Not necessarily. Sometimes you ask for a proposal opportunity and learn they’re not ready yet. That’s valuable information. Now you know where you stand and what needs to happen before they’ll be ready.

Sometimes you ask for a plant tour and learn they have concerns about confidentiality. That’s a buying signal – they’re worried about protecting their operation, which means they’re taking this seriously enough to think about implementation.  Be prepared to sign an NDA.  I’ve been in business over 21 years.  In the first fifteen years, the number of NDA’s I signed could be counted on one hand. In the last five years, it’s nearly become routine.

The point isn’t to strong-arm customers into commitments they’re not ready to make. The point is to get clarity on where you are in the process and what needs to happen next. That only happens when you ask.

What Sales Managers Need to Do

If you’re a sales manager, you need to reinforce this discipline constantly. Before salespeople go into calls, ask them: “What’s your objective for this meeting?” After salespeople come out of calls, ask them: “Did you achieve your objective? If not, what did you learn?”

Make this a standard part of your coaching conversations. Make it part of your sales meeting discussions. Make it cultural. When salespeople know they’re going to be asked about their objectives, they start thinking about them proactively. The behavior becomes habit.

The Bottom Line

Your prospects’ time is valuable. Your time is valuable. Every sales call should accomplish something meaningful or it shouldn’t happen. Figure out what you want from each meeting. Make sure it represents real progress in the Buyer’s Journey. Then ask for it before the meeting ends.

Will you always get it? No. But you’ll get a lot more than you’re getting now by wandering into meetings hoping something good happens. Stop “just checking in.” Stop scheduling meetings for the sake of meetings. Start every sales call with a clear objective and the discipline to ask for what you want.

Your prospects will respect you more. Your pipeline will move faster. And your results will prove that purposeful beats aimless every single time.

It’s January 2, 2026, and if you’re a salesperson or sales manager reading this, I have good news and bad news.  The bad news? The rapid changes reshaping our profession aren’t slowing down. They’re accelerating.

The good news? If you’re willing to adapt, you’re going to have a massive competitive advantage over the salespeople who are still pretending it’s 2015. Here are my predictions for what’s going to separate winners from losers in sales this year.

1. Adding Value Will No Longer Be Optional

It’s not enough anymore to just ask questions, make presentations, and sell product. Customers can do all of that without you – and they know it. The vital skill for 2026 will be your ability to become an expertise provider for your customers. Here’s the question you need to ask yourself after every sales call: When you ended that call, how was the customer better? Did you provide expertise that helped them, even if they don’t buy from you?

Customers can buy things without ever talking to a salesperson. They can research products online, compare prices, read reviews, and click “purchase” – all without your intervention. You need to give them a reason to do otherwise. And it’s not your ability to talk football for 30 minutes. That reason is the expertise, perspective, and insights you bring that they can’t get from a Google search.

If you’re not making your customers smarter and better informed through your interactions, you’re not adding value. And if you’re not adding value, you’re irrelevant.

2. AI is Changing How Customers Research You

While skepticism about AI-generated content will continue to increase – and rightfully so – the use of AI for research is exploding. More and more customers are using tools like Claude and Perplexity (my favorite AI tools, FYI) to research you, your company, and your products before they ever talk to you. They’re finding sources, reading reviews, and gathering information faster and more comprehensively than ever before.

Here’s what that means for you: Salespeople should regularly research themselves, their companies, and their products to see what AI is saying about them. Go into Claude or Perplexity right now and ask what it knows about your company. Ask about your products. Ask about common complaints or issues. See what comes up. Because I guarantee your prospects are doing exactly that before they agree to meet.

3. Customer Expectations About Pre-Call Prep Are Skyrocketing

Once upon a time, salespeople could walk into a call fat, dumb, and happy, knowing almost nothing about the customer and still succeed. You could ask incredibly basic questions like “What do you do here?” and customers would patiently explain their business to you. Those days are over. Research is too easy now. Information is too accessible. Customers expect you to have done your homework before you waste their time.

This doesn’t mean you stop asking questions – Investigation is still where 80% of the sale is won or lost. But here’s the shift: Use research for the basics and confirm, then shift into “asking to learn” mode for the specifics. Instead of asking, “What are the biggest trends you see in your industry?” try this: “I did some research, and here are the trends I found in your industry. How close did I get, and how are those affecting you specifically?” This approach demonstrates both knowledge and curiosity. It shows you cared enough to do research, and you’re smart enough to know that research only gets you so far – you still need their specific insights.

Make good use of the customer’s time. Demonstrate that you care enough to prepare. Then use your questions to get specific about their company needs, buyer motivation, and unique situation.

4. LinkedIn’s Role in Prospecting Will Become Even More Critical

Prospecting continues to get more challenging, and the role of LinkedIn in filling the sales funnel will increase throughout 2026. Yes, there are still a handful of industries where old-style door knocking works. But for most industries, modern security concerns and time management have made that obsolete.

Decreasing contact ratios are harming the effectiveness of phone prospecting. But here’s the interesting twist: Phone prospecting can be an excellent setup to LinkedIn prospecting, rather than vice versa. The search for authenticity is so important now that a voicemail from a real human being launches a relationship. And I advocate giving multiple points of contact in that voicemail, including “look me up on LinkedIn.” When prospects hear your voice, you become real. When they look you up on LinkedIn and see you’re actively sharing valuable content and engaging professionally, you become credible.

Smart salespeople will stay on top of these evolving trends and read and react to what their customers are doing. I fully expect that the prospecting I’m teaching at the end of 2026 might be tweaked or modified from what I’m teaching now – it’s evolving that fast.

5. Generic Email Prospecting Will Finally Die (We Hope)

I’ve been predicting the death of cold email for years, and 2026 might finally be the year it happens – at least for the smart salespeople. Spam filters are getting better. AI detection is getting smarter. And most importantly, prospects are getting more ruthless about ignoring anything that looks like mass outreach. If you’re still sending generic email blasts hoping for a response, you’re not prospecting – you’re just annoying people and damaging your brand reputation.

6. Video Communication Will Become Table Stakes

Video isn’t new, but its importance in sales communication will increase dramatically in 2026. Whether it’s personalized video messages to prospects, video proposals, or simply being comfortable and professional on Zoom calls, salespeople who can’t communicate effectively on video are going to struggle. Younger buyers especially expect comfort with video. If you’re still treating video calls like an awkward necessity rather than a normal communication channel, you’re behind.

One tip here:  Forget the digital backgrounds on Zoom calls.  It slows down the streaming and can make you pixelate or break up.  Instead, sit (or preferably stand) in front of an actual background that makes sense and doesn’t look bad.

7. The Gap Between Adapters and Non-Adapters Will Become a Canyon

This might be the most important prediction of all. The salespeople who embrace these changes – who invest in learning, who adapt their approaches, who stay current with how buyers are evolving – are going to absolutely crush it in 2026. The salespeople who cling to “tried and true” methods that stopped being true five years ago? They’re going to struggle more every month.

This gap has been growing for years, but 2026 is when it becomes undeniable. The winners and losers won’t be separated by talent or personality – they’ll be separated by willingness to adapt.

For Sales Managers: You Need to Stay Ahead

If you’re a sales manager, staying ahead of these trends in order to coach your salespeople effectively is non-negotiable. That requires time in the field with your salespeople – two days a week minimum. You can’t coach what you’re not seeing, and you can’t see it from behind your desk.

Here’s the critical thing: Be very careful before dismissing sales challenges as “excuses.” What might have been an excuse a couple of years ago could be a very real barrier now. The sales landscape is changing so fast that legitimate challenges emerge almost monthly.

Your salespeople have to be smart and versatile to keep current. You have to be a touch ahead of your salespeople to be effective. That means you’re constantly learning, constantly adapting, and constantly challenging your own assumptions about what works.

The Bottom Line

2026 is going to separate the salespeople who are committed to staying relevant from those who are riding the train until the track ends. The changes aren’t slowing down. Customer expectations aren’t decreasing. The bar for what constitutes “professional selling” keeps rising.

You can either complain about how much harder sales has become, or you can adapt and thrive while your competitors are still wondering what happened. Your choice. But choose quickly – 2026 won’t wait for anyone.

I was listening in on sales calls with a distributor of high-performance auto parts, along with their Inside Sales Manager. A customer had called asking about a particular engine wiring harness. The salesperson explained that yes, the harness would work on his engine just fine. Right as the customer was about to buy, the salesperson said, “However, it’s not designed as a stock replacement harness; it won’t work on your original 2000 Camaro.”

The customer stopped and said that what he wanted was a stock replacement harness for his Camaro. The salesperson explained that this harness was designed to swap the engine into an older car and wouldn’t support all the functions of the Camaro’s system. The customer thanked the salesperson and hung up.

The Inside Sales Manager came unglued. What happened next perfectly illustrates one of the worst outdated sales techniques still being taught today.

1. “Never Answer the Question the Customer Didn’t Ask!”

That’s what the Sales Manager yelled at the poor salesperson. “If you hadn’t volunteered that information, he’d have bought.”

The salesman was a rookie, so I stepped in. “If he’d bought,” I said, “that harness would have come right back as a return, and the customer would have been upset. What’s your win there?” As the manager stammered, I continued: “Or worse, he’d have tried to modify the harness to make it work, it still wouldn’t have worked, and then he couldn’t return it OR use it. He’s out $1,000. How does that help anyone?”

This technique is built around “get the order at all costs, and to hell with what happens afterward” transactional selling. It might have worked in an era when customers had limited information and options. But today? Especially with Millennial and Gen-Z buyers who can research everything, read reviews, and blast their experiences across social media? This is professional suicide.

Your role is to help the customer reach a successful buying decision. Here’s your new rule: If it’s information the customer needs to know in order to have a successful result, give it to them, whether they asked or not.

That’s not just good ethics. It’s good business in an age where one bad Google review can follow you forever.

2. The “Take Away” Close

This manipulative tactic works like this: At closing time, you say something like, “You know, you really shouldn’t buy this (for whatever noble reason).” The idea is that the customer now wants it so badly that they’ll justify why they should buy it, essentially selling themselves.

Here’s the problem. If you’ve been selling correctly, you’ve built trust and credibility with the customer. Based on that trust, one of two things happens when you use the “take away”:

First, the customer believes you because of that credibility – which means you lose the sale (or you have to re-close, making yourself a liar).

Second, the customer sees right through the tactic, realizes you’re manipulating them, and walks.

Modern buyers are especially adept at spotting manipulation. They’ve been marketed to since birth. They know every trick in the book. When you try to play games with them, they don’t just walk – they tell everyone they know. Just play the close straight. Only take it away if you’re really going to take it away – meaning it’s genuinely not a good purchase for the customer.

3. Never Ask a Question to Which You Don’t Know the Answer

This is the old “lawyer’s technique,” and it means the salesperson is terrified of being surprised by an answer.

There are two massive problems with this philosophy.

First, you must ask questions to which you don’t know the answer to properly discover and interpret needs. Be prepared for surprises and for the call to go in directions you hadn’t anticipated. That’s not a bug – it’s a feature. Those surprises are where you learn the most about your customer.

Second, by the time the lawyer gets into the courtroom, the witness has already been questioned numerous times. The lawyer knows what the witness will say. That’s not the case in a sales call.

Remember: 80% of your chance to win or lose the sale is determined by the time you ask your last question. You can’t ask good questions if you’re afraid of the answers.

This fear-based approach is particularly deadly with younger buyers who expect consultative conversations, not scripted interrogations. They want salespeople who are genuinely curious about their situation, not afraid to explore it.

4. The Salesperson Should Seek to Control the Customer

First, any salesperson who believes they have “control” over the customer is fooling themselves. The customer can always remove themselves from the process. This delusion was always problematic, but it’s laughable in today’s empowered buyer environment. Modern buyers – especially younger ones – have done their research before they ever talk to you. They know their options. They control the process whether you acknowledge it or not.

Whatever control we have is more aptly called “influence,” and it’s shown by the customer allowing or asking us to direct parts of the process.

Seek influence, not control. Earn it by respecting the customer’s intelligence, showing your expertise, and working side by side for a successful result. Anything else is a fantasy that will cost you deals.

5. The Up Front Contract

This technique opens the sales call with a closing question designed to lock the customer in with “intent to buy if things are right.” This ranges from the car salesman’s “Are you here to buy a car today?” to “If you like what you see today, is there any reason we can’t move forward?”

The problem is that this question occurs at the start of the selling process, before you’ve built any trust or equity, and before you’ve earned the right to ask a closing question. At this point your customer knows nothing of your offerings or pricing. Many times their needs haven’t even been defined and matched to a product or service – and you’re asking a closing question?

And if the customer says “yes” to the question and later says “no” to moving forward, what can you do? Whine about it?

Don’t worry about the buyer’s intent until the buyer has a reason to have intent. If they’re seeing you, they’re Motivated to enter a buying process – but that’s all. Let them complete their Buyer’s Journey.

The Common Thread

All of these techniques share one thing: they’re designed to maneuver and manipulate customers into places they don’t want to be. They come from an era when salespeople had information advantages over buyers. When customers had limited options. When bad experiences stayed local instead of going viral.

That world is gone.

Today’s buyers – and especially Millennial and Gen-Z decision makers – can smell manipulation from three states away. They have access to unlimited information, countless options, and platforms to share their experiences with thousands of people.

These outdated techniques don’t just fail with modern buyers. They actively damage your reputation in ways that follow you across your entire career. If you’re still using them, the ’70s called and they want their sales techniques back.

Focus on helping customers make successful buying decisions. Ask great questions. Build genuine relationships. Respect their intelligence and their process.

That’s not manipulation. That’s professional selling.  That’s Navigating the Buyer’s Journey.  And it’s what makes you successful in today’s world.

An objection is when a customer states a problem with your offering or asks a question that creates a clear barrier to the sale. Essentially, they’re saying “No” or “No, because.”

And by the time they say it, you’ve probably already lost.

That’s not what most sales managers want to hear. They like to think there are magic “objection responses” that will easily overcome any objection. When a salesperson comes back from a lost deal, the manager asks, “Well, did you say this? Did you say it with the right tone?”

I had a sales manager like that early in my career. His name was Bill, and every time I lost a deal, he’d drill me on whether I’d used the “right words” to handle the objection. Finally, after losing yet another deal, I yelled at him: “Bill, I know the words! I said the words! The words didn’t turn it around!” To Bill’s credit, he didn’t fire me – small wonder. Instead, we had a good conversation that started me thinking differently about objections.  Bill still thought there were magic words – but I knew that there weren’t.

What I Learned the Hard Way

Through trial and error over the years, I discovered something that changed how I sold and how I now teach salespeople to sell: Most objections aren’t won in the objection phase. They’re won in the questioning phase, much earlier in the Buyer’s Journey.

Think about where objections typically surface. Usually, it’s in the Decision phase – after you’ve made your presentation, after you’ve quoted your price, when you’re asking for the business. The customer says, “I need to think about it,” or “Your price is too high,” or “We’re not sure this will work for our situation.”

At that point, the problem has already taken a set in the buyer’s mind. You’re now trying to overcome an obstacle that’s been building throughout the entire sales process, even if the customer didn’t voice it until now. It’s taken a set in the buyer’s mind, and no scripted response is going to magically dissolve that concern.

The Power of the Buyer’s Words

Here’s a principle that should be tattooed on every salesperson’s brain: The words your customer uses are always more powerful than the ones you use. When you respond to an objection with your carefully crafted counter-argument, you’re using your words to fight their words. You’re essentially saying, “No, you’re wrong to think that.”

Even if you “win” the argument, you’ve lost something in the relationship.

But when you surface the concern early through questioning, and the customer articulates their needs and concerns in their own words during the Investigation phase, something different happens. You’re not fighting their concerns – you’re addressing them as part of your solution.

How to Minimize Objections Before They Happen

The real objection hack isn’t a better script. It’s a better process. When you ask comprehensive, customer-centric questions in the Investigation phase, you accomplish several things:

You surface potential obstacles early. The price concern, the implementation worry, the internal politics – these issues exist whether the customer voices them or not. By asking the right questions, you bring them to light when the buyer is still open and exploratory rather than defensive and decided.

You understand the buyer’s definition of success. When you know what success looks like to the customer, you can present your solution in terms that directly address their vision. This isn’t manipulation – it’s customization.

You present to the solution before the objection crystallizes. If you’ve uncovered during Investigation that budget is a concern, you can address ROI and value in your Solution presentation. If you’ve discovered implementation anxiety, you can build your implementation support into your proposal. By the time you get to the Decision phase, you’ve already addressed the concerns that would otherwise become objections.

The Questions That Prevent Objections

So what does this look like in the real world?

Instead of waiting to hear “Your price is too high” in the Decision phase, ask in Investigation: “What budget parameters are you working within? How are you measuring ROI on this type of investment?”

Instead of hearing “I’m not sure this will work for us” at the end, ask earlier: “What concerns do you have about implementing a solution like this? What would need to be true for this to be successful in your environment?”

These questions don’t eliminate all objections. But they bring potential obstacles into the open when you can still do something about them.

When You Should Walk Away

Here’s something else that needs to be said: Not all objections can be overcome, and not all objections should be overcome.

Sometimes the barrier is very real and indicates that bad business is in your future. Maybe the customer truly can’t afford your solution. Maybe their expectations are unrealistic. Maybe the timing is genuinely wrong. Bulldozing through these objections might get you a sale, but it gets you an unhappy customer who feels pressured, regrets the purchase, and becomes a problem down the road.

Salespeople need to be trained to know when to say “no.” Sometimes the best response to an objection is, “You know what? Based on what you’re telling me, I’m not sure we’re the right fit right now.” That honesty builds credibility for future opportunities and saves everyone from a bad experience.  I had an experience like that myself this week.  The business didn’t happen – but the relationship is intact.

When You Do Face Objections

Sometimes, despite your best Investigation, you’ll still face objections in the Decision phase. When that happens, understand what you’re dealing with: a concern that’s already taken a set in the buyer’s mind. Your best move isn’t a scripted response. It’s a question that takes you back to Investigation: “Help me understand where that concern is coming from. What specifically worries you about this?”

Then listen. Really listen. Because if you didn’t surface this earlier, you need to understand it now before you can address it – or decide if you should even try.

The Bottom Line

Stop looking for magic objection responses. Stop drilling your salespeople on whether they said the “right words” with the “right tone.” Instead, improve your Investigation phase. Ask better questions. Surface concerns early. Build your solution around the buyer’s definition of success. And recognize when an objection is telling you this isn’t the right deal.

When you do that, you’ll find something interesting: The objections that used to derail your deals in the Decision phase simply don’t come up anymore. Not because you got better at handling objections. Because you got better at preventing them. And when they do come up, you’re smart enough to know which ones to address and which ones to respect.

That’s not a script. That’s a strategy.

I saw a post from another sales trainer yesterday that annoyed me enough to write about it. He said:

“Pick one communication channel at a time. Email, voicemail, LinkedIn InMail, and text all go to the same place. When you give me the same bad reason to respond in 2, 3, or more of these at the same time, I’m out. Pick one. Next time, try another. Less is more.”

This is outdated nonsense from someone who’s clearly out of touch with how younger buyers operate. And if you follow this advice, you’re going to lose deals to competitors who understand modern communication.

The Fundamental Problem with “Less is More”

Here’s what this trainer misses: The salesperson did exactly the right thing. When you leave a voicemail or send an email, you should absolutely give the prospect multiple ways to respond—phone, text, email, LinkedIn. Why? Because you don’t know which method they prefer.

Some buyers live in email. Some never check voicemail but respond to texts within minutes. Others prefer LinkedIn. Still others want to call back. When you only say “call me at this number,” you’re forcing them into your preferred channel instead of letting them respond through theirs.

I used to agree with “less is more.” Twenty years ago, it made sense. Back then, there were two channels—phone and email. You left a voicemail with your phone number, or you sent an email with your email address. Simple.

But things have changed, and my viewpoint has changed with them. Today’s buyers—particularly younger ones—expect communication versatility. When you give them multiple response options, you’re not being confusing. You’re being respectful of their preferences.

What the Data Actually Shows

Here’s what I’ve seen in real-world selling: Giving prospects multiple response options increases response frequency. It’s not even close. When my clients’ salespeople say “respond however works best for you—call, text, email, or LinkedIn,” they get significantly more responses than when they only provide a phone number.

And here’s the kicker: The most common response method these days is text, not phone call. Think about that. If you’re following the “pick one channel” advice and only give them your phone number, you’re missing the channel that gets the highest response rate from younger buyers.

For every one prospect who gets confused by multiple response options, there are two who appreciate the flexibility and respect the courtesy. And that ratio is growing as generational dynamics shift the buyer population younger.

The Generational Disconnect

The trainer who posted this is obviously not a young man. His perspective reflects how Boomers and older Gen X prefer to operate—you leave a voicemail with a callback number, or you send an email and they email back. One channel in, same channel out.

Gen Z and younger Millennials don’t operate this way. They’re channel-agnostic. They might get your voicemail but prefer to text back. Or read your email but respond via LinkedIn. When you only give them one way to respond, you’re forcing them to use your preferred method instead of theirs. And in today’s empowered buyer environment, that’s backwards. – and the buyer just opts out of the process.

The Real Issue Isn’t Multiple Options—It’s Bad Messaging

Let’s address what the trainer actually said: “When you give me the same bad reason to respond in 2, 3, or more of these at the same time, I’m out.” Notice the key phrase: “same bad reason to respond.”

The problem isn’t offering multiple ways to respond. The problem is having a bad reason to respond in the first place. If your value proposition sucks, offering five ways to decline doesn’t make it better—it just gives them more options to ignore you. But if you have a genuinely compelling reason for the prospect to engage, giving them multiple response options increases the likelihood they’ll actually respond through their preferred method.

This is like blaming the return address options when the letter itself is junk mail. The issue isn’t the response mechanism. It’s the message.

How to Actually Do This Right

I work with salespeople who successfully reach decision-makers every day. Here’s what works:

First, craft a compelling, specific reason to engage that’s relevant to that prospect. Not generic messaging, but research-based outreach that demonstrates you understand their business.

Second, when you reach out—voicemail, email, or LinkedIn—give them multiple ways to respond. “You can call me at 913-555-1212, text me at the same number, email me at troy@example.com, or connect with me on LinkedIn. Whatever works best.”

One message. Multiple response options.

The response rate destroys the old “give them one number and wait” method. And responses come through whichever channel the prospect finds most convenient—which, increasingly, is text.

The Aging-In Effect

The communication preferences of younger buyers aren’t a temporary quirk. As Gen Z and younger Millennials move into decision-making roles, expecting multiple response options becomes standard, not exceptional.

Salespeople who give prospects flexibility in how they respond will win. Those who cling to “just give them one number” advice will find themselves shut out by buyers who view that rigid approach as out of touch and inconvenient.

What You Should Actually Do

When you reach out—voicemail, email, LinkedIn, whatever—give them multiple ways to respond. Don’t just say “call me.” Say “call, text, email, or message me on LinkedIn—whatever works best.”

Make it easy for them to respond through their preferred channel, not yours. This isn’t confusing. It’s courteous.  Remember, you aren’t the star of the show.  Your prospect is. And make sure your value proposition is compelling. If you’re getting pushback on offering multiple response options, the problem isn’t the options. It’s the message.

The world has changed. Buyers have changed. If your sales advice hasn’t, you’re teaching people how to lose deals to more adaptable competitors.

Less isn’t more. Flexibility is more.

There’s a fundamental truth about sales management that most leaders refuse to accept:

The right behavior can overcome the incorrect tools, but the right tools cannot overcome the incorrect behaviors.

Read that again. Let it sink in. Because if you’re a sales manager or business owner constantly frustrated by your team’s performance, this principle explains why all your “solutions” keep failing.  And if you’re a salesperson who’s asking for more and better “tools,” it might give you a window into your own path forward.

What You Need is Profitable Behavior Change.

The most important thing business owners and sales managers can do is produce what I call “profitable behavior change.” This is when a salesperson’s behavior is changed through coaching, direction, or other corrective means to produce a result that’s profitable for the company, the salesperson, and most likely the company’s customers as well.

The ability to coach and produce profitable behavior change is the most fundamental skill of management. Period.  When I interview potential managers, this is what I’m looking for.  And it’s not just the ability – it’s the willingness.

Yet everywhere I look, I see managers trying to fix systems instead of fixing behaviors. Rather than having the difficult conversation with a subordinate about changing what they do, managers tinker with CRMs, redesign compensation plans, and add more procedures to already bloated process manuals (I once saw a sales management process manual that was 490 pages, covering “every” possible eventuality). It’s easier to blame the system than to address the behavior. It’s more comfortable to implement a new tool than to have a tough coaching conversation.

And it doesn’t work.

Does Your CRM Need Fixing?

Here’s a conversation I’ve had more times than I can count:

Manager: “Our CRM isn’t working. We need a better system.”

Me: “What do you mean it’s not working?”

Manager: “Nobody’s using it properly. We’re not getting the data we need.”

Me: “Were they using the old CRM properly?”

Manager: “Well, no, but this new one will be more intuitive.”

Let me save you the six-figure investment and months of implementation headaches: If your salespeople aren’t using the current CRM, they won’t use the new one either. The problem isn’t the tool. The problem is that nobody has required, coached, or held your team accountable for using it. You have a behavior problem masquerading as a technology problem.

Fixing the CRM without fixing the behavior is like buying a treadmill for someone who won’t exercise. You’ll have a really expensive piece of equipment that nobody uses, just like you did before.  When I was a sales manager, my philosophy was, “If it’s not in CRM, it didn’t happen.”  And I’d enforce that.  Sometimes, a salesperson would come to me about a customer situation.  I’d look it up in CRM, and I’d find that the interaction he was referring to wasn’t in there.  I’d send him back to put it in before I’d help with it.  Was it a pain for him and a delay?  Yep.  But I didn’t have to do that too many times before everything made it into CRM.

Your Compensation Plan Won’t Fix Behaviors.

Another classic example: constantly reworking compensation plans to incentivize behaviors that management isn’t coaching or teaching.

“If we just adjust the commission structure, they’ll start prospecting more.”

“If we add a bonus for account growth, they’ll focus on upselling.”

“If we change the quota calculation, they’ll work harder.”

No, they won’t.

Compensation plans don’t teach people how to prospect effectively. They don’t show people how to identify upsell opportunities. They don’t give people the skills or discipline to do the work. What happens instead? You create a more complicated compensation plan that’s harder to track, more confusing to explain, and generates more disputes about payouts. Meanwhile, the behaviors you wanted to change remain exactly the same.

You cannot compensate your way out of a coaching deficit.

Over-Proceduralization is a Disease.

Then there’s the tendency to over-proceduralize and overcomplicate systems and processes rather than giving subordinates the mission of their position and coaching them to fulfill it.

I see this constantly in sales organizations: massive process manuals, endless checklists, approval workflows that require sign-offs from three different people, and standardized templates for every possible customer interaction. The theory is that if you make the process detailed enough, foolproof enough, and controlled enough, people will automatically do the right things.

The reality is that you’ve created a bureaucracy that slows everyone down, frustrates your best performers, and still doesn’t fix the underlying behavior problems. Here’s what’s missing: clarity about the actual mission and ongoing coaching to help people achieve it.

Instead of a 47-page process manual, try this: “Your mission is to identify and close new business that’s profitable for the company and valuable for the customer. Here’s what good looks like. Now let’s work together on how you’re going to do that.” Then coach. Daily if necessary.

Why Managers Choose Systems Over Behavior

So why do smart managers keep making this mistake?

Because fixing systems feels productive. You can have meetings about it. You can create project plans. You can show visible progress. You can say you’re “doing something” about the problem.

Coaching behavior change is harder. It requires difficult conversations. It means telling people their current approach isn’t working. It involves ongoing attention and follow-up. You can’t just implement it and move on.

Systems work is comfortable. Behavioral coaching is uncomfortable. But only one of them actually works.

What Profitable Behavior Change Actually Looks Like

Real behavior change starts with clarity: What specific behavior needs to change, and what does the new behavior look like?

Not “we need better CRM compliance.” That’s a system metric.

Instead: “You need to document every customer interaction within 24 hours with notes that include next steps and timeline. Here’s why that matters and here’s how to do it efficiently.”

Then comes the coaching part: Following up, reviewing, providing feedback, holding people accountable, and reinforcing the behavior until it becomes habit.

This takes time. It takes attention. It takes consistency. But it works.

Once the behavior changes, the right tools can amplify the results. A good CRM makes proper documentation easier. A well-designed compensation plan rewards the behaviors you’ve already coached people to do. Efficient processes support the mission you’ve clearly defined. The tools come second. Behavior comes first.

The Bottom Line

Stop buying new systems hoping they’ll fix your people problems. Stop redesigning compensation plans expecting them to teach skills you haven’t coached. Stop adding procedures thinking they’ll replace the management conversations you’re avoiding.

The right behavior can overcome incorrect tools. Your best salespeople will figure out how to succeed even with a clunky CRM, a mediocre comp plan, or imperfect processes.

But the right tools cannot overcome incorrect behaviors. No CRM, no matter how sophisticated, will make lazy salespeople diligent. No compensation plan will teach people how to sell. No process manual will replace actual management.

Focus on coaching profitable behavior change. Have the difficult conversations. Invest the time in teaching, following up, and holding people accountable. Get the behaviors right first. Then optimize the tools to support those behaviors.

Everything else is just expensive procrastination.

Your LinkedIn profile isn’t a digital resume. It’s not a placeholder. And it’s definitely not something you can set up once and forget about – but if you’re like many of the people I talk to, that’s exactly what you’ve done.  When I’m speaking, I’ll often ask, “Raise your hand if you’re on LinkedIn.”  Most, if not all, of the hands go up. Then I’ll say, “Keep your hand up if you have actively used LinkedIn in the last two days.”  I get a lot of sheepish looks and the hands go down.

More than half of the people reading this haven’t touched their LinkedIn profile in more than a year – unless it was to add a new job.  Your profile is making a business case for you every single day – whether you know it or not.

Your Buyers are Looking You Up.

Here’s what’s happening right now: A prospect is considering whether to take a meeting with your company. Before they respond to that email or return that call, they’re looking up your leadership team on LinkedIn. They’re not just checking job titles. They’re evaluating whether you and your team are engaged in the modern business landscape. They’re assessing credibility, expertise, and whether you understand the challenges they face.

A bare-bones profile with outdated information, maybe no profile picture, and no activity doesn’t just reflect poorly on you. It raises questions about your entire organization. If your leadership team can’t be bothered to maintain professional profiles, what does that say about how engaged you are with customers, with innovation, with your market?

Research shows that most B2B buyers are more likely to purchase when an executive’s profile demonstrates impact and achievement. Your profile is influencing buying decisions before you ever get the chance to present.

The Generational Factor Makes This More Pronounced.

This matters even more when you consider generational dynamics. Younger decision-makers – Millennials and Gen Z buyers who now make up a significant portion of B2B purchasing – expect to find robust professional profiles. They’ve grown up researching everything online before making decisions. When they can’t find substantive information about your leadership team, or when they find profiles that haven’t been updated in years, they move on to competitors who demonstrate they’re current and engaged.

Profile vs. Presence: Both Matter

A great LinkedIn profile is table stakes. But it’s only the beginning. Your profile tells people who you are. Your content and engagement show them how you think. The most effective business leaders on LinkedIn do both:

• They maintain profiles that clearly articulate their expertise and impact
• They consistently create content that demonstrates thought leadership
• They engage authentically with their professional community

You can have the perfect profile, but if you never post, never comment, and never engage, you’re missing the opportunity to demonstrate your expertise in real-time.

Building a Profile That Works

Here’s what separates profiles that generate business opportunities from those that sit idle:

Tell a story, not a resume. Your About section shouldn’t list job responsibilities. It should articulate the problems you solve, the value you create, and why you do what you do. Write it in first person. Make it conversational. Show personality while maintaining professionalism.

Lead with impact, not titles. Instead of “VP of Sales,” try “Helping B2B companies navigate generational dynamics to build high-performing sales teams.” Your headline should make someone want to learn more, not just identify your organizational position.

Use your experience section strategically. Don’t just list what you did – explain the outcomes you achieved. Quantify results where possible. Show progression and growth. Demonstrate that you’ve solved problems similar to what your prospects face.

Keep it current. An outdated profile signals you’re not engaged. Update your experience when roles change. Refresh your About section periodically to reflect current focus areas. Add new skills and certifications as you acquire them.

A Professional photo matters. This seems obvious, but the number of executives with outdated, unprofessional, or missing photos is staggering. Your photo should be recent, professional quality, and appropriate for your industry.

Quality Content Matters.

Once your profile is solid, the real work begins: consistent content creation and authentic engagement. LinkedIn isn’t a static advertising platform – it’s a networking site that is content-based.  This doesn’t mean posting daily motivational quotes, sportsball pictures, or sharing generic business articles. It means:

Sharing your perspective on industry trends. What are you seeing in your market? What’s changing? What should your prospects be thinking about?

Demonstrating expertise through original insights. You’re smart and you know things.  Show it.  Write posts that show how you think about business challenges. Challenge conventional wisdom when appropriate. Offer frameworks and actionable advice.

Engaging authentically with your network. Comment meaningfully on others’ posts. Ask questions. Share experiences. Build relationships through genuine professional discourse, not superficial “great post!” responses (yawn).

Being consistent. Posting once every three months doesn’t build visibility. Regular engagement – even just 2-3 times per week – keeps you in your network’s awareness and signals to LinkedIn’s algorithm that you’re an active, valuable contributor.

Lead by Example

If you’re a CEO or senior leader, your LinkedIn presence sets the tone for your entire organization. When leadership engages authentically on LinkedIn, it empowers employees to do the same. This creates an advocacy engine that attracts clients, talent, and opportunities. – but it has to be authentic. Employees can spot manufactured corporate messaging instantly, and it backfires. Share real insights, real challenges, real wins. Be human while being professional.  “I’ll just let the marketing department handle that” is a road to failure.

The Bottom Line

Your LinkedIn profile and presence are working for you or against you right now. There’s no neutral position. Every prospect who researches you, every candidate who considers joining your team, every potential partner who evaluates working with you – they’re forming opinions based on what they find (or don’t find) on LinkedIn.

The question isn’t whether you need a strong LinkedIn presence. The question is whether yours is opening doors or quietly closing them. Take an honest look at your profile today. Would a prospect who found it be more or less likely to take a meeting? Would a top candidate be impressed or concerned?  For that matter – would you be more or less likely to buy from yourself, based on your profile?

If the answer doesn’t make you confident, it’s time to invest in building a presence that reflects the professional you actually are – not the outdated snapshot from five years ago. Your profile is making a business case every day. Make sure it’s the case you want to make.

Sometimes the universe delivers perfect teaching moments right to your doorstep. Today, within the span of one hour, I experienced two prospecting approaches that were so spectacularly awful, I had to write about them.

These weren’t just bad sales calls. They were masterclasses in how to ensure a prospect will never, ever buy from you. And the scary part? I bet the salespeople involved think they’re being persistent and professional. They’re not. They’re being desperate and tone-deaf. And there’s a huge difference.

Disaster #1: The Uninvited Calendar Terrorist

A few weeks ago, I had a LinkedIn message exchange with someone who sells some sort of program to help speakers raise their profile. There are thousands of these people out there, and most of them just separate speakers from their money, but I was polite. I told her I might be interested in a conversation at some point, but that this wasn’t that point.

Clear communication, right? Apparently not clear enough. The next thing I knew, I received a Zoom meeting invitation from someone who works for her. Not a request to schedule a call. Not a follow-up message asking when might be convenient. An actual calendar invitation for a specific time and date.

I never asked for this call. I never agreed to this call. Someone just decided to put a meeting on my calendar without permission. I responded and declined, explaining that I was too busy to even devote head space to this topic right now. His response? He’d send a different invitation for a month out. I told him more vehemently that I didn’t appreciate the tactic and had no interest because of it.

Today – weeks later – I received and declined yet another unsolicited Zoom calendar invitation from this same guy. Let me be crystal clear about what this approach accomplishes: It ensures I will never, under any circumstances, buy from this company. Ever.

Disaster #2: The Incomprehensible Cold Caller

While I was still shaking my head about the calendar terrorist, my phone rang. It was a cold call from some company promising to get me in front of thought leaders. I’ve heard this pitch a thousand times from a hundred different companies.

But here’s where it got interesting. The caller spoke with a very heavy accent and spoke very quickly. I couldn’t understand most of what she was saying. So I did what any reasonable person would do – I politely told her I couldn’t understand what she was saying and asked her to restate it more slowly. She repeated the exact same well-rehearsed pitch in exactly the same way.

I tried again. “I’m sorry, but I still can’t understand you. Could you please slow down?” Same pitch. Same speed. Same result. Finally, I told her the truth: “If I can’t understand what you’re saying, I’m not going to buy anything. It’s not my job to understand you – it’s your job to speak clearly.”

She hung up.

The Common Thread of Tone-Deafness

Both of these disasters share the same fundamental problem: complete disregard for the prospect’s communication preferences and boundaries. The calendar terrorist heard “not now” and interpreted it as “send me unsolicited meeting invitations until I give up and take the call.” The cold caller heard “I can’t understand you” and decided that repeating the same incomprehensible script was the solution. Neither one of them was actually listening. They were both just executing their processes, regardless of what the prospect was telling them.

This isn’t persistence. Persistence means continuing to provide value over time while respecting boundaries. This is just being pushy and annoying.

What These Approaches Actually Accomplish

Let’s be honest about what tactics like these really achieve:

They damage your reputation. Every unsolicited calendar invitation, every ignored request to slow down, every boundary you cross makes you look desperate and unprofessional.

They eliminate future opportunities. I might have been interested in that speaker program at some point. Not anymore. The approach killed any possibility of a future conversation.

They waste everyone’s time. How much time did that guy spend sending me multiple calendar invitations? How much more productive would it have been to respect my initial response and follow up appropriately later?

They reinforce negative stereotypes about salespeople. Every pushy, tone-deaf interaction makes it harder for professional salespeople to get the respect and attention they deserve.  Honestly, this one makes me madder than any of them.  Our profession doesn’t NEED any more negative stereotypes.

The Right Way to Handle These Situations

Here’s what should have happened in both cases:

Scenario 1: When I said “not now,” the appropriate response would have been, “I understand. When would be a better time to revisit this conversation?” Or even better: “No problem. I’ll check back with you in a few months to see if your situation has changed.”

Scenario 2: When I said I couldn’t understand, the appropriate response would have been to slow down, speak more clearly, or even suggest we continue the conversation via email where language barriers might be less of an issue.

In both cases, the salespeople should have adapted their approach based on what the prospect was telling them. That’s what professionals do.

The Bigger Picture Problem

These two disasters highlight a broader issue in sales today: too many people are following scripts and processes without thinking about the human being on the other end.  Good prospecting requires reading the room, adapting to feedback, and respecting boundaries. It requires treating prospects like human beings with preferences and priorities, not just names on a list to be processed through your system.

When someone tells you “not now,” that’s valuable information. When someone asks you to slow down, that’s helpful feedback. When someone sets a boundary, that’s important data about how they prefer to be approached. Ignoring all of that in favor of your predetermined process isn’t persistence – it’s professional malpractice.

The Bottom Line

Both of these salespeople probably think they’re being diligent and thorough. They’re probably tracking their “touches” in their CRM and reporting to their managers about their consistent follow-up. What they’re actually doing is burning bridges, damaging their company’s reputation, and ensuring that prospects will go out of their way to avoid doing business with them.

Professional selling means adapting your approach based on what your prospects tell you. It means respecting boundaries. It means listening more than you talk. If you can’t do those basic things, you’re not in sales. You’re in harassment. And there’s a big difference between the two.

Your prospects know the difference, even if you don’t.