I saw a Reddit post last week where someone asked “How much of sales is luck?”

I see sales being alot like poker in that you can't control the cards you're dealt, but if the game were really just luck, you wouldn't see the same names showing up at the World Series of Poker final year after year.

There was a popular book about 10 years ago called “The Power of Habit,” by Charles Duhigg, where one chapter looks at decision making at the poker table and how it relates to life decisions. The basic thesis was that the best poker players think probabilistically and how this perspective applies to many of life circumstances. In sales for example, bad luck happens just as often as blistering runs that light up the dashboard. In either circumstance, both the expert poker player and the best salesperson recognizes it each for the ebb and flow that it is and regardless, they don’t deviate from their overall system and principles.

Think about how easy it is to do the opposite. You close three deals in a row and suddenly you’re convinced you’ve cracked some code, so you start freelancing on your process, even cutting corners. On the opposite side, you lose two deals in a row and suddenly you’re questioning everything, second guessing a pitch that’s worked a hundred times before. Neither reaction is really about skill. It’s about mistaking a short stretch of variance for a greater signal. The best players, and the best reps, know the difference between noise and a real pattern, and they don’t let a hot or cold streak talk them into abandoning what actually works statistically over time.

A couple of specific principles from that chapter and how they apply to sales:

• Expert poker players see losses as experiments: Duhigg’s study concluded that the top poker players still lose often, but they use these losses to learn better how to read the room. They view the losses as experiments for data gathering and the loss is an investment in future success and how to adjust their perception of the table. This aligns with the advice I received from an outstanding sales manager when I asked him how to handle the demo situations where you can just tell in advance that they’re not going with us. He advised me to just use them for practice on how to position us against the competition and don’t hold back.

• Expert players are comfortable with the unknown: The best poker players weren’t looking for certainty at the table and they’re comfortable with the fact that they don’t know the outcome. However, they know that as the game goes on, as long as they stick to their principles and adjust them based on the incoming data (learned from the losses), the odds are going to turn in their favor. Intermediate players, by contrast are looking for certainty and thus tend to play conservative, get discouraged, abandon their system entirely or even just cash it in early.

I think about the first point every time a deal falls through. It’s tempting to treat a loss as just a loss, close it out in the CRM, and move on. But the reps who actually get better are the ones asking what that loss taught them and how to use that lesson going forward, not just the outcome itself.

The second point might be the more important one. New reps want certainty. They want to know a deal is going to close before it closes, and that need for certainty makes them chase the wrong signals or panic at the wrong moments. Experienced reps make peace with not knowing. They trust that if they keep running the same sound process on enough opportunities, the math eventually works out in their favor, the same way it does for a poker player who’s willing to sit through a losing stretch without changing how they play the hand.

I hear debate when it comes to discounting. Some people talk about it freely and early and some like to announce a hard line, ie. “we don’t discount, etc.” Like most sales principles, alot of it depends on some variables. Your market, your product moat, your client, conditions, the fit for the purpose; all of these and more are conditions where discounting or lack of can make sense. Most of us are in competitive industries where discounting is prevalent and yes, it works. However, you need to be careful when you do it as it’s a vehicle that is easily misused and can backfire, reducing the perceived value of your offering.

The easiest principle to remember: I’ll always negotiate with someone who has a pen in their hand.

Here’s how discounting goes wrong. You’re in a demo with a lower level individual just gathering information to take to a deicsion maker. They ask about price. You throw out your number and then a “softener,” ie. “but we can be flexible there, we could probably get it down to more like X.” You’ve now just given up your leverage just to stay in the game…and you’re probably wondering now why you haven’t heard from them (they now know what they need to know).

I’ve had over 1500 Zoom meetings for competitive SaaS offerings and here are a few rules that have proved successful through trial, test, error and success.

1. Never offer a discount without the decision maker being involved: Otherwise you’ll be discounting twice.

2. Never discount until you know you are the vendor of choice: first they need to decide yours is the product they want, until we get there, a discount is a moot point.

3. Always get something in return: Usually this is in exchange for a swift commitment. A discount with nothing coming the other way isn’t a negotiation, it’s just giving away margin.

4. Give it a deadline: Not: “let me think it over and circle back next month.” If that’s where they are, it’s not time for the discount discussion yet. This is off the menu pricing. It exists because they’re ready to move now, not because it’s a standing offer they can cash in whenever. Leave it open indefinitely and you haven’t given a discount, you’ve just created your new price.

Discounting isn’t a bad thing…but the client needs to walk into it. You’re not discounting to be liked. You’re discounting because they gave you something worth trading for. That’s the whole difference between a real negotiation and just being generous with somebody else’s margin.

People know Pat Tillman, rightfully, for his military service and sacrifice. Fewer people know how interesting his football background actually was before that.

Despite being named one of the top high school players in the state of California, Tillman’s measurable didn’t jump off the page. His height, weight, speed, agility times…none of it screamed future star. As a result, he went very much overlooked and only received three scholarship offers: Arizona State, BYU and San Jose State. He went on to Arizona State, and even though he was one of the best players in the country in his final season, he still was not selected until the seventh round of the NFL draft, for the same reason; his physical numbers on the page just did not appear to be the type of player to translate to the NFL. You had to physically see Pat play and witness it for yourself. The ferocity that he hit with, his omnipresence on the field, the way he lifted the team and achieved the desired result; the traits that don’t show up on paper.

When he got to the NFL, he was a solid producer, but he was still on just a one-year contract with the Arizona Cardinals and largely an unknown name around the league.

All that changed before the 2000 season, when a Sports Illustrated analyst named Dr. Z used a unique dataset to isolate the right variables and determine a player’s actual value, not just the traditional measurables teams had leaned on for decades. Z’s model concluded that Pat Tillman was not only good, but he was the best in the entire NFL at his position…and it wasn’t close. Dr. Z published his reaction as “What shocked me was the margin by which he was superior…he is clearly the best in the NFL at his position.” Only then did teams come calling, including the St. Louis Rams, who offered him more than double his pay from the Cardinals. For better or worse, Pat was loyal and remained with the Cards, but I’m assuming there were some contract renegotiations.

Tillman obviously left a legacy far more significant than being a standout NFL player. But his football career is still a great example of something I often think and have seen in sales and in quantitative measures of performance. The right data, used the right way, can reveal real value that the obvious, surface level numbers completely miss.

A few examples of revealing metrics that are rarely measured:

• Revenue per Inbound Lead: (the result here may surprise you…who’s really crushing with what they have to work with and who is driving your customer acquistion cost up)

• Dollars per Hour: Who on your outbound team is producing relative to their time on the clock. This is especially useful for hourly, outbound employees.

• Growth Rate Percentage (Territory or Book of Business): Who’s really building their territory, vs. who is turning and burning.

Top line alone doesn’t tell the entire story and you may find sometimes the top performers are hiding in plain sight. It just takes someone willing to look past the conventional scouting report.

This is where anchoring comes in, and it’s one of the most useful things I do in a demo and it happens long before pricing ever gets mentioned.

An anchor is simply a reference point you plant earlier in the conversation so that your actual price, when it finally comes up, feels small by comparison.

Say I’m walking someone through the part of the platform that builds out a model of their best fit potential clients, essentially telling them who to go after next. Instead of just showing the feature and moving on, I’ll make clear the fact that a consultant doing this manually would routinely charge over $50,000 and take a month or more to deliver something far less complete than what they’re looking at on the screen in real time. Now that number is sitting in the room.

Another example: If the data surfaces 600 target individuals, I would state the fact that “each of these tagets could make a purchase of over $10,000, and you’ll typically have at least a 10% conversion rate with these prospects.” (Which would be about $600,000)

When pricing comes up later and I say the investment is $16,000, it’s being compared to $650,000. Suddenly it sounds like the deal it actually is.

The key is that the anchor has to be true and it has to be relevant, not just a big, unrealistic number thrown out for effect. If a prospect can tell you’re inflating a comparison, you lose the credibility you spent the whole demo building.

I try to anchor against something specific to what I’m actually showing them in that moment, a real cost of doing it manually, a real cost of a consultant, a real cost of the staff hours it would take internally, and the lost new business of $600k. That way the anchor takes care of two things: it justifies the price and it reinforces the value of the featur.

The other thing I’ve noticed is that anchoring works best when it’s dropped naturally, in the middle of showing value, not as a hard sell. In the consultant example, I’m not saying “this is worth $50,000” I’m saying “this is the kind of thing people pay consultants over $50,000 for,” and letting the prospect do the math themselves.

By the time we actually talk numbers, the real price isn’t the shock. The absence of a $50,000 invoice is the nice surprise.

I’ve seen this at work with sales teams and the same concept proves true.

There’s a story about Miles Davis that gets at the same idea from a completely different direction. Davis was known for being bluntly honest with the musicians in his band, and he expected the same honesty back. His guitarist John McLaughlin once said of him, “He never told you what to play. He would throw you curveballs to make you think about it. He always wanted to get your honest response. He was the most blunt, honest person I ever met.”

Notice what Davis wasn’t doing. He wasn’t handing out sheet music and demanding it be played note for note. He was creating a space where honest, sometimes uncomfortable, creative response was not just allowed but expected.

Sales teams work the same way. You can manage a process. You can hand someone a call flow and a set of stage gates, pull out a rubric and rigidly hold them accountable. Anytime I see this approach, the result back is compliance. Reps start doing the minimum just to “check the box.” Compliance becomes so paramount that the actual goal of sales revenue becomes secondary to the process. What you don’t get is a rep who tells you honestly that a deal is dying, or that the pitch isn’t landing, or that they disagree with the approach, because they don’t feel safe saying so. The vicious cycle then goes on.

Salespeople don’t need to be managed into following steps. They need to be led into thinking for themselves, the same way Davis pushed his band, with honesty going both directions. That’s the real difference between a manager and a leader. One builds compliance. The other builds a team that will actually tell you the truth in order to make real, actual progress towards the goal.

If you receive an inbound lead, that buyer is likely 70% down the road with his/her decision. They’ve read the reviews, got their AI summary, talked to a peer, skimmed the websites, maybe watched a demo video at 1.5x speed. Your “discovery call” is often just a formality wrapped around a decision that’s already been made and often times this decision is not you.

So how do you get inside that remaining 30%, turn the tables and beat the odds? After giving about 1,500 Zoom product demonstrations and analyzing all the results, it’s three things, in this order:

1. Compelling differences. Not features. Not “we’re the leader in X.” Something genuinely different that a competitor can’t say with a straight face….but they’re difference that have…see #2….

2. Relevance to them, specifically. A compelling difference that doesn’t map to their actual problem is just noise. It has to land on something they already feel, not something you wish they felt. This is where your discovery will help for real.

3. Direct delivery to the Decision Maker. Differentiation that never reaches the DM might as well not exist. I’ve watched brilliant messaging die in a middle manager’s inbox more times than I can count. If you’re not meeting with the decision maker, (which most of the time we aren’t), we need to inspire our contact to come to the table internally and say “I may have found something interesting.”

Everything else, the rapport, the follow-up is table stakes; It does not win the deal.

If you want to actually move a number that’s already 70% set, stop polishing your pitch and start asking: is this different, does it matter to them, and is it reaching the person who can say yes?

Side Note: this applies to nearly all industries. A close friend of mine is a car dealer and I asked him recently, “How often does someone walk in the door randomly and walk out with a car?” His reponse was that “Probably 85% of buyers these days, by the time they walk in they already know what they’re doing and they’re pretty much there to ask some basic questions, look it over and pick it up.”

A study cited in Fox News says that most managers believe it takes about six months before a new rep is fully trained and really running on their own. That’s half a year…a little scary if you have an annual number to hit. Ramping a new rep quickly matters and the better the foundation the more likely the new rep is to succeed. It’s a foundation with a positive compounding effect over time. This effect also cuts the other way with the loss of a rep who doesn’t work out and who maybe the training didn’t “click” with. There is actually a way to minimize this risk and likely compress a rep’s ramp-up time. It takes 10 minutes and it should be done before training even begins.

A friend of mine who is a professor at Vanderbilt turned me onto a brief online test he suggested we all should take, which shows us our most effective ways of learning. After a small amount of questions, it generated a learning profile, which measures how you most effectively take in and process new information. (The test itself is here ).

It turns out that there are four unique ways people learn.

• Visual: learns best through symbolic/graphic information: charts, diagrams, flowcharts, color-coding, spatial layouts. Does not include video or photos. Let’s say you bought a new piece of furniture that requires assembly. These people focus on the diagrams that come with the assembly directions.

• Aural: learns best through listening and talking: discussion, being talked through something, explaining ideas out loud, phone calls, audio. These people will find a youtube video of how to put the new furniture together.

• Read/Write: learns best through the written word: lists, manuals, bullet points, documents, glossaries, reading, slide decks and writing things out. These are people who like to read the directions to put the furniture together.

• Kinesthetic: learns best through hands-on experience: trial and error, real examples, demonstrations, practice, doing the actual task rather than reading or hearing about it. Video is a split between aural and kinesthetic. Kinesthetic learners throw the directions aside and just get started. They’ll pull up a youtube video when they hit a snag.

I’m bimodal, Aural and Kinesthetic. I need to try things hands on, hit my own walls, give mock presentations and talk things through before it clicks. Meanwhile my read/write is very low: A binder full of information and a slide deck full of bullet points will nearly evaporate once put aside.

Most sales training and onboarding is built for one type of learner. A lot of it leans heavily on the written word: onboarding docs, playbooks, battlecards, scripts, written quizzes for certification, etc. That works great for someone with a strong Read/Write preference. It does very little for someone who might be a Visual and needs a diagram of the sales process, or someone who’s Aural and needs to sit in on real calls and talk it through afterward, or someone Kinesthetic who needs to just get in the product and break things before it makes sense.

None of these reps are weaker learners. They just take in information differently, and if you only train one way, you’re only reaching a fraction of your team effectively and efficiently.

Invest the 10 minutes to diagnose the learning style and give reps options. Some reps should watch demo recordings. Some should shadow calls and talk through what they heard. Some need to just run a demo themselves, badly, a few times, before it sinks in. Identify the mode rather than force one mode on everybody.

This isn’t just a sales training problem. Think about it for clients. A client may light up at a verbal explanation of a concept, but tune out when shown the concept on the screen…thats an Aural. That client who didn’t seem enthused over the demo, but is heavily engaged in your post-demo emails? Thats a read/write. The client that cuts to the chase and asks for a trial? A kinesthetic. We can now adjust our follow through accordingly.

Think also about the lost art of ongoing training. Battlecards have become the de facto for competitive intelligence. Those reps who barely look at them? Theyre likely wanting it synthesized into a competitive landscape discussion, or watch a Zoom call where a competitor was overtaken and practice it themselves.

There is a larger pattern at play here and it even pertains to our education system. Our entire education system runs on a Read/Write and lecture heavy model, and we wonder why so many capable kids get labeled as struggling students. Some of them just needed to build it, discuss it, talk through it or try it.

Try it with your team, introduce it to your enablement and you’re likely to see more engaged reps, more successful new hires, shorter ramp times and an exponential payoff.

I use both of these constantly on my demos, and if you can combine both effectively, you’ll be a step ahead.

Social norming is simply that people want to know what people like them are already doing. I don’t necessarily just say our platform is great, but I’ll say something like, “organizations that come to us from X competitor tell me they were missing opportunity that was sitting right in their own backyard.” Or, when I’m talking with a performing arts organization, I’ll mention that other well known cultural institutions in their region already use a tool we offer. None of that is a feature pitch. Once a prospect sees themselves reflected in a peer group they respect, a lot of the decision starts making itself, because now the question isn’t “should we do this” but “why haven’t we done this yet.”

Loss aversion; the other lever. It’s underused in sales typically because people are afraid of sounding pushy with mission driven organizations, but there’s a real difference between manufactured urgency and true urgency. If I mention for example, that our fiscal year ends in September, It’s a real deadline with real flexibility attached to it while it’s open. Losing that window is a real cost to the prospect, not an invented one. I would rather show someone clearly what they are leaving on the table by waiting than oversell what they stand to gain by acting.

Bonus points when you can combine the two in a single phrase. For example: “Most organizations do sign on September, that way they lock in the current rate and not miss out on the client opportunities they can capitalize on at by end of the year.”

Every demo I run, I’m quietly asking myself two questions in the background. Where is the mirror, meaning who else like you is already doing this. And where is the window closing, meaning what does waiting actually cost them. Get those two things right, communicated honestly, and you’ll likely have a prospect with momentum.

Although you may not know Ron Popeil’s name, you know his work and have probably seen him if you have ever stayed awake past midnight flipping channels. He’s regarded as the infomercial pitch king, the creator and promoter of such products as the Ronco Showtime Rotisserie, the Ronco Pasta Maker and GLH hair replacement. Remember the spray-on stuff that “looks just like real hair!?” That was Ron Popeil.

Ron embodies the American dream. He created products in his kitchen, went out and pitched them on his own. Ron was heavily influenced by another pitchman named Arnold “The Knife” Morris, a mesmerizing pitchman, who could draw large crowds but more importantly, keep them. Arnold said that one of the keys to retaining the audience was anticipation. To do this, he used a pineapple. Throughout the entire pitch, a big beautiful pineapple was perched on the cutting board while Arnold sliced, diced and impressed. Every now and then Arnold would say “and just wait until you see what it can do to this pineapple.” After some exciting demonstrations, he would offer a promo price and people would literally swarm Arnold holding out their cash, afraid the item would sell out.

To this day, Arnold has never cut the pineapple. “Why would you cut it?” he says. “As soon as you cut it they’ll leave.”

One of our biggest challenges as a sales rep is getting the client to spend enough time engaged with us to build trust enough to make a sale. This can be done in just a couple minutes, but sometimes a couple minutes is tough to come by. Every now and then, be aware of when you have a pineapple, a special recommendation, a feature that can’t be announced yet, but you know they’ll love. Use it strategically to keep them engaged.

For example:

“Based on what you’re saying, I’ve got an add-on I think would be perfect for your team, but let’s get your core setup locked in first and then I’ll tell you about it.”

“We just rolled out a new integration you might like, but let’s go through the rest of the platform first and maybe you can add it on.”

“If you’re interested in the analytics module, there’s another feature I think you should see, but let’s get the rest of your package finalized and then I’ll tell you about that one.”

Getting the buyer’s attention is one of the first and most important steps, but keeping it is just as important. Ask Ron Popeil.

We need to use this same concept in selling, the concept of scarcity. The less of something there is, the more valuable it is perceived to be.

Trader Joe’s grocery stores use this to great effect. TJ’s has the highest rate in the industry of multiple “same product” purchases. The store is ruthless about discontinuing products, creating a “get it while it’s here” effect. Anytime people see that block of Gouda that they love, they’re buying three or four of them because it may not be there again.

This is a simple and powerful concept to apply to selling anything.

Scarcity equals value. It is why the Hope diamond is expensive, why it’s cool if Brad Pitt walks into your restaurant and even cooler if he sits at the table immediately next to you. Your product may not be one of a kind, but you can create a situation where the opportunity is.

• Do not hesitate: Don’t stop to make any last minute calculations or check for accuracy, don’t say “hang on….ok…it looks like the whole thing will be just $6,500.” If you hesitate at all when it’s time to quote price, even for a few seconds, the client thinks they’re getting worked and the once-hot buying cognitions go cold.

• Preface it with the positives: Make it brief so it doesn’t appear you’re trying to mask the price, but remind the client of a few key benefits they will be receiving right before getting to the number.

• Price should be an “all-in” number: Any fees, implementation costs, etc should be included. This is simpler, increases the chances of a finalized transaction and reduces buyer remorse.

• Use it to close: Quoting price at the end of the presentation is a great time to gain the client’s commitment to the order.

Example: Let’s say you’re about to sell an annual SaaS subscription to a business owner. The price quote may sound like this:

“So the full platform, includes all core modules, you get unlimited seats, priority support, onboarding, and the integrations add-on: your grand total all in is $6,500, annually...and we can even break this into quarterly payments of $1,625 if you like.”

How you do the price quote should signify confidence in the product, which will transfer to the buyer. If it doesn’t, you probably need to go back and sell yourself on the offer first.

Two rules I used to follow about breaking bad news to a client:

• It should always be a phone call.

• It should happen right away.

Most of the chargebacks were people who were disappointed with their seating and, deep down, were upset they were not given a personal call with an explanation. When we transitioned the process to phone calls, the retention rate of these scenarios increased.

This is applicable to any business and any setting. You’ll keep the client and you will actually strengthen your relationship.

This is also true in your sales pitch. As soon as you go down “cold cognition” paths (too much data, unnecessary details) you’ll lose them and they’re checking their watch while you’re looking at your powerpoint.

In 2002 a movie came out called “Comedian,” which was a documentary about comedians on the road, including Jerry Seinfeld. During an interview with Seinfeld, he was asked how the process is different for him, given his status as perhaps the most famous comedian in the world. He said that he felt like his stardom and celebrity mega-status buys him about three minutes of stage credibility when the show begins. Meaning the fact that he is America’s most powerful and recognizable comedian earns him the audience’s undivided attention and agreeable mindset for just the first three minutes of the performance, and after that, he needs to be just as funny and entertaining as any other comedian.

The same is true in sales. Say you live in Pittsburgh and you are selling suites for Heinz Field. When you call a business and identify that you’re with Heinz Field, a reputable and well known city landmark, that probably buys you about 15 seconds with the client. 15 seconds of credibility and after that you need to keep it interesting and keep the momentum in order to maintain the client’s attention.

Too many salespeople think that who they work for can buy them 30 minutes, an hour, or even the entire sale. All you are is in the door. If you want to stay, keep it interesting and keep it moving.

Sigmund Freud claimed that the adult personality was fully developed by the age of five. Selling is no different and from my experience as both a middle school teacher and as a sales manager of 13 reps, adults are not much different from children. Too many choices leads to either paralysis or disaster. Realizing this, I changed the procedure. Remember what philosopher Soren Kierkegaard said: “Anxiety comes from the possibility of possibility.”

Just like any good sales person, I realized that I am the expert when it comes to picking out the outfit. I know the weather outlook for the day, the activities being done at school, the seasons and any other variables that go into the best decision. I pick out the best two options, hold them up in front of her and ask her confidently “Presley, which one?” She then points at one, the process is over and she’s better off for it.

The same goes for selling. There is far too much emphasis with sales people these days on “customization” and “we can do it however you want it.” This is lazy. Overwhelm a client with choices and they’re in no-man’s land. As the expert, lead them to the optimum one or two options. The sale will move faster and they’ll be better off for it.

It’s always a red flag to me when a rep puts a client on hold and asks “how long are we doing this promotion for?” That tells me they’re allowing the buyer to hold all the power, rather than leveraging the urgency that the entire promo is built around. My advice is to simply tell the buyer the truth, as in “It’s a short term sale only; we simply sell them until we run out. I could come in tomorrow and it’s out of the system. Plus the early buyers are the ones that will get the best seats.”

Some sales reps get caught up in feeling the need to be completely honest and transparent in every discussion with every client. You should be honest, because this helps your conviction come through, but you don’t need to be transparent. The inner workings of the deal is your business, that’s your magic formula and you should use it to bolster the value of the offer so the client realizes how valuable it really is.

This is honesty at work:

“If it were my money, I would take the seats on the main floor. Even though it’s less money than the balcony, I’ve sat there before and it’s just a better vantage point for this type of act. If you want to grab those now, I’ve got a promo today I can apply.”

This is unnecessary transparency:

“There are a lot of seats available for this concert. I can get you a promotional price that we’ll probably be running for a couple of weeks if you decide you want to go.” The buyer won’t even like this because it signals that the product they have interest in is in low demand, causing them to question their preferences.

No one wants to see how their steak is made, they just want it to taste great, look nice when it comes out, be served promptly and with a smile. That makes me feel like it was worth the money and that’s a restaurant I’ll go back to every time.

1. They have an unshakeable belief in the product: The reps that succeeded really believed in the product and don’t second-guess what they’re selling. For example, let’s say that we are selling a promotion that offers a 20% discount if a client purchases a full series of concerts. The rep who is on his way to failure is the one who gets on the website, reads all the fine print and questions “can we really say it’s a 20% discount? I mean, if you truly calculate the savings, it’s more like 15% because they sort of get a 5% discount if they buy online.” Lack of conviction will equal lack of sales; it’s as consistent as gravity. For this type of reason, it raised a flag to me when a candidate revealed in the interview that they were detail oriented. Top sales reps are wired differently, they think generally; they are “big picture” people. People who are detail oriented have a hard time keeping their pitch simple and buyers will tune out their complex approaches, in addition, they will often not see the direct psychological path to the sale. They’re often “paper shufflers,” appearing to be “getting organized” instead of selling. If you like splitting hairs, go to law school, but sales is not for you.

2. They have a concrete financial need to produce: The best reps feel their own pressure. They create their own urgency. Whether it’s kids, a family, a mortgage or a payment on a Mercedes, the best reps need to make money and will thus be personally invested in their improvement and success. The reps who don’t need the money are the ones who like to call in sick or mail it in once they hit their minimum quota.

A secondary trait that can be helpful, but yet is non-essential: organization. Organization is a wild card. My top two reps were highly unorganized; their desks were basically trashed, while at the same time, I also had reps who had organizational systems that enabled them to do very well. My conclusion on organization was that it can be used as an equalizer. A B-player can progress to an A-player by having an outstanding system for callbacks, segmented buyer interest, taste in performance, etc.

For example, I once had a team responsible for fundraising and series subscriptions for a major performing arts organization. We would call patrons and introduce them to the benefits of being a subscriber and if all goes well, we get them seated in a package of performances. Seat locations are a common discussion point. The reps that fail are often the ones who present the entire hall to the patron and then leave it up to them. These are the deals that go into the black hole of callbacks because the buyer is unsure of what to do and the risk now outweighs the benefit of committing.

Like philosopher Soren Kierkegaard said, “Anxiety comes from the possibility of possibility.”

The reps that succeed however, are the ones who believe in their expertise enough to lead that buyer with confidence, to the location that is optimum for him. Be an expert and lead.

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Why the Human Voice is Now More Valuable than ever…..

Twelve years ago I wrote a version of this post arguing that “Permission Marketing,” the idea popularized by Seth Godin, that you should never interrupt a prospect and instead wait for them to opt-in, was overrated. Back then the pitch was simple: build a list, send emails, and the money will roll in. Alot of companies believed the pitch and many missed quota that year. Fast forward to 2026, and we’re having the same argument with a new concept; AI. AI SDRs, AI-written sequences, automated outbound at a scale no human team can match. The promise sounds familiar. Let the algorithm find your buyers and write to them, and the deals will find their way to you.

Here’s the irony that would’ve surprised me twelve years ago: the flood of AI-generated outreach is making the human voice more valuable, not less. When every inbox is full of auto-personalized messages that all read the same, a real person on the phone stands out more than it did a decade ago.

None of this means nothing’s changed. High-volume, script-based calling is dying, and it should be. AI is genuinely useful for research and timing; what it can’t replace is the moment a real person has a frank conversation with another real person about whether your product solves their problem.

Marketing still matters; targeted lists and compelling messages still matter. What hasn’t changed is the trap: building a brand and running campaigns, then never picking up the phone to close the loop. That’s still like leaving a football game at the end of the third quarter.

Selling in the age of AI doesn’t mean handing the job to a bot. It means using the tools that save time while doubling down on the part AI still can’t do: the actual conversation, the actual trust, the actual close. Nothing happens at any company until somebody sells something. That was true twelve years ago; AI hasn’t changed it.