One Terrifying Lesson in Sales

Halloween was just upon us. Costumes, candy, screaming children, and spooky stories. And if you’re lucky, a glass of wine to soothe the nerves after a long evening of trick-or-treating. You might ask yourself, “How does this relate to sales?”

And you’d be right. It’s not easy.

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But let me try: there’s nothing more scary in sales than getting blindsided by reality.

Think back to a deal you thought was a layup.The prospect sounds excited during the Zoom demo. Their high energy is palpable. You can feel them leaning in. They seem eager to learn more. They ask you a bunch of buying questions. Pricing is even brought up. You allow yourself to think, “Wow, this is headed in the right direction. I can feel them pulling at me.” You can smell the sweet aroma of the commission check headed your way. As they run to their next call, they implore you to follow-up via email to schedule the onboarding session.

As a dutiful salesperson, you comply within fifteen minutes of hanging up. Superhuman indicates they’ve opened your email the next day. But no response. Five days go by. You reach out once again, trying to provide incremental value.

Dead silence.

You’ve gone from salivating at the celebratory steak dinner you’d enjoy to the crushing shame of missed expectations.

So what caused you to go from thinking you had a deal done, to their pulling a Casper on you?

In most cases: faulty tracking of the prospect.

Tracking the prospect is one the hardest things to do in sales. You’re supposed to take the current temperature of the deal all the while juggling the pitch, leading the sales interaction, driving to a close, and a number of other things.

“Is the prospect ready to buy?”

“Am I selling beyond the close?”

“Have I given them an opportunity to surface any objections?”

“Do they trust me enough to buy?”

Those are just some questions rattling in your head as you’re interacting with your prospect. You’re like an NFL quarterback; sensory inputs are coming at you from all angles. And you have to remain calm, self-aware, and execute methodically, despite the chaos around you and inside your noggin.

Fast forward a few months. You and I happen to work together, as you’re having issues closing the opportunities in your pipeline. As we start our engagement, you pull out a recording of this demo, and we launch into game film review. As we peer into recorded footage together, we observe a few things. At the tail end of the call, the prospect rushes as he leaves, and his energy actually feels a bit unsettled and almost dismissive. We notice something else: the prospect’s initial excitement about your product cools off after you introduce pricing. What we had originally thought of as a very positive call now seems difficult to negotiate.

Regrettably, we weren’t able to catch it live, as we were bumping up against our allotted thirty minutes for the call. Poor time management caught up to us. As we rushed to wrap up, we were in the midst of the action, and couldn’t fully perceive what was happening in front of us. Our inability to accurately track our prospect ends up killing our deal. Had we been more turned in, we would have spotted these issues and either addressed them head on during the demo, or scheduled more time to tackle them.

Tracking the prospect is a little bit like a Chef tasting a dish in the mayhem of a busy restaurant kitchen. You’re orchestrating the graceful chaos of making delicious food for a savvy urban clientele, and you need to keep your eye on the ball. The dish needs to be exquisite right as it hits the plate. This means you need to be fully present to taste the dish at all of its stages. If anything feels off, you need to adjust and right the ship. A pinch more salt. Too al dente. More sauteing needed.

If you’re not able to taste the dish accurately, you can’t be expected to make the right adjustments and deliver the succulent entrée to Table 6. Your gustatory discernment needs to be on point all evening long. Same goes with sales. If you don’t see your prospect’s intent and mindset accurately, you won’t be able to deal with their reality as it is. And without inhabiting their world, you’re likely to lose the deal. The Chef’s equivalent of putting together an unsavory pièce de resistance.

But if you’re on the money with your awareness of your prospect, you spot the gaps that need to be filled to bring the deal home. Sometimes, all that’s needed is a little Cayenne pepper to deliver the flawless dish. It’s on you to figure what’s missing or needed in your sales interaction, and then provide it. If you do, you’ll land a lot of deals that previously had you befuddled. Quite possibly, the difference between having a crappy quarter and seeing your name at the top of the leaderboard.

1 Myth, 1 Home Run & 1 Lesson

Myth: When writing outbound copy, being formal or professional is helpful.

We’ve all seen them: stiff emails dressed up with ‘formal’ or ‘professional’ words. We reach for the Delete button before we’ve finished reading the entire subject line. 

Here are some examples:

“Introducing [BrandName]”

“[BrandName] will solve [YourProblem]”

“[BrandName] is part of Gartner’s Magic Quadrant”

There’s two reasons these emails don’t work: they feel like sales pitches, and they look like every other sales email clogging up your inbox.

Professionalism is important in business, but ironically the best, most successful sales emails are personal and informal. They’re crafted to feel catchy and elicit your curiosity. 

Here are example subject lines:

“how are you solving [YourProblem], [FirstName]”

“you alive, [FirstName]?”

“feeling like Tom Cruise yet, [FirstName]?”

These spell out your first name, which naturally captures your attention (and is more than can be said for 90% of cold emails).

The same rules apply for the email body. Write as if you’re dashing off a note to a close friend. Let your personality out. Include humor. Don’t hesitate to write sentences all in lowercase. This is an opportunity for you to loosen up that necktie and put on your loafers. 

Here’s one I wrote wearing my weekend shoes:

Hey [FirstName] — how’s normal life Post-COVID? For me…it’s been exhausting interacting with friends more…I’m sure that’ll pass soon. I used to think I was an extrovert haha…

Speaking of exhaustion…how’s your accounting team performing? This time of year work is a little hectic and productivity is under a microscope. People like you keep telling us they’re not getting enough from their existing headcount. 

We’ve built software that organizes your accountants’ work and allows them to be a lot more efficient…36% on average. Disney, Coca-Cola, and BCG are among the teams that already use us. 

How about a quick call early next week to see if there’s a fit? All it’d take is 10-15mins. How does Tuesday afternoon look to you…?

Let me know…would love to connect!

Take care,


Now…how did that feel? Quite a bit more personal right? It could even pass for an email that’s not automated. And yet that’s the key to success in automation. You want to industrialize your process, all while your touch points feel personalized. Be as colloquial and as casual as possible.

At the end of the day, prospects want to buy from a human being, not a faceless corporation. To see your reply rate increase, write like you would to a friend, and let your humanity shine through.

Home run: Last year, while many companies were spinning their wheels figuring out how to survive, my client 3x’ed their MRR in 12 weeks.

A trends startup approached me late Q1 last year with a major problem. They were getting a ton of inbound interest — including from household names — but very little was converting to actual sales. The founder pair had garnered a ton of attention through PR, content and thought leadership, but next to nothing was hitting their bottom line. Recognizable brands said they wanted their product, but traction was minimal. The few deals they were able to land were far too small. The founding team wondered if they were ever going to hit product market fit, as they had been floundering on the sales front for over a year. Their runway was limited. So, they needed to get to ramen profitability before time ran out. One co-founder told me, “We need to make more money…for the survival of the company.” To make matters thornier, the pandemic slammed into us as we started our engagement. Would our customers suffer from budgetary contractions? Would fear play a role in their buying process?

As I stared into their sales funnel, I spotted major leaks. Folks were initially interested in the platform but weren’t jumping on a call with us. They came to the site and signed up for access to the platform, but somehow didn’t want to talk to us. We had little shot at making the sale as things stood. Once prospects did join us on the initial call, most of them didn’t stay in our sales funnel. Free trials were not converting to paying customers. We needed to patch things up. And quickly. 

What could we use as a lure for that first call? I wanted something that would compel them to attend. Without much delay, we came up with a consultation session. That first call was not only an introduction to the platform, but also a consultation where the salesperson delivered trends and insights. The prospect left that first meeting not only intrigued but wowed by the understandings they had gotten. They could walk into their next team meeting and flex their newfound industry knowledge, “Did you know that we’re seeing increased demand in [product category]? A 37% increase in North America over the next 2 months, as a matter of fact.”

Before ending our first sales meeting, we promised them even more on our next call: we’d help them answer some of their company’s major strategic questions. This second call was about unveiling the platform tailored to their needs. It was also about us getting them started on their credit card activated free trial. And setting them up for success for that initial stretch and beyond. 

Once changes were in place, our two punctures were plugged and our sales process started humming. All of a sudden, our steady flow of inbound leads now turning into greenbacks, and we were off to the races. 

The biggest lesson here is this: we transformed the customer experience. Offering demos to folks that had been curious about our data product wasn’t enough to get leads to convert. No prospect wants to sit through yet another product demo. Delivering personalized, actionable insights on a silver platter was the key to having them make their way down our sales funnel. And ultimately to a closed deal.

Lesson: The selling part is easy. It’s the “not selling” part that’s hard.

This gem was uttered by my coach several months back, in the context of selling my sales coaching services. It stuck with me ever since. Here’s what he meant. We all know the major selling points of our product or service. At a basic level, we know how to articulate those value props, and even handle major objections. And once we have some sort of sales process in place, we know how to lead the prospect through it, and get the deal across the goal line.

What’s much harder is to recognize what’s happening in our prospect and pull back at the appropriate times. Sales is about recognizing when to pour it on, when to sprinkle in a pinch of selling and when to not sell at all. Just like a good sauce, it must taste just right. A top-level Chef will intuitively know when to make the necessary adjustments to her dish. She’ll keep tasting things, tunes into her senses, and steps in with a pinch of salt at exactly the right time amidst the madness of her kitchen. Sales works the same way. Despite the many things going on around you, the feelings you’re managing on both ends, you need to be acutely tuned into your prospect. You might ask yourself the following questions, “Are they already sold?” “Are they ready to move on to the next step?” If you’re getting resounding “Yes’s”, then it’s time to move things along.

The last thing you want to do is keep selling when the prospect is either already sold, or is selling themselves. If the deal is already closed, you want to discuss next steps; which typically include things like payment, contract, and onboarding. If the prospect is selling themselves, you want to get out of the way. Few forces are as strong in sales (or otherwise) as someone convincing themselves of something. In those cases, you want to let them do the work for you. Adding in anything at that stage is only intruding on their cognitive journey. You risk derailing them. That’s when you want to let them talk and work their way through to a closed deal.

That doesn’t mean prospects won’t get to a point where they need a little nudge from you. They might even run into Everest-sized objections that you’ll get them over. But, the key here is to recognize when you need to intervene and when you can let the prospect close themselves. The ability to recognize when not to sell and actually shut up is an advanced form of sales.

Which leads us to the counterexample: a terrible sales experience. Most of us have felt the pain of a salesperson not being in-tune with their environment. They fail to understand what’s happening in front of them. They keep pushing something that doesn’t need to be pushed. You might already be convinced that you need their product, but they haven’t switched off their sales pitch. They lean in and insist, “You should really consider our solution for the issues you’re facing.” And you think to yourself, “I’ve been giving you buying signals that I want this thing for the past thirty minutes. Let’s move on already!” Depending on the prospect’s patience, the salesman’s tone deafness could end up costing him the sale. Had he known that his sales sauce tasted delicious, he might have left the dish alone, and been on the way to closing a deal.

So next time you’re selling, keep your antenna up. Track your prospect. Taste the sauce. What are they telling you? Are they sold already? Can you move on? If so, it’s time to use restraint. Adding in more selling would only ruin the dish. And the deal.  

Selling Through Crisis

It’s been a series of tidal waves. First came the news of a virus coming out of Asia’s wet markets. Then came the cruise ships that were floating petri dishes. Then the growing number of cases in countries like Italy and China. Then our sheltering in place orders across most US cities. And now the growing number of domestic and global cases.

There’s no question it’s a terrifying time for all of us. A natural instinct may be to crawl up in a big ball and hibernate. Or even worse: panic. When this quarantine first hit us, my therapist told me, “The Chinese character for crisis is composed of danger plus opportunity.” We are undoubtedly faced with a dangerous situation. But our only choice lies in how we respond. Despite the chaos around us, we always have the option to pull ourselves up by the bootstraps and establish a plan of action. We need to make the conscious choice of seeing opportunities where they lie, and pursuing them relentlessly. Here’s how I would think about sales in this Coronavirus reality.

It’s Prime Time for Building Pipeline

TV executives have known the concept of captive audience for the longest time. They have programmed their best bits for the boob tube on nights where folks are at home. Just look at television schedules today. The most successful shows are more than likely on nights where folks are at home: Monday, Thursday, and Sunday nights, for example. It’s no secret the NFL — who routinely has the majority of the top television shows by ratings any given year — has ended up on those nights. Radio executives have lived by this as well, putting their best programming during “drive time”, when folks commute to and from work in their cars. Commuters are captive in their cars, and in desperate need for entertainment. Radio is their best and perhaps only option. 

More than any other time in recent history, you have a captive audience of folks confined at home, with unprecedented access to technology platforms we can broadcast to. Our shelter in place orders have forced us in quarantines and have severely limited our in-person social interactions, so we’re seeking connection online. As social animals, we are confined in tight spaces and are craving social interaction and mental stimuli more than ever. And it’s happening all over the world. That’s a clear and gigantic opportunity for you to come in and create conversations.

Barring having small children that need constant attention, most adults will want to chat and will be open to doing so. Their distractions and outside activities have been dwindled to next to nothing. If you nail tone in your outreach (more on that later), you’ll be able to build up a glut of pipeline in Q2, which you’ll be harvesting in Q3 and Q4. 

Now, going through procurement or even closing complex sales is going to be tougher as folks are more disconnected than ever. Yes, we’re getting better at working remotely, but most organizations haven’t worked out the wrinkles of that yet. It’s also tougher right now to create urgency down your sales funnel and drive deals to a close. If I was a founder or a head of sales, I would put a lot of my energy into starting a lot of conversations and building pipeline. I would actually double down on it. I might even move some of my AEs to prospecting. This abundance of opportunities is something you’ll collect on in the latter portion of the year when things start getting back to normal. Companies that adopt this strategy will end up saving their year. 

If you thought this was only theoretical, I’ll submit that we’re seeing early signs that top of the funnel activities are generating more results right now. Within my consultancy, we have seen a decrease in Cost-per-Lead on Facebook, and also an increase in open and reply rates on outbound email in the past few weeks. 

Communication: Nail Your Tone

If you’re going to focus your efforts on generating opportunities, your only risk is not nailing tone in your communications. People are especially touchy these days, and reaching out with messaging that could be considered insensitive can turn people off very quickly. So you’re going to want to be extra careful. Lead with empathy. 

Your stance is going to be that of a waiter at a restaurant with a general message of “How can I help?” rather than “This is why you should use our product!” You’ll score points being extra friendly and informal during this time. Remember, people are most likely starving for human communication and intellectual stimulation. Think hard about that as you’re putting together your messaging. Salesy emails are not likely to land well during this time. Don’t push the sale, but tell prospects it might be worth having a quick conversation to see if there’s a fit. Think about including a personalized video message to your prospects. Seeing other human faces matters to all of us; particularly right now. Think about honoring each person’s humanity. Build relationships. In our startup community, founders are well known for asking each other out to coffee to share best practices and exchange feedback on their respective products. That’s the type of feel your messaging must have. If you go about formulating your outbound emails this way, you are going to start booking a lot of introductory calls for yourself, during this time of crisis. 

And remember, when you do chat with folks, make it about them, and their pain points. Nobody wants to have a product shoved down their throats. Nobody wants you to tell them about your product’s benefits, unless it applies to them. Especially now. You’re going to want to lead with pain points more than ever. As a close friend of mine told me a few nights ago over FaceTime, “This is a good time to get back to fundamentals.” This climate will be less forgiving to faux pas’, or clumsy communication. If you’re buttoned up, you’ll do just fine. 

Closing Deals: Focus on ROI

Now what if you did want to close deals during this time? What things do you need to consider to actually get deals moving down the funnel, and across the goal line? 

Three letters: R-O-I. 

With the contraction happening in the economy, your prospects are getting very cost-conscious. There’s no room for fluff. Selling with charisma or personality will not suffice. The rubber has met the road. And we need to make sure that products generate a positive ROI. And it’s important to articulate that in very simple, digestible terms. 

Let’s take a quick detour to illustrate my point….Hiring freezes and layoffs have already commenced. And more are coming. If you sell a tool that is supposed to enhance or empower a group of people within a business, this is your time to act. Folks will be looking to increase the productivity of their existing teams, without the need to add headcount. If you can prove to them that you can add a team member’s productivity, then you need to make that case right away. That will ensure that you close deals, even in this climate. Several years ago at Whitetruffle, where I ran sales, we used to sell an Agent package, which leveraged our talent sourcing platform and layered on a human component. We would have a person internally that would have a quick conversation with sourced candidates, in order to prequalify them, before we sent them to our employer clients. Our pitch to employers was that we could delay their hiring of a sourcer. Instead of paying a $80K – $90K salary per year in a city like San Francisco, or New York, you could hire us on a month-to-month basis for $3K/month. The ROI case was easy to make: it was $36K on demand versus $80K for a full-time hire, not counting benefits. And you could delay any real hiring. If you can make a similar case in this climate, you will have a good chance of closing.

If you’re formulating your sales strategy (like a few of my clients are currently doing), it’s time to think hard about the newer constraints that have been thrown into the mix. Folks are going to be more skittish about spending a large amount of cash in the immediate future, unless you are able to convince them there is positive ROI. You might have to extend trials or offer flexible payment terms to prove even more value upfront. If you can find a way to land and expand right now, I’d highly recommend it. The idea is this: if you can get people on the sauce at a lower price tag — without going through procurement — you’ve got a shot to land and expand later on. Think about pricing per seat and allowing people to pay for your product with their own credit card, before recruiting more members to join once you have delivered a ton of value. Lower the bar for entry, and let your product do the selling. That type of strategy is more than likely going to succeed in these difficult times. 

Spring Cleaning: What can we do better? 

You hear of people doing “spring cleaning” activities during this hiatus. It’s your chance to do the same thing within your sales organization. Look at your tool stack. Do you really need that Nth tool? Is it delivering value? Is there a different tool you’ve been meaning to try, that could provide a productivity boost or eliminate operational inefficiencies? Now might be the time to get on a demo with the vendor and/or sign up for a trial. 

Examine your sales funnel. What conversion rate can you take a stab at improving? What things can you install to make it better? Review your staff. Who needs extra training right now? Who can I help level up? What can I do to make them better salespeople? These are questions you should be asking yourself at this time. 

We’re usually so busy running around and chasing deals, that we don’t take enough time to take stock and regroup. This is just the time to engage in that type of thinking and strategizing. Tidy things up within sales. This little bit of slow down allows you to take stock in your sales model and work out some of the wrinkles you might have been ignoring for quite a while. Take the space to see what’s working and what’s not, and start putting in place initiatives that can fix your issues. 

Overall, it’s most important to be flexible with your approach. Many rules have been thrown out the window in a matter of weeks, and adaptability will be a major factor for companies that emerge from this period. Resistance to change, or clinging to old strategies will be an impediment to survival.

If you need help during this trying time, email us for a free consultation about how to set your startup up for a successful 2020. Feel free to drop me a line at to schedule a time. Be well and stay safe!

Always Be Listening

We’ve all been seduced by a good sales pitch in movies or in TV series. By the strong close or the moving speech. Michael Douglas as Gordon Gekko convincing Teldar Paper (and us) that Greed is good. Or Alec Baldwin in Glengarry Glen Ross instilling fear to motivate his real estate sales team. Or Jon Hamm as Don Draper delivering another convincing advertising pitch to his clients in Mad Men.

These expressions are about persuading the other side. About winning them over. About getting them to buy you or buy your product or just buy in. You get another human being or a group of them to do what you would want them to do. In the above examples, it’s the force of pure charisma that does the convincing. And we often think of salespeople as charismatic powerhouses that will others into seeing the world the way they do. Because that’s how they’re usually portrayed on film.

However, some of the best salespeople on the planet don’t rely on their capability to overpower. What they’ve cultivated is the ability to listen. And listen well.

Because, without listening, you never earn the opportunity to deliver the pitch.


Corey Myers, a close friend, and one of the best salesmen I know, once told me over lunch, “Sales reps are basically just waiters.”

In social settings, Corey is charming and animated. Some might even say he has an energetic mouth. A short time into our friendship, we scheduled a call to discuss my startup’s tech hiring. Corey was to sell me on his agency filling one or two of our open job reqs. I can remember what I was thinking when I fielded his phone call. I was bracing myself for a lecture from a caffeinated pitchman arguing his way into a new contract. What I got was drastically different.

After exchanging pleasantries, Corey began asking succinct, pointed questions about my young start-up. After each inquiry, he would just shut up. I couldn’t believe Corey wasn’t chewing my ear off. I could barely hear him. I even wondered if he had pressed the “mute” button, on the other end of the phone line. Gradually, I became more engaged in the conversation, as I answered each of his questions. Instead of getting yet another pitch, I had someone on the other end that sounded interested and concerned about my needs.

Imagine yourself selling as a waiter. You approach your prospect with a short inquiry, “Is there anything I can do to help?” or “How can I best help you?” The conversational dynamic shifts. Instead of being the predatory sales guy yelling into the phone, telling the customer what they need, your disposition is quite different. You’re not here to convince. To persuade. To push your agenda. You’re here to help. Who doesn’t want help?

The ability to listen well helps in other realms. In dating, listening gives you an upper hand. Your date is thrilled to be talking. You’re offering your full attention. Your date feels you empathizing, bit by bit. You both start to open up gradually. You’re vulnerable with one another. Closeness and intimacy emerge from this dance. And trust ends up being woven into the relationship.

The same goes with sales.

Asking questions and listening allows you to get to know your customer better. You’re the other party who is paying attention to them, and trying to solve their problems. Your prospect feels understood, and even take care of. All of a sudden, you’ve become very likable.

Now that you’re a likable caretaker to the prospect, and that you have changed the conversational dynamic, you are gradually earning your prospect’s ear. They have gone from protecting themselves from an upcoming pitch to opening up to you about their problems and concerns. Little by little, through attentive listening and natural curiosity about your prospect, you become a trusted confidant.


As you start getting closer to your prospect, they will start spilling the beans about their challenges and concerns. It’s time to dig in. What are their pain points? What keeps them up at night? What preoccupies them as they drive into the office every morning? What potentially threatens their job, and their ability to pay the mortgage? What will earn them their next promotion or year-end bonus? And finally — as a maitre d’ might ask — where and how can you help? And how can you help most effectively?

By understanding your customer’s aches and pains intimately, you will be able to develop a more tailored pitch, when the time comes. It will fit them like a glove and feel less like a pitch and more like a solution or in this case, a panacea to their problems.

We’ve covered how listening will both get you to empathize with your prospect and inform your pitch. Are there any other benefits to keeping your ears open and mind engaged?

There are plenty.

First, you maintain total control of the conversation by asking questions and listening intently. If, at any point, you manage to think that your solution won’t be a fit for a particular prospect, you can politely bow out instead of pushing things any further. It might avoid an expensive trial, or deployment. You can disqualify the prospect fast and avoid deploying further resources into a customer that might make your life difficult over the long haul.

Second: in many instances, your job as a salesperson is to be the eyes and ears of your company in the market. You’re usually one of the first people on the ground. The knowledge you bring back to internal company meetings might end up informing product strategy, marketing, or even recruiting.

By listening carefully, you might get crucial industry information from a prospect. They might tell you about a competitor’s product roadmap, and their plans to develop a new feature which could threaten your business. Or they might alert you to a competitor losing a key executive. Salespeople are relied upon to bring back these important bits of information back to headquarters. That data can shape company strategy at the board level.

Third, you can listen inward. Although I’m a big fan and practitioner of mindfulness, I am talking about listening to what is happening internally at your company. A colleague needs help on a complicated deal. The #1 sales rep on your team is offering tips on dealing with enterprise customers and their last-minute objections. Or a managerial opportunity opens up to lead a sales team of 4 reps. Tuning in to what happens inside the walls of your office building is sure to pay dividends.

We can all become enamored of the strong pitch on the silver screen. There’s something truly alluring about it. It’s okay to be drawn to it. But, what really makes the difference is cultivating the empathy and relationship between the prospect and the sales rep. You don’t hop on the phone for the first time with the right to pitch your prospect. You earn that right over the course of one call (or several calls) by listening to cultivate empathy and to build trust.

The best salesperson is not the one that can best explain the product or service to others. Or the one that gives the best demos. The best salesperson is the one that listens to the prospect, the market, and her surroundings; processes the information, and produces a tailored pitch. On the receiving end, the prospect feels understood, opens up the purse strings, and happily buys the product.

The tone of the relationship is now set: both parties are upbeat and pleased to be in business with one another. That’s an invaluable leg up when onboarding a new customer. It’ll ensure you get the benefit of the doubt from your new client if speed bumps arise as the relationship develops. As a salesperson, there’s no better way to ride into the sunset, as you hand the account off to Customer Success.