The Cold Opener

In any sales opener, the customer is going to ask themselves a series of questions, including:

• Who is this person?

• Are they professional?

• Am I comfortable?

• Are they relevant to my need?

• Would I like to continue the conversation?

So, how do we satiate this need:

1. Introduction: Say your full name, where you are calling from, and ask them how they are doing.

“Hi is this Frank? Hi Frank, this is Jennifer Marcus from Acme, how are you doing today?

2. Relevancy Statement: This is your mini-description of why you are calling this person at this time.

“Great, the reason for my call is I know you spoke to my associate “insert SDR” last week, and she mentioned you were interested in learning more about toner”

3. Disclaimer + first open question: This is what we call a “stop-sell” to disarm the customer and put our cards on the table that we are willing to walk away.

“Cool, so we primarily work with companies who are actively searching for toner, and I’m not sure if that is a priority for you right now, but can you tell me a little more about what led to your conversation with “insert SDR”?”

4. Agreement to move to discovery: Assuming there is a fit and the customer hasn’t hung up yet, now is the time to get buy-in to engage in a line of questioning.

“Totally understand, it sounds like there could be a mutual fit, but I need to dive a little deeper to fully understand, do you mind if I ask some questions about the business?

Moving to discovery

Prescription without diagnosis is malpractice. If the customer is still speaking to you it’s time to get as close to the customer's need as we can and develop an emotional link to solving the problem (also known as the “e-link”). There are two main principles to consider when doing discovery:

1. Create an atmosphere of cooperation: Customers should perceive your conversation as something they can get value from whether or not they buy your product.

2. 90% listening: The worst salespeople “hear” and then “talk”, but the best “listen” and then “ask”. This is the customer's time to share, and your time to digest whether you can solve their problem.

There are two types of discovery questions:

1. First-level questions that uncover facts about customers. They provide us with the tactical reasons a customer is in the market for a solution.

2. Second-level questions go deeper and uncover the true motivation for a buying decision. Almost all buying decisions are made off an e-link to the problem.

The art of discovery is moving seamlessly between first-level to second-level questions and drilling down when you strike gold - i.e. the customer reveals a key motivation. Drilling down has three parts: first-level question, second-level question, and an exploration of consequences

“So where do you buy Toner today?” - First Level Question

“How have prices changed with your current supplier?” - First Level Question

“I’m sorry to hear that, a lot of my customers tell me it’s hard to generate a profit margin when they need to spend so much on their day-to-day operation. Have you felt anything similar?”- Second Level Question

“Ok, it sounds like we’ve got a serious situation on our hands, and we need to get you toner at a price that doesn’t break the bank” - Consequence Exploration

This is obviously a simple example, but the key is to continue drilling down as long as you have the customer's permission to do so. Be self-aware and don’t push customers beyond their limit. Work to collaborate with your customer and get to a focal point on which a deal can close.

All great customer relationships start with an initial disarming and asking good questions.

✌️

1. Don’t talk down to your buyer.

   • Assume your buyer is intelligent. They might not share the same expertise that you do, but they likely have an existing knowledge base to work off of.

   • Respect your buyer and do your research. Don’t assume that because you’ve sold to similar people, the same rules will apply to this person. Draw parallels to previous sales you’ve made, but work to build in originality.

   • Don’t talk down to your buyer. It’s easy to assume that someone you’re speaking to is just another door to get through towards getting the deal closed. Assume that all those you come in contact with, whether it’s a receptionist or the CEO, will be heavily involved in the buying decision (multi-threading!!).

2. Everyone has an opinion. Present research.

   • If there’s one thing a decision-maker is good at, it’s parsing opinion from fact.

   • Opinions are as easy as they are lazy. A qualified decision-maker doesn’t much care for your or anyone else's opinion on what you’re selling (at least not early on in the process). Their job is to determine whether or not this purchase will benefit the bottom line. Presenting opinions rather than facts (or worse, opinions disguised as facts), wastes both your time and theirs.

   • Avoid saying, “Our product is better,” or “Using our technology will increase your demand.” Provide concrete examples, case studies, and facts for why a buyer should move forward with your offer.

   • Good research and solid data take time to produce, as well as a great salesperson to present in a digestible and memorable form. The payoff, however, is well worth it.

3. Tell a story

   • This is among the first pieces of advice any salesperson receives, but it’s one that is so often overlooked or cast aside.

   • Everyone loves a story. Stories are how we’ve related to one another since the beginning of everything. Research alone does not keep a buyer engaged. Stories offer a dual opportunity. You can both inform your buyer and entertain them at the same time. That’s valuable real estate to occupy.

   • If research is the science, presenting it as a story is the art.

4. Ask better questions

   • An average salesperson gets to the end of a pitch and, facing no questions or objections, thinks they’ve done a great job. A good salesperson knows that there is much more work to be done.

   • Asking your client complex and thoughtful questions early and often will pay dividends down the road when it comes time to close the deal. It also emphasizes to the client that you care about their needs and are aiming to find them a solution rather than sell them a product.

   • Take nothing at face value, and do not be complacent. If you sense that there’s more to be done to close the deal, you’re probably right. Don’t assume that your buyer is being 100% forthcoming with you. Use your questions to poke and prod until you get to the truth, then use it. Questions that get you to the core of an issue are the better questions.

5. Focus on wordcraft

   • “A person's name is, to that person, the sweetest, most important sound in any language.” - Dale Carnegie. Any salesperson who’s worth their weight knows this to be true. People love hearing their own names. People love knowing that you know their names. The trick in sales becomes deploying a buyer’s name at the right time. Underusing their name is bad, but overusing it might be worse. A good salesperson should be strategic about when, where, and how they use a client’s name.

   • Whether you’re speaking to a client or writing to them, the words you use should always be at the forefront of your mind. This is where there truly is no one-size-fits-all all approach. The best thing you can do is mirror the language a client is using. You don’t need to use the exact same words (though there is a time and a place), but you can aim to use words and phrases that are similar.

   • Think about great writing. Sentences are not all the same length. Great writing uses sentences of all different lengths to draw the reader in and engage them. Whether you’re speaking or writing, manipulating the way you use language can be just as powerful as the words that you use.

6. Be persistent

   • “It’s so hard to beat someone who keeps coming back for more.” -Ben Aldis. While that motivational tidbit does come from a Peloton instructor in the middle of a workout, it rings true in so many aspects of life, especially sales.

   • Persistence is the name of the game, yes, but persistence without intelligence is a big waste of everyone’s time. Persistence is where you weave in the previous five bullet points. Don’t talk down to your prospect, present research to them and tell it in an interesting way (like a story). If it “isn’t the right time,” ask questions and find out why it isn’t a good time. Use mirroring and wordplay to make yourself more interesting to talk to. And, if it is, in fact not the right time, keep some light pressure on for whenever the right time might be.

   • Be persistent because, as every salesperson knows, getting to a “yes” after a tough battle is about as rewarding a feeling as there is.

✌️

Decision-making in large organizations is a long, tortuous process due to legacy technology deployments, internal politics, entrenched homegrown solutions, the sunk cost of integrations, account control by incumbent vendors, and the sheer size and scale involved. In many ways, enterprise sales aims to help customers get through their own internal buying processes. Even the best and most popular product can’t make a typical enterprise buyer change the way it does procurement.

Some people think the sales force’s job is communicating value to customers. They’re wrong. The true purpose of sales is to create new value for customers, and in our case, customers can be several people inside of one organization.

Multi-threading is the concept of building relationships with multiple stakeholders within your deal. Top salespeople use this approach in every deal to build momentum and strengthen their influence when they’re not around. Data shows, on average, winning deals have at least three people from the buyer’s side included in meetings across the sales cycle. By contrast, losing deals often struggle to get more than one point of contact to attend their meetings. The first person they connect with is often the only person they ever speak with.

These insights confirm the behavior of buyers we’ve all heard – they make group decisions. There are two factors in determining whether your deal will make the jump in engagement:

1. If the prospect views your offering as interesting enough to socialize internally (and invite their colleagues to the next call)

2. If the sales rep navigates the org and includes additional stakeholders proactively.

#2 is where most sellers get this wrong while waiting for a reactive add to an email chain or meeting. You have to invest in the multithread before you need the return, which is why this is often called “deal insurance.”

When you rely on a single person to win your deal, you’re only one person away from losing it. This is single-threading, the unhealthy opposite of multi-threading. Investing in their direct reports is worthwhile even if your champion is the decision-maker or economic buyer. You may have a verbal yes, and it may feel like the deal is pretty much done.

But that can quickly flip from “I got this” to “I’m screwed.” Here’s how:

• Your decision-maker suddenly stops responding to texts, calls, and emails.

• Your champion forgets to tell you they are going on paternity leave, and you don’t have a point of contact to work with until he returns.

• Your champion switches jobs before you can connect with other stakeholders.

Enterprise deals are often lost by being stretched vertically inside an account without being wide. You need additional contacts in case your champion disappears. That’s precisely why multi-threading is deal insurance.

Tip#1: Ask how-to questions. When looking for new contacts, don’t ask, “who’s involved in this decision?”. Your prospect may hear you asking who you need to speak with to sign a contract and then put their defenses up. Instead, ask who decided to buy the solutions yours will replace or who made a recent, similar purchasing decision.

Tip#2: Context > titles. Context roles are more important than titles. The organizations you sell to don’t adhere to your internal buyer personas - those are OUR constructs we create to influence building and internal decision-making and are more directional than precise. When you multithread, you must understand who’s who regarding responsibilities. For example, “operations” means something different at every company, from customer service to finance.

Going dark isn’t the only risk that can plague your deal. Healthy deals can quickly turn downward when priorities shuffle, budget restraints set in, or bandwidth becomes limited. Each circumstance can potentially hold up your deal, but multi-threading can tackle them all. It’s a game-changer because instead of fighting these hurdles alone, you have numerous champions battling internally on your behalf, preventing hiccups from becoming showstoppers. The ability to tackle several threats at once is essential for companies attempting to go up-market and for sellers chasing more significant, more complex deals.

Common reasons you may end up single-threading:

1. You’re introduced to a new point of contact, and you let go of your original contact.

It’s common to break into an account through a senior leader and get immediately punted to someone on their team to dig in and see if there’s a fit. You might have a first meeting with the new contact and assume they’re your new path forward without ever going back to the original contact. As time passes, the senior leader forgets about the intro, their interest in your offering fades to zero, and it’s impossible to get back on their radar.

Turn that around.

Go back to the leader who was your starting point. Give them updates and keep them in the loop. You’ll need them to step back to approve the deal later.

2. If you didn’t ask for an additional contact to work with.

You need to ask well. Ask poorly, and the best-intentioned multi-threading will quickly be interpreted as going around or over your prospect. That earns you enemies as soon as it gains you new contacts. There are non-threatening ways to make the initial request, follow up on it, and bring more people into the conversation.’

Tip#1: Write emails to your original contact to keep the lines of communication open without asking for anything. The best sellers continuously offer insights to their buyers to keep them engaged. Share the high-level evidence of what you uncover without asking for anything in return.

Hopefully, by now, you are seeing the light at the end of the tunnel on multi-threading! But before we get to the finish line, we must remember one thing - buyers lie. It’s not malicious. Most of the time, it’s completely accidental. Sometimes, their truth simply isn’t the truth. We’ve all sold to someone who seems just a little too chipper. That said, it’s your job to decode reality.

Every deal in your pipeline has a surprise — a hidden truth you have yet to uncover. That’s why you’re never truly in control of your deal until you learn the full truth, and that requires numerous information sources.

No one is immune to champions who — despite their best intentions — accidentally coach you inaccurately. You can’t see behind-the-scenes blockers or defend yourself against unknown procurement officers who were angry pigeons in a previous life.

If you get any of the following answers while navigating your closing motion, it’s a red flag for a flimsy truth:

• “I’m the only decision-maker.”

• “This is my first time purchasing at this company.”

• “It’s an easy/quick procurement process.”

Unknowns are out there, waiting to derail your deal. Master sellers know to uncover these surprises proactively to maintain insurance in their deals and eliminate what would otherwise become barriers. You uncover unknowns by triangulating the truth with your stakeholders.

This means asking the same questions to multiple contacts and seeing whether the answers align. If all the answers are the same, excellent! You’re on the right track. Continue vertically until everyone from the end-user to the executive sponsor is aligned.

Suppose the answers aren’t the same, excellent! You found a potential hurdle before it found you. When you uncover an unknown in your deal, you’re a step ahead in terms of finding a solution. Alternately, if you wait for false truths to find you, they’ll greet you with a smack in the form of increased risks. You’ll feel the sting of an elongated sales cycle and a lack of control. That will leave you just hoping the deal will come in, and hope is not a strategy.

Find the truth through multiple stakeholders and nail down the win.

✌️

At the end of a performance cycle, there are really four potential outcomes (not two): 1) system-hit, 2) lucky-hit, 3) system-miss, and 4) perfect-miss.

1. System-hit: Things were done correctly. The top of the funnel was consistently filled, deals moved stages at appropriate ratios, and discovery, qualification, and objection handling were all on point. This is a deserved win.

2. Lucky-hit: This one is more complicated. The pipeline might be a mess, and customer experience could be in the toilet, but there is one massive deal that comes in, or back-to-back high intent inbounds that don't require selling. This is a loss, masquerading as a win.

3. System-miss: This has all the properties of the lucky hit, however, we are not so fortunate to have the pipeline whale. This is a loss, that looks like a loss.

4. Perfect-miss: Things were done correctly. Process, pitch, and attitude were above board on all fronts. Unfortunately, we fall on the wrong side of circumstance and for whatever reason don't hit. This is a win, masquerading as a loss.

Earlier in my career, I made the biggest mistakes coaching after the perfect-miss. I would come up with plans and ghost-feedback that didn’t make much sense, because in actuality the process and pitch didn’t need any alteration, the person just needed the encouragement to repeat the same thing over again, knowing that performance should shake out statistically. Sales lightning can and will strike, but rarely 2, 3, or 4 times in a row.

If I could go back and give myself feedback in these moments, it would be to normalize this statement. “Being unlucky sucks, but unfortunately it happens. You did great, and you are excellent at this job, regardless of what the dashboard reflects. Go out and do exactly what you did again”

Celebrate the perfect miss.

Managing and effecting lasting change is a five-point formula:

1. Vision

2. Skills

3. Incentives

4. Resources

5. Action Plan

Missing any of these creates a unique team blisters, and blisters f*cking suck. They look like this:

False starts happen if you don’t convert your thinking, meetings, and conversations into a clear action plan with clear assignments and responsibilities.

Frustration happens when you under-resource a critical initiative. People are stretched too thin and feel like they can’t win. This is a morale suck.

Resistance happens when payments, bonuses, promotions, and glory don’t align with the project goals. Incentives drive behavior.

Anxiety happens when participants don’t have the skills to execute. They start work, and management immediately comes down on them for poor execution. They are playing a rigged game.

Confusion happens when teams don’t have a clear vision of success. There is no charter for everyone to work from, so everyone develops their own charter.

I’ve accumulated all of these blisters in my career. Planning for them is a little more work, and might slow things down by a day or two, but it’s a fair price to pay for effective change management.

✌️

Reps who are star earners often find themselves on PIPs later in their tenure, while managers get to go to exec offsites, talk to the board, etc. It's not about the job change. It's about the perceived shift in value. I have a voice, or I don't. So, how do we fix it? I recommend all organizations adopt the "Commercial Principle" as a role in the hierarchy—the next layer up from the most senior AE seat.

What is different about the Commercial Principle role? First, it sits on equal footing with a second-line manager in seniority and base comp band. They are added to the revenue leadership slack channels and email distros, and consulted on key changes. Their skip-level is with the CEO.

They are ABOVE standard performance management. They have earned the right to miss a quarter. They must continue performing, but their drop-down is not getting fired but losing the Commercial Principle badge. There is more padding between a miss and losing their job.

They are a revenue partner to the organization and have carry on their deals. In addition to OTE, 1-3% of their revenue in an end-of-year bonus. Carry increases with tenure.

They are the sales team API for other departments. Product, marketing, and finance should make the Commercial Principles their first stop when gathering feedback on a release or campaign.

I don’t know why you wouldn’t want your star performers, who want to stay star performers, at the table for a long long time.

Here is what worked:

Smart prospecting. SDRs don't fail because they don't know what to say. They fail because they don't know who to call. I would spend most nights creating "hot lists" of leads in my territory. These calls had an incredibly high hit rate.

Aggressive time management. Block everything in your calendar—every follow-up, every call blitz, every coffee break, etc. Don't bog yourself down with microdecisions on what to do next. You can't afford the lost time. It looks like this:

Blue for call blocks, orange for hard follow-ups, green for AE meetings, and red for non-sales work.

No wheel spinning. If I knew someone was not going to set a meeting, I pretty much hung up on them. I didn't see the ROI in spending an hour trying to be a hero and selling them in a different direction.

Nurture the AE relationship. I treated my AE’s time with respect and their deals with urgency. At peak, I was supporting 18 outside field reps. They each wanted their meetings set differently and had different requirements. I followed all of them - and in return, they fed me back. When they had hot leads that needed follow-up, they sent them to me.

Inbounds are a gift from god. I remember once sprinting from the lunch table back to my desk to make sure I got to the customer within a minute of hitting the site. Don't f'up free money.

Personalize every email. This was 2012, so there was no sequencing or sales engagement yet. You had to write your own follow-ups. It worked better than some of the generic comms and cadences I did later in my career.

Nothing ever beats the phone. Pick up and start dialing.

The SDR role is the most challenging role in tech. You need to optimize your chances for success by calling the right people, being present and available to get lucky, forming allies, and working your ass off.

Until next time.

It wasn’t.

He looked at me and said, "Congratulations, you are fucked."

I responded with a version of what looked like this: 🧐🥺

He replied, "If you miss your numbers this year, the board will ask me to fire you. If you hit your numbers this year and in subsequent years, the board will ask me to replace you with someone more senior. It's on you to make sure neither of those happens."

There was a pit in my stomach, but this turned out to be some of the best advice I had ever received. It was clear that if I wasn't consistently prepping for the next growth phase, even doing well in my job was a suicide mission.

Here are some strategies that worked:

Study your positive future. We were crossing 1M in revenue when this happened to me. Therefore, I would need to study 1-10M, 10-25M, and 25-50M. What did companies go through? What bottlenecks and challenges existed? What resources were required? And most importantly, who were the people who failed at making these transitions and why?

Find mentors. I found two who had gone through the two stages ahead of me. I picked their brains on what to expect and got their written plans and playbooks. It was like getting a syllabus six months before your course started.

Make growth a team sport. I shared this with my reports. At the end of each year, I'd share "the new sales org" vision and ask each manager and director to "fire themselves" because most of their skills wouldn't be relevant for our next phase.

Communicate upward. I never wanted the CEO to doubt I could do whatever came next. I constantly communicated what I was doing to get better and shared ideas on how we could make our business better in the future.

Deprecate and replace. To keep growing as a leader, especially at a startup, you must constantly get rid of or update your work. This can be taxing on the ego, but you must admit things you did successfully at one stage may not scale to the next.

Hire owners. My life was made easier by finding amazing sales directors and managers to share the burden with.

The moral of the story: if you join a growth company, you must think about your job as something different each year. Companies grow exponentially, but humans grow linearly. Figure out a way to kink your own growth curve and stay ahead of yourself.

Unfortunately, exaggeration is common from most business functions back towards the product and engineering team. It makes sense. There are limited resources, and you must make a case on why yours is more important. That is unfair to our friends on the product and engineering teams. How can you prioritize when everything is a level-10 fire? And, if what you shared is not a level-10 fire, how are you to be trusted again? To provide great product feedback, you must shepherd the process and ensure that information is packaged to be received, understood, and prioritized. The communication breakdown in this direction usually takes one or multiple forms: fire drill feedback, recency feedback, or no evidence feedback.

Fire-drill feedback is when we skip right to ringing an emergency bell. Sometimes, it's warranted, like being unable to do your job because an API is down or having customers locked out of their accounts. However, crises like these are usually few and far between, and in most situations, problems feel more urgent than they are. This manifests for a product manager as an attempt to decipher the problem while trying to solve it simultaneously. To use an analogy, imagine waking someone up in the middle of the night whose house is on fire, but instead of asking them to escape, you ask them to figure out where the fire started, how to put it out, and how to save the household members - tough gig! The stakes are not nearly as high in business, but everyone needs orientation to solve problems. The heavy hyperbolic and emotional tinge usually accompanying this feedback can make it hard.

Recency feedback is when you react to a recent, isolated incident to prove a larger hypothesis that something is broken or needs updating. This frequently happens on sales floors and usually comes from a customer request. Salespeople live and die by each deal, and although these requests are one-offs, if they cause a lost deal, it will create the feeling that the issue at hand is the most important thing for a company to solve. In this case, product managers have to spend time trying to recreate the problem and research whether it's something that, if solved, solves for everyone or just for one customer or sales rep.

No-evidence feedback is precisely what it implies: providing feedback without supporting data. This will often look like a bug duty or feedback request without a customer link, description, or any supporting material on what happened. It's difficult to solve a problem without a whole story. In this case, rightfully so, product managers will generally de-prioritize the request as the lift of piecing together the entire picture may be too high.

The next time you give your product team feedback, keep the above in mind. Present information that is thoughtful, calm, and collected with evidence on what happened and the impact a fix might have. You don’t want to be known as the salesperson who cried bug.

This is what we’re told when stepping into a leadership role. Be the rock. Be the force. Never stand irresolute. I get it, and I agree these are important traits. As a leader, you must move the immovable, and you can’t do that if you’re wavering from your post.

I had an experience when I was younger, training with a soon-to-be UFC fighter. We would grapple, and it would be like wrestling a rabid dog. He would kick my ass. You would see his skill and stature and assume he would be a hardened man, but that wasn’t the case. He was sweet, calm, and gentile, and in one instance, he felt so poorly about his performance against me (that he clearly won) that he asked if I’d help him drill moves. It was a lesson. He could dominate without making others feel dominated and move himself and everyone else forward.

Vulnerability and leadership are not usually two things we put together. While it may seem counter-intuitive and sometimes a little scary, the new generation of workers requires us to be authentic and show as much of our true selves as possible.

So how might we do that?

1) Admit and own your mistakes. We all make them. Leadership is about home runs, not batting average. You will fail more than you win. The more willing you are to admit and own your mistakes, not make excuses, point fingers, or avoid responsibility, the more others will trust you.

2) Don’t take yourself too seriously. Not everything is profound or requires a reaction. Sometimes, the only response is humor, which is especially powerful as it can give a group a healthy perspective when times are tough.

3) Share your own process, journey, and challenges. You didn’t arrive at leadership by accident. You did things - some really good and some really bad. Everyone goes through a process of growth, discovery, and challenge. The more transparent we are about our methodology, the more we let others know who we are, give them insight into how we operate, and create an environment conducive to individual and collective growth.

4) Ask for help. Requesting help is not an admission of weakness. It is a sign of strength. You are willing to put yourself in that vulnerable space to get to the best version of right.

Now, I want to caveat everything I’m saying. All of your team members will regress to your worst habits. Allowing yourself to be vulnerable only works if you are excellent at the more tactical parts of your work. The time you log on is the time your team will log on. How you make a document will signal the minimum requirements for everyone else. The effort you put into a customer call will become the minimum standard, and so on.

Being a leader is unusual. Being a fantastic leader is never something you attain but strive to achieve. It requires hard work, dedication, and constant and never-ending improvement. The goal of a leader is not an extraordinary amount of wealth but an extraordinary amount of respect. You are not training a team to hit this month's quota. You are training a team of exceptional individuals who will be lifelong partners in your professional journey. That only happens with trust.

Until next time.

Subscribe now