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Todd Caponi: The Transparent Sales Leader

The Transparent Sales Leader

As you have graduated to the role of sales leadership, there is a quick realization that the two roles of sales and sales leadership could not be more opposite: Sales is the ultimate independent role. You are your organization’s voice to the prospective buyer. You are the Sherpa to the prospective buyer’s journey. You define your own success. You are transferring confidence to the buyer. Sales leadership is the ultimate dependent role. Your success is dependent on the success of those you lead. You are transferring confidence to your sellers.

To maximize sales team and organizational performance, we need to optimize five core areas required to build, maximize, and maintain revenue capacity.

There is a set of core responsibilities, which we will explore, that can quickly become your structure when categorized. There are also a core set of drivers to intrinsic inspiration.

The Transparent Sales Leader challenges long-held sales leadership standards, providing a modern, cards-faceup, science-backed, easy-to-implement framework for today’s sales leaders.

The Transparent Sales Leader Framework

Transparency Defined

AS HUMAN BEINGS, WE ARE PREDICTION MACHINES. FROM THE TIME WE are babies, our brains are wired to predict.

Could the secret of revenue leadership success begin with something as simple as accurate expectation setting? It’s a great place to start.

A prediction is hard to come by when the recipient is having trouble trusting the source.

In 2016, we engaged with Northwestern University to investigate how consumers interact with a website when that website is acting as the salesperson.

When a website is acting as a salesperson:

  • Data point 1: Almost all (96 %) of consumers read reviews before purchasing a service or product they haven’t bought before.
  • Data point 2: As many as 82 % of consumers seek out negative reviews.
  • Data point 3: The optimal average star rating for purchase probability is between 4.2 – 4.5 on a 5 – star scale.

At even a subconscious level, we know that perfection isn’t probable.

The negatives act as a disarming mechanism. It works online. It works in human-to-human selling. It works in leadership.

Transparency sells better than perfection, retains better, upsells and cross-sells better, creates advocates better, and leads better.

Tyra Banks. Banks, a television personality, model, business mogul, producer, and actress, often uses the word “flawsome”: “An individual who embraces their ‘flaws’ and knows they are awesome regardless.”

In one study, the relationship between leadership “transparency” and “employee happiness” had a .937 correlation coefficient.

Traditionally, sales organizations have kept their team members on a need-to-know basis.

However, sales leaders monumentally underestimate their sales team members’ ability to see through a muddling of the facts. It may be one of the top skills of a great salesperson. The result is disengagement and likely turnover.

Transparent leadership is living the following values every single moment, consistently: Taking a cards-faceup approach to leadership. Setting proper expectations, consistently meeting them, and embracing the idea that those expectations are not always just rainbows and cotton candy. Embracing the idea that you do not have all the answers. Embracing the idea that you have weaknesses, and it’s ok for others to know that. Embracing the idea that you are no more important than anyone else on the team, you just have different responsibilities.

A considerable portion of our responsibility as sales leaders centers around expectation setting: helping our team predict their day, week, month, and even future; helping our managers and leaders predict; helping our board predict; helping our investors predict. Overpromising and underdelivering is, of course, an unsustainable policy. However, consistently underpromising and overdelivering is also unsustainable.

Expectation inflation is when we consistently underpromise and overdeliver. There is magic in setting expectations and consistently meeting them.

Being authentic is to “be true to the self.”

However, as a sales leader, it can be the downfall of your effectiveness for your team and your company. Becoming an authentic leader heightens the risk of becoming preoccupied with yourself versus focusing on the needs and wants of others.

If authenticity is bringing your true self to every interaction, as a friend of mine once asked, “What if your true self is an imbecile?” What if you are lacking in experience, respectfulness, and tact? What if your team doesn’t yet respect you? What if you’re an authentic incompetent?

Don’t buy into the hype that authenticity in leadership is the solution to future aspirational leadership. Yes, you should always be yourself. However, prioritize transparency over authenticity.

You are a sales leader. Your number one job is to move people toward successful outcomes — professionally and personally. That begins with trust.

Trust begins with transparency through the setting of accurate expectations.

Reveal to your team your specific responsibilities as a leader, your strategy, your plan, and the way you think about the role. Build trust through transparency, then use that same transparency to set proper expectations.

The Five F’s Framework

Transferring confidence to your sellers is a key function of your role.

But you must have the right amount of confidence. A lack of confidence becomes a germ that travels through your team and onto your prospects and clients. However, have you ever been around someone with too much confidence? That may be even worse!

Confidence begins with the words from the first definition above — an “appreciation of one’s own abilities.” Knowing your job, with a predictable structure, a plan, and a way to communicate it will set you far apart from others with similar responsibilities. You’ll have confidence. That structure, created and used in a transparent way, will create the confidence your sellers so need through “the feeling or belief that one can rely on someone or something.”


This, the Five F’s, is the scope of your role. Every responsibility you have fits into it. It is your ultimate responsibility, and it is never perfect. But with a structure, you are no longer the dog chasing the car; you are the car with the map.

You will make sure your team is working on the right opportunities at the right time through your efforts to hone the team’s focus. You’ll lead the field each day with the right people in the right roles in the right places with the right tools and the right resources through your efforts to build it. Your team will consistently execute through your efforts to drive the fundamentals. You will predict the future through measuring the right KPIs and metrics engrossing your responsibility to forecast. And you will drive fun through the creation, management, and optimization of an environment where your team is intrinsically inspired, so they’ll show up, do their best, stay, and tell their friends.

  • FOCUS. Ensure the team has focus, spending their time on the right opportunities in the right places at the right time. The individuals you will lead have an inventory of time. It is the most valuable asset they own. How is that inventory being allocated? You are responsible for establishing, maintaining, and optimizing your team’s effort so none of it is wasted.
  • FIELD. Structure your field organization to maximize effectiveness, efficiency, and output. Ensuring you are deploying the right team with the right tools and the right resources to best address your focus.
  • FUNDAMENTALS. It’s on you to ensure the field organization you’ve invested so much into is doing the fundamentals right. Maximum output requires the right execution, done consistently. Start with the foundational elements.
  • FORECAST. Quite possibly the most obvious of your assumed responsibilities, you must be able to hone your psychic abilities, your ability to forecast.
  • FUN. Building and delivering a culture where your team not only shows up every day, but they are intrinsically inspired to do their best every day, too.


Our natural inclination seems to be toward selling to anyone interested in buying. However, the focus, when done correctly, optimizes your return on time in such a dramatic way.

Focusing that time on the right opportunities and the right individuals within those opportunities is the first step to optimizing that inventory.

What are the ideal firmographics (company sizes, verticals, geographies) and demographics (titles, levels) of the companies and individuals within those companies which will grant us the easiest path to the highest reward? Which will we say yes to, which will we say no to, and what criteria will we use to determine the gray areas?

TAM (total addressable market), which is a calculation that theoretically answers this question: If we sold everything we have to every possible company that could derive value from our solutions , what would that dollar amount be?

The ICP answers the question for investors and potential referrers, “What is the profile of customer that is ideal for your organization? In a perfect world, if you could only work on one type of customer where the mutual impact would be optimal, what would that profile look like?”

Baader-Meinhof, also known as the frequency illusion or frequency bias, once you as a human being establish a focus, it stays top of mind. You notice it everywhere.

Firmographics are the attributes of the organizations or companies; their sizes, verticals, and geographies.

When we look at our customer base, which verticals have the highest win rate and/or the highest average contract value and/or shortest sales cycle.

As you begin your new leadership role, spend the time to identify the firmographics of the organizations your team should prioritize. During your tenure, an important responsibility will be to not only maintain that focus, but also to consistently consider and adjust that focus as warranted. You will do this at the team level, but also at the individual level during one-on-ones.

With extreme firmographic focus, you begin by doing the work, research, and measurement on which key subsets of the overall target market are most ripe for opportunity, maximize deal sizes, win rates, and most efficient cycle lengths.

Not all individuals within your target companies are equally desirable, either. As a sales leader, understanding where your team and your organization’s focus should be extended to the functions and levels of individuals worth pursuing. And even more important, identifying the individuals not worth pursuing.

What do you do if an inbound lead comes in from a function or level that doesn’t match? Will you pursue them? Will you refer them out?

That is your responsibility as a leader: to find the more efficient path to the highest value opportunities in terms of cost of acquisition and profitability. Cost of acquisition and profitability draw a direct line from opportunity flow, deal sizes, win rates, and sales cycle lengths.

The final category in your focus responsibility is to understand the soft or hard prerequisites an organization must have to make it worth pursuing. What are the things a company must have, or must have in place, to make it a valuable opportunity for your team and business?

While the average sales leader seeks to cast a wide net of potential clients and work every opportunity where the prospect has interest and budget, the world – class sales leaders embrace the idea of “no science projects,” and help their team maximize their results through embracing an extreme focus on the ideal pursuits.


Based on your focus, your next responsibility is in building, maintaining, and growing the field organization, which is putting the right people in the right roles in the right places with right tools and the right resources.

Just like salespeople need to always be on the lookout for great prospects, as a sales leader, it’s likely you will always be recruiting. The team that takes the field each day will need to be the optimal team to play the game you are playing — your focus. How will you align your search with your focus?

Should you create a formal structure in your interview process? Should you establish consistent processes and questions asked to everyone? Those are two very difficult questions to answer, and I believe the optimal way is somewhere in between. Interviews that are a free-for-all lend themselves to bias. In a free-for-all interview, we, as human beings, create a first impression of the individual we are interviewing.

Interviews that are highly structured, where the questions are predetermined, and every individual is asked the same questions, creates a different dilemma. A structured interview process includes four core elements:

  • question consistency,
  • evaluation standardization,
  • question sophistication, and
  • rapport building.

When you have an experienced rep for the role, your focus is: what intrinsic and extrinsic things can we provide to keep this person motivated, and will they fit in and succeed here?

I’ve found this collection allows me to get at the real drivers of engagement, passion, fit for the role, fit with the team, potential longevity, and ultimately mutual success.

  • QUESTION 1: TELL ME YOUR STORY. If they are not able to tell their own story, how will they be able to tell a story where the client is the hero?
  • QUESTION 2: WALK ME THROUGH THE LAST X YEARS OF YOUR RESUME. WHY DID YOU TAKE THE JOBS YOU DID? WHY DID YOU LEAVE? With this question, I’m listening for: (a) how the individual assessed whether an opportunity was worth committing to, (b) what the individual missed during that assessment, and (c) what the individual learned from each.
  • QUESTION 6: (FOLLOW-ON TO THE LAST QUESTION) WHAT’S GOING TO STRETCH YOU? MEANING, WHAT DO YOU THINK WILL BE THE GREATEST CHALLENGE YOU WILL FACE HERE? I’m looking for authenticity and transparency from their answers. I’m also looking to understand whether this person is looking to stretch themselves, or just looking for a wheelhouse position that aligns perfectly to their skills.

We appear to be amid a “sales stack” revolution. The sales stack, a term used to represent the “stack” of sales software that a team uses to optimally perform their role, has become a hot topic given the hundreds of technologies now available.

It was the second week of July 1916. The World Sales Congress was taking place in Detroit, Michigan. The primary keynote speaker? None other than the sitting President of the United States of America, Woodrow Wilson. The sales profession was trusted, respected, and even admired in the early 1900s. What happened? Technology happened. Its misuse devolved the profession back to its deplorable reputation which permeated the late 1800s.

Back in the early 20th century, to make a sale, it required a face-to-face interaction. While the telephone had been invented, it wasn’t until the 1950s that it became more pervasive in the sales world.

The greatest “sales stack” revolution of all time happened. While you might consider call recording, list building, or enablement tools to be a revolution, what about the proliferation of the telephone? Would you not consider it to be the greatest game changer in the history of sales? No longer did we need to leave the office to connect with prospects. But we ruined it. Unwanted generic pitches. Metrics and call targets incentivizing quantity over quality. Aggressive tactics. Auto dialers. Robocalls. Call prevention technologies weren’t enough. The government had to step in, creating legislation including the “Do Not Call Registry” in 2003.

Then came the sales professionals’ next great gift, email. But we ruined it. Generic spam messages, unrelenting reach outs, scams, and trickery made email the next target of even more technology innovations. Those email sales-prevention strategies weren’t enough, either. And, once again, the government had to step in, creating legislation through the 2003 CAN-SPAM Act.

The five-letter dirty word is S-C-A-L-E. Sales leaders and organizations prioritizing volume over quality, relationships, and focus. The great gifts of technology sullied by our forgetting that we’re selling to human beings.

The great gifts kept coming. Just prior to the signing of the CAN-SPAM Act, LinkedIn began — an incredible gift for salespeople, where hyper-targeting became possible.

You must be trusted to be respected. Trust and respect require a shift back to humanness in our profession.

The best way to make a customer and/or prospect believe we truly care about their outcomes is to truly care about their outcomes.

Build, maintain, and grow your field organization to best serve the focus, not the other way around.


Your ongoing sales leadership function is to drive the fundamentals that maximize the field’s effectiveness. Defining and now driving your team’s focus on the right opportunities at the right time, building a team to take the field filled with the right people in the right roles in the right places, with the right tools and the right resources is just the start. Now they must execute, and you must ensure that execution is aligned around the right fundamentals, imparted in the most efficient and effective way possible. The word fundamentals is used on purpose. These are the central principles of which consistent execution is founded. You have a responsibility to ensure that your team members are executing consistently optimal, the right execution in the right situations.

What are fundamentals? The fundamentals are the simple things we must get consistently right. These are the 100-level skills. At a high level, it’s categories like:

  • Messaging: Are we consistently messaging to prospects and customers correctly?
  • Prospecting: How effective are we at inspiring the interest and engagement of our focus targets?
  • Discovery/Qualification: How good are we at identifying the fit for both the potential customer and our organization?
  • Presenting: In the more formal engagements with prospects and customers, how are we at maximizing audience engagement, driving action, telling stories, and leading to our solution instead of with it?
  • Negotiating: Do we overdiscount? Do we erode trust at the goal line of our deals using techniques taught in hostage negotiation classes? Are we exuding pricing integrity?
  • How about sales process execution? Hand-offs to post sales — the team that executes the transaction, the team that cares for the customer longer term? Deal strategy?

Messaging: If you were to ask five members of the team the following question, how would they do in answering it? You go to a party. You run into a few friends you haven’t seen in a while, who are also in the business world. One asks, “Hey, I heard you got a new job. XYZ Company? What do they do?” How would you answer this question so that the listeners would understand it, be able to relate with it, and remember it?

Prospecting: How would you assess your team’s ability to engage with your focus targets, drive their engagement, and lead them into a buying process? Are they “we-ing” all over the prospects? Are they eroding trust before they’ve built any to begin with?

Discovery and Qualification: How would you assess your team’s ability to do proper, effective discovery and qualification?

We will lose deals, but what percentage of our time are we spending on opportunities we should have known we were going to lose?

For you as a leader, there are two things I want you to consider when assessing the choreography and execution of your presentations: Do our presentations lead to us, or do they lead with us? Do our presentations offer a collection of logic, or do they tell a story where the prospect/customer is the hero?

Negotiating: When you look across the deals you’ve done, how do you feel about your team’s ability to build trust through to the close? Are they building trust or eroding it? How do you feel about your team’s ability to maintain pricing integrity, and not just give things away in the form of a discount, resulting in a charitable contribution to the prospect’s bottom line?

The reward doesn’t look as sweet when the journey to get there doesn’t match our expectations. Our brains stack the deck toward the easier path when deciding.

To do sales enablement right, those three primary and essential responsibilities are: amalgamate, orchestrate, and evaluate.

Every department in an organization wants to enable salespeople. Beyond the sales department itself, your marketing team wants to enable salespeople.

They need time to teach positioning, lead qualification, and processes; and to work on upcoming events, branding, and so on.

Your product team probably wants to enable salespeople, too. They want to gain alignment to ensure salespeople are aware of current and future product features and functions, roadmaps, and gotchas.

Your finance team wants to enable salespeople through: expense policies, legal requirements, and sometimes even stock option plans and compensation intricacies. Your human resource team wants to enable salespeople on: values, onboarding, and workplace-required training like harassment prevention.

Establish an initial list of the requirements salespeople must have to be effective and efficient in their roles.

Categorize those into four areas:

  • Sales skills
  • Product knowledge
  • Business/industry acumen
  • General company policies, processes, and requirements

Second, establish the priorities.

Once in place, the third step is establishing those priorities as the mantra for sales enablement.

By definition, orchestrate means “to arrange, organize, or build up for special or maximum effect.”

Based on the desired outcome: What is the right format for delivery? Who should deliver it?

Within the orchestration, it is also your responsibility to ensure that you optimize the delivery for how individuals pay attention, engage, consume, and ultimately learn and consolidate.

The third category of responsibility for your enablement function is to evaluate; to assess the effectiveness and success of delivering the priority.

Invest in enablement. Invest in the fundamentals. Enablement is an investment, not a cost.

In an environment where the demand for sales talent so exceeds the supply, you’ll find yourself needing to cross out lines on your job description requirements, hire lower, and invest.


There were five ways we bucked traditional approaches to driving a forecast, which, when put together, can’t help but drive forecasting breakthrough: We rethought traditional forecast stages and milestones. We rethought traditional qualification criteria. We celebrated the wins and the losses. We eliminated the word commit from our vocabulary. We rethought traditional key performance indicators.

The point of a forecast is to predict when the buyer will sign, and for how much!

  • A buyer first decides “Why change?” Is their status quo no longer sustainable?
  • Once the buyer embraces their need to change, they then move on to the question of “Why you?”
  • After you have been able to confirm that your solution is the chosen path to change, the final step from a forecasting perspective is “Why now?”

I should refer to it as qualifying whether a prospected is appropriately TEMPTed , as defined by five buyer-centric perspectives on deal qualification:

  • Trigger: Does the buyer see that their status quo is no longer sustainable? Do we believe it to be the case?
  • Engagement: An engaged buyer is evidenced in their willingness to put you on their calendar.
  • Mobilizer: This concept comes from The Challenger Customer, but are we attached to someone who is capable of mobilizing change within their organization?
  • Plan: An engaged buyer is also willing to chart a path. Are they willing to take a journey with us, and discuss/collaborate on what that journey will look like?
  • Transparency: Are they okay with what we don’t do? Have we addressed the elephant in the room? Will the truth sell it?

Traditional sales leadership approaches to what is measured and enforced disincentivizes sellers from quickly qualifying out of opportunities they are likely to lose. A lost deal is one where we were outsold. We prioritize pipeline loads over pipeline quality. We prioritize prospecting skills over qualification skills.

We must also throw out the concept of the “pipeline-to-quota requirement ratio”.

Quality over quantity is often said but rarely practiced amongst sales leaders.

Deal qualification seller development is an oft-overlooked skill but could arguably be one of the most important to maximize the revenue capacity of an individual rep. Working the right deals, at the right time, with the optimal mutual outcome is what often sets apart the top performers from the middle of the pack.

The second-best thing behind winning is losing quickly. We can foster an environment where losing quickly isn’t a punishable offense. The result is an optimized use of our team’s time and a more accurate forecast.

When a customer says yes, guess what? The odds of that deal closing are still not 100 %. They’re likely closer to 75 %.

A customer has said yes and has now gone through a round of contract redlines. The odds are now around 90 % of the deal closing.

Our wiring as human beings drives an avoidance of short-term pain over the avoidance of long-term pain. We’ll lie now to avoid a short-term pain (or receive a short-term reward) and will concern ourselves with the long-term consequences later.

Transparency isn’t just something that works when working with prospects and customers. It’s even more magical within the four walls of your organization. So, instead of commits, why not spend the time coaching them, honing the fine art and science of owning their territory forecast, like you, their leader?

The goal of sales forecasting is to be in range.

If you are measuring everything, are you measuring anything that matters? By gaining a focus on the metrics that truly drive results, then sharing those metrics, you: (a) focus, and (b) build confidence in those around you.

The results of your sales organization are a combination of:

  • Number of opportunities your team has to work on (O).
  • The dollar value of each of those opportunities ($).
  • What percentage of those opportunities you win (%).
  • How long it takes for you to win the opportunities you win (CL).

These four core metrics are volume, size, win rate, and time.  That’s all.

Under each buyer behavior stage are the individual stages you and the buyer are going through together. In each column, there are two categories of activities:

  • Them: If you were to ask the prospect / buyer what they are doing, thinking, or believe is coming next, what would be their answer? Their answer might be different depending on where they are along the buying journey. This row aligned under each forecast stage column can be your guide.
  • Us: Based on where the buyer is along their journey, this row describes the activities the seller should consider or be focused on to confirm where the buyer is in their journey.


  • Suspect (0 %): These are the organizations and opportunities where the prospect appears, from the outside, to meet the criteria of what would constitute a good potential client for your organization.
  • Discover (10 %): In this stage, the prospect understands your value proposition and continues to be engaged.
  • Confirm (25 %): This is where mutual learning occurs. The prospect has communicated the reality that doing something different tomorrow than they are doing today is necessary and desired.
  • Decide (50 %): You have reached the decision phase when the mutual learning is all but completed. Your prospect is deciding, and that decision should be focused on, at most, one or two alternatives.
  • Selected (75 %): The prospect has communicated that you are the selected solution for change within the prospect’s organization.
  • Negotiation (90 %): Once the agreement process has begun and the prospect’s organization sees no deal breakers.
  • Closed/Won (100 %): The relationship is now formalized, typically in the form of a mutually signed agreement.

Ask yourself the question, how long, on average, should an opportunity stay in this stage? Then, determine how long before an opportunity sits in that stage before you should truly question whether it belongs there.

Buyer-behavior focused versus seller-activity focused will always win in your sales forecasting. Coupling that with the environment you create around forecast accuracy, and you have the recipe for a more accurate forecast.


Engagement comes from you, the leader, and is the key to performance, the mental health of both yourself and your team, predictability, reduced turnover, and even speed to hire.

The fun factor correlates directly with your state of mind.

Intrinsic inspiration is your actions being driven without any tangible reward for doing so. You are engaging in behavior driven by something inside of you, versus an external motivation provided outside of you.

The Behavioral Science of Intrinsic Inspiration

You as an individual and those on your team are subconsciously engaged by these six categories of feelings that, when maximized, result in low voluntary turnover and maximized team revenue potential. Balance these six.

They happen to spell out the word praise:

  • Predictability: We do our best work when we can predict the future.
  • Recognition: We do our best work when we are recognized for our efforts, validated for the impact, given status in front of others, and provided regular feedback.
  • Aim: Do your reps know what their work means to you? Do your reps know what their work means to your customers? Do your reps know what their work means to your customers’ customers?
  • Independence: We do our best work when we have autonomy, trust, resources, and independence.
  • Security: We do our best work when we are a part of a team. Packs outperform individuals.
  • Equitability: We do our best work when we feel like “the juice is worth the squeeze.” Are the rewards I receive equitable to the output?

Variable compensation wins when it’s the REWARD, not the MOTIVATOR.


We, as human beings, do our best work when we’re able to predict.

When we are in an uncertain environment, it is taxing on the brain. Our IQ goes down, as our energy-burning brains seek to make sense of the information it is taking in.

Individuals tend to be less productive when they have feelings of uncertainty, inconsistency, and instability.

Consistent leadership does not have to mean being consistently warm, consistently gracious, or consistently engaging. Being consistently grumpy and distant is better than being inconsistent.

You are setting the prediction in the minds of your team from your first interaction. Often, that first interaction is happening during the interviewing process.

There are some ways sales leaders tend to overpromise during the first interaction — where the prediction is being created.


For your salespeople to be successful, part of your role is to transfer confidence. Confidence begins with transparency, honesty, and accurate expectation setting.

The focus of the sales interview is to seek a mutual understanding of fit. Hiring a candidate is not about getting the sale. Hiring a candidate is about finding and developing mutual alignment around achieving each other’s goals — both professionally and personally.


AS HUMAN BEINGS, WE ARE OPTIMALLY DRIVEN TO PERFORM OUR BEST when recognition, status, and feedback are available.

Regarding the first lesson, when delivering a critique of a team member, deliver one positive and only one opportunity to improve at a time.

Always remember to provide praise in public, critique in private.


Individuals are less likely to do their best when they feel their aim at work does not matter.

Salespeople on a mission, with a true purpose beyond just striving to hit a number, making an impact daily that is a benefit to society will achieve more. They will stay longer. They will advocate.

The quota, originally designed as a measure to understand whether a salesperson has paid for themselves, has evolved to a rite of passage that occurs at the beginning of every organization’s new fiscal year. It’s the “starting over at zero” tradition.

The practice of starting over at zero each year reengages and rewards your underachievers. The practice of starting over at zero each year reduces the intrinsic inspiration of your achievers and overachievers.

For your sales personnel who bring new logos in the door, is it possible to create a visual for the rep to see their name associated with that account in a place where the rest of the organization can see it? Forever? Can you give quota achievers a lower quota that following year, or start them part of the way to their target, based on their previous year’s overachievement? You want those overachievers to stay, right? There’s a significant cost to their leaving, right? This investment is likely worth it!


We are driven toward control, autonomy, and the trust of others. Remote work maximizes that feeling of control. However, as a sales leader, we are also driven to predict. We are driven toward certainty. Our struggle to predict and gain certainty is multiplied when we cannot oversee those who control our destiny — our sales teams. Remote sales environments are great for salespeople but inherently are not great for organizational and sales leadership.

If you’re a human being, which I’m assuming you are, you probably get your best ideas while taking a shower. There’s a particular reason why. Showers are a perfect combination of three things required to create an optimized, creative brain: distractions are lowered, relaxation is maximized, and dopamine is released.

Performing in front of other people creates anxiety. Making prospecting calls creates anxiety. Neurologically speaking, maximizing brain comfort and focus is vital to creating top performance from your selling organization.

As sales leaders, creating an environment of autonomy, control, and free from anxiety is vital for fostering a culture of activity and productivity.

Multiple studies show that if you believe you are a lucky person, you are more likely to perform better than those who think they are extraordinarily unlucky. With your team, their perception of luck becomes a self-fulfilling prophecy, and as a result, impacts their performance.

I’ve seen many sales leaders not take the concept of peak performance time into account, and quite literally steal productivity from their team.

Align with the members of your team to optimize their independence to when they do their best work. Provide the freedom for your team members to optimize each day. We all have pockets of time each day when we feel our most productive, and times we don’t. As a sales leader, don’t steal those productive times.


As a sales leader, fostering security and safety, being part of a pack, or being part of a team directly correlates to higher performance, lower turnover, and faster time to hire.

Threats to your security and feelings of loneliness get even worse as a sales leader. The role itself is inherently lonely. The original definition of “social distance” refers to rank and authority — where the greater the distance, the greater the level of isolation.

As a sales leader, make sure you’re addressing your own level of disconnectedness.

There are three core ways to build and maximize the feeling of security between your team members. At the highest level, there’s simply hanging out. The connection between team members gets deeper when they can have shared experiences together. When you can combine hanging out and sharing experiences with having shared goals, the opportunity to maximize this feeling can be achieved.

Sales meetings with the following four elements provide an opportunity to maximize the bonds that can take place:

  • Fun
  • Recognition
  • Education
  • Motivation

Sales, for the hundreds of years before it, was a commission-only environment. It had to be. As a salesperson, it was you against the world. As a sales leader, you had to trust that your salespeople were extrinsically motivated — primarily by dollars. There were no quotas for those individuals.

Quota and quota achievement was solely about bringing in enough revenue to pay for yourself — your salary and the expenses associated with you being in the employ of the company.

Sales in the modern sense was born as an individual sport.


Equitability comes about through the fairness of monetary rewards balanced with the intrinsic inspiration categories such as predictability, recognition, aim, independence, and security. The effort and output are what we give up in order to get all that reward by goodness.

Like our children’s perceptions, the second we feel like there are politics, favorites, or others receiving a larger reward for an equal or lesser effort and output, our brains start to go a bit crazy.

The office environment for salespeople is biased toward extroverts. These extroverts are people who feed off the energy of others. They like to talk through ideas out loud, brainstorm, and strategize informally around just about everything.

Remote work favors introverts. These introverts do best when they have uninterrupted focus and don’t feel as though others are looking and listening as they’re making calls and working their opportunities.

What you’ve experienced is something I like to call expectation inflation. Once we’ve received an additional perk, no matter how out of the ordinary versus others it is, taking it away reduces our overall satisfaction. Our expectations of normalcy have been inflated.

There’s potential for a strong case of subconscious bias to appear in the hybrid environment. A bias toward the individuals who are in the office. You are likely to have a distance bias because “We prefer people or things closer in space or time than what’s farther away.”

Equitability is maximized through transparency and empathy.

Myths and Applications

The Three Myths of Motivation

Learning helps individuals achieve higher levels of recognition via performance and improved status, and helps individuals achieve greater independence through added personal resources.

The Application

There are times when the economy is booming. Sales leaders have two core jobs to bring revenue in the door: recruit and report.

When the economy is not booming, the job of sales leadership becomes five-fold, requiring a disciplined foundation. Embracing a structure for sales leadership allows you to extend your lead in the good times and continuing to grow in the bad. That foundation can be the Five F’s.

It was the summer of 2009. I had been in my role serving as the vice president of worldwide sales for an initially small tech company headquartered in the Valley for probably 18 months. Our success led to a capital raise in early 2009. The best advice I can give you is, “Don’t miss your first-quarter forecast following a fundraise.” Unfortunately, that is exactly what we did.

“Todd, we need you to fly out today. Bob [our lead investor/chairman] needs to meet with us at the office in Menlo Park, California, at 8 am tomorrow. It’ll be you and me, plus Bob … and they’re bringing in a forensic sales expert. Bob started in. “Todd, we just raised a substantial investment in (your organization) and promptly missed the first-quarter number. That’s a problem. As such, we have allocated the next four hours to look at every aspect of your go-to-market strategy to figure out what happened and make sure we have the right people in place to maximize this investment.”

  • We discussed every region: the targeted accounts by geography, by vertical, by size, and by prerequisite (i.e., the focus).
  • We discussed the field in excruciating detail, providing a diagnosis of every single rep’s positives, opportunities for improvement, and what drives them.
  • We dove into the tools and resources in place today and how they are used. We discussed the sales process, our messaging and positioning, our pricing strategy and negotiation approach, and where investments needed to be made in terms of fundamentals.
  • We dove into metrics and all our key performance indicators (KPIs). We worked through the current pipeline, and together thought through what a true forecast should be.
  • We finished by talking about my management style, my approach to driving engagement, and oversight given that our entire sales team was enterprise level (big deals, multiple buyers, long sales cycles), older than I was, but an even bigger deal at the time, all remote (i.e., the fun).

You’re being interviewed for a sales leadership role, and you’re asked, “How would you go about tackling the first 30, 60, 90 days of your tenure in the role?”

Lessons Learned from “The Great Resignation”

Considering the elements that make up our intrinsic inspiration, the best leaders will use them naturally or keep them as a checklist. Am I helping the team with predictability through transparency, consistently considering recognition through feedback and praise, helping them recognize their aim means more than just their numbers, giving the team independence via trust and space to succeed, building security by showing the team I/we have their back, and treating them equitably?


We, as human beings, crave predictability — to have certainty. We crave control and autonomy. We thrive when we’re trusted and provided the resources to do our jobs. A balance was achieved. Self-aware leaders settled into a new balance between their own need to predict and their team members’ need to have independence.


Changing sales jobs became like changing streaming TV service providers for your team members. The physical cost of changing jobs is practically nonexistent. Commute doesn’t change … I still get out of bed, expend a few steps to the kitchen, then a few steps more into their home office. The emotional cost of changing jobs is practically nonexistent. It’s a whole lot easier to leave someone you’ve only met over the phone and video.


  • Do your reps know what their work means to you … on a personal level?
  • Do your reps know what their work means to the company? Can your salespeople see their impact?
  • Do your reps know what their work means to your customers?
  • Do your reps know what their work means to your customers’ customer?
You may also like
The Transparancey Sale
Todd Caponi: The Transparency Sale
Frank V. Cespedes: Sales Management That Works
Graham Yemm: The Sales Book
Walter A. Friedman: Birth of a Salesman; The Transformation of Selling in America

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