Obsess over the Non-Obvious
I’ve been fortunate enough to build a consultancy that only solves one problem over and over: turning average sales teams into best-in-class, category-defining sales teams.
Firsthand, I've noticed that companies with a great sales team earn better valuations in some instances, which can be 3X-5X a valuation or better.
I first experienced this as an operator and sales leader in 2015. The largest hospital company in the US acquired our business. This publicly traded Fortune 300 healthcare system paid a premium to buy our business because of the sales team they would now own and operate.
I continue to see elite sales teams serve as a value multiplier in my consultancy.
In early 2024, one of my consulting clients notified me that they would be taking the company to market, hoping to find a buyer and finalize a transaction within the year. During my coaching calls with the sales leader, we spent a lot of time demonstrating that the “asset” was the sales team.
I showed him how to position all past revenue growth as a dependable annuity that would continue to produce dividends for the acquirer and how to ensure the team would continue to perform and improve over time.
Within six months, the company had sold at a premium to a great buyer, and my client (the sales leader) could walk away with a pile of immediate cash vs. a long earn-out period.
He walked away without any golden handcuffs because he demonstrated that he wasn’t special, but the system he built was. This machine was loaded with elite salespeople and sales managers who were happy to stay, serve the new owner, and continue representing a noble offering that aligned with their life’s plan and purpose.
*Sales talent isn’t the only component required to build a category-defining sales team. The sales leader must understand the importance of territory design, compensation, technology, coaching and performance management, refining the offering, etc.
But without exception, the category-defining sales teams have the best sales talent. Their worst-performing salesperson might be better than your top performers.
How do they build their category-defining sales team?
Well, they don’t fill it with sales performers like myself.
I was an average, middle-of-the-pack salesperson
I consistently hit quota, but it was never easy, and what skills I possessed were only borrowed from other, much better salespeople.
Like any new salesperson, I introduced myself to everyone on the team and asked them, “If you were a recently hired salesperson like me, what would you do?”
What’s interesting to me is that some of the nicest salespeople eager to share ideas, advice, and perspectives weren’t that great at selling. If I were to rank the helpfulness of each rep on the team, it would look like the direct inverse of sales performance. It wasn’t that the top salespeople weren’t nice or didn't want to be helpful, it’s that they didn’t tell me anything different from what the average sellers told me. They told me what I already knew about selling:
Make more calls than anyone else
Become an expert on our offering
Listen well
Ask great questions
Never take no for an answer
It didn't add up.
The answers only focussed on the obvious
Every professional salesperson, even the bad ones, can:
Hold a conversation
Make prospecting calls
Ask good questions
Overcome objections
Mentally reset after a bad meeting, lost deal, or bad month
These are all obvious things any salesperson should be able to do, but they aren’t indicators of being elite. Even the average salesperson (like me and many others) should be able to develop a strong sense of competency in the obvious skills.
These obvious skills will get you to middle-of-the-pack performance, hitting quota some months and years, but won’t propel you to the top of the leaderboard.
If the best and worst salespeople have the same advice for a new rep, why aren’t they all achieving the same results?
Were the best reps withholding secret tactics from me?
At first, I thought so, but I found the truth as I spent more time with the top performers. My career as a forgettable football player helped me see the non-obvious truth about elite salespeople.
College football is full of people who are 6’5”, 225 pounds of muscle, lightning quick, and strong as an ox. But according to the NFL, only 1.6% of college football players will play in the NFL. All supremely athletic, but those athletic, obvious talents aren’t enough to make it to the NFL, let alone have a long and notable career.
Physically, is Patrick Mahomes better than every other college player who failed to make the cut? Probably not because it’s not the obvious characteristics that make him world-class. It’s the non-obvious. Speed of thought, a 360-degree view of play, for example, is not obvious.
The sales profession has non-obvious skills that are required to be elite, and most elite salespeople and sales leaders don’t know what these skills are or, if they do, how to interview for them.
So, what are the non-obvious skills?
1. Self-Awareness
Every sales leader wants a self-aware salesperson, but it’s difficult to spot self-awareness during the interview process. Focus on a few key areas: past failure, understanding of strengths and weaknesses, and structured professional development.
Past Failure
I like to ask candidates to describe a past failure and what they learned from it; self-aware salespeople can provide genuine insights. Be aware, though, that the quality of the question determines the quality of the answer. Let me show you.
"Can you describe a past failure and what you learned from it?" is a softball question and usually leads to a benign answer.
Instead, ask something like, “We’ve all blown deals. Tell me about a time in your current role where you blew what should have been a straightforward deal. Pricing was fine, the offering was what they needed, but YOU found a way to screw it up.”
Most candidates will be shocked that you would even ask this question. Pay attention to how their body language shifts immediately after you ask the question. If they can’t think of a recent example, that's a red flag. Even elite salespeople sabotage straightforward deals from time to time. The difference between the elite and the average is that they keep a close inventory of their mistakes, and more importantly, they aren’t ashamed to discuss them.
Their self-awareness reminds them that no single deal (good or bad) defines them and that mistakes happen. What’s more important than the mistake is how they respond to it. You’re looking for a candidate who isn’t ruffled by the question and can quickly give you an example, with details, plus a plan to mitigate this mistake from happening again.
Understanding Strengths and Weaknesses
Conduct a behavioral assessment as part of every interview process. The market has plenty of tools for this exercise. The more popular ones include Strengths Finder, DiSC, Myers-Brigg, and, my favorite, The Predictive Index.
The tool doesn’t matter as much as the exercise of conducting the assessment. It’s a good practice to share the results with the candidate to determine their self-awareness by how they react to the results and the questions you ask about them.
If you look at my Predictive Index results, you can see that I am intense, restless, not good with rigid structure, and assertive.
These characteristics are neither good nor bad, they just explain who I am.
Talking about a candidate’s results with them (regardless of the results) will tell you about their self-awareness, and that’s all that’s relevant for now. When a candidate challenges the results, that’s a red flag. It means they aren’t self-aware.
Here’s how I lead the conversation:
If you ask, “What did you learn about yourself from the behavioral assessment?” That's a good start, but I like to pick an element of their results that I think they might not like and take the conversation in that direction.
If I were interviewing me to assess self-awareness, I would ask, "Tell me how your intensity gets you in trouble," and "Does your self-confidence coupled with your informal nature ever cause you to not be as prepared for a meeting as you would like?"
Self-aware candidates won’t be offended or rattled by these types of questions. The elite candidates will be aware of their strengths and weaknesses and have a professional development plan intended to amplify their strengths and mitigate their weaknesses.
Another great question to ask the candidate to finish this statement “I wish I were someone who…”
Structured Professional Development
My behavioral assessment shows that I’m very independent. Early in my sales leadership career, I received feedback from the CEO that I didn’t want to hear, but it was true.
“Needs to seek counsel more often and proceed with process planning and analysis more comprehensively before leaping.”
I was independent and confident, which was a recipe for operating in a silo and not collaborating with my other leadership peers. If I wanted to be an elite sales leader, this needed to be improved. So started a learning journey to figure out how to better seek counsel before leaping.
When you interview salespeople ask about professional development. One of my favorite questions that points to their eagerness to learn and grow is, "When it comes to selling, how do you improve your craft? Who do you study? Where do you turn?"
I’ve learned that the best salespeople have a learning plan. They're reading a sales book or taking a course, or they love listening to podcasts on a sales-related topic.
2. Self-competitive
Sales is competitive. Your offering competes with other offerings to win customers and market share. So naturally, competitive people, riding on the highs of winning and learning from the lows of losing, will do well in sales. That's why so many ex-athletes do well in sales careers.
But being competitive is obvious.
What’s not so obvious is how elite salespeople define winning. They aren’t striving to just win the next deal or climb the leaderboard. They don’t compare themselves to other salespeople on the team, and they don’t celebrate much when they close a deal.
The elite salespeople compete with themselves, and all their competitive energy is focused inward. It's a never-ending game that gets harder to play with time because every new personal best becomes the new standard.
One of my favorite questions to examine a candidate's sense of self-competition is, "Do you like to win or hate to lose?" Elite salespeople hate to lose. They know that the sweetness of victory fades (quickly), but the bitterness of defeat lingers.
Why do they hate losing more than they like winning?
Winning is expected. It's a data point that all the training and preparation came together well in the situation. They know that a won deal, one great quarter, or a good year is over instantly, and the scoreboard returns to zero.
One of the best things about leading an elite salesperson is that the standard they set for themselves is so high that even when they don’t meet their personal standard, they still exceed your expectations. If you expect a certain amount of activity or revenue, the elite salesperson quietly expects more and won’t be satisfied to merely meet your expectations. The elite salesperson is trying to put themselves out of business because they know that all the work and talent that got them this far might not be enough to get them where they want to go.
But where are they going?
3. A Life Plan And Purpose Bigger Than Work
Every elite salesperson has a plan for their life.
Work is integral to the plan, but it's not everything. They know what they want from life and have a plan to achieve it. I've never interviewed a candidate who turned out to be elite and didn't have a written plan for the next season of life.
Maybe the season was three years, five years, or ten years, but regardless of the period, there was a plan. The elite salesperson is eager to share that your job is just a step in a larger stairwell to a future them.
An elite salesperson might say something like, “I plan to stay in this role for 2 years, then I’ll move on to leadership or start my own company.”
Instead of operating out of fear, dig into what this job means for their larger purpose and career. Who knows, maybe their success in two short years will show that they could be much more valuable to your business than you originally thought. You might be interviewing your replacement.
To try and learn about a candidate's greater purpose and plan, I ask
“Who do you want to be when you grow up?”
“What will success in this role make possible for you?”
"How much money did you make last year, and what did you do with it?"
"What's your personal monthly burn rate?"
These questions can only be answered (well) by someone who has a plan for their life and devotes time to sticking to it.
4. Productive Paranoia
Since the bitterness of defeat lingers longer than the sweetness of victory, elite salespeople are paranoid about losing—they fear not being the best, losing a customer, or not meeting the standards they’ve set for themselves.
Paranoid behavior is enormously functional if fear is channeled into extensive preparation and calm, clearheaded action; hence, the term "Productive Paranoia."
Productive Paranoia is a concept developed by Jim Collins in the book Great by Choice.
The only mistakes you can learn from are the ones you survive. Salespeople who stave off decline and navigate turbulence assume that conditions can unexpectedly change violently and fast. They obsessively ask, What if?
By preparing ahead of time, building reserves, preserving a margin of safety, bounding risk, and honing their disciplines in good times and bad, they handle disruptions from a position of strength and flexibility.
They’ve spent the effort to develop self-awareness and, in some instances, self-mastery. They're in a never-ending competition with themselves to get better every day and achieve their life's purpose, so of course, they ask, "What if?" all the time.
For a person who hates losing, the loss of not achieving their life’s mission is enough to make them obsess over the threats that could keep them from being who they really are.
But the paranoia doesn’t paralyze them, it propels them. During the hiring interview, I ask “What keeps you up at night?” I’m looking for an answer that reveals someone living in a world of constant danger.
Here’s an example from a salesperson coming off back-to-back President’s Club years, “What keeps me up at night is thinking about what a waste it would be to have worked this hard, making all these sacrifices, to only get this far.”
Another helpful question to ask during the interview is, "What time do you start your day? What does your daily routine look like?" I recently had a salesperson tell me that they don't set an alarm but trust that their dog will wake them up no later than 7:30 a.m. so they can walk them and be at work by 8 a.m. That’s not how an elite salesperson lives.
Not all elite salespeople are early risers, but without exception, they start their day hours before work starts. Why? They know that to be elite, they need to take care of their body, mind, and spirit before work starts. Professional athletes don’t wake up an hour before the game starts. Instead, they’re at the stadium hours before the game starts, stretching, getting settled, and visualizing the game.
Elite salespeople do the same thing. They start their day with exercise, reading, meditation, writing, planning, etc. Listen for candidates who start their day well before the workday start time.
But paranoia isn’t always productive. When the paranoia paralyzes a salesperson, it becomes problematic. Problematic Paranoia occurs when a salesperson allows the paranoia to misguide their energy, efforts, and attention. Instead of using mistakes and missed opportunities as learning events, they spiral. Here’s what it looks like:
Incessantly seeking security and affirmation from the sales leader vs. focusing on closing more deals
Looking for another job vs. looking for new customers
Complaining about how hard the job is vs. asking other reps for help
This paranoia is easy to spot when they work for you but harder to identify during the interview process.
I first learned about the difference between productive and unproductive paranoia when I discovered the concept of Locus of Control in Charles Duhig’s book The Power of Habit. The book references Julian B. Rotter’s work, which says a person's "locus" is conceptualized as internal (a belief that one can control one's own life) or external (a belief that life is controlled by outside factors that the person cannot influence, or that chance or fate controls their lives).
Individuals with a strong internal locus of control believe events in their lives are primarily a result of their own actions. For example, when receiving exam results, people with an internal locus of control tend to praise or blame themselves and their abilities. People with a strong external locus of control tend to praise or blame external factors such as the teacher or the difficulty of the exam.
Asking questions that reveal if the candidate is in charge of their lives or if they believe circumstances beyond their control play a big role in their success or failure. You are looking for a candidate that uses "what if" to inform their next, controllable action vs. focusing on uncontrollable aspects of their life and career.
Insatiably Curious
I know the best salespeople are the most curious salespeople. You know this, too; it's obvious. But how to interview to gauge a salesperson's curiosity isn't as obvious. There are two good ways to see if a candidate is insatiably curious during the interview process. I need to clarify that asking great questions (an obvious skill) isn't the same as being insatiably curious (non-obvious). The distinction is how they ask questions and what they do with your answers.
Did They Just Interview Me?
In a good sales discovery meeting with a prospect, the prospect should do most of the talking, not the salesperson. Good salespeople ask great questions that create the atmosphere for the prospect to do most of the talking. As the prospect talks, the salesperson makes useful discoveries about the prospect’s situation. This is simple to replicate in the interview process, yet too many interviewers don’t use the process as an opportunity to judge a candidate's curiosity. You ask the candidate question after question, but rarely do you encounter a candidate that interviews you.
Elite salespeople have a way of gently and politely taking charge of the questions asked during the interview process. It’s very subtle, and when it’s done well, the untrained interviewer doesn’t see it coming. You walk away feeling like you’ve just left the therapist's office and have a better sense of what you’re looking for in a candidate, all because the elite candidate pulled the clarity from you with great questions.
If you walk away from the interview and you’ve answered questions that no other candidate has asked, you’ve just been interviewed by an elite salesperson. Here are some questions an elite salesperson won’t ask:
What’s the typical day like?
What’s your vacation policy?
Can I work remotely?
What’s training like?
They don't ask these questions because they already know the answers and/or because the answers will not help them determine whether they can be successful in your sales organization.
What's the typical day like? Probably meeting with prospects or trying to meet with prospects. What’s your vacation policy? What elite salesperson is thinking about a vacation while trying to make a career move? Work remotely? They will work where they can be the most productive and have the best access to customers, other reps, and internal resources. Training? Because of their strong internal locus of control, they already know the responsibility is theirs, not the company’s.
Don’t be surprised if they ask questions that make you feel uncomfortable. They’re just curious. Expect questions like “Why should I work for you? How will you make me a better salesperson?” “Who’s the best rep? Why are they successful? Can I chat with them about what it’s like to work with you?” “What’s the dynamic with marketing or customer success?” “How many reps did you fire last year? Why?” “Which current rep ramped the fastest? Why?”
Never Stop Learning
The other way to spot curiosity is to ask, “What are you currently reading or studying?” Elite salespeople are always learning something related to their craft.
Look, I know most people don’t read anymore, especially books. Instead, they watch YouTube and social media reels, listen to podcasts, and scroll LinkedIn for articles and courses on a subject. Great, that’s learning, too.
Learning is powerful because it changes your perspective and arms you with new ideas. Elite salespeople have learned that it’s not what they know that makes them successful, its that they have so much more to learn–that kind of curiosity is what makes them successful. I read this quote in Ego Is The Enemy and it pretty much sums up the importance of learning.
“As the island of Knowledge grows, so do the shores of our ignorance –the boundary between the known and the unknown. Learning more about the world doesn’t lead to a point closer to a final destination but to more questions and mysteries.”
―
Marcelo Gleiser,
The Island of Knowledge: The Limits of Science and the Search for Meaning
Once you know these non-obvious skills elite salespeople possess, the natural follow-up question is: how and where do I find these people?
That’s what’s coming in the next article.
Until then, I’d love to know what you found most useful in this article. Anything you’d like me to expand on? Drop me an email at nigel@nigelgreen.co.
