How do sales reps build skill and confidence?

Doug Adamic · Sep 8, 2023

Sales is a learnable craft, though it requires an entrepreneurial spirit to enter it.

Once you understand that sales is about improving a customer's business by driving specific outcomes, you see how complex and intricate it is — and that complexity can be learned over time.

Scope: requires entrepreneurial spirit as a starting disposition

3:03 20Sales: Why Everyone is Responsible for Demand Generation, How to do Great Sales Discovery, How to Reduce Sales Cycles and Create Urgency and Deal Reviews; Good and Bad Reasons to Lose a Deal with Doug Adamic, CRO @ Brex

AJ Tennant · Oct 23, 2024

Sales skills can be learned rather than being innate personality traits

Humans can learn anything if they're taught and motivated; he has seen people at Facebook and Slack who lacked a gregarious nature succeed through work ethic, desire to learn, and focus on inputs

Scope: requires motivation and work ethic

2:03 20Sales: Biggest Lessons Scaling Slack from $6M to $1BN in ARR | How to Build a Customer Success Machine and Where Most Go Wrong | The Framework to Hire All Sales Reps: Take-Home Assignments, Hiring Panels and more with AJ Tennant @ Glean

Matt Plank · Dec 20, 2024

Some innate traits (competitiveness, tolerance for losing) are needed for sales, but the actual skills of a good salesperson can be taught

In sales you lose the majority of the time, so you need the right raw ingredients; from there skills are learnable

Scope: requires the right underlying attitude

2:55 20Sales: Rippling's CRO on Why Founders Should Not Create Sales Playbooks | Why Discounting is BS and How to Create Urgency in Deals | The Biggest Lessons on Pricing and How to Win the Pricing Game with Matt Plank

Carlos Delatorre · Jan 24, 2025

Selling is mostly learned rather than innate; what people call a 'born salesperson' is usually just charisma and a big personality, which are not the core of sales ability

Charisma and big personality don't hurt but aren't what makes a great salesperson; empathy and genuine curiosity are innate attributes that help, but most of the job is learned

Scope: empathy and curiosity are innate and do help

3:07 20Sales: Why Every Sales Rep Should Do Pipeline Generation & How to Teach Them | Verticalised Sales Playbooks: When and How | How the Best Sales Reps and Leaders Structure Their Time with Carlos Delatorre, CRO @ Harness

Frank Fillmann · Mar 22, 2023

Starting a career in a competitive sales role, where every account doesn't want to talk to you, is a great way to enter sales

It builds a bulletproof skin because you're constantly talking to accounts that don't want to speak with you

3:02 20Sales: The 3 Profiles of a Sales Rep, How to Negotiate in a Sales Process, How to Sell to a CFO & How You Should Shift Sales Messaging in a Downturn with Frank Fillmann, CRO @ Salesforce Australia

Mark Goldberger · Apr 19, 2023

Not enough salespeople have confidence today, and the cause is lack of reps — junior sellers constantly hit situations they've never seen, whereas hundreds of deals build 'scar tissue', i.e. pattern recognition that lets you act on instinct instead of analyzing every decision.

Pattern recognition removes the need to reason through every novel situation, which is what makes junior reps fearful.

21:08 20Sales: Why You Should Never Hire a VP Sales First, How To Create Urgency in a Sales Process, How to Do Traditional Outbound 10x Better, Why Revenue Doesn't Matter with Your First Customers | Mark Goldberger, Head of Enterprise Sales @ Ramp

Harry Stebbings · Jun 27, 2025

Door-to-door sales is the best possible training ground for a seller because it builds tolerance for rejection

Nobody welcomes a stranger on their doorstep, so you learn to absorb constant rejection

36:02 20Sales: How to Layer Enterprise Sales on PLG | How to Sell AI Tools To Enterprises That Are Scared | Should Reps Own Their Own Pipeline | Mistakes All Founders Make When Moving From Founder-Led to Rep-Led Sales with Kim Graves

Frank Fillmann · Mar 22, 2023

Being an alpha in sales is valuable, but two alphas paired together will crash and burn; the right pairing is an alpha with a less experienced rep

Ego at the expense of others destroys the pairing, whereas a junior paired with an alpha can get three years of education in a year

Scope: alpha traits are healthy individually, just not in combination

19:53 20Sales: The 3 Profiles of a Sales Rep, How to Negotiate in a Sales Process, How to Sell to a CFO & How You Should Shift Sales Messaging in a Downturn with Frank Fillmann, CRO @ Salesforce Australia

Steve Goldberg · Dec 13, 2023

Some of the best relationship sellers cannot close because they can't have the tough conversation, so the manager must have it for them and pair complementary strengths

He managed world-class relationship sellers as a first-time manager who couldn't close, and had to have those conversations himself

39:16 20Sales: How to Close Sales When Selling to CFOs, How to Guarantee You Win Every Renewal, Core Questions All CFOs Ask Today When Buying, Why Revenue Operations is the Most Important Role in a Company with Steve Goldberg, CRO @ Salesloft

Larry Shurtz · May 10, 2024

High-end EQ and empathy cannot be trained; they are the irreducible art of sales and separate the incredible sellers from the merely great

He has tried to train it and failed; when empathy isn't core to someone you are asking them to work outside their DNA, which is uncomfortable and a bad spot for them

Scope: extends beyond reading customers to interactions with coworkers and bosses

9:31 20Sales: How to Build Vertical Sales Teams, Why No Customer Success is BS and Everyone Needs it, How to Hire, Train and Retain the First Reps and Lessons Scaling to $2.1BN Revenue and 1,300 People with Larry Schurtz, CRO @ Genesys

Harry Stebbings · May 10, 2024 · hedged

Sales is becoming more science-based (structure, frameworks, analytics, call recordings, outbound tools), and the only art left may be the EQ of reading people and building relationships

Structure, frameworks, analytics, call recording and outbound tooling have systematized most of the rest of the job

Scope: stated as an outsider's view

9:04 20Sales: How to Build Vertical Sales Teams, Why No Customer Success is BS and Everyone Needs it, How to Hire, Train and Retain the First Reps and Lessons Scaling to $2.1BN Revenue and 1,300 People with Larry Schurtz, CRO @ Genesys

Carlos Delatorre · Jan 24, 2025

Sales is more science than art

We call something 'art' when we don't yet understand it; as with Picasso, gifted people connect dots others don't see, but those patterns can be broken down, learned and replicated

Scope: candidly / his own read

3:55 20Sales: Why Every Sales Rep Should Do Pipeline Generation & How to Teach Them | Verticalised Sales Playbooks: When and How | How the Best Sales Reps and Leaders Structure Their Time with Carlos Delatorre, CRO @ Harness

Ron Gabrisko · Aug 4, 2025

Enterprise sales is a learnable system and a science, not a black box

In complex organizations decisions are made by committees, so the work is navigating the org — identifying decision makers versus influencers — which can be taught through frameworks like MEDDPICC, playbooks, and hiring profiles

Scope: specifically for selling into large, complex enterprises

6:13 20Sales: $0-$3.7BN: The Databricks CRO's Playbook to Build the Fastest GTM Engine in SaaS History | How Databricks Beat Snowflake | How To Build a Sales Org of 5,000 and Close $190M Deals with Ron Gabrisko

Chad Peets · Aug 23, 2024

A new sales rep should invest in their own career development — reaching out to people to learn and working as hard as possible — and doing so will make them better than their peers

Learning fast and outworking others is what separates a rep from everyone around them

58:16 20Sales: How Snowflake Built a Sales Machine | Why You Have to Hire a CRO Pre-Product | Why Most Sales Reps Do Not Perform | Why Hiring Panels are BS in Interviews | Why Remote Sales Reps Do Not Care About Their Development with Chad Peets

John McMahon · Nov 28, 2025

Adaptation is self-driven: after coaching, the rep must look in the mirror and train themselves on the how-to skill, which is the hardest part to acquire.

Reps often know what the play is but not how to execute it, and only repetition on the skill closes that gap.

25:17 20Sales: John McMahon on How to Hire, Train & Retain the Best Sales Reps | How Sales Changes in a World of AI | Sales Lessons from Snowflake and MongoDB | How to Create and Drive a Sales Process with Urgency

Larry Shurtz · May 10, 2024 · hedged

Sales talent is hardwired by about age 13; everything learnable after that is skill and belongs in the science bucket

You can pivot, adjust and learn new things later, but the underlying hardwiring is fixed early

Scope: framed as his own possibly-wrong categorization

8:15 20Sales: How to Build Vertical Sales Teams, Why No Customer Success is BS and Everyone Needs it, How to Hire, Train and Retain the First Reps and Lessons Scaling to $2.1BN Revenue and 1,300 People with Larry Schurtz, CRO @ Genesys

Chad Peets · Aug 23, 2024

Salespeople are born, not made — you can coach someone to be better, but without innate selling ability they cannot sell

Some people are simply petrified of picking up the phone; he never had that fear and could naturally anticipate needs and objections three steps ahead

Scope: training can improve someone who already has the innate ability

5:14 20Sales: How Snowflake Built a Sales Machine | Why You Have to Hire a CRO Pre-Product | Why Most Sales Reps Do Not Perform | Why Hiring Panels are BS in Interviews | Why Remote Sales Reps Do Not Care About Their Development with Chad Peets

Harry Stebbings · Oct 23, 2024

Sales is innate for the top 1% of performers but otherwise teachable, as is true of most skills

Roger Federer's tennis ability is in his bones — the very top of any field is native talent

Scope: only applies at the top 1%

59:08 20Sales: Biggest Lessons Scaling Slack from $6M to $1BN in ARR | How to Build a Customer Success Machine and Where Most Go Wrong | The Framework to Hire All Sales Reps: Take-Home Assignments, Hiring Panels and more with AJ Tennant @ Glean

AJ Tennant · Oct 23, 2024

Only the top ~5% of sales talent is innate; below that, people can reach elite level purely by grinding at it

LeBron James's level is innate, but players like Steve Nash showed no obvious early innate NBA ability and got there by grinding

Scope: top 5% is the innate echelon

59:18 20Sales: Biggest Lessons Scaling Slack from $6M to $1BN in ARR | How to Build a Customer Success Machine and Where Most Go Wrong | The Framework to Hire All Sales Reps: Take-Home Assignments, Hiring Panels and more with AJ Tennant @ Glean

John McMahon · Nov 28, 2025

Coachability is not enough — many reps accept coaching but never actually adapt, and those are the people who hit a wall as the product, market and buyer change with scale.

Adapting means changing the skill set, not just acquiring knowledge, and most people don't do it.

21:55 Adaptation not coachability separates reps

John McMahon · Nov 28, 2025

Becoming a world-class sales leader requires a great mentor plus intelligence, drive, coachability, adaptability, hard work and discipline

You need somebody to teach and coach you, and you have to be coachable enough to absorb it

28:37 Great mentor plus innate drive and discipline

Carles Reina · Feb 14, 2026

The most valuable thing a sales leader can do is have new reps watch them pitch and watch them deliver on every promise to customers

Trust with your customers is the best asset you have, and modeling it sets the right culture and way of operating in the team

53:13 Leader modeling pitching and promise keeping

Frank Fillmann · Mar 22, 2023

The scalable way to specialize a sales team is to put a been-there-done-that 'quarterback' at the front of a two-to-three-person team and place high potentials inside it, so the team teaches the team

Teaching every seller one by one is impossible for a sales leader; following a leader gets high potentials there far faster and drives scalability and repeatability without the leader doing everything themselves

9:59 Quarterback plus high potentials team teaches team

Ben Fiechtner · Aug 2, 2024

Sellers should play to their own strengths and be authentically themselves rather than replicating a company's model seller personality

Not everyone is the gregarious relationship person or the data-driven ROI seller; a Salesforce exec telling him to just be himself was the biggest unlock in his career

50:41 Authentic self beats replicating a companys model seller persona

Kim Graves · Jun 27, 2025

Confidence in how you present yourself is the decisive skill for a new sales rep, especially when calls get hard.

Talking to happy users is easy; insecurity shows up when the customer asks for a discount or raises a competitor, and you have to remind yourself you earned the role for a reason.

6:19 Confidence under pressure is the decisive skill

Harry Stebbings · Jun 27, 2025

Confidence is everything in sales, and reps should defuse the pressure by recognizing the worst case — losing one deal — is survivable because there are more clients.

He draws on his own experience fundraising, where confidence was the deciding factor.

7:01 Reframe worst case as survivable to build confidence

Mark Goldberger · Apr 19, 2023

The key to sales mentorship is helping people see their blind spots rather than teaching a fixed playbook, since the dynamics and buttons to push change from rep to rep.

The goal is to make the mentee more well-rounded; e.g. showing a founder he had all his eggs in one opportunity and needed more pipeline.

22:15 Blind spot mentorship over fixed playbooks

Chris Degnan · Nov 10, 2023

Sales talent is best developed by a leader who takes feedback themselves and who enlists other leaders to mentor people, rather than developing everyone personally.

Because he does it one way doesn't mean it's the best way; it's like a family raising people versus being a single parent, and he learns daily from his own reps and leaders.

37:13 Distributed mentorship across many leaders

Steve Goldberg · Dec 13, 2023

The differentiator in sales careers and big deals is obsession — with learning, improving, the customer, and winning — not raw talent

Analogy: the lion isn't the strongest, fastest or smartest animal but is king of the jungle because it's obsessed with winning; the people he sees closing big deals are maniacally focused on the customer and relationship

43:31 Obsession beats raw talent

Ashley Kelly · Jun 7, 2024

A new SDR should shadow and copy the team's top performer exactly before adding their own twist, rather than trying to reinvent the wheel

There's no asterisk on hitting quota because you mimicked a top performer; too many new reps try to make a name by doing it differently

47:00 Copy the top performer before adding your twist

Matt Rosenberg · Oct 4, 2023

In the earliest days every sales call should be recorded and reviewed together by the sales leader and reps, using a three-by-three framework (three things that went well, three things you'd do differently, from the caller, the listener, and the leader)

Like an athlete breaking down tape, joint review produces alignment, best practice and pattern recognition, which scales the team faster than any other mechanism because it multiplies exposure and at-bats

22:05 Joint call tape review multiplies at bats