The Human Side of Selling with Jeff Jaworski

Welcome back to Snafu with Robin Zander.

In this episode, I’m joined by Jeff Jaworsky, who shares his journey from a global role at Google to running his own business while prioritizing time with his children.

We talk about the pivotal life and career decisions that shaped this transition, focusing on the importance of setting boundaries—both personally and professionally. Jeff shares insights on leaving a structured corporate world for entrepreneurship and the lessons learned along the way.

We also explore the evolving landscape of sales and entrepreneurship, highlighting how integrating human connection and coaching skills is more important than ever in a tech-driven world. The conversation touches on the role of AI and technology, emphasizing how they can support—but not replace—essential human relationships.

Jeff offers practical advice for coaches and salespeople on leveraging their natural skills and hints at a potential future book exploring the intersection of leadership, coaching, and sales.

If you’re curious about what’s next for thoughtful leadership, entrepreneurship, and balancing work with life, this episode is for you. And for more conversations like this, get your tickets for Snafu Conference 2026 on March 5th here, where we’ll continue exploring human connection, business, and the evolving role of AI.

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Early life and first real boundary

• Jeff grew up up in a structured, linear environment

• Decisions largely made for you

• Clear expectations, predictable paths

• Post–high school as the first inflection point

• College chosen because it’s “what you’re supposed to do”

• Dream: ESPN sports anchor (explicit role model: Stuart Scott)

• Reality check through research

• Job placement rate: ~3%

• First moment of asking:

• Is this the best use of my time?

• Is this fair to the people investing in me (parents)?

• Boundary lesson #1

• Letting go of a dream doesn’t mean failure

• Boundaries can be about honesty, not limitation

• Choosing logic over fantasy can unlock unexpected paths

• Dropping out of college → accidental entry into sales

• Working frontline sales at Best Buy while in school

• Selling computers, service plans, handling customers daily

• Decision to leave college opens capacity

• Manager notices and offers leadership opportunity

• Takes on home office department

• Largest sales category in the store

• Youngest supervisor in the company (globally) at 19

• Early leadership challenges

• Managing people much older

• Navigating credibility, age bias, exclusion

• Learning influence without authority

• Boundary insight

• Temporary decisions can become formative

• Saying “yes” doesn’t mean you’re locked in forever

• Second boundary: success without sustainability

• Rapid growth at Best Buy

• Promotions

• Increasing responsibility

• Observing manager life up close

• 60-hour weeks

• No real breaks

• Lunch from vending machines

• Internal checkpoint

• Is this the life I want long-term?

• Distinguishing:

• Liking the work

• Disliking the cost

• Boundary lesson #2

• You can love a craft and still reject the lifestyle around it

• Boundaries protect the future version of you

• Returning to school with intention

• Decision to go back to college

• This time with clarity

• Sales and marketing degree by design, not default

• Accelerated path

• Graduates in three years

• Clear goal: catch up, not start over

• Internship at J. Walter Thompson

• Entry into agency world

• Launch of long-term sales and marketing career

• Pattern recognition: how boundaries actually work

• Ongoing self-check at every stage

• Have I learned what I came here to learn?

• Am I still growing?

• Is this experience still stretching me?

• Boundaries as timing, not rejection

• Experiences “run their course”

• Leaving doesn’t invalidate what came before

• Non-linear growth

• Sometimes stepping down is strategic

• Demotion → education

• Senior role → frontline role (later at Google)

• Downward moves that enable a bigger climb later

• Shared reflection with Robin

• Sales as a foundational skill

• Comparable to:

• Surfing (handling forces bigger than you)

• Early exposure to asking, pitching, rejection

• Best Buy reframed

• Customer service under pressure

• Handling frustrated, misinformed, emotional people

• Humility + persuasion + resilience

• Parallel experiences

• Robin selling a restaurant after learning everything she could

• Knowing the next step (expansion) and choosing not to take it

• Walking away without knowing what’s next

• Core philosophy: learning vs. maintaining

• “If I’m not learning, I’m dying”

• Builder mindset, not maintainer

• Growth as a non-negotiable

• Career decisions guided by curiosity, not status

• Titles are temporary

• Skills compound

• Ladders vs. experience stacks

• Rejecting the myth of linear progression

• Valuing breadth, depth, and contrast

• The bridge metaphor

• Advice for people stuck between “not this” and “not sure what next”

• Don’t leap blindly

• Build a bridge

• Bridge components

• Low-risk experiments

• Skill development

• Small tests in parallel with current work

• Benefits

• Reduces panic

• Increases clarity

• Turns uncertainty into movement

Framing the modern career question

• Referencing the “jungle gym, not a ladder” idea

• Careers as lateral, diagonal, looping — not linear

• Growth through range, not just depth

• Connecting to Range and creative longevity

• Diverse experiences as a competitive advantage

• Late bloomers as evidence that exploration compounds

• Naming the real fear beneath the metaphor

• What if exploration turns into repeated failure?

• What if the next five moves don’t work?

• Risk of confusing experimentation with instability

• Adding today’s pressure cooker

• Economic uncertainty

• AI and automation reshaping work faster than previous generations experienced

• The tension between adaptability and survival

• The core dilemma

• How do you pursue a non-linear path without tumbling back to zero?

• How do you “build the bridge” instead of jumping blindly?

• How do you keep earning while evolving?

• The two-year rule

• Treating commitments like a contract with yourself

• Two years as a meaningful unit of time

• Long enough to:

• Learn deeply

• Be challenged

• Experience failure and recovery

• Short enough to avoid stagnation

• Boundaries around optional exits

• Emergency ripcord exists

• But default posture is commitment, not escape

• Psychological benefit

• Reduces panic during hard moments

• Prevents constant second-guessing

• Encourages depth over novelty chasing

• The 18-month check-in

• Using the final stretch strategically

• Asking:

• Am I still learning?

• Am I still challenged?

• Does this align with my principles?

• Shifting from execution to reflection

• Early exploration of “what’s next”

• Identifying gaps:

• Skills to acquire

• Experiences to test

• Regaining control

• External forces aren’t always controllable

• Internal planning always is

• Why most people get stuck

• Planning too late

• Waiting until:

• Layoffs

• Burnout

• Forced transitions

• Trying to design the future in crisis

• Limited creativity

• Fear-based decisions

• Contrast with proactive planning

• Calm thinking

• Optionality

• Leverage

• Extending the contract

• Recognizing unfinished business

• Loving the work

• Still growing

• Still contributing meaningfully

• One-year extensions as intentional choices

• Not inertia

• Not fear

• Conscious recommitment

• A long career, one organization at a time

• Example: nearly 13 years at Google

• Six different roles

• Multiple reinventions inside one company

• Pattern over prestige

• Frontline sales

• Sales leadership

• Enablement

• Roles as chapters, not identities

• Staying while growing

• Leaving only when growth plateaus

• Experience stacking over ladder climbing

• Rejecting linear advancement

• Titles matter less than skills

• Accumulating perspective

• Execution

• Leadership

• Systems

• Transferable insight

• What works with customers

• What works internally

• What scales

• Sales enablement as an example of bridge-building

• Transition motivated by impact

• Desire to help at scale

• Supporting many sellers, not just personal results

• A natural evolution, not a pivot

• Built on prior sales experience

• Expanded influence

• Bridge logic in action

• Skills reused

• Scope widened

• Risk managed

• Zooming out: sales, stigma, and parenting

• Introducing the next lens: children

• Three boys: 13, 10, 7

• Confronting sales stereotypes

• Slimy

• Manipulative

• Self-serving

• Tension between reputation and reality

• Loving sales

• Building a career around it

• Teaching it without replicating the worst versions

• Redefining sales as a helping profession

• Sales as service

• Primary orientation: benefit to the other person

• Compensation as a byproduct, not the driver

• Ethical center

• Believe in what you’re recommending

• Stand behind its value

• Sleep well regardless of outcome

• Losses reframed

• Most deals don’t close

• Failure as feedback

• Integrity as the constant

• Selling to kids (and being sold by them)

• Acknowledging reality

• Everyone sells, constantly

• Titles don’t matter

• Teaching ethos, not tactics

• How you persuade matters more than whether you win

• Kindness

• Thoughtfulness

• Awareness of the other side

• Everyday negotiations

• Bedtime extensions

• Appeals to age, fairness, peer behavior

• Sales wins without good reasoning

• Learning opportunity

• Success ≠ good process

• Boundaries still matter

• Why sales gets a bad reputation

• Root cause: selfishness

• Focus on “what I get”

• Language centered on personal gain

• Misaligned value exchange

• Overselling

• Underdelivering

• The alternative

• Lead with value for the other side

• Hold mutual benefit in the background

• Make the exchange explicit and fair

• Boundaries as protection for both sides

• Clear scope

• What’s included

• What’s not

• Saying no as a service

• Preventing resentment

• Preserving trust

• Entrepreneurial lens

• Boundaries become essential

• Scope creep erodes value

• Clarity sustains long-term relationships

Value exchange, scope, and boundaries

• Every request starts with discernment, not enthusiasm

• What value am I actually providing?

• What problem am I solving?

• How much time, energy, and attention will this really take?

• The goal isn’t just a “yes”

• Both sides need to feel good about:

• What’s being given

• What’s being received

• What’s being expected

• What’s realistically deliverable

• Sales as a two-sided coin

• Mutual benefit matters

• Overselling creates future resentment

• Promising “the moon and the stars” is how trust breaks later

• Boundaries as self-respect

• Clear limits protect delivery quality

• Good boundaries prevent repeating bad sales dynamics

• Saying less upfront often enables better outcomes long-term

• Transitioning into coaching and the SNAFU Conference

• Context for the work today

• Speaking at the inaugural SNAFU Conference

• Focused on reluctant salespeople and non-sales roles

• Why coaching became the next chapter

• Sales is everywhere, regardless of title

• Coaching emerged as a natural extension of sales leadership

• The origin story at Google

• Transition from sales leadership to enablement

• Core question: how do we help sellers have better conversations?

• Result: building Google’s global sales coaching program

• Grounded in practice and feedback

• Designed to prepare for high-stakes conversations

• The hidden overlap between sales and coaching

• Coaching as an underutilized advantage

• Especially powerful for sales leaders

• Shared core skills

• Deep curiosity

• Active listening

• Presence in conversation

• Reflecting back what’s heard, not what you assume

• The co-creation mindset

• Not leading someone to your solution

• Guiding toward their desired outcome

• Why this changes everything

• Coaching improves leadership effectiveness

• Coaching improves sales outcomes

• Coaching reshapes how decisions get made

• A personal inflection point: learning to listen

• Feedback that lingered

• “Jeff is often the first and last to speak in meetings”

• The realization

• Seniority amplified his voice

• Being directive wasn’t the same as being effective

• The shift

• Stop being the first to speak

• Invite more voices

• Lead with curiosity, not certainty

• The result

• More evolved perspectives

• Better decisions

• Sometimes realizing he was simply wrong

• The parallel to sales

• Talking at customers limits discovery

• Pre-built pitch decks obscure real needs

• The “right widget” only emerges through listening

• What the work looks like today

• A synthesis of experiences

• Buyer

• Seller

• Sales leader

• Enablement leader

• Executive coach

• How that shows up in practice

• Executive coaching for sales and revenue leaders

• Supporting decision-making

• Developing more coach-like leadership styles

• Workshops and trainings

• Helping managers coach more effectively

• Building durable sales skills

• Advisory work

• Supporting sales and enablement organizations at scale

• The motivation behind the shift

• Returning to the core questions:

• Am I learning?

• Am I growing?

• Am I challenged?

• A pull toward broader impact

• A desire to test whether this work could scale beyond one company

• Why some practices thrive and others stall

• Observing the difference

• Similar credentials

• Similar training

• Radically different outcomes

• The uncomfortable truth

• The difference is sales

• Entrepreneurship without romance

• Businesses don’t “arrive” on their own

• Clients don’t magically appear

• Visibility, rejection, iteration are unavoidable

• Core requirements

• Clear brand

• Defined ICP

• Articulated value

• Credibility to support the claim

• Debunking “overnight success”

• Success is cumulative

• Built on years of unseen experience

• Agency life + Google made entrepreneurship possible

• Sales as a universal survival skill

• Especially now

• Crowded markets

• Economic uncertainty

• Increased competition

• Sales isn’t manipulation

• It’s how value moves through the world

• Avoiding the unpersuadable

• Find people who already want what you offer

• Make it easier for them to say yes

• For those who “don’t want to sell”

• Either learn it

• Or intentionally outsource it

• But you can’t pretend it doesn’t exist

• The vision board and the decision to leap

• December 18, 2023

• 45th birthday

• Chosen as a forcing function

• Purpose of the date

• Accountability, not destiny

• A moment to decide: stay or go

• Milestones on the back

• Coaching certification

• Experience thresholds

• Personal readiness

• Listening to the inner signal

• The repeated message: “It’s time”

• The bridge was already built

• Skills stacked

• Experience earned

• Risk understood

• Stepping forward without full certainty

• You never know what’s on the other side

• You only learn once you cross and look around

Decision-making and vision boards

• Avoid forcing yourself to meet arbitrary deadlines

• Even if a date is set for accountability (e.g., a 45th birthday milestone), the real question is: When am I ready to act?

• Sometimes waiting isn’t necessary; acting sooner can make sense

• Boundaries tie directly into these decisions

• They help you align personal priorities with professional moves

• Recognizing what matters most guides the “when” and “how” of major transitions

• Boundaries in the leap from corporate to entrepreneurship

• Biggest boundary: family and presence with children

• Managing a global team meant constant connectivity and messages across time zones

• Transitioning to your own business allowed more control over work hours, clients, and priorities

• The pro/con framework reinforced the choice

• Written lists can clarify trade-offs

• For this example, the deciding factor was: “They get their dad back”

• Boundaries in entrepreneurship are intertwined with opportunity

• More freedom comes with more responsibility

• You can choose your hours, clients, and areas of focus—but still must deliver results

• Preparing children for a rapidly changing world

• Skill priorities extend beyond AI and automation

• Technology literacy is essential, but kids will likely adapt faster than adults

• Focus on human skills

• Building networks

• Establishing credibility

• Navigating relationships and complex decisions

• Sales-related skills apply

• Curiosity, empathy, observation, and problem-solving help them adapt to change

• These skills are timeless, even as roles and tools evolve

• Human skills in an AI-driven world

• AI is additive, not replacement

• Leverage AI to complement work, not fear it

• Understand what AI does well and where human judgment is irreplaceable

• Coaching and other human-centered skills remain critical

• Lived experience, storytelling, and nuanced judgment cannot be fully replaced by AI

• Technology enables scale but doesn’t replace complex human insight

• The SNAFU Conference embodies this principle

• Brings humans together to share experiences and learn

• Demonstrates that face-to-face interaction, stories, and mutual learning remain valuable

• Advice for coaches learning to sell

• Coaches already possess critical sales skills

• Curiosity, active listening, presence, problem identification, co-creating solutions

• These skills, when applied to sales, still fall within a helping profession

• Key approach

• Use your coaching skills to generate business ethically

• Reframe sales as an extension of support, not self-interest

• For salespeople

• Learn coaching skills to improve customer conversations

• Coaching strengthens empathy, listening, and problem-solving abilities, all core to effective selling

• Book and resource recommendations

• Non-classical sales books

• Setting the Table by Danny Meyer → emphasizes culture and service as a form of sales

• Unreasonable Hospitality by Will Guidara → creating value through care for people

• Coaching-focused books

• Self as Coach, Self as Leader by Pam McLean

• Resources from the Hudson Institute of Coaching

• Gap in sales literature

• Few resources fully integrate coaching with sales

• Potential upcoming book: The Power of Coaching and Sales