How to Sell Yourself – A Workshop

Robin Zander hosted a Snafu webinar for the Sidebar community on non-sales selling—think self-promotion for career transitions, freelancers, entrepreneurs, and product people. The goal: learn to “sell yourself” without the ick factor.

 

Participants shared fears: follow-ups feel intimidating, sales feels slimy, and success seems like a numbers game. Robin reframed it: selling is really about enrollment—being a chief evangelist for your work, not begging for attention.

 

Drawing on stories from his childhood pumpkin patch, his time as a personal trainer (where desperation lost him clients), and opening Robin’s Cafe in San Francisco (raising $40k, serving multiple stakeholders, training staff with Danny Meyer’s principles), he showed the difference between selling from need vs. service. Long-term success comes from genuine connection, curiosity, optimism, and passion.

 

Attendees explored their “authentic attitude” and reflected on times self-promotion felt good versus slimy. Exercises included mapping all the people who benefit from your work—employees, customers, managers, mentees, community—and practicing generosity in selling (a “Miracle on 34th Street” mindset: help customers even if it means sending them elsewhere).

 

In Q&A, Robin tackled:

• Asking for promotions as modeling for others, especially women and minorities

• Persistence in follow-ups (yes, emailing Mark Benioff 53 times counts)

• Relationship-based enterprise selling

• Avoiding fear-based AI marketing by knowing who you serve and what problem you solve

Recommended reading: Setting the Table (Danny Meyer), Unreasonable Hospitality (Will Guidara), The New Strategic Selling.

 

Robin also shared upcoming Snafu conference details (March 5, Oakland Museum of California) and reminded everyone: Snafu = situation normal; all fucked up.

00:00 Start

01:06 Audience Fears About Selling

• Robin Zander welcomes 93 participants to the webinar

• Notes the session is interactive with exercises planned

  • Encourages participants to drop questions in chat or interrupt him

• Last 15–20 minutes reserved for questions

• Robin introduces himself briefly

• Focuses on storytelling as a tool for self-promotion

• Shares experience as a community builder

• Runs a conference called Responsive since 2016 (not Snafu)

  • Tools, structures, and company cultures for resilient organizations

• Two-day event each September on the future of work

• Focus on building resilience in organizations

• Observations on rapid change

• Technology and work-life changes happening at a fast pace

• Questions about resilience in individuals

• Traits needed in careers, personal relationships, professional relationships

• Ability to stay resilient through change

• Robin frames his expertise

  • Emphasizes his strength in asking questions and fostering honest conversations

• Labels himself a reluctant salesperson

• Not the world’s leading expert on self-promotion or selling

• Key lessons from research and interviews

• Two buckets matter in business and life:

  • Example: Sidebar community forming coalitions for learning and action
    
    

• Operational excellence: being competent and at least as good as others
  Promotion/enrollment/sales: standing up, saying what you want, building coalitions

• Started interviewing people about influence and persuasion

• Started a weekly newsletter called Snafu

• Written by hand, not AI

• Shares lessons from his life and others about self-promotion and resilience

• Focus on courage to take action: raising hand, offering something valuable

• Core characteristics of self-promotion and selling yourself

• Connecting with others: art of connection
  Courage to ask: inspired by Amanda Palmer’s TED Talk and book The Art of Asking

• Opposes traditional “always be closing” sales mentality

• Advocates for simply asking for what you want

• Current work mostly involves storytelling for large companies

• Clients include Supersonic, Airbnb, Zappos, and others

12:25 Service as the Core Principle

• Robin introduces the concept of storytelling for self-promotion

  • Stories used to:

  • Get promotions

  • Build coalitions

  • Propel career or organizational growth

• Emphasizes turning personal, career, or company stories into “commercials”

• Focus of today’s talk: self-promotion with impact

  • Core principle: service

  • Showing up from a place of helping others

  • Through helping others, also helping oneself

• Distinguishes between sleazy salespeople and effective self-promoters

• Childhood anecdote: Robin’s pumpkin patch

  • Tended plants all summer, learned responsibility and care
    
    

  • Harvested pumpkins and sold them using a small red tin box labeled “money”

  • Ran “Robin’s Pumpkin Patch” for five to seven years

• At age five, father had him plant pumpkin seeds

• Engaged neighborhood kids for fun, collaborative promotion

  • Explained product (pumpkins) enthusiastically to potential buyers

• Used scarecrow costumes and creative gestures to attract attention

• Lessons learned from pumpkin patch:

• Authentic enthusiasm creates value

• Helping people do what they were already inclined to do

• Early experience of earning and serving simultaneously

• Self-promotion is most effective when it’s service-driven, not manipulative

• Applying childhood lesson to career and business

  • Asking for a raise

  • Persuading companies to choose one service over another

  • Promoting oneself or others (e.g., Evan, web developer)

  • Key principle: approach self-promotion from delight and service, not need or fear

• Authentic enthusiasm as foundation for:

• Interactive exercise for participants

  • Not influenced by sleep deprivation or stress

  • Could be inspired by childhood or adult experiences

  • Opposite of fear; personal and unique for each participant

• Question posed: what is your authentic attitude when self-promoting?

• Examples shared from participants:

• Curiosity

• Passion

• Inspiration

• Service to others

• Observation

• Possibility

• Insight

• Value

• Helping others

• Creativity

• Belief in serendipity

• Optimism

• Key takeaway from exercise and story

  • Promoting from delight, enthusiasm, and service

  • Promoting from need or fear

• Two versions of self-promotion:

• Effective self-promotion aligns with authenticity and enthusiasm, creating value for others while advancing oneself

18:36 Gym Job and Needy Selling

• Robin shares the next story and sets up the next exercise

  • Gym culture is sales-heavy

  • Initial motivation: love of fitness, desire to help people

  • Quickly realizes environment incentivizes personal trainers to sell aggressively

• Timeframe: ~20 years later, at age 20, moved to San Francisco

• First post-college job: personal trainer in gyms

• Early experience at gyms

  • Key lesson from early failure

  • Selling from need feels gross

  • Promoting oneself from fear or desperation leads to poor results

  • Recognizes similarity to unwanted sales calls received personally

  • First authentic success in self-promotion

• Worked at Petro and World’s Gym in San Francisco, Pilates instructor

• Owner confronted Robin after two weeks: no clients, potential clients being lost to others

• Threatened termination by Friday if no clients acquired

• Robin froze under pressure, approached clients but with needy, desperate energy

• Outcome: fired by Friday, left gym

• Encounters man in pain on Valencia Street, offers help as personal trainer

• Approach comes from genuine care, desire to serve

• Leads to three-year working relationship, consistent sessions, good income

• Next client: world-famous photographer Michael Light at UCSF swimming pool

• Client comes from natural connection, not pushy salesmanship

• Dichotomy observed:

• Pushy, need-based self-promotion → freeze, poor results

• Service-oriented self-promotion → natural connections, sustained relationships

• Exercise for participants

• Prompt: identify two moments:

• One time self-promoting felt slimy → what were you doing?

• One time self-promoting felt good → what were you doing differently?

• Two-minute reflection / chat participation

• Participant reflections/examples

• Slimy examples:

• Interviewing for a job during layoffs, giving desperate energy

• Selling P&L at a hyperscaler

• Selling computers and printers in UK post-college

• Sales emails getting ghosted

• Feeling inauthentic or performative, taking advantage of someone

• Good examples:

• Offering services out of care and love rather than ROI

• Showing impact of work to junior child

• Knowing services add real value and solve a challenge

• Being clear on what the other person needs

• Key takeaway

• Self-promotion feels different depending on intent and knowledge
  
  

• Slimy → desperate, inauthentic, unclear value to recipient

• Authentic → service-driven, clear value, connection-focused

• Effective self-promotion combines knowing your value and serving others, not just pushing for personal gain

25:35 Miracle on 34th Street Lesson

• Feeling good in self-promotion comes from genuinely helping, solving problems, and sharing information

  • Santa Claus hired at Macy’s to hold kids and give candy canes, but real goal: persuade parents to buy from Macy’s

  • Santa instead sends parents to competitor to truly serve them

  • Macy’s manager initially furious

  • Outcome: customers feel genuinely served, return praising Macy’s, become loyal fans

• Robin references Miracle on 34th Street (original version)

• Key insight: providing real value, even if it benefits someone else, eventually returns value to you

• “Put enough bread across the water, eventually good things come back”

• Participant reflections

• Slimy: knowing audience expects judgment, catering to them for approval

• Good: giving the gift of knowledge, providing service freely

• Takeaway: authentic self-promotion is rooted in service, generosity, and sharing expertise, not manipulating for immediate gain

27:45 Starting Robin’s Cafe Through Service

• Robin shares a major professional turning point: opening Robin’s Cafe in 2016

  • No restaurant experience beyond college busing tables

  • Opened in three weeks, eventually grew to 15 employees by 2018

• Worked in multiple industries: Pumpkin patch, personal trainer, circus performer

• Opened a café/restaurant in Mission District, San Francisco

• Courage and conviction came from clear focus on service to others

  • Employees: create a great workplace, go-giver culture
    Investors: $40k raised from friends/family, provided value and potential return

  • Landlords (ODC, nonprofit dance center): wanted success of business to support community

  • Customers: diverse—tech workers, kids in dance classes, local community

  • Robin himself: financial sustainability, learning, personal growth

• Key audiences served by Robin’s Cafe

• Approach to challenges

  • Used Danny Meyer’s Setting the Table as a service-focused framework for employees

  • Philosophy: “giving in order to get paid”

  • Examples: spouse, kids, dog, manager, peers, mentees, clients, community, customers, extended family, mentors

• Served multiple stakeholders during crises: break-ins, flooding, city permitting, neighborhood issues

• Exercise: identify all the people who benefit from your work or success

• Key idea: the more stakeholders served, the easier self-promotion becomes, because it comes from service, not need or pressure

  • Show up thinking: does this serve the person I’m talking to?

• Principle: selling yourself from a place of service

• Consider multiple stakeholders simultaneously

  • Audience question: elaborate on applying this service mindset specifically to asking for a promotion

  • Tying service to self-promotion in career advancement

• Result: asking for a raise, applying for jobs, pitching clients—all easier and more authentic

38:11 Promotion As Service

• Asking for a promotion from a place of service

  • Example: doing the role already, deserving recognition, asking for what you believe you’ve earned.

• Personal perspective: advocating for yourself is a form of service to yourself

• Recognize other stakeholders in the process:

  • Modeling courage and advocacy for the next generation

  • Authority enables ideas to be taken more seriously

  • Stories gained from new responsibilities enhance value to clients or teams

• People you mentor, especially women or underrepresented groups

• The organization: your promotion can make it stronger

• Your family or children: showing them what it looks like to advocate

• Concrete examples

  • Outcome: trajectory of career positively influenced, demonstrated courage, modeled behavior

• Asking first time for a manager role

• Later asking for VP title as a director

• Courage and small steps

• Courage = acting despite fear, not absence of fear

• Practice by taking incremental steps toward what scares you

• Avoid masking or hesitation; direct action builds confidence and results

• Persistence and follow-up

  • Busy people require patience and multiple nudges

• Example: Mark Stubbings emailing Mark Benioff 53 times before a yes

• Persistence = respectful, consistent follow-ups

• Role modeling for women and minorities

  • Demonstrates that asking is a normal, expected, and service-oriented act

• Many don’t ask for promotions or raises due to upbringing or cultural norms

• Modeling advocacy teaches the next generation, including children, to speak up

• Service mindset in practice

• Approach self-promotion by asking: is this good for the other person?

• Keep intention aligned with service, not desperation
  
  

• Books for guidance:

• Setting the Table – Danny Meyer: service-driven sales and employee culture

• Unreasonable Hospitality – Will Guidara: lessons from the restaurant world on giving value and delight

• Key takeaways for promotion and asking

• Serve yourself, your mentees, your organization, and your broader audience

• Take small, courageous steps to ask for what you deserve

• Follow up respectfully and consistently; don’t assume silence = no

• Self-promotion becomes easier and authentic when rooted in service, not fear or need

• Snafu Newsletter

• Weekly newsletter written by Robin

• Covers influence, persuasion, and modern workplace dynamics

• A resource for ongoing learning and practical insights

56:55 Where to Find Robin

• Robin’s newsletter covers influence, persuasion, and modern work.

• Snafu Conference

• Responsive Conference
• Robin Zander on social medias