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