Scaling Up summit takeaways: relationships, wisdom, and sales playbooks

Executive overview

A panel of Scaling Up coaches recap their favourite speakers and lessons from the October 2019 Scaling Up summit in Anaheim. The core themes are consistent: build genuine relationships with customers and employees, tap hidden wisdom inside your organisation, and create repeatable systems for sales.

Emotional connection — with customers, employees, and yourself — is the most durable competitive advantage.

Gender equality and the underdog

• Katika Roy opened the summit; her core message: women aren't the problem, they're the solution.
• The talk extended beyond women — it covered any underrepresented voice, including fathers who can't take parental leave.
• Leaders often grant themselves flexibility they deny their teams; Roy made that double standard visible.
• Ignoring diverse voices means ignoring a large share of the customer base.
• 50 women entrepreneurs in Costa Rica gave Lisa's team firsthand evidence of the hurdles female founders face.

The modern elder: wisdom as a strategic asset

• Chip Conley joined Airbnb as a mentor after selling Joie de Vivre Hotels; the founders wanted his judgment, not just his industry knowledge.
• Wisdom is the ability to navigate a process regardless of subject matter — experience compounds across domains.
• 75% of Millennials want a mentor; only 2% have one — a large, mostly untapped opportunity.
• Ask "Who do you learn from besides your direct manager?" — the answers are rarely the obvious names.
• Heat-mapping informal knowledge holders surfaces hidden experts who deserve a broader platform.
• Pairing the youngest champion of an initiative with the most experienced team member as advisor is a practical implementation.
• Don't waste innovation energy reinventing proven frameworks; apply it to real market or operational problems.

Molly Bloom: resilience and customer obsession

• Bloom ran high-stakes celebrity poker games from her mid-twenties; her story is a case study in perseverance.
• She memorised 20 players' individual preferences and anticipated needs before they were voiced — extreme customer intimacy.
• When her boss fired her mid-game, she immediately pivoted: she knew the strategy and became the competition.
• Lapses of integrity (taking a rake, making the game illegal) created existential risk — small compromises compound.
• Recovery arc: stripped of everything, then rebuilt from scratch — self-belief and reinvention as repeatable skills.
• Early dreams (near-Olympic skiing, ended by scoliosis and a twig on the course) set the pattern for her resilience.

The relationship economy

• John DeJulius defines the relationship economy as emotional connections that make your brand one customers cannot live without.
• Discounting is the tax you pay for being average — price becomes irrelevant when connection is strong enough.
• The FORD framework (Family, Occupation, Recreation, Dreams) gives anyone four safe on-ramps to genuine conversation.
• Everyone walks around with an invisible banner: "I want you to ask about me."
• FORD works in sales, hiring, and leadership — the same questions reveal personal values and cultural fit.
• ~60–65% of leaders know very little about their team members on a personal level; there is a direct correlation between that gap and team effectiveness.
• Relationship-building is a trainable skill; invest in it across all employee levels.

Listening as a discipline

• David Meerman Scott's rule: four questions for every one statement.
• Asking a question then answering it yourself signals you weren't listening — and destroys trust.
• Silence after a question is valuable; resist the urge to fill it.
• Fierce listening requires active restraint, especially for high-D, activator-type leaders.
• Words either build trust or erode it (Judith Glasser's conversational intelligence framework).
• The three W's of words: they can wow, win, or wound.

Stagility: stable and agile simultaneously

• Judy's coined term captures a core tension: stability enables execution, agility enables survival.
• Jim Collins called the underlying idea "the tyranny of or vs. the genius of and."
• Change is now one tweet away — organisations must hold both capacities at once.
• No plan survives contact with the enemy; iterate, listen, adjust.

Employee engagement and purpose

• Santiago Jaramillo: culture, leadership, and a clear path for growth are what retain people — especially where $20/hour can lure someone away.
• Apathetic employees are the real risk; they leave or disengage without signalling why.
• Asking "Are you happy in your job?" opens a diagnostic conversation about trust, meaning, and belonging.
• Purpose is not a soft add-on — it is the primary differentiator when compensation is comparable.
• Bill's open offer: if you can't see how purpose applies to your company, call him and he'll help for free.

The inner voice: whisperer vs. whiner

• Alden Mills distinguished two inner voices — the whisperer (encouragement) and the whiner (self-doubt).
• Most people's default leans whiner; the whisperer is quieter and needs deliberate cultivation.
• A structured morning routine — meditation, affirmations, gratitude journaling, inspiring content — builds the whisperer before the day erodes it.
• Reframe the whiner: for many, it functions as risk-mapping ("what could go wrong?") rather than pure self-sabotage.

Jack Daly: the sales playbook

• Fewer than 10% of sales teams have individual playbooks; the rest improvise, with inconsistent results.
• A playbook is a process flow and checklist — it captures what already works and makes it repeatable.
• Practice before you're in front of the customer; top performers in every other field don't rehearse on their audience.
• Three Ps: Playbook, Practice, Professional coach — all three are present in elite athletic performance; most sales orgs use none.
• Structure sets you free — a playbook is a living document to iterate on, not a once-and-done artefact.
• Even LeBron James and Tiger Woods have coaches; ego is the main reason leaders resist the same.

Boutique hotels and brand differentiation

• Chip Conley's Joie de Vivre took neglected inner-city motels and repositioned them by identifying the intersection of two target magazine audiences.
• The approach "un-genericised" properties — giving them a defined identity rather than a lowest-common-denominator offering.
• The major hotel brands now invest heavily in boutique sub-brands; Conley was a forerunner.
• Core scaling principle: find one thing that works, understand why, then repeat it with discipline.