Do entertainment-based relationship tactics still win enterprise deals?

Doug Adamic · Sep 8, 2023

Entertainment-based enterprise selling (concerts, Super Bowl tickets) works less well now, and challenging a customer's status quo with insights earns more relationship respect

Most organizations now have gift-acceptance policies; and customers value being taught something and having their ideas challenged through constructive tension

Scope: a relationship between seller and buyer is still necessary

47:54 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

Chris Degnan · Nov 10, 2023

The relationship sale — golfing, wining and dining to win deals — is dead, and relying on it means you're in trouble.

52:21 20Sales: Five Lessons Scaling Snowflake to $1BN ARR, Why Customer Success is BS and Should Be Removed, Why All Sales Reps Should Do Eight Calls Per Week & Why You Should Hire a Head of Sales Sooner Than You Think with Chris Degnan, CRO @ Snowflake

Steve Goldberg · Dec 13, 2023 · hedged

Entertainment-based selling — golf outings, weekend hangs, long lunches — has largely died out because buyers now guard their time

People look at their time differently now

40:59 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

Harry Stebbings · Aug 4, 2025

Long, unhurried, phone-free formats like a four-hour golf round with several big enterprise customers together are rare and unusually valuable

Four uninterrupted hours where customers hang out with each other and with you is something you almost never get

64:27 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

Ron Gabrisko · Aug 4, 2025

Multi-day customer experiences like spring training trips with golf and dinner create a fundamentally different relationship with customers, but only if you invite the right ones

That amount of shared time changes the relationship; targeting matters because the spend is only justified with the right accounts

Scope: you have to make sure they're the right customers

64:40 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

Carles Reina · Feb 14, 2026

You build community by giving customers direct personal access (WhatsApp, Slack) and letting them downscale commitments even when it costs you money

Doing what is right for them builds a real relationship, and relationships beat transactions because no one wants to be sold

55:44 Direct personal access builds community over transactions

Carlos Delatorre · Jan 24, 2025

People over-index on relationship building, charisma and having a big personality as drivers of sales success — those traits don't hurt but aren't very impactful.

56:44 Charisma and relationships are overrated drivers

Shaunt Voskanian · Mar 21, 2026 · hedged

Sending gifts to prospects is an outdated sales tactic — it reads as transparently transactional, effectively a bribe

It feels so transparent that it comes across as a bribe rather than genuine relationship building

55:39 Gifts read as transparent bribes not relationship building

Steve Goldberg · Dec 13, 2023

Small personal gestures that reach a buyer on vacation can be what gets a deal signed, provided they stay on the right side of creepy

Buyers' timelines aren't your timeline; a thoughtful reminder gets you back top of mind when they come up for air

41:18 Small personal touches still close deals

Ashley Kelly · Jun 7, 2024 · hedged

Handwritten notes have died as a sales tactic and are now more of a waste of time than they used to be

Not a lot of people are in the office anymore to receive them

45:54 Physical personal touches died with the office

Patrick Forquer · May 11, 2026

The steak-dinner era of enterprise selling has evolved — buyers now prefer activities over formal dinners — but relationships remain essential and conferences are the highest-leverage venue for Legora

He graduated in 2008 into the steak lunch/dinner entertainment era and has watched the format shift; the legal space has so many conferences and events that showing up matters

44:10 Format shifted to activities and conferences but relationships still decide