Ask Why: Uncover Boardroom Drivers Behind Priorities
The best discovery question I ever learned: "What's going on in the business that's driving this to be a priority?" It sounds innocent. But it gets prospects to reveal the boardroom conversations that led to their budget approval.
Ask for Decision Steps, Not Vague Processes
Never ask: "What's your decision-making process?" Instead ask: "What steps does your company need to take to make a confident yes or no decision?" Same intent. Completely different depth of response. Then DON'T take their answer at face value.
Quote Big Numbers Casually; Confidence Sells High‑value Deals
Quote a $600,000 proposal with a straight face. That's a superpower. The best salespeople talk about money like it's nothing. "$600,000. Pass the salt." The worst salespeople tremble when price comes up. The turning point: realizing your value is a tsunami compared to the tiny...
Master Decision Dysfunction to Earn Enterprise Sales Premium
The single most underrated enterprise selling skill: Navigating decision dysfunction. Always assume that dysfunction is the status quo. And that it's your job to make it as functional as possible. That's why you get paid the big bucks in enterprise.
Coffee
3 years ago, almost to the day, I sat down for coffee in Los Altos with a man who earns $100M per year in SaaS. Yes, you read that right. 9-figures. Every year. Here’s what struck me:
Relentless Focus on Top Accounts Beats Mass Outreach
Chet Holmes managed a magazine dead last in market share out of 15 competitors. He found 167 accounts drove 95% of industry revenue. He stopped pursuing the other 1,833. Cold turkey. Every 2 weeks: direct mail + phone call + fax. 4 months later:...
Skipping Negative Impact Costs Wins, AI Shows
I’ve written 1,394 LinkedIn posts about Discovery. But according to the data… I still have more to learn: Last week, we released AI Skill Intelligence on a limited basis. It measures your proficiency against industry-standard revenue skills. So I ran my own discovery calls...
Speed Wins: Faster Follow‑Ups Accelerate Sales
Sun Tzu said: "Fall like a thunderbolt." In sales, this means respond FAST. If you take 2 days to follow up after a demo, your buyer takes 2 days to respond. If you respond in 2 hours, they mirror that speed. Money loves speed. Speed...