Leadership & Delegation

Words I like: “Make a customer, not a sale.” – Katherine Barchetti Many CEOs measure sales performance using a linear sales funnel that ends when a customer signs a contract. A signed contract doesn’t mean you’ve won and the race is over. It means you’ve been permitted to deliver on your promises, and the easy, lucrative, and fun activities are just getting started! Traditional sales funnels drop the ball the moment a deal closes, leaving customer success teams to pick up the pieces. Winning by Design’s Revenue Architecture, aka the Bowtie Model, changes that. It turns the old funnel on

Words I like: “An overabundance of choices often leads to a paralysis of decision.” – Barry Schwartz Most CEOs pitch investors and rally employees all day, then go quiet in front of a paying customer, because selling from the top feels pushy. So they list a few features and hope the deck closes the deal. There’s a better sequence, one that answers the buyer’s questions in the order they ask them: PASTO. Shout-out to my dear friend and mentor, Joe Rojas, for teaching me all about PASTO… Problem Accentuate the problem Solution Transformation Offer Here’s how to run it. Problem:

Words I like: “If you want to do a few small things right, do them yourself. If you want to do great things and make a big impact, learn to delegate.” – John C. Maxwell When you started your company, you took the title of founder, and nobody trained you for it. It worked for years regardless, because you taught yourself how to build the product by shipping bad versions of it, and you learned to sell by losing deals. Once you hit the 20-employee mark, the founder’s role changes. You hire people more senior than yourself, and you fire

Words I like: “Execution is the ability to mesh strategy with reality, align people with goals, and achieve the promised results.” – Larry Bossidy When you delegate decisions, your team sees the outcome but misses your hidden reasoning, non-negotiable constraints, and trade-offs. This thinking gap causes critical alignment failures under pressure or when choosing between two defensible options. To prevent this, you must make your reasoning visible. Here’s how to do it. 1. Write your intent before the decision happens Before delegating any significant task, write a single paragraph detailing your objective, your non-negotiables, and what success looks like. Taking

Words I like: “Without data, you’re just another person with an opinion.” – W. Edwards Deming Every day, CEOs review performance numbers to decide where to push, where to cut, and where to hold. When you see a 40% increase in revenue, you would immediately think about expanding. But before you move, you need to ask: 40% compared to what? Most metrics are presented without enough context to support a decision. People naturally assume that large numbers are important simply because they are large. In practice, a number only becomes useful when it is placed in context. Hans Rosling studied

Words I like: “Before addressing a situation, leaders need to recognize which context governs it, and tailor their actions accordingly.” – Dave Snowde Most management frameworks assume that problems can be solved using a repeatable standard process. But in 1999, Dave Snowden developed the Cynefin Framework to start from a different assumption: different types of problems require different approaches. The framework was originally developed during Snowden’s work in knowledge management at IBM and later popularized through the Harvard Business Review article A Leader’s Framework for Decision Making, co-authored with Mary Boone. The word Cynefin (pronounced kuh-nev-in) is Welsh for “habitat”

Words I like: “A man who chases two rabbits catches neither.” – Confucius You did not build a company to spend half your week on everyone else’s priorities. But that is exactly where most CEOs end up. In 2006, Harvard Business School professors Michael Porter and Nitin Nohria launched a landmark study of how 27 CEOs spent their time in 15-minute increments. Across 60,000 hours of data, they found that the average CEO worked 62.5 hours/week and advanced their own agenda only 43% of the time. Email alone earned the label “dangerous time sink.” You do not need a Harvard

Words I like: “We don’t give discounts. We buy value.” – Todd Caponi Almost every CEO has done it. A deal is close, the client pushes on price, and to keep things moving, you knock a few thousand off. It feels like progress. What actually happened is you taught that client your price was never real, and you handed away gross margin you’ll never get back. Do that enough times and your pricing stops meaning anything. Here’s how to fix it. The framework comes from Todd Caponi’s work on transparent negotiation. It rests on one idea worth sitting with: your