Real Talk About Selling
Start With Who’s Already at the Table
Before you go looking for new customers, take a hard look at the ones you already have. Most reps take their best accounts for granted, counting on them for the lion's share of growth expectations while doing almost nothing intentional to develop them. The revenue feels reliable until it isn't. What's missing isn't effort. It's a plan.
You Don't Have a Prospecting Problem
I start hearing some version of this every March. Q1 closes out, the numbers look softer than expected, and the instinct is immediate: get out there and prospect. Fill the funnel. Make some calls. But confusing the channel you have the most control over with the most effective channel is one of the most expensive mistakes a sales team can make.
When the Secret Sauce Walks Out The Door
Bob's been your top performer for 20 years. Sarah's been here 15. Between them, they account for close to 35% of the team's revenue. Everybody knows they're good, but nobody can explain exactly why. Then they leave. And all of that knowledge walks out the door with them.
The Onboarding Problem
Ramp time is a function of clarity. The clearer you are about what success looks like, the faster new reps can get there. If your onboarding is "shadow Bob and figure it out," you're guaranteeing a long ramp. You're finding good people. You just keep setting them up to fail.
The Assumptions Running Your Sales Team
You're in an executive team meeting, and the sales team is on the docket. Reps are taking too long to ramp. Revenue is concentrated in a few veterans. Something needs to change. So you make decisions based on... what, exactly? A hunch. A pattern you think you see. Without validation, every decision is a guess.
The Growth Ceiling
You were growing. Revenue was up. The team was hitting numbers. And then it stopped. When you can't grow by throwing money at the problem, you have to grow by getting better at what you already do. You can't replicate what you can't explain.
The Real Cost of Bad-Fit Customers
Some deals aren't worth winning. That customer you knew you should have walked away from? They're still costing you. A bad fit doesn't just kill your margins, they crush your soul at the same time. When you know who you're for, you also know who you're not for.
Go-to Market or Go-to-Network?
It's an arms race for access, and as the tech advances, so do the obstacles placed between our prospective clients and us. Going to your network is a massively underutilized way to grow your book of business. 89% of customers would be willing to provide a referral if asked, but only about 10% of sales reps are willing to ask. Choose your hard.
Make It Stick
You've excavated what your best people actually do. You've validated it with your best customers. Most companies never get this far. But you have. Now what? Without integration, the knowledge stays in a slide deck. That's not transformation. That's a workshop.
Assumption vs. Evidence
If I asked 100 salespeople why their best customers buy from them, 5 would actually know, 15 would guess correctly, and 80 would be completely shocked by the real answer. Everything is an assumption until you meet reality. Here's how to stop guessing and start knowing.
The Boardroom Work
The best salespeople do things that many others don’t, but few can actually explain what those things are. It takes work to excavate these differentiators, and you need to go 2-3 levels deeper than you think you do. You know you're still on the surface when your differentiators sound like "relationships," "trust," and "we really care." Those aren't wrong, but they're not different. Here's how to excavate what's underneath.
Measuring The Stuff That Matters
The biggest problem in sales isn't effort. It's knowing when your effort is actually enough. In 2008, I discovered a simple point system that transformed how I approached sales. By tracking four key activities with a weekly point goal of 25, I tripled my territory revenue in 17 months while cutting my work hours in half. That's a 9x return. The system helped me focus on leading indicators—prospecting, scheduling meetings, meaningful conversations, and getting commitments—instead of obsessing over lagging indicators like revenue. More importantly, it gave me peace of mind. I finally knew when "enough was enough," which let me stop spinning my wheels and start actually growing. Whether you're carrying a bag or leading a team, this scorable sales system can help you measure what matters and know exactly when your efforts are sufficient to drive results.
Your Secret Sales Weapon
Most companies struggle to articulate what makes them different. They talk about "white-glove service" and "deep expertise"—things their competitors also claim. When everyone says the same thing, no one says anything. The solution isn't just knowing your value proposition; it's being hyper-specific about it. And there's a cheat code most people ignore: writing. When you're forced to put words in black and white for someone outside your business, you can't hide behind shared context or assumptions. You have to be precise. That's where real clarity happens.
The Best Negotiation is No Negotiation
Most salespeople think it's inevitable—they'll have to discount near the end to close the deal. They plan their concessions instead of laying proper groundwork upfront. But here's what that assumption costs you: margin, leverage, and customer trust. The best negotiation is no negotiation at all. When you build an airtight business case from the start, you rarely need to make concessions. And when discussions do happen, you hold all the cards.
It's Bigger Than Your People
Most mid-market B2B companies have a couple of reps who consistently crush it. But getting anyone else to that level? Nearly impossible. Here's why it's not a people problem—it's more systemic.
The Goo Stage
Adopting new skills and frameworks feels uncomfortable because real change requires you to become unrecognizable for a while. Welcome to the goo stage.
Like Talking To Myself, Only Better
Working with an LLM isn't just helpful—it's transformative. Here's why arguing with Claude has made me a better thinker.
Two and a Half Hours
I used to sell with a guy who would say, "Jeff I can sell our product in 2 1/2 hours. The problem is I only get it 5 minutes at a time."
It was an important dose of perspective to a young seller like myself.
"What Am I Supposed To Do Now?"
I was standing in an operating room with someone who had been a surgeon longer than I had been alive.
He turned around and asked me, "What am I supposed to do now?"