The Boston Red Sox have been "wicked embarrassing" this season. 21 wins, 27 losses. A fired manager. Way too many injuries sitting in the dugout. Not exactly the championship energy Fenway was expecting in May.
Yesterday's Peanuts strip hit me right between the eyes. Lucy's in the outfield, ball dropping behind her, and she says with complete sincerity: "I've been wrong a lot lately."
My standard response — the one I use constantly with sales and marketing teams — is this: if you want to stop losing, you need to change what you're doing.
The good news for all of us in sales? We're not at the end of the season. With a long Memorial Day weekend ahead and a second half of the year still very much in play, here are three specific changes you can make right now.
Baseball has rules, positions, innings, and a very specific way the game is played. Sales is no different. There needs to be a formal, disciplined process for moving a prospect from an MQL through Qualify, Discovery, Validation — and whatever additional stages your team uses — to a closed deal.
One process. Practiced, understood, and committed to by everyone on the team. "This is the way we sell" — no exceptions, no freelancing.
The reality of Sales today is that success is built on the Science of Sales. There's a small role for individual artistry, but it's tiny — and more importantly, it can't be replicated, tracked, or taught at scale. Process can.
No professional team walks onto the field without a playbook. It's the religion, the science, and the discipline — all formalized into something the team actually uses every day.
The old model — a detailed annual sales plan that got dusted off at the January kickoff and never touched again — is dead. What you need today is a living playbook: always-on, AI-infused, and loaded with real-time CRM data, individual plays, training videos, templates, value propositions, and business use cases — all configurable to specific prospects and situations. If your playbook lives in a binder on a shelf, it's not a playbook. It's a monument.
You'll bring everything you have — skills, experience, training, coaching — to get every player to "A" level performance. That's your job and you should do it relentlessly.
But decades of working with sales teams has taught us one hard truth: nothing gets better by itself, and waiting only makes it worse — for the individual and for the team.
The Red Sox made their move 21 days ago. Most observers would say management waited too long through seven seasons of underperformance, but at least they made the call before Memorial Day. Be realistic. Look at the stats. And don't wait for the problem to solve itself — it won't.
Have a great long weekend — and come back Tuesday ready to change your score.
— Jack
Jack Derby is Managing Partner of Derby Management, a strategy consulting firm, and founder of the Derby Entrepreneurship Center at Tufts University, where he has taught for 20 years. Every semester's content is significantly updated, with heavy emphasis in 2025 and 2026 on the use of AI in Marketing & Sales. At Derby Management, Jack and his team architect and build business strategies focused on sales and marketing processes, tools, and technology platforms.
"Writing the Winning Sales Plan" | "Writing the Winning Business Plan" | www.derbymanagement.com | Derby Entrepreneurship Center at Tufts