Wins & Losses: How did it go?


First, and most importantly, I hope you had a superb July 4th holiday topped off by a successful end of the quarter.

In my last post on July 1st, I wrote about Ben Franklin, my favorite blogger, who — in addition to being an outstanding statesman — was just an exceptional sales and marketing guy.

At the Constitutional Convention of 1787, which met in secret from May through September of that year, half of the delegates were under 40. Franklin was 81. A superb orator, he had written a compelling speech meant to rally his colleagues to sign the newly drafted Constitution they'd negotiated and battled over for four months behind closed doors.  But due to his declining health, Franklin couldn't deliver it himself, so he passed that job to James Wilson, a fellow Pennsylvania delegate. Franklin wasn't about to waste the marketing opportunity, though: after the signing, two delegates put his speech into the Massachusetts and Maryland newspapers, from which it was reprinted up and down the country building the pressure that finally got the Constitution ratified in June 1788.

Yea, I know — a lot of history for a Friday before the weekend. But after binging 12 hours of Ken Burns' PBS documentary on the Revolution over the 4th, I was fascinated by just how much I didn't know.

That weekend, as I balanced my time between the air-conditioned house and the 100-degree beach outside the door, I found myself piecing together the various dates and the seasonal rhythms of the summer and winter campaigns, trying to make them line up. Here's an example: before that documentary, if you'd asked me how long the Revolutionary War lasted, I'd have said — embarrassedly — "around 5 years." In fact, it lasted 8.

For us in sales, we're not going into battle with our prospects and customers, but the discipline is the same: track your time exactly, know your available days to sell, and do the math on moving each deal from that first qualifying step through to a closed deal. It's all about managing your time and selling the business value.

For Franklin and his band of revolutionaries, the value was never the Constitution as a document — that was just the contract at the end. The real value was the political power it would secure for a few and the economic prosperity it would unlock for many, built on a newly discovered abundance of raw materials.

 

In our own lives as salespeople, having closed the first half with lots of points on the board, it's time to take a deep dive with the team this Monday and plan out, in detail, the next 58 available-days-to-sell in Q3.  And before you get comfortable with 58...or you just round it up to a cozy 60, you need to subtract the equivalent of 5ish days caused by the reality that some of those critical people that you need are going to be on vacation.

 

As you go through your Beginning-of-the-Quarter Meeting next week, here are a few things to consider and hand out as assignments, to be worked during the balance of the week and reported back on Monday the 20th:

    • What's our true "Available-to-Sell Day Count"?
    • Does everyone have a 30- and 60-day tactical plan for those days? No excuses!
    • Do your Value Propositions need retuning? If so, assign someone and give them until the 20th.
    • Same question, same assignment for your Q3–Q4 Playbook. Want examples? Give me a call.

Just maybe, on this beautiful Friday morning here in Vermont — where I arrived at 6:00 for a day of sales calls, I've overstepped on the war-and-sales comparison. War and selling aren't the same thing, but one of the primary metrics we measure ourselves by every month is Wins & Losses.

So, as we count these next 58 days, just like General Washington winning the Revolutionary War, success will come to those of us who plan the best while demonstrating the most continuous leadership over time.

Have a great week next week putting points on the board while planning out the details for your wins!

Enjoy the weekend!

Jack is a 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 is significantly updated, with heavy emphasis in 2026 on 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.

| www.derbymanagement.com | Derby Entrepreneurship Center at Tufts

 

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Tags: 4th of July, Derby Entrepreneurship Center at Tufts, 2026 Sales Planning, 2026 Business Planning, 2026 Marketing Planning, 2026 Sales Best Practices

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