In the profession of Sales, we always have a sharp eye on both the clock and the calendar. Measured by months, weeks and quarters, points go up on the scoreboard every day, and you can either fight time ... and be very unsuccessful...or fully embrace it and let the natural rhythms of both the seasonal and budgetary calendars work for you.
Since I spend time each month living in the tiny town of Winhall, VT (pop 1,133) where six generations of my family have lived in this valley of the West River, I know very well that Vermont has many more than the normal four seasons we all know. One of the most critical of those "extra" seasons is the four weeks of "Leaf Peeping" when the buses run up and down the state producing 25% of VT's annual tourism revenue.
Nowhere are seasons more pronounced than in the business of education. Here it is just at the beginning of August, but for weeks now, we've been seeing Back-To-School ads at Target.
As a professor at Tufts and founder of the Derby Entrepreneurship Center, my own seasonal calendar for teaching in September begins in early May. In my teaching, I introduce my students to the language, the processes, the tools, the math and the seasonal rhythms of business. This semester's schedule:
- June 1: syllabus was sent to the registered students.
- June 8: a simple assignment was required. If no response: students were dropped from the course.
- June 9: team assignments were given for the six companies that signed up for marketing plans.
- Before September 8: there's a requirement to complete HubSpot's Inbound Marketing Certification.
As sales execs, this particular turn of the calendar today into August marks the sharp reality that there's just not much that's going to happen in this last month of the Dog Days of Summer. By its own definition, August is going to be a period of difficult sales funnels due to vacations planned way back in January over which we have zero control. And those are the planned vacations, which don't take into account the reality of the unplanned three-day weekends for the next four weeks.
Bottom line: although the August calendar technically shows 20 workdays, the reality between your own time availability and that of your prospects who are currently in the bottom half of your pipeline, the math says you will lose 25% of those available days.
It is what it is, so what you are going to do come Monday?
1. Count the days you personally have available to sell and rigidly protect that time. Move the dentist to September and just tell the finance manager that she will need to wait until next month. Absolute focus on selling! Everything else can wait!
Here's an example: rationalize the travel! Every trip should have two objectives! Yesterday, I spent seven hours driving back and forth for a four-hour board meeting, which I could have done by Zoom, but it would have been the wrong thing to do culturally. So, I switched it up asking one of my leads in London to call me at 5:00AM and then had an intensive discovery call with an existing customer on the return trip.
2. Unless, you're in the final step of a big deal with a new prospect where you're presenting a fully rationalized business use case, spend all of your time in August either upselling or extending existing customers.
Have a great day selling!
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
