Summer Preparation for Next Year's Revenue Planning

Plan Now, Win Later: A Strategic Plan for Sellers, Managers, and Owners. Post #2

Hi,

Revenue success doesn’t start in January; it starts now. Summer offers a strategic window to get ahead while competitors slow down. 

This workshop is designed to help sellers sharpen their pipeline, managers align their teams, and company owners build systems that scale. 

Planning now means fewer surprises, better forecasting, and more value delivered to customers when it counts. 

Whether you're carrying a quota, leading a team, or steering the whole ship, this workshop gives you the clarity and direction to enter next year with confidence.

THE 3-STEP WORKSHOP

Step 1: Write Your Upcoming January Memo Summarizing Your Current Year

Prompt:
Imagine it’s January 15, 20xx. You’ve hit your prior year revenue goals. What happened?

Instructions:
Write a 1-page memo from your future self to your team or leadership. Include:

  • Total revenue booked

  • Key wins or new clients

  • Challenges overcome

  • What made it all possible

Open a Word Doc or Google Doc and start writing. Don’t wait… Push yourself to do this!

Step 2: Reverse Engineer the Milestones

Prompt:
What had to happen in Q3 and Q4 to make your January memo a reality?

Instructions:

  • Work backward from your memo to identify:

    • Key pipeline moments

    • Marketing pushes

    • Hiring or enablement actions

    • Strategic meetings or investments

  • Break your milestones down by month and assign owners.

Milestone Tracker Template

Month

Milestone Description

Owner

Status

September

Finalize Q4 outbound targets

Sales Manager

Not started

August

SDR team launches test sequence or learn about drip campaigns with your marketing team

SDR Lead

In progress

July

Create next year revenue forecast

Each seller and sales manager

Complete

Step 3: Activate Your Summer Sprint Plan

Prompt:
What 3 things can you do between now and Labor Day to build momentum into next year?

Instructions:

  • Identify 3 high-impact activities

  • Assign owners, due dates, and success criteria

  • Share with your team or accountability partner

Sprint Plan Template:

Action

Owner

Due Date

Success Criteria

Re-engage top 10 stale opportunities

Account Exec

August 15

3 meetings booked

Align CS and Sales on handoff process

CS Lead

August 30

Updated SOP published + shared

Map ideal next year team org chart

Founder / CEO

July 25

Hiring plan reviewed by investors

Tips for Completion + Real-World Examples

Tips:

  • Block off 60–90 minutes of quiet time to complete the workshop

  • Use visuals like whiteboards, Miro, or FigJam to sketch ideas

  • Discuss outputs with a team member, mentor, or manager to refine them

Example 1:
A mid-market AE wrote her memo in July, envisioning a big Q1 deal with a retail giant. It inspired her to schedule an August discovery call. The deal closed in Q4 and accounted for 18% of her annual quota.

Example 2:
A SaaS founder ran this exercise with their executive team. It revealed that Marketing and Sales had no Q3 alignment on enablement content. They fixed it fast, leading to a 19% lift in Q1 next year demo conversions.

Further Reading

  1. The 12 Week Year: Get More Done in 12 Weeks than Others Do in 12 Months
    Brian P. Moran & Michael Lennington (2013, Wiley)
    Tactical frameworks for executing with urgency and precision, ideal for time-boxed sprint planning.

  2. Playing to Win: How Strategy Really Works
    A.G. Lafley & Roger L. Martin (2013, Harvard Business Review Press)
    A clear guide to making strategic choices about where to play and how to win in competitive markets.

  3. The Sales Tactician: Spycraft Techniques For Revenue Success
    Mort Greenberg (2025, digitalCORE Publishing)
    The Ultimate Sales Playbook Inspired by Spycraft Techniques

==

The Revenue Workshop isn’t theory. It’s a field-tested system used by real leaders, in real markets, under real pressure.  

Each newsletter is based on one of over 300 workshops and worksheets found in the eight books of the RevenueVsSales.com and TheFocusedSeller.com book series.

To contact us, email [email protected]

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