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26 August 2025

In this Issue

🏃    Sprint to Year End
💰    Sell Bigger Deal
💼    Close the Briefcase
“If you’re not first, you’re last.” It may not be that binary, but September is the time to step on the gas to sprint to year end. | Columbia Pictures

🏃  Sprint to Year End

Labor Day is the unofficial end of summer. It’s back to school and back to work.

I’ve got mixed emotions as I write this. It’s been a phenomenal summer, and I am not quite ready for it to end. But I am also feeling amped for the next four months.

It’s a sprint to year end. Now is your chance to close this year on a high note.

2025 has been a tumultuous year. From a trade war to market manipulations to wild swings in customer demand, many of us have been on a rollercoaster ride.

Hit this September hard and fast. This is your opportunity:

  • If you had a rough first half of the year, turn the corner and close the revenue gap.
  • If you’ve outperformed in the first half, step on the gas and crush your targets.

Approach the next four months with purpose:

  1. Objective: What do you need to achieve by December 31, 2025?
  2. Priorities: How will you achieve your objective? Be deliberate and clear. Define three to five priorities to move the needle.
  3. Metrics: How will you measure progress towards your objective? Choose lead and lag measures that will show your progress.

September is a time of renewal and energy. It’s like a mid-New Year. Hit this moment with rigor, purpose, and the strategy you need to make 2025 an outstanding year.

One Stat to Watch

43%

Only 43% of salespeople hit quota in the first half of 2025, according to RepVue.

💰  Sell Bigger Deals

There are four ways to grow your business:

  1. Volume: Acquire more customers.
  2. Velocity: Sell faster to increase inventory turns.
  3. Value: Increase your average size sale.
  4. Variety: Increase the share of wallet with more products.

Volume, acquire more customers, is the default growth strategy for most companies. They assume, “We just need to sell more deals…”

This is logical, but impractical. Increasing Volume is one of the harder growth strategies to implement, because it requires structural change:

  1. Increase lead generation
  2. Increase productivity of the sales team
  3. Increase productivity of operations

Sales is usually the weak point in this mix. Salespeople have predictable rhythms. You can analyze the number of transactions a sales rep performs and discover that pace is pretty consistent and predictable over time.

Changing your sales reps’ pace is easier said than done. It requires structural changes to your sales process, technology, and value proposition to increase.

Instead of relying on Volume to drive growth, the easier place to focus is Value: sell bigger deals.

Going up market to sell bigger or more complex deals usually puts less strain on the organization and is faster to implement. Salespeople often lament, “It’s just as hard to sell a big deal as it is to sell a little one.” Lean into that.

💼  Close the Briefcase

Closing the briefcase is a powerful sales technique. It’s about saying “no” and being prepared to walk away from a sale.

The name comes from a time when salespeople carried a briefcase. Closing one’s briefcase was a sign that the meeting was over.

The technique works for three reasons:

  • Know Your Value. It’s really easy to get caught up in a sale and try to win at all costs, but not all customers are good customers. Know your value, take pride in it, and sell it. If a prospect doesn’t recognize or want what you have to offer, then don’t try to convince them. Walk away.
  • Save Time. Negotiating is a step in the sales process. There’s no point wasting your time trying to convince someone to buy when all they care about is getting the cheapest price.
  • Position of Power. No one likes to hear, “No.” The thing that surprises me most about the Close the Briefcase tactic is how many customers reverse their position after they know you’re prepared to walk from the deal. You are taking back control by saying “no,” and showing the boundaries of how far you will negotiate.

Closing the briefcase is a power move. You don’t use it often, but it’s incredibly effective when you do.

It takes intestinal fortitude to walk away from a prospect, and sometimes it means losing a deal. But if you’re willing to be strong and proud of your brand, you can walk away from a bad customer. And you should.

🤔  Thoughts on Today’s Issue?

We’d love to hear your feedback. Message with any thoughts, comments, or ideas for future issues.

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