4 Tips For Selling in The Summer

How to sell to prospects when it feels like everyone's out of office

Good Morning! Yesterday, Apple announced a new feature that will let you translate conversations in real time across text, FaceTime, and even live phone calls. Which means we’re now just one software update away from every sales rep being able to say “just following up” in 43 languages. Now let’s get into today’s Follow Up. 😁 

Sales Tip of The Day 💡

When a prospect says, ‘We’re just gathering information right now,’ it might just be a cop-out.

Ask them what that really means:

 Cool, happy to help. Let me know when you’re ready.
 Makes sense. When you say ‘gathering info,’ is there a specific problem you’re trying to solve right now, or just comparing options?

This separates curiosity from intent and lets you in on their criteria early.

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These aren't theoretical best practices. They're battle-tested messages used by successful sales teams to land meetings and close deals.

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4 Tips For Selling in The Summer

Summer is here. Your prospects' email replies are set to "Out of Office." And your pipeline is starting to feel it.

If it seems like deals slow down every July and August, you're not imagining things. Nearly two-thirds of B2B companies report a summer sales slump, with 75% seeing sales drop by 20% or more.

But that doesn’t mean there’s nothing you can do about it. The best sales reps get creative and turn the season into an opportunity.

We put together 4 actionable tips to keep closing deals while everyone else is slacking off.

1. Keep Prospecting (Even When It Feels Pointless)

It's tempting to ease off outreach when buyers aren’t responding. But don't.

The work you put into filling your pipeline now pays off in a few months, when those contacts are back and ready to engage.

Stopping outreach during a "slow" summer will hurt you next quarter.

Here's the alpha: Many competitors assume summer is a dead zone and take their foot off the gas. That's your cue to keep pressing.

You might catch decision makers with more breathing room. And far less sales spam.

Consistent prospecting through summer helps you stay top-of-mind, even if it feels like no one’s seeing your outreach.

2. Add a Summer Twist to Your Outreach

If your usual emails are getting crickets, try shaking up your messaging.

Inject a little summer flavor to stand out.

Start a voicemail with: "You're probably on a beach right now, but..."

And if you have insight on their summer plans, personalize with context.

A sales rep at Slack did this by recommending local restaurants to a prospect who was on vacation. It worked, and the rep managed to connect with the prospect when his competitors couldn't.

Fewer prospects may be around, so make each interaction count.

3. Use the "Out of Office" Message to Your Advantage

Those automatic "I'm away till next week" replies are your secret roadmap.

First, take note of when your contact returns. Set yourself a calendar reminder to follow up the day they're back (or the day after).

No one wants to feel overwhelmed with work right when they get back.

A friendly "How was vacation?" email scheduled for their return can land just as they dig out of their inbox backlog. Perfect timing.

Next, read their OOO message carefully. Did they mention another point of contact?

That's an opportunity to multi-thread the deal. If your original prospect says, "contact Jane in my absence," go ahead and reach out to Jane.

She might be a stakeholder you need on board.

And even if you don't push the deal forward immediately, you've expanded your network in the account.

Lastly, get creative on social. While your prospect’s OOO, see if they're still posting on LinkedIn.

Prospects still sneak a scroll between mai-tais. Engaging with their posts or commenting can keep you visible without being in their inbox.

4. Create Urgency Right Now

Summer has a way of making everyone procrastinate. Your job is to reignite some urgency.

One tactic is to remind prospects of looming fall deadlines or goals that can't wait.

A gentle reminder like: "September will be here soon, and if you need XYZ in place by Q4, we should talk now."

Another approach is to see if you can sweeten the deal with a time-bound incentive.

Talk to your manager about a summer special. Maybe a limited discount, added free service, or flexible start date.

Many sales orgs find that offering a small discount or incentive for a quick summer close can nudge buyers over the line during a slow season.

Just use it sparingly. You still want them buying for value, not just a coupon. (:

What's your biggest sales challenge in the summer?

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