[12] The Follow-Up Formula: Turning 'Maybe' into 'Yes'
Let me set the scene: I once went on a first date with a guy who showed up 15 minutes late wearing a backwards hat that said “IYKYK.” He spent the evening talking about crypto losses, referred to his mom as his “roommate,” and when the check came—poof—he suddenly had to “take a call.”
Needless to say, I never heard from him again. Ghosted harder than a Halloween haunted house.
But you know what? That same “now you see me, now you don’t” energy shows up all the time in sales. You have a killer discovery call, they nod like you’re the second coming of SaaS, say they’re “so excited to move forward,” and then… inbox silence.
If dating is just sales in heels, then following up is where the real courtship begins.
But here’s the thing: turning a “maybe” into a “yes” doesn’t mean blowing up their inbox or turning into a LinkedIn lurker. It means thoughtful timing, messaging that actually earns a reply, and a little sprinkle of sass.
So if your deal is ghosting, grab a glass of wine (or a triple-shot espresso if it's quarter-end), and let’s break down the follow-up formula that turns radio silence into “Let’s do this.”
Step 1: The Waiting Game
AKA: How to follow up without sounding like you camped outside their office with a boombox
Let’s not confuse “high touch” with “high alert.” I know it’s tempting to send a follow-up email before your Zoom tab even closes, but let’s keep our cool. You’re not desperate—you’re deliberate.
People are juggling audits, last-minute board decks, and trying to remember their Slack password after PTO. So before you assume you’ve been ghosted, assume they’re drowning in digital noise.
Here’s how to break through without breaking a sweat:
Follow-Up Timing Cheatsheet (Now with Strategy & Sass):
After a great call or demo
Send your thank-you/follow-up within 24 hours (you’re polite, not passive).
If you don’t hear back, set a calendar reminder for 4 days later—enough time to let them breathe, but not so much they forget your name.
Use that second touch to bubble up value again
“Still thinking about your comment on automating evidence collection—it’s giving free time and fewer headaches. Can we pick this back up?”After they hit you with the “Let’s circle back”
Translation: Not now, but maybe later if I don’t get promoted or pulled into a re-org first.
This is your chance to follow up with flair. Reference something specific (and human!) from the call. Show them you were listening, not just nodding while updating Salesforce.
“Circling back like we said, and yes—I still think Secureframe can save you more hours than your team spends in Zoom each week.”
“Following up like a true Swiftie—just like you mentioned during the call—back and better than ever with a new integration update you might love.”
“You said your CFO hates surprises, so I figured I’d pop back in before Q2 sneaks up.”
Pro Tip: Humor, specificity, and timing > “Just bumping this up.” Every. Time.
End of quarter or renewal season
This is your golden window. Use urgency without the pressure:
“We’re seeing a lot of teams push final security tooling decisions before Q2 hits—any room on your side to revisit?”
Deals in Heels wisdom:
“The best follow-ups don’t chase—they saunter back in with confidence, value, and just the right amount of sparkle.”
Step 2: The Message Matters
AKA: You can’t just say ‘bumping this up’ and expect hearts to flutter
Raise your hand if your inbox is 70% “just checking in” messages. 🙋♀️
Now burn that phrase with fire.
The truth is, your follow-up message should bring value, vibe, and maybe even a laugh. We’re not robots—we’re relationship builders (in heels).
Here’s my no-fail formula:
Context — “Last time we chatted, you mentioned X...”
Hook — “Thought of you when this update dropped…”
Soft CTA — “Want to carve out 15 mins next week?”
Bonus moves:
Use humor when appropriate. (I once followed up with a meme of a tumbleweed and the subject line “Me waiting for your reply 👀”—they responded instantly.)
Include a real reason to re-engage (a new feature, case study, or timeline nudge).
Deals in Heels wisdom:
“Make your follow-up so good they feel guilty for ghosting you.” And maybe a little impressed too.
Step 3: When It’s a “Not Now,” Not a “Never”
AKA: Playing the long game like a high-stakes rom-com
Not everyone’s ready to commit on the first try. Sometimes they need to “figure things out” or “see where next quarter leads.” Sound familiar?
And while I do not endorse texting your ex, I do endorse strategic check-ins with prospects who said, “Not right now.”
How to Stay Top of Mind:
Set a calendar reminder to follow up in 30, 60, or 90 days.
Personalize it—reference something real: their hiring plans, their recent launch, or even their favorite coffee (yes, I keep notes).
Give them a reason to say yes now: “Hey Sam, we just dropped a feature that automates the workflow you mentioned—worth a peek?”
Soft touches like these keep the spark alive without sounding like you’re lurking in their LinkedIn views (even if you are).
Deals in Heels wisdom:
“You’re not chasing them—you’re just letting them remember what they’re missing.”
Step 4: Respect the No
AKA: When to stop texting him—and your prospect—and walk away with your dignity (and LTV) intact
Look, not every deal is The One. Some prospects are like that guy who “just got out of something serious” but still wants to “stay in touch.” Sis… no.
Sometimes you really have been ghosted. Or worse, friend-zoned with a “We’re going with another solution, but you were great!” It stings. But let’s not pull a rom-com meltdown on the sales floor.
Here’s your power move: bow out gracefully, leave the door cracked, and let them remember you as the one that got away—wearing red lipstick and holding a killer QBR deck.
How to Gracefully Exit Stage Left:
“Totally appreciate the transparency—timing is everything. If priorities shift or the spreadsheet life gets old, I’d love to reconnect. Wishing you and the team a strong quarter!”
Bonus? These notes often get saved, forwarded, or magically resurrected when their new platform goes poof or a new head of security joins and says, “Wait, why aren’t we using Secureframe?”
Because you, my friend, planted that seed like the confident queen you are.
Deals in Heels wisdom:
“Every 'no' is just a 'not yet'... probably from someone who still uses Excel like it’s 2012. You? You exit like it’s a runway. And they’ll remember you when they’re ready for the real thing.”
Step 5: Build Your Follow-Up Arsenal
AKA: Set it, style it, reuse it (and make it fabulous)
Let’s face it: you’re too busy being a pipeline powerhouse to reinvent the follow-up wheel every time someone ghosts you. That’s why every sales queen needs a swipe file of stylish, strategic, and slightly savage follow-up templates.
Think of them like your signature lipsticks: one for every mood, every moment, and every type of buyer. From “I saw you looking 👀” to “Let’s seal this deal before EOW,” your messages should feel personal without being painstaking.
Here’s my go-to rotation:
The Feature Drop
For when your platform just rolled out something chef’s kiss and you need an excuse to slide back in.
Use it when: You’ve got new functionality that aligns with something they mentioned on a call (or something you know will trigger major FOMO).
Example:
“Hey Mia! We just launched a new dashboard that lets you automate third-party vendor reviews—instantly thought of you and your team’s backlog. Want a quick peek before word gets out?”
Vibe: Helpful, timely, and just a little exclusive—like a VIP product drop.
The Funny Nudge
Because sometimes the best way to get a reply is to be the most memorable email in their inbox.
Use it when: You’ve followed up once or twice already and want to stay top-of-mind without sounding pushy.
Example:
Subject: Still here. Still fabulous.
“Not trying to win an award for Most Persistent (unless there’s a trophy), but I figured I’d bubble this up in case it slipped through. Still think we can save your team serious hours—and maybe even your sanity.”
Bonus points for: Using a relevant meme, GIF, or callback to something funny they said in your last convo.
The Executive Ping
For when it's time to escalate gently and speak the language of leadership—ROI, compliance risk, and bottom-line benefits.
Use it when: You’ve got a gatekeeper or champion, but decision-making power sits with someone higher up.
Example:
“Looping in Rachel here, as we touched on the budget piece during our chat. Happy to walk through how Secureframe can help reduce manual hours across IT & Security and cut audit prep time by 70%. Let me know if you want to run the numbers together.”
Vibe: Smart, confident, data-backed. You’re not pushing—you’re aligning.
The End-of-Quarter Closeout
Time’s ticking, the CFO is lurking, and you’ve got a quota to close. Let’s make it count.
Use it when: You’re approaching quarter-end and want to inject urgency without turning into a discount gremlin.
Example:
“Quick heads up—we’re closing out Q2 and holding a few spots for teams looking to lock in support and onboarding by next month. If now feels right, I can make the process smooth as butter. Shall we?”
Optional add-on: “This also lets you expense the deal before budgets roll over 😉”
Bonus Template Naming Vibes
Because follow-up should be just as fun to send as it is to get. Name your templates like lipstick shades or happy hour cocktails:
Red Alert Follow-Up – When urgency is the move, but style is still required.
Espresso Yourself – Your witty check-in after a slow reply week.
Quarter-End Quencher – For the final nudge before EOD.
Tequila Timeline Touchpoint – For when they say “next quarter” and you actually followed up 90 days later.
Bubblegum Budget Bouncer – A soft way to ask if they actually have budget yet, with personality.
Deals in Heels Wisdom:
Templates don’t make you lazy—they make you legendary. With a little personalization and a lot of charm, your follow-up game can go from forgotten to fabulous faster than you can say, “Just circling back.”
So next time a prospect ghosts you, don’t spiral. Channel your inner Elle Woods, flip your hair, and send a follow-up so polished it belongs in Vogue.
And remember: great saleswomen don’t beg. They build pipelines.