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📞 dialing mastery
Unlock prospect callbacks with strong opening lines
Daily Sales Newsletter July 08, 2025 |
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Welcome - this is your daily dose of sharp, tactical sales advice.
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In today’s issue:
Sheriff Shahen: Follow-ups that actually book meetings
Will Aitken: Opening cold calls that never feel awkward
James Bissell: Your calling openers need a permission ask
Giulio Segantini: Use this pitch strategy for conversations
Follow-ups that actually book meetings
Sheriff Shahen breaks down how to master cold calling with practical strategies that actually work, helping you book more meetings without sounding robotic and pushy:
Cold calling that books meetings
Begin with a sniper-focused ICP.
Don’t call anyone with a pulse.
Your list should be clear on:
✔ Who exactly to call (roles, industries, specific pain)
✔ Why they actually care (real triggers, problems)
✔ When to reach out (funding, hiring, tech changes)
Ditch the script — use a blueprint
A rigid script makes you sound like a robot.
Instead of just reading from a dialing script:
➤ Outline key components: Opener, 2-3 discovery questions, short value-based pitch, objection responses, and closing deal statement.
➤ Practice doing conversations until it feels natural, not rehearsed.
Nail your dial openers with clients
Forget “Did I catch you at a bad time?” immediately.
Use this structure instead:
➤ “I know you weren’t expecting my call, so I’ll keep it super brief.”
It signals respect, confidence, and professionalism, and it works.
Tonal control when speaking matters
Sound curious, not desperate when talking with prospects.
Curiosity drives people inside. Desperation pushes them away.
Make everything about them, not you
The primary goal is simple: make sure your clients are talking.
Focus on their challenges and experiences, not your pitch.
Objection handling = FFF formula
⇒ Feel: “Totally get why you’d say that.”
⇒ Felt: “Others have felt the same.”
⇒ Found: “But they found that after we [insert success example], it worked really well.”
Push for at least 3 no’s before considering to end.
Mindset is half the sales calling battle
Rejection is data-packed evidences, not failures.
Every “no” gets you slowly closer to a “yes.”
Stay detached, always play the long game.
Talking with clients like a peer, not a pest
Skip the begging part of your conversation
Instead say:
↳ “Seems like there could be a fit. Why don’t we book 20 minutes next week to explore?”
Peers are setting frame atmosphere.
Pests are showing never-ending games.
Outworking the possible result averages
Volume always still wins.
No magic hack replaces:
✔ 50+ calling prospects daily without failure
✔ More conversations = faster improvement
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Opening cold calls that never feel awkward
Will Aitken delivers ld calling tutorial stripping away the awkwardness and pressure — replaceing it with a simple, confident process booking meetings and real conversations:
Start with mindset, not a script
↳ Most people won’t pick up.
↳ Most calls will be short-lived
↳ Most won’t result in a meeting
The primary goal isn’t to win every call attempt.
It’s showing up, have conversations, and stacking wins over time.
Smile confidently when dialing
⇢ Smiling when dialuing changes your tone instantly.
⇢ You sound warmer, more human, and less “salesy”
⇢ A mirror on your desk helps you stay aware of energy.
The perfect cold calling opener
Skip the fake-sounding intros.
Lead with preparation and curiosity.
Example:
⇒ “Hey Jenny, I was just looking at your [LinkedIn, website, job ad, or recent funding news]. It’s Will over at [Company]. Can you help me out for a quick second?”
✔ Gets a small “yes” fast instantly
✔ Shows you did some homework.
✔ Lowers defenses immediately.
How to frame prospect conversations
When they say yes, follow with:
⇒ “I noticed you [insert observation] — figured [insert challenge] might be top of mind. Mind if I share a couple of common challenges I’m hearing from others trying to [insert goal]?”
This method earns your second “yes” — where the real conversation begins.
Position the problems, not the product
State 2 relatable problems with simple impacts.
Example:
❖ “Some teams are struggling with [problem one], which causes [impact]. Others don’t have that issue, but [problem two] is a big one, usually caused by [common cause].”
Then consequently ask:
❖ “Curious — can you relate to either of those? Or are you just totally crushing this right now?”
↳ Light, conversational, and pressure-free.
Objection handling: The 3-step formula
Acknowledge → Permission → Split
If they say, “We’ve got this covered”:
❖ “Totally fair — figured that might be the case. Before I let you go, mind if I ask a cheeky question?”
❖ “Is it that you’ve genuinely got this dialed in… or are you just being polite because you get loads of calls like this?”
↳ This surfaces prospect’s truth without creating tension.
If it’s a genuine ‘no,’ exit deal gracefully
✔ Offer to send email attachments for future reference.
✔ Bonus tip: Ask random questions:
“What’s your favorite pizza topping?”
→ Use as the subject line in the follow-up email.
Keeps things light, human, and memorable.
When there’s a fit, set up touch meetings
If they persuasively lean in:
➤ Clarify:
“How long has that been a challenge?”
➤ Then:
“If I could show how others are solving that, with or without our help, would that be worth a quick chat?”
Lock it in:
“Would it be totally out of the question to grab 20 minutes next week?”
Confirm time availability, email confirmation, and send a final recap — done.
Bonus calling advice that matters most
The number one reason people fail at cold calling isn’t bad scripts — it’s bad energy.
→ If you sound nervous, desperate, or rushed — buyers feel it on you
→ If you’re calm, playful, curious, and detached — buyers relax too
This isn’t a graded performance.
It’s a conversation. Have fun with it.
The more yourself you are, the more meetings you’ll book.
Your calling openers need a permission ask
James Bissell provides an effective cold call structure s built around control, and fast qualification testing urgency, helping his team scale from 6 to 60 meetings a month:
1. Permission opener
Start introduction with a calm, respectful ask:
“Hi [Name], we haven’t spoken before—can I take 30 seconds to explain why I’m calling?”
✔ Most prospects usually accept invitation, saying yes
✔ Gives you room to continue without sounding pushy
2. Get to your problem
Use soft phrasing to surface relevance fast:
“I don’t suppose you’re struggling with [problem] too?”
Or:
“I don’t suppose this market-wide problem impacts your team too?”
⇢ Makes it safe to say “yes” without pressure
⇢ Lowers their guard and making clients think
3. Short, quick discovery
Gauge their urgency quickly:
“What are you doing to try and solve that?”
⇢ Helps you know if solving is a priority
⇢ If they fumble, it’s likely not that urgent
4. Personal customer story
Use proof when building trust and sparking curiosity:
“This reminds me of [title or name]. They were trying to [goal] but couldn’t because [barrier]. We helped them go from A to B.”
⇢ Make primary outcomes be the hero
⇢ Avoid technical jargon, keeping it short
5. Soft close + double option
End things with a no-pressure check-in:
“Curious—do you think this approach could help your team too?”
Then immediately:
⇒ Offer them various time slots
⇒ Stay quiet, wait for response
↳ This combo makes it easy to say yes without feeling sold to
↳ The silence creates space for prospects to give you a response
Cold calling still works when it’s centered on the buyer—not the pitch.
If you’re hitting walls, try rewriting your openers and discovery around this format.
Make it conversational. Keep it short. Always test for urgency early.
TO-GO
Giulio Segantini: Use this pitch strategy for conversations
Josh Braun: Bypass resistance with one simple dialing shift
Tom Alaimo: How calling blindly ruin potential connections
Aaron Margolis: First impressions are everything to clients
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QUOTE OF THE DAY
"Your whole goal making a dial is simply to have a conversation."
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