The Truth About Prospecting
It’s All About Starting Conversations
Hi, it’s Vince and I’m back with another edition of Early Wins, my newsletter that delivers actionable insights and lessons to help startups close enterprise deals, achieve market fit, and confidently scale.
Here’s the truth about prospecting: it’s not about selling, it’s not about pitching, it’s not about perfect email templates or slick outreach sequences.
Prospecting is about starting conversations.
The best conversations feel natural, genuine, and human. Whether you’re a founder landing your first customers or a seller trying to build a pipeline, your goal is simple: open the door to a real dialogue. Once you start a conversation, the relationship—and eventually, the sale—can follow. First, you need to earn the right!
Here’s how to make it happen.
Step 1: Update Your LinkedIn Profile (Because They’ll Check It)
Before you send your first message, take 10 minutes to clean up your LinkedIn profile. Why? Because as soon as you reach out, your prospect is going to check it out.
Make sure your profile communicates who you are and what you do. This isn’t about bragging—it’s about making it easy for someone to understand why they should connect and talk to you.
✅ Headline that’s clear and specific (Not just “Founder” or “Sales Manager.” Say what you do.)
✅ About section that shares your expertise and the value you bring
✅ Up-to-date photo (Not a blurry headshot or a cropped vacation pic)
✅ Relevant content or wins in your Featured section
A polished profile builds credibility and shows you’re someone worth talking to.
Step 2: Connect on LinkedIn (No Need for a Personal Note)
If you’re not already connected, start by sending a connection request—and don’t overthink it. Studies show that blank connection requests are accepted slightly more often than personalized ones. but, make sure your profile is up to date!
Once they accept? That’s your opening to start a conversation.
Step 3: Make It About Them (Not You)
Nobody wants to read another pitch email. The fastest way to kill a conversation is to make it all about you. Instead, focus on them.
Start with something simple and genuine:
Find a hook – Did they just post something interesting on LinkedIn? Get promoted? Raise funding?
Ask a question or share an observation – “I saw your post about X—curious how you’re thinking about Y?”
Lead with value, not your product – “We helped [similar company] solve [pain point]—happy to share if it’s relevant to you.” worth exploring?
The key is to keep it natural and conversational. If your outreach feels like a form letter, they’ll treat it like one—by ignoring it or deleting it.
Step 4: Mix It Up (Use Multiple Channels)
The best prospectors don’t just rely on one channel—they show up where their prospects are. Some people respond to emails, others to LinkedIn, and sometimes it takes a phone call. Here’s a simple playbook:
Engage on LinkedIn – Like or comment on their posts to get on their radar.
Send a short, direct email – Under 100 words. Ask one question, make it easy to respond.
Leave a voicemail – Keep it short and curious: “Saw your post about X—wanted to connect and hear more.”
DM on LinkedIn – If they viewed your profile or engaged with your content, follow up here.
Messaging - text or WhatsApp app works well but timing is critical, too soon and it’s creepy
Go Old School - get crazy and send a handwritten note or card and blow their minds.
You don’t need to be aggressive—just consistent. Your goal isn’t to sell; it’s to start a conversation.
Step 5: Move to a Call or Meeting (That’s Where the Real Connection Happens)
At some point, you need to take the conversation off the keyboard and into real life. The best way to build a connection is through a live conversation—whether it’s a phone call, Zoom, or (ideally) an in-person meeting.
When the timing feels natural, send your prospect a calendar invite:
"Hey [Name], I’d like to hear what you’re working on and see if I can help. Here’s a link to my calendar—feel free to grab a time that works for you."
Once you’re on the call, make it all about them. The best conversations start with curiosity:
What are their goals?
What challenges are they facing?
What have they tried?
What are their priorities right now?
No pitching. Just listen. The more you understand their world, the easier it will be to connect their challenges back to the value you provide at the end of the call.
Before ending the call tie back your value to their challenges (pain). You’re looking to confirm a mutual fit i.e. we have a solution that can solve your pain.
Don’t forget to set the next step!
Final Thought: Prospecting is a Conversation Game
The best sellers and founders don’t focus on making sales in the first message. They focus on starting conversations. Conversations build trust. Trust opens the door to relationships. And relationships lead to deals.
Keep it simple: Show up consistently, stay curious, and keep it genuine. The rest will follow.
Featured Early Wins Podcast Episode
This is a spotlight clip from my full conversation with Mark Kosoglow. Mark shares how he helped Outreach go from $0 to $1M ARR in only six months.
Watch the Full Episode on our YouTube channel.
Whenever you're ready, there are 3 ways I can help you:
Deal Coaching: I lead 1:1 and Group sessions to increase your win rate by focusing on large winnable deals through peer-to-peer reviews and deal construction reviews.
Fractional Sales Leader: I'm a temporary sales leader for organizations that are in a transition or in need of help scaling.
Advisor: I help companies with their GTM strategy for near-term results and long-term success.
Vince Beese Coach, Advisor, Fractional CRO
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