Dearest Reader,

Most founders won’t come out and say, “I’m scared of selling.”

What they do say is: “I don’t want to sound salesy.”

But here’s the real tell—
That feeling shows up in their behaviour: being too passive.

Waiting for the prospect to lead the call.
Waiting for referrals to magically roll in.
Waiting for sales to “just happen” if the offer is good enough.

And then wondering why deals stall...

Here's a simple fix: if you don't want to "be salesy"....the don't.

Somewhere along the way—think Glengarry Glen Ross scripts, Wolf of Wall Street boiler rooms, and late-night infomercials promising six-pack abs in 6 minutes—sales became synonymous with manipulation. Marketing picked up the baton with countdown clocks that mysteriously reset, or those “but wait, there’s more” offers. Advertising piled on with stock-photo handshakes and spray-and-pray billboards.

Cheap thrills. Shiny, hollow, and over fast. Like a bad Tinder date where the photos looked great but the conversation had nothing behind it.

You don’t have to sell like that and if no one taught you another way, come sit by me—I’ll show you a couple.

If I had to start from scratch tomorrow, I’d double-down on three things:

1) Define what sales means (to you)

Sales is neutral—the intersection where supply meets demand. Your job is to light the crossing so buyers can see what’s ahead. Streetlights aren’t sleazy (except the ones telling us to “smile more”). They exist so we can move safely and make good decisions. That’s you.

Some of my clients define sales as:

• Advocacy: micro-moments that champion women into leadership—deal by deal, room by room.
• Service: every sale adds a thread to the customer’s internal story so the org can move.

Once you commit to a definition aligned with your values, the “icky” feeling drops. You’re not tricking anyone; you’re guiding traffic.

Try this (1 minute):​
Finish this sentence and say it out loud:

Practice rep: Write your one-sentence definition. Share it with your team. Use it to open calls (“Here’s how we think about sales and today’s conversation…”). Reps make it real.

2) Build pipeline daily (so you’re never desperate)

The fastest way to feel desperate is to be desperate. When there’s only one deal on the table, you show up tight. Tight sellers don’t listen; they pitch.

You don’t need 50 tactics. Pick two you can do consistently and turn them into habit.

Minimum Viable Pipeline (MVP) recipe (30 minutes/day):

• 10 minutes research: add 5 right-fit names to your list.
• 10 minutes outreach: send 5 targeted messages with a tiny, specific ask.
• 10 minutes nurturing: 3 replies, 1 referral ask, 1 “thought-of-you” share.

Micro-CTAs you can ship today:

• “Want the 3-step checklist we use for first-call prep?”
• “Curious if this is worth it for you? I’ll send two quick questions.”
• “Want me to send you the 3 questions I use to test if a sales process is working?”

Pipeline isn’t pushing—it’s planting. Seeds become shade.

Practice rep: Add one standing CTA at the end of your next post or email (not a buy button, an invite). Track responses for a week. Adjust the wording; keep the behaviour.

3) Run a simple, repeatable process

Winging it isn’t a process. The “talk about yourself for 40 minutes and hope” flow isn’t selling; it’s stalling.

Use a 5-step Streetlight Process:

1. Pre-call (5–10 min): Write a one-line problem hypothesis + a short agenda.
   “If nothing else, I want to learn X and confirm Y.”
2. Open (2 min): Safety + context.
   “Here’s what I understand, here’s the agenda—what would make this time valuable for you?”
3. Discover (15–25 min): 70/30 listen/talk. Validate the problem now, not the product later.
   • “What have you already tried?”
   • “What happens if this slips another quarter?”
   • “Whose day actually changes if we solve this?”
4. Decision path (5 min): Co-create next steps. Offer an easy out.
   “If we’re wrong fit, say so—I’ll still send you the notes and a resource.”
5. Follow-up (same day): Summary, decisions, dates, owners. Include one question that requires a reply.

Practice rep: After your next call, spend 3 minutes on a debrief (solo or with a peer):

• Where did I truly listen?
• Where did I jump to solutioning too soon?
• What single sentence moved the call forward?
• What will I do differently on the next call?

Reps turn a process into muscle memory.

We don’t rise to the level of our goals; we fall to the level of our reps. You can white-knuckle this alone, or you can practice in a room designed for it.

Focus on these three (and actually practice), and by year’s end selling will feel different. Because sales is a lag measure, by January you won’t recognize the seller you used to be.

Until next time, Happy Selling!
Talica

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