Intro

Most sales outreach blends into the noise not because sellers lack effort, but because they approach prospects the same way everyone else does. In this episode, Ashley Winston breaks down why traditional outreach tactics fall flat and how sales professionals can stand out by leading with relevance, clarity, and genuine curiosity. We explore how to create conversations that feel natural, human, and worth responding to.

Why Prospects Ignore Most Sales Outreach (00:02:10 – 00:03:35)

Ashley explains that buyers aren’t ignoring messages because they’re rude, they’re overwhelmed.

Generic outreach, vague value statements, and self-focused messaging give prospects no reason to engage.

The real issue isn’t volume, it’s relevance.

The Biggest Mistake Salespeople Make in Messaging (00:03:35 – 00:05:10)

Most outreach talks about the seller instead of the buyer.

Ashley shares why messaging that leads with credentials, features, or company history immediately creates disengagement.

Prospects care less about who you are and more about whether you understand them.

How to Personalize Without Overcomplicating It (00:05:10 – 00:06:55)

Personalization doesn’t mean writing long messages.

Ashley explains how small signals like role relevance, timing, and context, dramatically increase response rates without extra effort.

Relevance beats creativity every time.

Using Curiosity Instead of Pressure (00:06:55 – 00:08:30)

Rather than pushing meetings, Ashley encourages sellers to spark curiosity.

Open-ended questions invite conversation and reduce resistance, making prospects feel in control instead of sold to.

Pressure ends conversations. Curiosity starts them.

How to Earn Replies Without Chasing Prospects (00:08:30 – 00:10:05)

Ashley breaks down why follow-ups fail when there’s no value added.

Each touchpoint should introduce a new insight, observation, or reason to respond not just “checking in.”

Silence is feedback. Adjust accordingly.

What High-Performing Sellers Do Differently (00:10:05 – 00:12:10)

Top performers focus on quality conversations, not activity metrics.

Ashley explains how intentional outreach, patience, and consistency lead to better pipeline health and stronger relationships.

Selling is about connection, not coercion.

Key Lesson: Make It About Them, Not You (00:12:10 – 00:13:55)

When outreach is centered on the buyer’s world, challenges, and priorities, responses come naturally.

Sales success comes from empathy, relevance, and respect, not persistence alone.

“If your message doesn’t immediately answer ‘Why should I care?’, it won’t get a reply.” – Ashley Winston

Resources

Want help applying these strategies directly to your pipeline and hitting your quota?

Join The Sales Evangelist Mastermind, a 90-day program designed to help you close more deals and hit your number.

Learn more at thesalesevangelist.com/mastermind

Sponsorship Offers

This episode is brought to you in part by HubSpot.

With HubSpot Sales Hub, your data, tools, and teams come together on one platform to help you close deals faster. Try it at hubspot.com/sales.

This episode is brought to you in part by LinkedIn.

Tired of prospects not responding? Get a free 60-day trial of LinkedIn Sales Navigator at linkedin.com/tse.

This episode is brought to you in part by the TSE Sales Foundation.

Improve your LinkedIn outreach and land 3–5 appointments with our LinkedIn Prospecting Course.

Visit thesalesevangelist.com/linkedin.

Credits

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Join us for future episodes on Apple Podcasts, Google Podcasts, Stitcher, or Spotify. Audio provided by Free SFX, Soundstripe, and Bensound. Music credits include The Organ Grinder written by Bradley Jay Hill, performed by Bright Seed, and produced by Bright Seed and Hill.