The Challenges Checklist

Many of Jason’s clients arrive at The Coaching Hour after wrestling with one—or many—of these common problems. Sound familiar?

You’re not alone…

• You’re explaining your capabilities, and buyers seem impressed—but they don’t invite you into an engagement.

• You’re using communication patterns that worked in corporate—but fall flat in business development.

• You’re not selling solutions—you’re selling leadership—but no one told you that.

• Your sales conversations stop at “interest” instead of moving into action.

• Buyers say “this is great”—but then go silent when they see the proposal.

• You’re networking with dozens of people… and not getting introduced to opportunities.

• You get stuck talking about your experience instead of creating urgency around a business problem.

• You turn over control of the conversation too early—asking buyers what they want to do next.

• You’re trying to educate and impress instead of guide and discern.

• You’re waiting for buyers to be “ready,” instead of helping them get ready.

• You’re showing up with experience—but not presence, clarity, or leadership.

• You’re using job interview communication habits instead of business-building habits.

• You’re not sure how to lead from the outside—without a title, role, or org chart.

• You feel confident in your abilities… but not in your ability to create consistent income.

• You’re not sure how to turn a great conversation into a paid engagement.

• You feel like you’re guessing—about your market, your offer, and what to say next.

• You’ve held leadership roles… but no one taught you how to lead a buying conversation.