E39 From "I Suck at Sales" to Sales Coach: How Howard Wolpoff Transformed His Sales Skills and Built a Thriving Consulting Practice | Howard Wolpoff

Are you struggling to sell your consulting services because you feel like you're "bad at sales" or don't have formal sales training?

In this episode, host AJ Riedel talks to Howard Wolpoff, a sales coach who works with sales leaders and individual salespeople. What distinguishes Howard is his dramatic personal transformation from someone who openly admitted "I suck at sales" to becoming a successful sales coach who helps consultants and business owners master the art of selling.

Why You Should Listen to This Episode: Self-employed consultants will discover how to overcome their sales anxieties and develop the confidence needed to grow their practice. Howard shares practical strategies that any consultant can implement, regardless of their current sales experience or comfort level.

What You'll Learn in This Episode:

You'll discover how to build sales confidence through early wins and systematic analysis of what works.

Howard explains his unique podcasting strategy for lead generation that allows consultants to have natural conversations with prospects before making any sales pitch.

You'll learn the critical importance of getting all decision-makers involved in sales conversations and specific techniques for making that happen.

The episode covers how to handle objections by addressing them proactively throughout your sales process rather than waiting until the end.

Howard shares his "confusion technique" for cold calling that immediately disarms prospects and creates rapport.

You'll understand why personality assessment is the most transformative sales skill for consultants and how to adapt your approach to different personality types.

Finally, you'll get practical advice on follow-up frequency and the mindset shifts necessary for sales success.

Listen to These Key Moments:

[1:02] The Psychological Shift That Changed Everything Howard explains how getting early wins and analyzing what made them successful built the confidence foundation for his sales transformation.

[7:43] Using Podcasting as an Unconventional Sales Strategy Learn Howard's systematic approach to using podcast interviews as a natural way to have sales conversations with ideal prospects.

[9:05] The Follow-Up Conversation That Closes Deals Howard reveals his exact script for transitioning from podcast guest to sales prospect in a second conversation.

[14:09] Getting Decision Makers in the Room Discover the process Howard uses to ensure all key decision makers are present before making any sales presentation.

[17:23] How Many Times to Follow Up Before Giving Up Howard shares why the answer has evolved from 5 times to 20+ times and how to think about follow-up like a television advertising campaign.

[22:58] The Confusion Technique for Cold Calling Get Howard's exact script for opening cold calls that immediately creates rapport and disarms defensive prospects.

[25:18] Three Essential Pieces of Sales Advice for Consultants Howard's practical guidance on having a plan, saving money before starting, and understanding that selling is fundamental to every business.

[26:55] The One Sales Skill That Transforms Everything Learn why understanding personality types is the most powerful sales skill and how it helps you adapt your approach to any prospect.

Connect with Howard Wolpoff on LinkedIn: https://www.linkedin.com/in/howardwolpoff/