Boldness and Humility: The Yin & Yang of High-Performance Selling


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Yin and Yang. The universal symbol of “how seemingly opposite or contrary forces are interconnected and interdependent in the natural world.” (source: Wikipedia)

Boldness and Humility: The Yin and Yang of High-Performance Selling

The more I learn about selling, the more I believe that the most successful sales professionals have a unique combination of two powerful character traits: boldness and humility.

We often think of these two things as opposites; you are either bold or you are humble. Two different personalities for two different people.

I disagree. I think these two forces actually work more like a battery. A battery creates electricity by combining chemicals and throwing off electrons. The main chemicals mix together to cause a powerful charge.

This is what great salespeople do: they create a charge around them. They are at once bold in their approach, and humble in their interactions. They are unafraid, confident, direct, concise. They push. And then they listen, ask questions, tell stories, wonder why. They pull.

Boldness and humility have so many powerful applications in our day-to-day selling efforts. Here are just a few of my favorites.

Where Salespeople Can Apply Both Boldness and Humility

Handling objections

Great salespeople are bold in seeding objections into a conversation. They know that the “We can’t afford this” objection is coming, and they don’t sit around in fear and wait for it. They seed that objection into an otherwise great sales meeting by saying; “John, we should discuss the costs involved here. How do you feel about the investment we are asking for versus the return you will see??” That’s bold. Great salespeople don’t wait for it; they put it out there and tackle it head-on.

But once that objection is out on the table, they don’t bully the answer. When they get the inevitable response “Well, I see the return, but we just can’t budget that in right now,” they demonstrate humility by asking questions. “Tell me more about that. Has the entire budget for this year been spoken for by priorities that are higher than this one? If so, what kinds of returns are you anticipating on those other initiatives?”

They shut up and listen. They don’t just jump right to the answer, but instead let the client move through his thought process. In doing so, they are much more credible and customer-centered than the usual response to budget objections; “I don’t think you are seeing the big picture here. The ROI on this project is clearly in your favor. That makes sense, right?” You can be both bold and humble in the way that you handle objections as a salesperson.

Working a room

Great salespeople know how to work a room. We all go to trade shows, events and dinners, but do we really work them? Or do we walk around, collect thumb drives and have a few drinks?

Great salespeople exhibit boldness by being unafraid to make a cold approach. They know what to say and how to say it such that they get quickly into a sales conversation. But then the high-performers switch gears. They ask impact questions, share stories (even failure stories!) and brainstorm without portraying that they’ve got all the answers. They are humble in spending more time listening and asking questions than telling.

High-performing salespeople remember the ratio of two ears to one mouth.

Sales Leadership: Giving feedback

Great sales leaders never miss an opportunity to give feedback. They do ride-along’s, join conference calls and sit in on presentations. And often, these situations require them to give direct feedback to their sales people. But many sales leaders whiff on this because giving feedback can be awkward.

Great leaders are bold in the sense that they see an opportunity for feedback and they have the guts to take it. They say; “Bill, here’s one thing in that presentation that I would like you to do differently. You were long-winded, and I think the team lost the thread of what you were saying. How do you feel about that?” This type of feedback is uncomfortable and often awkward. But, so is hard work. Bold sales leaders get it done. Then, in the midst of that feedback conversation, they exhibit humility in acknowledging how they too have been accused of being long-winded and sharing feedback they have received over the years.

Be bold. Be humble.

Are you bold and humble? Are there certain situations that call for more boldness or humility?

Let me know how you try to be simultaneously bold and humble in the comments below or on Twitter.

Republished with author's permission from original post.

Craig Wortmann
Craig Wortmann is the CEO and Founder of Sales Engine, a firm that helps companies build and tune their sales engine(s). He is also a renowned professor of entrepreneurship at the University of Chicago's Booth School of Business. His course, Entrepreneurial Selling, was ranked by Inc Magazine as one of the Best Courses of 2011. Craig published his book What's Your Story?: Using Stories to Ignite Performance and Be More Successful in the same year and continues to speak on the topic of using stories in the sales process.


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