Copyright to Andrew Sobel © 2012
Published here September 2012

Editor's Note | Introduction | Dealing with your Customers or Stakeholders 
Personal Predicaments | The End of the Road


At work, at home, with friends, and even with perfect strangers, it isn't uncommon to find yourself suddenly entrenched in a tough, tense conversation. Instead of trying to stutter and mutter your way out of it, and risk permanently damaging an important relationship, I suggest you ask your way through it by using key Power Questions.

We've all experienced moments when we feel at a loss for words. Your boss criticizes your work. A customer demands a discount. Your presentation gets off on the wrong foot and tempers flare. Every time, you're left thinking, I wish I had been able to think of just the right thing to say to that person! What should I have said?

No interaction, regardless of how tough, is ever completely lost. I suggest transforming tough conversations - and the relationships they affect - by asking a few power questions. In these situations, when there's a lot on the line, it's not all about finding the right thing to say - it's about asking the right questions. By posing just one or two thoughtful questions, you can turn even the most difficult conversation around, shift the focus back to the other person, and give yourself invaluable breathing room to gather your thoughts.

Read on for a look at ten of the toughest, most awkward conversations you'll ever have, and the powerful questions that will help you manage them with ease.

The First Challenging Question

1.  A prospective customer says, "Tell me about your firm. What's different or special about you?"

Even the best salespeople seem to choke up when they are asked this question. Usually, they spout a bunch of unconvincing statistics, talk about all their offices around the world, and tout their unique, "collaborative" approach - the same stuff anyone else can and does say. A better response - which will engage your prospect - is to first seek additional information. You might ask, "I'm curious, have you had any past experience with our company?" or, "What particular aspect of our business would you like me to talk about?"

Often, prospects have something specific they want to know about you or a doubt they harbor, and this second question will help draw it out. This way, you'll focus in on what's most important to that particular customer. Finally, you should add, "The best way to talk about our firm is to share a couple of examples of recent work we've done with clients in your industry. Would that be helpful to you?" Skip the boring facts and figures and go right to engaging examples that will capture your prospect's imagination.

Editor's Note  Editor's Note

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