Asking Questions: Pushing Past Discomfort to Find Trust

Many Presales and Sales professionals I've mentored say they feel uncomfortable asking questions. Most are concerned they'll come across as rude or pushy.

Asking questions honestly and engaging with the answers from the perspective of wanting to help elevates the conversation.

Henry Thoreau summed up the correct approach: 

"𝘛𝘩𝘦 𝘨𝘳𝘦𝘢𝘵𝘦𝘴𝘵 𝘤𝘰𝘮𝘱𝘭𝘪𝘮𝘦𝘯𝘵 𝘵𝘩𝘢𝘵 𝘸𝘢𝘴 𝘦𝘷𝘦𝘳 𝘱𝘢𝘪𝘥 𝘮𝘦 𝘸𝘢𝘴 𝘸𝘩𝘦𝘯 𝘴𝘰𝘮𝘦𝘰𝘯𝘦 𝘢𝘴𝘬𝘦𝘥 𝘮𝘦 𝘸𝘩𝘢𝘵 𝘐 𝘵𝘩𝘰𝘶𝘨𝘩𝘵, 𝘢𝘯𝘥 𝘢𝘵𝘵𝘦𝘯𝘥𝘦𝘥 𝘵𝘰 𝘮𝘺 𝘢𝘯𝘴𝘸𝘦𝘳." 

𝘽𝙚 𝙜𝙚𝙣𝙪𝙞𝙣𝙚 𝙞𝙣 𝙮𝙤𝙪𝙧 𝙙𝙚𝙨𝙞𝙧𝙚 𝙩𝙤 𝙝𝙚𝙡𝙥. If you establish that your motivation is to solve their problem and demonstrate that you care about their answer, you're not just asking questions - you're offering help. This builds trust and earns you the right to investigate deeply without breaching boundaries.