Don’t Focus on the Sales Process … Create Challenging Conversations

What conversations do your sales teams have today? Odd question – perhaps, but perhaps not. How well do we listen to the conversations our sales organizations have with prospects and clients? Are the conversations respectful, intellectual, valuable, filled with new creative ideas, authentic, and thought provoking? Or are they directive, guarded, calculated, and non-engaging, addressing only your product with no tie back to each client’s unique issues?

What stimulates a conversation? It is a question grounded in your clients or prospects industry and business, not yours. This creates trust which is the cornerstone to any successful relationship. To have credibility you need to demonstrate that you have done your homework prior to the call, and that you have: reviewed their website, reviewed their annual report, researched their industry, and read about their competition. At this point you can focus your conversation on “points of clarification” on what you have learned about their business instead of “education” about what they do.

Asking challenging questions to provoke new ideas, different thinking, or more curiosity helps those around us see us as leaders. Great questions take time to answer. To create them we need to really listen carefully and craft questions that do not elicit an obvious answer or be an apparent step to sell your product.

Challenging questions force you to look beyond the obvious, to analyze, assess and make decisions and demonstrate your expertise, while enhancing your credibility. Most important, they can’t be answered without seriously considering their business situation.

To encourage more engaging conversations in your organization and with your prospects have a look at some of these ideas and share them with your sales team. Perhaps you can collectively shift the culture and engage more people, simply by improving their approach to conversation. As your team becomes courageous in asking challenging questions, you may find that your sales cycle shortens and your win rates increase.


Seek knowledge rather than demonstrate it – it’s not about you.

All too often, sales people ask questions that are designed to demonstrate their knowledge, rather than expand it. Unfortunately, such questions actually tend to make the questioner seem arrogant and provide no real information to either party. Challenging questions are designed to elicit information and actually tend to open your prospect even more as they will be more willing to share their issues and concerns with you. Most important? You leave with more client knowledge than you came with.

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The rule here is to never be afraid to admit what you don’t know or understand. Most people are complimented when asked questions about their business and their roles – as this demonstrates their knowledge – rather than discussions about your product or solution. Here are some tips to help your reps encourage prospect engagement:

  • Explore a new topic. Search for a new mutual topic of interest, either about the business or possibly mutual outside interests. Gain agreement to explore it intensely. Do it together and notice how the engagement between you expands.
  • Ask someone to teach you. Notice someone who knows about a subject you would like to learn. Be attentive, curious, and encouraging as they share with you some new knowledge.
  • Listen deeply. Engage your client in conversation by giving 100% focused, present, and deep listening. When someone feels heard regarding their value, engagement rises quickly.
  • Allow silence. When the person you are speaking with pauses, allow the silence to hang suspended and continue to hold a focus with them. They will take a breath, realize you are truly engaged and continue sharing their thoughts.
  • Coach. If someone expresses a need to work towards a goal ask if you can coach them. Use gentle, powerful, and thoughtful questions to engage them in conversation, listen well, and suspend your own judgement helping them to find their own answers.
  • Explore – When faced with an issue or problem – instead of immediately going into problem-solving mode – ask questions about what does work. Dig deep to find the gems of good ideas, good processes, and excellent work. It engages your prospect in new ways.
  • Notice someone’s passion. When you know someone has a certain passion, find an article, an object, an idea, or piece of information and share it with them. This enables you to sell not only the business value of your solution, but also your personal value to the client.

Using challenging questions is a great way to encourage open thinking amongst your opportunity stakeholders. This will help to surface ideas, values, issues and perceived constraints. Once these thoughts and issues have surfaced, they can be discussed and solutions can be explored and created.

To view a partial list of suggested “challenging questions” follow this link.


About the Author

James HaleJames Hale
Founder and CEO, Mprove Sales

Jim Hale is a recognized sales leader with broad success in Entrepreneurial and Corporate environments. He has developed and led worldwide sales and operations and has extensive experience with selling and managing teams in the Americas, EMEA and Pacific Rim. Jim has both channel and direct sales organizations consistently improving revenue and margins while implementing profitable cost controls. Extensive network of executive contacts in major reselling organizations as well as corporate accounts. Jim has hired and developed sales organizations at IBM, Oracle, Ernst & Young and Vantive as well as a number of startup companies.


James Hale

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