Tough Questions – by Barbara Weaver Smith

In my continuing series on rehearsing for team sales presentations, today’s post is about preparing for the tough questions.

Sometimes you are tempted just to hope they won’t ask questions for which you don’t have a good answer, but that is a path to disaster. Everyone involved in the presentation needs to know WHO will answer each tough question and HOW the team will answer it. You need to anticipate and even welcome the tough questions

Here’s an example. You are a marketing company presenting to a new brand new prospect, a company that also happens to be in an industry that you haven’t worked in before. Of course, you can’t gain experience in new industries unless a company in that industry will trust you enough to be the first! So that is a logical question and an inevitable question that they will ask: have you ever worked in the automotive industry before?

Faced with a question to which the actual answer is “No”–your team is likely to hem and haw, look around the table to see who is going to field that question, and appear embarrassed and inexperienced. If you are prepared for the question, your designated person can answer promptly and confidently, a response like one of these for example:

  • “You would be our first automotive client. Our team has been actively researching marketing trends in your industry in order to prepare for our planned move into this arena. Would you like to see what we’ve learned?” [present a bullet list, infographic, or other chart of your findings]
  • “We have a plan to move into new industries strategically, and yours and signage is one we’re prepared for. I’d be glad to put you in touch with a couple of customers whose companies were our first in their industry, so that you can ask about their experience. We have handled it well!”
  • “You know, we have learned that the differences between companies in the sale industry are more important to our delivery than differences in the industry vertical. So our proposal includes an up-front process of learning about your company’s current marketing status at our cost, not yours. Here is a process document to illustrate how that works.”

It’s less important WHAT you say but that you’ve anticipated the question and your response is prompt and appropriate.

How do you anticipate tough questions? There are three kinds:

  • questions you want them to ask, because they lead you to great selling points
  • questions you hope they won’t ask, because you don’t have good answers
  • questions you’ve already answered but that you want to change your response

Brainstorm these categories with your team as you’re preparing your presentation. A good source is your list of whale fears and fear busters. If you’re preparing to present a very big deal, invest the time to convene a Murder Board, small group of very knowledgeable people whose job it is to put you on the spot with tough questions.

How do you prepare to handle tough questions? Please comment to share your own great ideas. Thanks!


Barbara Weaver Smith is founder and CEO of The Whale Hunters®, co-author of Whale Hunting: How to Land Big Sales and Transform Your Companyand author of Whale Hunting with Global Accounts: Four Critical Sales Strategies to Win Global CustomersHer business development process is based on the collaborative culture of the Inuit people and how they engaged their entire village to land whales. Barbara works with companies to grow their business by making bigger sales to bigger customers. She has directly helped dozens of privately-held companies and B2B franchise owners to implement The Whale Hunters Process™ to dramatically increase their sales, deal size, and predictability. 95% of them do so! She reaches thousands of business leaders in workshops, seminars, and keynote speeches. Barbara also produces books, articles, podcasts, webinars, and online training programs for entrepreneurs who want fast, consistent revenue growth.


Get your free preview of Chapter 1 from Selling Fearlessly.

Check out the 86 reviews for Selling Fearlessly at