--- title: Gaining Trust By Asking the Difficult Questions | The Sales Blog description: Being a trusted advisor means asking the difficult questions. The one question the answer to which will often do the most to help you help your dream client is why they haven’t already found a way to achieve the outcomes they need. The answer is sometimes that your competitor, the one sitting in your chair, […] image: https://www.thesalesblog.com/hubfs/Imported_Blog_Media/Screen-Shot-2014-03-01-at-8_10_47-PM.png --- ### [Now booking SKO meetings for 2026/27! 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The one question the answer to which will often do the most to help you help your dream client is why they haven’t already found a way to achieve the outcomes they need. The answer is sometimes that your competitor, the one sitting in your chair, simply won’t give them what they want. But more often it is something more complex, more challenging, and more difficult to resolve. Sometimes the reasons your dream client doesn’t already have the results they want is because they are unwilling to do what is necessary. Sometimes your dream client is unwilling to make the [investments](http://thesalesblog.com/blog/2012/04/16/how-to-keep-your-client-from-underinvesting/) that would rocket them forward. Being a trusted advisor, Level 4 Value Creator™, consultative salesperson means you have to tell them they are underinvesting—and help them make the appropriate investment. You have to be the one to tell them they can’t have [better, faster, and cheaper](http://thesalesblog.com/blog/2014/01/24/better-faster-cheaper/). Sometimes your dream client can’t reach consensus within their own four walls, and [the status quo](http://thesalesblog.com/blog/2012/02/28/the-status-quo-the-most-dangerous-threat-to-your-deal/) wins the day. If you want to be your dream client’s strategic advantage, their partner, you have to go inside and help them find the trade offs that can get a deal unstuck. You have to have the difficult conversations about what the obstacles and hold outs are putting at risk. And you have to help those who will benefit most to make trade-offs and mitigate the impact of change on those who don’t really support it. And sometimes your dream client is just too [afraid](http://thesalesblog.com/blog/2013/09/27/a-short-meditation-on-fear/) or too complacent to move. Being trusted means you have to [help them become dissatisfied](http://thesalesblog.com/blog/2014/01/28/on-latent-dissatisfaction-and-dissatisfaction/) enough to change. You have to help them understand the price they will pay if they don’t take action, as well as the rewards for taking action. These conversations aren’t easy. They sometimes don’t make you as popular as telling your dream client they can have what they want without changing. But if you want to be a trusted advisor, you have to have these difficult conversations. Even though they’re tough, your dream client’s respect for you grows when they know they can count on you to tell the truth—and to really help. #### Questions Why is your dream client really struggling to get results? What answer do they need to hear, even though they will likely resist it? Why does honest but uncomfortable answers generate trust? What do you risk by not having these conversations? ###### Tags: [Sales](https://www.thesalesblog.com/blog/tag/sales) [2014](https://www.thesalesblog.com/blog/tag/2014) Post by [Anthony Iannarino](https://www.thesalesblog.com/blog/author/anthony-iannarino) on March 1, 2014 Written and edited by human brains and human hands. ![Anthony Iannarino](https://www.thesalesblog.com/hubfs/ai-blog-profile-crop.jpg) Anthony Iannarino is an American writer. He has published daily at [thesalesblog.com](https://www.thesalesblog.com) for more than 14 years, amassing over 5,300 articles and making this platform a destination for salespeople and sales leaders. Anthony is also the author of four best-selling books documenting modern sales methodologies and a fifth book for sales leaders seeking revenue growth. His latest book for an even wider audience is titled, The Negativity Fast: Proven Techniques to Increase Positivity, Reduce Fear, and Boost Success. Anthony speaks to sales organizations worldwide, delivering cutting-edge sales strategies and tactics that work in this ever-evolving B2B landscape. He also provides workshops and seminars. Connect with Anthony on LinkedIn, X or Youtube. You can email Anthony at [iannarino@gmail.com](mailto:iannarino@gmail.com) [Follow me on my website](https://www.thesalesblog.com/anthony-iannarino) [Follow me on Facebook ](https://www.facebook.com/thesalesblog) [Follow me on LinkedIn ](https://www.linkedin.com/in/iannarino/) [Follow me on Twitter ](http://www.twitter.com/iannarino) [![AISA-square-ad-SKOs-26-27](https://www.thesalesblog.com/hs-fs/hubfs/AISA-square-ad-SKOs-26-27.jpg?width=400&height=400&name=AISA-square-ad-SKOs-26-27.jpg)](https://www.thesalesblog.com/authority) [![ai-cold-calling-video-sidebar-offer-1](https://www.thesalesblog.com/hs-fs/hubfs/ai-cold-calling-video-sidebar-offer-1.jpg?width=318&height=179&name=ai-cold-calling-video-sidebar-offer-1.jpg)](https://www.thesalesblog.com/free-cold-calling-video) ![salescall-planner-ebook-v3-1-cover (1)](https://www.thesalesblog.com/hs-fs/hubfs/salescall-planner-ebook-v3-1-cover%20(1).jpg?width=768&height=994&name=salescall-planner-ebook-v3-1-cover%20(1).jpg) ### Free Sales eBook: Sales Call Planner Planning your sales call improves the likelihood of making a successful call, and it demonstrates to your dream client your professionalism. 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What we’re doing right now **is working**, even in this challenging economy. **Would you like some help?** [![Solve for Sales](https://no-cache.hubspot.com/cta/default/2922376/d3a4938b-2008-4a27-8b44-7b2223f6d035.png)](https://cta-redirect.hubspot.com/cta/redirect/2922376/d3a4938b-2008-4a27-8b44-7b2223f6d035) ### Join my Weekly Newsletter for Sales Tips Join 100,000+ sales professionals in my weekly newsletter and get my *Guide to Becoming a Sales Hustler* eBook for FREE! --- ```json { "@context" : "http://schema.org/", "@type" : "BlogPosting", "author" : { "@type" : "Person", "name" : "Anthony Iannarino" }, "dateModified" : "2021-09-17T2:37:02 PM", "datePublished" : "2014-03-01 20:43:13", "description" : "Being a trusted advisor means asking the difficult questions. The one question the answer to which will often do the most to help you help your dream client is why they haven’t already found a way to achieve the outcomes they need. 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