Gaining Trust By Asking the Difficult Questions

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, 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 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.

Sometimes your dream client can’t reach consensus within their own four walls, and the status quo 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 or too complacent to move. Being trusted means you have to help them become dissatisfied 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.


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?

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