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Sales Fear and Timidity: Obstacles to Sales Success

Posted by Mark Trinkle on Fri, Nov 28, 2025
 
 As a sales coach, I have lots of experience helping salespeople dig into their inner beliefs that are getting in the way of them having greater sales success. And without question, the top two issues within those beliefs are:
  1. Fear

  2. Timidity

At Anthony Cole Training Group we teach our clients to have bold and assertive (not aggressive) conversations with their prospects. We teach our clients to ask lots of questions and to make sure that those questions are tough questions. In our training and coaching sessions, we talk about challenging the norms of conventional conversations by pushing the edges of the conversation all the way to the ultimate boundary of clarity. That way the salesperson will leave the sales call with beautiful clarity in terms of whether their prospect is really a prospect, instead of letting sales fear cloud the conversation.

We encourage them to make sure they are in front of all the decision-makers and to make sure that they know exactly what the decision-making process looks like. We even coach our clients to inquire about the decision-making criteria so they know for sure how their proposal is going to be compared against other options. When sales fear takes over, these important questions often get skipped.

How Sales Fear Limits the Conversation

In short, we teach salespeople to ask about everything.

But that rarely happens. Sometimes salespeople don’t even ask about anything.

Why, you ask? Why would a salesperson know the right thing to do and then not do it?

If you guessed fear as the reason, you are correct. While they have been coached on the right things to do, they succumb to their fear of either asking the question or their fear of hearing the answer. In essence, they are afraid. And yes, that could be due to a weak pipeline. As my colleague Jack Kasel is fond of saying, weak pipelines make cowards of us all. A weak pipeline only amplifies sales fear.

But here is what they should fear more than the fears listed above. They should be very afraid of not being bold and assertive. Specifically, they should fear the outcomes that are typically the result of not getting to the decision-makers or not getting all the truth in terms of whether or not the prospect is really compelled to change an existing relationship. Afterall, you can either lose, or you can be afraid.  Just don’t be both.

Fear has two acronyms:

  1. False Expectations Appearing to be Real

  2. Face Everything And Rise.

The choice is yours.

 

Can we help you find the right  approach for your company?

 

FAQ: Sales Fear and Timidity

What is sales fear?
Sales fear is the hesitation or anxiety salespeople feel when asking tough questions, confronting decision-makers, or seeking clarity during the sales process.

How does sales fear impact sales performance?
Sales fear often leads to incomplete conversations, missed questions, weak qualification, and an overreliance on hope instead of clarity. This results in stalled deals and poor outcomes.

Why do salespeople avoid asking tough questions?
Many salespeople know what to ask but fear hearing the answer. A weak pipeline also increases sales fear, making reps more timid and less assertive.

How can sales fear be reduced?
Building a strong pipeline, practicing assertive conversations, and learning structured questioning techniques help reduce sales fear and increase confidence.

What role does clarity play in overcoming sales fear?
Clarity allows salespeople to understand whether a prospect is truly qualified. When clarity becomes the goal, fear loses its power over the conversation.

 

Topics: sales fear


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    Anthony Cole Training Group has been working with financial firms for close to 30 years helping them become more effective in their markets and closing their sales opportunity gap.  ACTG has mastered the art of using science-based data and finely honed coaching strategies to help build effective sales teams.  Don’t miss our weekly sales management blog insights from our team of expert contributors.

     

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