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.

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.

The 9 Skills to Sales Coaching Success

1. Debriefs Effectively
Great coaches do more than ask how the call went. They dig into what actually happened. This skill focuses on structured, consistent debriefs that uncover the salesperson’s execution, thought process, and patterns. It emphasizes understanding the how rather than focusing only on the outcome.

2. Is Effective on Joint Calls
Coaches who only attend closing meetings miss the valuable learning moments. This skill highlights how to observe early stage calls, set expectations before the meeting, and avoid stepping in to rescue the salesperson so they can learn and strengthen their process.

3. Asks Quality Questions
Powerful coaching is built on powerful questions. Instead of interrogating or correcting, this skill focuses on using open ended questions that help reps identify gaps in their performance, reflect on their approach, and take ownership of their development.

4. Understands Impact of Sales DNA
Challenges such as fear of rejection, need for approval, discomfort discussing money, or an unproductive buy cycle can quietly influence sales behavior. This skill explains how effective coaches spot these issues and help reps address the root cause rather than the surface level problem.

5. Demonstrates an Effective Selling System
A coach cannot reinforce what they cannot model. This skill outlines how coaches demonstrate the core selling system, teach the reasoning behind it, and use examples and stories to help reps understand why the system works.

6. Is Effective at Getting Commitments
Improvement requires commitment. This skill helps coaches connect reps’ personal goals to their required behaviors, identify the gap between current performance and desired outcomes, and guide the rep toward committing to meaningful change.

7. Consistently Coaches Skills and Behaviors
Coaching should not be a once in a while activity. This skill focuses on establishing dedicated coaching time, emphasizing how the rep executed each step, and using repetition, role play, and drill for skill to build mastery.

8. Understands Impact of Will to Sell
Desire, commitment, outlook, motivation, and responsibility shape how a salesperson approaches their role. This skill explains how a coach can help reps strengthen these elements, eliminate excuses, and maintain the mindset needed for consistent performance.

9. Effectively Onboards New Hires
Success begins the moment someone joins the team. This skill emphasizes clear expectations, weekly coaching, pipeline inspection, and early identification of choke points so new hires ramp up more effectively and avoid developing bad habits.

You can access our audio clips on the 9 Sales Coaching Skills for free HERE!

These nine skills serve as the foundation of strong sales coaching. Our audio library gives you a clear and direct explanation of each skill, making it easy to learn, apply, and strengthen your coaching approach. Whether you are working to improve your team’s consistency, develop new managers, or sharpen your own leadership style, these short audio clips provide practical guidance that helps coaches lead more effectively and support the long term success of their sales teams.

In this article, we discuss the 3 rules every successful salesperson must follow in order to eliminate stalls and objections during the sales process. These rules create the structure needed to consistently have powerful sales conversations.

The Difference Between Typical and Powerful Sales Conversations

There is an important distinction between having a powerful sales conversation and a typical sales discussion, and it starts with a position of trust. If your salespeople have done the due diligence of researching the prospect or client and understanding what their industry and company challenges may be, then they have a better chance of having a powerful sales conversation.

But the prospect must be coming from a position of trust and hopefully some curiosity about what your salesperson can do for them. These conversations require thoughtful preparation, personalization, and a structured approach that guides the discussion from understanding problems to presenting value and ultimately closing the sale.

The Two Taboo Topics That Block Powerful Sales Conversations

In our work helping clients develop their sales talent, we know there are two topics consistently avoided, and both are to the detriment of the salesperson. Those two taboo topics are:

1. Discussing the incumbent

2. Uncovering the budget

There is an age-old debate about which came first, the chicken or the egg. While that debate may never be solved, there is one “which comes first” situation that shouldn’t be up for debate, and that is whether you should show the solution first or know the budget first.

Our definition of budget is broader than just the monetary investment. It includes three categories commonly known as TMR: Time, Money, and Resources. What is the prospect willing to commit in the context of time, money, and resources to make their problem go away or achieve their goals? Stronger sales professionals don’t shy away from this discussion. They are successful because they follow these rules.

Rule #1: Have the Conversation

The 800-pound budget gorilla is in the room, so talk about it. Don’t make it part of your opening conversation, but don’t ignore it either. If the need is big enough and your solution fixes it, most of the time they will find the money.

Rule #2: Provide Context

Regardless of the investment your prospect needs to make to fix their problem, it needs to be framed in the context of their pain and your ability to eliminate it. If the pain is minimal, then your solution won’t seem that meaningful.

We have had prospects tell us their problem is a “two-comma problem,” meaning their cost of turnover was over one million dollars. That is context. Skillful salespeople who know how to have powerful sales conversations understand their prospect’s cost and level of personal pain before proceeding.

Rule #3: Don’t Show Your Solution Until You Know the Budget

It’s really that simple. If you have ever provided a solution to a prospect only to hear them say, “That’s more than we intended to spend,” then you have an issue discussing the budget.

Does it make sense to know their appetite for change, including budget, before you provide your solution? Here is where strong sales professionals stand apart. If the prospect doesn’t want to discuss budget, it is usually for one of two reasons. They haven’t uncovered enough pain, or the prospect simply wants to use them as a pencil sharpener for the competition. Your salespeople don’t get paid to be pencil sharpeners, so don’t let them become a means for prospects to get a better price from their current provider.

Salespeople do not need to be afraid of the budget or incumbent conversation. They must initiate and welcome these discussions because they are the basis of powerful sales conversations. In our history of working with companies, once they instill this with their people, relationships deepen and their salespeople move one step closer to being in an advisory position.

FAQ: Powerful Sales Conversations

Why do powerful sales conversations matter?
They help salespeople move beyond surface-level discussions and uncover the real issues driving a prospect’s need for change. When conversations are structured and intentional, it becomes easier to eliminate stalls and objections.

How do I know if my team is actually having powerful sales conversations?
If your salespeople consistently uncover pain, explore the prospect’s investment capacity, and address the incumbent early, they’re on the right track. If they avoid those topics, they are likely stuck in typical sales discussions.

Why do salespeople avoid talking about the budget?
It usually comes down to discomfort or fear of losing the opportunity. But strong sales professionals know that avoiding the budget leads to mismatched expectations and stalled deals.

When should the budget conversation happen?
Not at the very beginning, but well before presenting a solution. The prospect’s level of pain and commitment should guide the timing.

Is discussing the incumbent really necessary?
Yes. Without understanding who the prospect currently works with and why, the salesperson can’t position themselves effectively or eliminate the risk of becoming a “pencil sharpener.”

Can powerful sales conversations work in any industry?
Yes. The principles apply to any sales role where trust, preparation, and uncovering the truth behind a prospect’s challenges matter.

What if a prospect refuses to discuss budget?
It typically means one of two things. Either the salesperson hasn’t uncovered enough pain yet, or the prospect is gathering prices to negotiate with their current provider. Both situations can be handled with stronger process and questioning.

The Cost of Tolerating “Pretty Good”

Let’s pretend that you just invested $500,000 in the latest technology to “tighten up” the reporting on your company’s payables, receivables, compensation reports, taxes, and forecasting. The company you bought the service from told you that it would take about 90 days to work any bugs out, but certainly, by year-end, your expectations would be met.

Around the 90-day mark, you meet with your CFO and ask, “How’s it going?” She responds, “Pretty good!” You then inquire, “Pretty good means?” She replies:

• Our payable reports are about 66% correct, but trending in the right direction.
• Our overdue receivables still average 45 days, but we’re making progress.
• Our compensation expenses are off by about 5% and we’re not sure why, but we’re working on it.
• Taxes? Well, my best guess is that we are going to owe between 10% and 20% more than last year.
• As far as forecasting revenue, our pipeline shows $5,000,000 to be closed in the next 6 months, but we’re not yet confident that the number is accurate.

How do you feel about your investment? What is your reaction to a lack of success at meeting expectations? How long would you tolerate the continuance of this failure? I’m not sure you’d fire your CFO, CTO, HR, or consultant, but I’m pretty sure you wouldn’t say, “Okay, let’s give it another 60 days.”

What Nobody Talks About in Building a Successful Sales Environment

This is a bit of a stretch scenario, but the point I want to make is that you probably get a report like this about your sales team; you just don’t know it. What isn’t revealed in a sales meeting or in your monthly meeting with your sales manager is the detail behind the big numbers you talk about.

You talk about YOY results, sales YTD against plan, and maybe even how you’re doing against other sales divisions or peers in your industry. What you don’t see or hear about is this:

• Over 90% of your results are probably coming from 36% of your sales team.
• The bottom 36% of your sales team is likely responsible for less than 4% of your total sales.
• Of the last 4 hires, only 1 of them is doing better than the people they replaced.
• The cost of putting the other 3 in the market for 12 months and then replacing them is a two-comma problem over 5 years.
• If you really wanted to drive profit, you could probably eliminate the bottom 36% and increase profitability significantly.
• Some of your more senior people are not performing nearly as well as some of your new people.

The challenge to organizations (and what matters most) is the answer to the question: Are we hitting our numbers? If that answer is yes, you’re okay. BUT if you are unwilling to accept 90% correct in your tax estimate or compensation projections, why are you settling for anything less than 100% execution from your entire sales team?

3 Steps to Building a Successful Sales Environment

These three tools will help your organization build a successful sales environment and correct what’s broken.

1. Speed to Failure
With your new hires, do your best to find out quickly if both of you made the right decision. Make sure that, as you are making the offer, you let them know everything they are going to have to go through, how they will be managed, and all that is expected of them in the first 90 days and the following 6 months.

2. Conversation is King
Despite all the technology that is available to help your salespeople create opportunities, nothing yet has replaced the value of quality conversations and coaching. This means you need to have a very high standard for training, practice, and preparation before you put people out into the market. These consistent conversations are the foundation of building a successful sales environment.

3. Use Sales Technology That Supports Selling
The technology that you buy to support sales must support sales first, then finance. Your sales technology should make it easy for salespeople to communicate with suspects, prospects, and clients. It should be easy to use and provide extremely useful information for both the sales manager and salespeople. It should make it simple for your team to consistently follow your sales process and help you predict, with a high level of validity, what is actually going to get sold over any given time frame.

Implementing these three steps will go a long way toward building a successful sales environment and improving the productivity of your entire team.

FAQ: Building a Successful Sales Environment

Q: What is a “sales environment”?
A: A sales environment refers to the systems, culture, and tools that influence how your sales team performs. A strong environment promotes accountability, communication, and clear expectations.

Q: How long does it take to build a successful sales environment?
A: While quick wins can happen within 90 days, building a truly successful sales environment requires consistent coaching, clear metrics, and leadership commitment over time.

Q: What’s the biggest mistake leaders make when trying to improve sales performance?
A: Many leaders rely too heavily on technology or metrics without focusing on conversation quality and accountability. The best results come from combining strong systems with daily coaching and real dialogue.

Q: Can smaller teams benefit from this approach?
A: Absolutely. Whether you have 5 salespeople or 50, these same steps—speed to failure, consistent conversations, and the right technology—can transform your results.

Here are three examples of highly successful people and a brief summary of their “story of failure” through risk-taking. (The names have been changed to protect privacy.)

Doug had been working on an insurance account in Eastern Pennsylvania. He had a strong relationship with an inside contact and, in a very short period of time, leveraged that relationship to develop strong connections with the decision-makers who provided commercial insurance for their firm.

Doug was attempting to take the account over from one of the “BIG 3” national insurance brokers and definitely faced a fear of failure in sales. While many of his peers scoffed at his effort, he had great support from his sales manager and agency president. I worked with him as he attempted to position himself and the agency to take over the business.

He didn’t get the business. It took a lot of his time, the time of his team, and the underwriters who tried to underwrite the case. When he got the news, he was disappointed but stayed clinically detached. He didn’t get emotional, upset, or walk around feeling sorry for himself. Instead, when he got the call, he said something like, “Throw me a bone. Give me a chance to work on some aspect of your insurance needs. Give me a chance to prove we can work with you and handle your account.”

He told them he had worked hard on this account, had proven his dedication, and wanted something to show for the effort. The account gave him an opportunity to write a small portion of another aspect of their insurance needs. A year later, he wrote the entire account for more than $500,000 in revenue.

Risks taken by Doug:

1. Called on a large account

2. Competed against a much larger player in the market

3. Was not afraid to leverage a relationship

4. Made sure he was in front of decision-makers

5. Asked for business even when denied the initial opportunity

John: Turning Rejection into Opportunity

John had been working with an account on the West Coast. He had an engagement for a year, and at the end of that year, the client told him that his services were no longer needed. The company felt that the work he and his company had done over the last year had little impact on their sales and sales management results. The needle hadn’t moved on sales, and there was no compelling reason to continue the relationship.

As the president put it, “I just don’t see how continuing this relationship is going to help us. Our business is completely different. We’ve talked to our people, and the majority doesn’t believe you really understand our business.”

This was a first for John and his company, but he fought his fear of failure in sales and engaged with the president of his company to work on a strategy to maintain a relationship. He continued to stay in touch with an inside champion and would visit the former client whenever he was on the West Coast doing other work.

Changes began to take place for the company. There were leadership changes—though not at the very top where the previous decision had been made. There were new acquisitions and a feeling that they couldn’t handle it all (new hires, new offices, new leaders) without some help.

John was in the habit of consistently reaching out to his internal champion, and when he heard about the problem, he suggested coming out to talk about it. Maybe there was something they were missing. Maybe there was something he could do that was a bit different from the previous engagement.

Less than 12 months after John had been “fired” from the account because neither he nor his company “understood” the business, he was hired again by the company—and the account generated over $150,000 a year.

Risks taken by John:

1. Invested time and his own money to visit and stay in touch, even though the chance of re-engagement was remote

2. Took the risk that his new approach to one-on-one coaching could be met with the same rejection

3. Accepted the possibility that, if things didn’t work out, his reputation in the marketplace could be tarnished

4. Relied on his inside champion, which was also a risk that person took with their executives

Steve: Building Success Through Consistent Action

Steve was a senior executive and partner in a financial services firm in one of the country’s top 30 metropolitan areas. The story about Steve is short but powerful. As it was told to me, Steve made 20 phone calls a day to prospects, dealt with daily rejection, and faced his fear of failure in sales head-on.

Not just once in a while. Not just when he thought about it. Not just on Wednesdays. Every day that Steve worked—in or out of the office—he made his 20 calls. If the business of running the company kept him busy all day, he would still not go home, leave the office, or quit for the day until those calls were made.

Risks NOT taken by Steve:

1. Failing to reach the goals he set for his company and family

2. Being a poor example to his team

3. Neglecting the responsibility of helping the company meet its revenue goals

Steve was willing to overcome rejection 20 times a day. Assuming he worked 240 days a year, that’s 4,800 opportunities for failure to reach someone. Of those 4,800, he probably spoke to at least 480. In the services business Steve was in, he probably wrote about 10 clients a year—that means facing a lot of people telling you, “no.”

Steve remains today one of the most respected professionals in his market and his industry.

Are You Helping Your Salespeople Overcome Their Fear of Failure in Sales?

Are you encouraging your salespeople to take the risks that may include failure? Are you doing the same in your sales coaching role?

“It’s fine to celebrate success, but it is more important to heed the lessons of failure.”
— Bill Gates