There is one skill that can help you become a better leader, producer, parent, spouse, friend, and communicator. It is one of the most important skills you can develop, but many people do not work on it. In fact, many people really do not like it.

That skill is silence.

Most people are uncomfortable with silence. Even a few seconds can feel awkward. You may wonder if something is wrong, if you should jump in, or if the conversation has stalled. But in sales, leadership, negotiation, and conflict resolution, silence can do a lot of heavy lifting.

Why Silence Matters in Sales

When you are in a conversation with a prospect, client, employee, or team member, silence gives the other person room to think and respond. If you are willing to sit in the quiet instead of rushing to fill it, the person across from you may keep talking.

And when they talk, you learn.

That is where silence becomes powerful. You uncover more information. You hear what is really going on. You gain insight into the issue, the objection, the emotion, or the opportunity in front of you.

Salespeople often feel pressure to respond quickly, explain more, or keep the conversation moving. But you do not learn when you are talking. You learn when you listen.

Silence Can Help You Handle Difficult Conversations

Silence is especially useful when conversations become emotional or tense. In those moments, your instinct may be to defend, explain, or respond right away. But sometimes the best thing you can do is pause.

Jefferson Fisher, a well-known communicator, offers this advice: let your first word be a breath.

That pause can help you stay calm, avoid reacting emotionally, and respond with more intention. It also gives the other person space to finish their thought instead of feeling interrupted or dismissed.

Let People Finish Their Sentences

Another way to get better at silence is to practice letting people finish their sentences.

Many people struggle with this because they think they already know where the conversation is going. They want to jump in, respond, or move the discussion forward. But interrupting too soon can cause you to miss important information.

If you want to become a better listener, a better salesperson, and a better leader, practice waiting. Let the other person finish. Then pause before you respond.

That small habit can change the entire tone of a conversation.

Practice Silence Before High-Stakes Conversations

Like any other skill, silence takes practice.

Chris Voss refers to this as low-stakes practice for high-stakes results. In other words, do not wait until you are in front of a major prospect, a frustrated client, or an employee in a difficult conversation to try it for the first time.

Practice in everyday conversations. Try it with the barista at your local coffee shop. Try it with your mechanic. Try it with friends or family. Notice how often you want to jump in, and work on becoming more comfortable with the pause.

The more you practice, the less uncomfortable it becomes.

Your Best Sales Skill Might Be Being Quiet

People are not born naturally great listeners. Most people are not naturally comfortable with silence either. These are skills, and skills have to be practiced.

If you want to improve your conversations, your negotiations, your coaching, and your sales results, start by getting better at being quiet.

Ask a good question. Let the person answer. Let the silence sit. Listen to what they say next.

You may be surprised by how much you learn.

Sales organizations typically have plenty of sales data due to the growth and usage of CRM systems, which have become critical to capturing the activities occurring with the sales team. But using sales performance data to run effective sales meetings is often the greater challenge for sales managers and leaders. In our coaching platform, we offer several tools to help in this area, and one of the most effective, easy-to-understand, and easy-to-use tools is the sales data insights that come from holding regular Sales Huddles.

Why Huddles Help Coaches Run Effective Sales Meetings

Huddles, as defined by Verne Harnish, founder and president of Gazelles, are:

1. A communication process or system that allows for the sharing of real-time information
2. An opportunity to focus on "burning platform" issues for a team or company
3. A way to bring sharp focus and attention to a critical business driver
4. The most important 15 minutes in any company meeting

Each company should start by determining the most important sales activity data points to capture in their huddle regularly each week or month, such as contacts, appointments, proposals, COIs, sales, etc. If a sales manager does not schedule a regular means to monitor what is going on in the field in real time, they cannot coach, adjust the play, or get in front of any client issues or trends.

Huddles provide real-time information so that sales managers can make real-time decisions and provide real-time feedback or coaching. This is vastly different than waiting for month-end or quarter-end reporting on results because huddles capture what is happening now, this week. The sales performance metrics that are captured in Huddles are a means to run effective sales meetings and can then be used to coach salespeople to impact current deals.

Coaching with Sales Data Insights from Where’s Walter

We suggest a technique that we call “Where’s Walter,” pictured and explained below.

Coaching a salesperson’s activities can be simplified into two areas: their effort vs. their execution. Effort is described as evaluating if they are doing whatever it takes in the area of outreach and working hard to attain their goals. Execution evaluates their effectiveness in the sales process. Are they doing the right things to take a prospect through an effective sales process, or do they have a problem?

Using Where’s Walter for Coaching

As a coaching approach, we recommend sales leaders place their people into one of the four boxes noted above and then have the conversations below with the salespeople in each quadrant. These are guidelines, of course, and can be adjusted. One word of caution: do not soften too much. Leaders must be tough and direct at times to identify real areas of concern and development.

Execution Results & Effort

“Bob, thank you for the results you are generating. You must be thrilled, as this will help you achieve your personal goals and objectives. Just as important, though, I also want to thank you for your consistent effort. You may not realize this, but others on the team look to you and follow your lead. The way that you execute on sales skills week in and week out sets a great example for the rest of the team. Thank you. Now, Bob, what else can I do for you?”

Execution Results but Lacks Effort

“Bob, I want to thank you for the results you are generating. You must be thrilled, as this will help you achieve the personal goals and objectives you have for your family. I am worried about one thing, though; can we talk about that? Bob, how long is our sales cycle? (120 days).

Okay, so based on that and looking at our success formula, then the results you are getting today are a result of what? (The activity I did a while back).

That’s what I was thinking, and that is why I am concerned. Based on the activity here (show them the data), you are headed for a slump. Is that where you want to be?”

Effort Is There but Poor Execution Results

“Bob, obviously, based on the numbers you see here, you are not on schedule to achieve the extraordinary year you committed to managing yourself toward. But this is where I’m confused. The data I have, which tells me about your effort, indicates that you should be at or above your goals, but that isn’t the case.

My experience tells me that it can only be because of one of two things: either the data you are entering is not accurate, or you are failing to execute properly. Which one do you think it is?”

Lack of Effort and Results

“Bob, I have to tell you that I cannot figure this out. Your effort and results are a total surprise to me. If several months ago, someone said to me that you would be failing, I would have said, ‘No way.’ (Show Bob the job posting you used for the position he is in and his resume, then show him his current sales activity and results.)

Bob, I take a look at this (job info) and I think, ‘This is what I hired.’ I look at this (the results), and I’m thinking, ‘This is what I got.’ Bob, did I make a mistake?”

Collecting the right data utilizing Huddles can help leaders run more effective sales meetings. Then, using the Where’s Walter platform gives sales coaches a framework to use performance metrics from Huddles to generate conversations, identify areas for salespeople to focus on, and gain insights for immediate coaching. This helps improve skills, performance, and results.

One of the competencies of top salespeople is the ability to get to the decision-maker. When this is a strength, producers find a way to reach the person responsible for deciding to purchase the products or services offered, even at the risk of seeming pushy. Of course, it is key to be in front of the decision maker before you can begin to help your prospect make a decision.

We have come to recognize how essential it is to understand the buyer’s journey and how a prospect recognizes that they have a problem, how they search for a solution, and how they evaluate those solutions to make a resource choice and a decision. Salespeople have a great deal of influence on this entire process, and they must be adept at helping their prospect make a decision, whether it means they gain the business or not.

The customer’s decision-making process may be the most important step in the buyer’s journey. Salespeople can gain a great deal of information from CRMs, lead-nurturing data, and best practices from industry research systems like RelPro and IBISWorld. However, these tools will not give them insights into a prospect’s specific decision-making process.

There are nuances in every company as to how they approach an important purchase. Elite salespeople are skilled at asking the right questions in order to help their prospect make a decision.

Questions to Ask About Your Customer’s Decision-Making Process

One best practice is to be direct and ask the question simply. We coach salespeople in the commitment step of the sales process to ask:

“When you’ve made a decision like this in the past, what was your process?”

The question is simple enough, but the prospect may give a surface answer, making it seem less complex than it really is. There is rarely just one person deciding on a complex buying decision. Usually, the decision impacts others whom they will want to gain input from.

Salespeople who are skilled at helping their prospects make decisions help them think through this by drilling down from their surface answer and asking further questions such as:

• “Will that be the same process you follow this time?”

• “How long does that normally take?”

• “Who will this change impact in the organization?”

• “Who all needs to fall in love with this solution to gain approval?”

• “Can I go with you to present to the committee?”

• “How will you tell your current provider?”

It may not matter how much your direct contact likes the solution you have recommended. If the customer’s decision-making process is unknown, you risk losing the deal.

Those important questions need to be asked, and salespeople who master them close more sales. It takes courage, yes, and finesse as well, to ask these questions in a helpful, guiding manner.

Coaching Your People to Help Prospects Make a Decision

One of the findings from our partners at Objective Management Group is this: Managers who are effective at helping their salespeople get prospects to commit to a decision have 40% more top performers than managers who are ineffective at coaching on decision-making.

Why is this so predictive of success?

If managers are helping their team regularly uncover the decision-making process and gain commitment, then they are probably coaching to an effective selling system. Helping your prospect make a decision means you have uncovered a compelling reason for them to buy, thoroughly qualified the opportunity, and presented a need- and cost-appropriate solution at the right time.

This takes active listening, many insightful and challenging questions, and the ability to push back appropriately on potential stall tactics.

It is difficult to create and maintain a competitive edge in financial services sales. It requires continuous improvement and the refinement of skills. Group training sessions offer many advantages, but the transformative potential of personalized 1-on-1 sales coaching from a skilled manager is key to sustaining and implementing what is learned.

With decades of experience in the financial services sector, we have discovered that tailored, individualized coaching can be the catalyst for unlocking your producers’ full potential.

Personalized Coaching Creates Faster Growth

1-on-1 sales coaching delivers a highly personalized learning experience. Each financial services sales professional possesses unique strengths, weaknesses, and learning preferences. Coaches must invest time in understanding these distinct attributes and adapting their coaching strategies accordingly.

This personalized attention leads to accelerated skill growth and enhanced knowledge retention. Then, the real work begins. Leaders should establish a schedule of 1-on-1 sales coaching sessions, identify areas where their relationship managers might be falling short, such as lead generation or closing deals, and engage in practice sessions to refine their approach. This ensures they are more effective when engaging with real prospects.

Coaching Helps Develop the Right Skills

Because group training often encompasses a wide array of topics, not all are critical to every team member. 1-on-1 sales coaching permits a more focused approach, honing in on the specific skills that need to improve.

This kind of coaching empowers sales leaders to help their people fine-tune prospecting techniques, master consultative selling, or elevate negotiation skills. Breaking down an activity and concentrating on a particular facet, whether in golf or business development, can lead to improvement and exceptional outcomes. Consistent practice in this focused area can transform it into a habit, altering behavior and improving results.

Real-Time Feedback Improves Performance

One of the most remarkable advantages of 1-on-1 sales coaching is the immediate feedback loop it establishes. As producers work on their pre-presentation strategies, coaches can provide feedback on their approach and help facilitate quick adjustments.

This timely guidance expedites skill mastery and nurtures confidence. Leaders must set aside coaching hours, either in person or through virtual platforms, where they are available for salespeople to discuss ongoing deals, pre- or post-presentation strategies, and next steps. Such timely input can transform an average sales encounter into a strong consultative dialogue that uncovers the prospect’s true concerns.

Confidence Builds Through Practice

Attracting new clients and expanding existing relationships can be demanding, with confidence serving as a pivotal factor in achieving success. 1-on-1 sales coaching nurtures a safe environment for relationship managers to practice new techniques, role-play challenging scenarios, and receive constructive feedback.

Acknowledging accomplishments is also an integral part of 1-on-1 sales coaching. With heightened confidence in their capabilities, your salespeople will approach client interactions with greater assurance, resulting in better outcomes. Clients prefer to work with financial services professionals who are knowledgeable, self-assured, and confident in their recommendations.

Coaching Creates Accountability

Accountability is vital for the consistent growth of your producers, even if the process is not always met with enthusiasm. 1-on-1 sales coaching enables coaches to collaborate closely with their people in defining actionable objectives and monitoring progress.

Establishing specific performance standards is not just crucial for the individual; it is equally valuable for the entire team. Regular check-ins ensure that goals are achieved and challenges are promptly addressed.

Why did the relationship manager fall short of their new business target? What hindered their progress? How can they approach things differently next time? Was it a matter of effort or execution? This accountability-driven approach maintains momentum and empowers your team to pursue continuous improvement.

Sales Coaching Helps Teams Adapt to Change

The financial services landscape is characterized by its dynamism, with shifting market trends, evolving competition, and changing customer preferences. 1-on-1 sales coaching equips your team to better adapt to these transformations.

Coaches assist individuals in staying current with the latest industry insights, analyzing competitors, and responding to market shifts, ensuring that your team remains flexible and competitive. Producers can also relay insights from client interactions, helping leaders grasp the evolving nature of the financial services marketplace.

One of the pivotal roles of leadership is to assist team members in recognizing, adjusting to, and capitalizing on market changes. While the objective of cultivating and deepening relationships remains, the approach and methodology may require adjustment.

Conclusion

In the realm of financial services, leveraging every interaction can make a significant impact, and investing in 1-on-1 sales coaching is a strategic move that can yield substantial returns.

Let us know if we can help your bank, credit union, or insurance company.

Contact our Financial Services Sales Training Experts →

This article was originally published by Objective Management Group and written by Staci Matt. It is shared here with permission. Anthony Cole Training Group is a Certified OMG Partner, helping organizations hire and develop high-performing sales teams using OMG’s industry-leading assessments and insights.

Financial conversations are central to every sale, yet many salespeople avoid them or handle them too late. Objective Management Group data shows an average score of 67% in comfort discussing money, with 59% of salespeople considered comfortable. On the surface, this appears to be a strength. In practice, it reveals a gap. A meaningful portion of salespeople still struggle with money conversations, and even those who are “comfortable” often handle them inconsistently or too late in the process. Research shows that buyers increasingly expect pricing discussions early, while many sellers hesitate or defer. This misalignment creates friction, stalls deals, and reduces win rates.

The Hidden Gap Behind a “Solid” Score

At first glance, a 67% average score in comfort discussing money looks acceptable.

And with 59% of salespeople considered comfortable, it would be easy to assume this is not a major issue¹.

The reality is more nuanced.

In a competency that directly impacts:

• Qualification

• Value positioning

• Deal control

A 67% average means a large portion of salespeople are either:

• Avoiding or delaying money conversations

• Having superficial conversations about financial impact (“What’s your budget?”)

• Discounting or renegotiating deals where they have not uncovered value to the buyer

That gap becomes costly over the course of a sales cycle.

The Real Problem: Avoidance Shows Up Earlier Than You Think

Avoidance rarely looks like outright refusal to discuss price.

It shows up in more subtle ways:

• Skipping budget questions during discovery

• Waiting until late-stage conversations to introduce pricing

• Over-focusing on solution details before confirming that the product actually improves revenue or decreases costs for the Buyer

Research shows this behavior is widespread.

According to HubSpot, 58% of buyers want to discuss pricing on the very first call, while only 23% of salespeople are prepared to do so².

This creates immediate misalignment.

Buyers are looking for clarity.
Salespeople are often trying to delay the conversation.

Why Salespeople Avoid Talking About Money

There are both behavioral and learned reasons behind this pattern.

1. Cultural Conditioning

Many people are raised to view money as a sensitive or inappropriate topic.

Research highlights that discussing money is often considered socially uncomfortable, which carries into professional settings³.

That discomfort does not disappear when someone enters a sales role.

1. Fear of Losing the Deal

Salespeople often worry that introducing price too early will:

• Scare off the prospect

• Reduce perceived value

• Trigger objections

As a result, they delay the conversation, hoping to “build value first.”

1. Lack of Confidence in Value

When salespeople are not fully confident in the value they deliver, price becomes a point of tension.

Industry guidance reinforces that without a strong value conversation, price becomes the default focus, which weakens positioning and increases pressure to discount⁴.

The Cost of Avoidance

Avoiding financial conversations does not protect deals. It weakens them.

When money is not addressed early and directly:

Deals Stall

Prospects continue conversations without clear alignment on budget or investment expectations.

Late-Stage Surprises Increase

Pricing objections emerge late in the process, when more time and resources have already been invested.

Discounting Becomes More Likely

Salespeople who delay financial conversations often rely on price reductions to close deals they should have qualified differently.

Research shows that avoiding or delaying financial conversations contributes to misalignment and lost opportunities in the sales process⁵.

Comfort Alone Is Not Enough

Even among the 59% who are considered comfortable discussing money, performance varies.

Comfort does not guarantee:

• Timing the conversation correctly

• Asking the right financial questions

• Maintaining control of the pricing discussion

In many cases, salespeople are willing to talk about money, but only after:

• Presenting the solution

• Building rapport

• Advancing too far into the process

At that point, the conversation becomes reactive instead of strategic.

What Effective Salespeople Do Differently

Top performers approach financial conversations with more precision.

They:

• Introduce budget and investment discussions earlier

• Confirm both willingness and ability to spend

• Tie price directly to business and personal impact

• Address financial concerns before advancing the opportunity

Sales research consistently emphasizes that early financial alignment improves qualification accuracy and sales outcomes⁶.

This creates:

• Stronger qualification

• Shorter sales cycles

• More predictable outcomes

Implications for Sales Leaders

This data highlights an important leadership opportunity.

Rather than assuming financial conversations are being handled effectively, leaders should:

• Evaluate when pricing is introduced in the sales process

• Coach how financial discussions are framed and navigated

• Reinforce the connection between value and investment

Most importantly, leaders should recognize that:

• A “comfortable” salesperson may still be avoiding critical moments

• Timing and execution matter as much as willingness

The Bottom Line

Financial conversations are not a minor part of the sales process. They are central to it.

While a majority of salespeople appear comfortable discussing money, the data and behavior patterns suggest otherwise in practice.

The opportunity is not simply to increase comfort.

It is to:

• Improve timing

• Strengthen value alignment

• Ensure financial qualification happens early and consistently

Salespeople who address money directly and effectively gain clarity faster, qualify more accurately, and close more consistently.

Those who avoid it often pay the price in longer cycles, lower win rates, and unnecessary discounting.

Sources

1. Objective Management Group: Finding Statistics Tool. Sales Evaluations Conducted January 1, 2025-March 30, 2026. Results percentage for average scores and proficiency scores of Comfort Discussing Money competency. Internal dataset.
2. HubSpot – The First Call Conundrum
   https://blog.hubspot.com/sales/the-first-sales-call-conundrum
3. Money conversation discomfort and cultural norms
   https://thejpbusinessacademy.com/why-you-must-control-the-money-conversation-not-avoid-it/
4. ValueSelling Associates – Value vs price conversations
   https://www.valueselling.com/resource-blog/if-you-dont-discuss-value-all-you-can-do-is-talk-price
5. Financial conversation timing in sales
   https://www.lushin.com/blog/the-dangers-of-assumptions-in-sales
6. Financial conversation avoidance impact on deals
   https://suitebymonitor.com/why-most-dealers-lose-sales-by-avoiding-the-money-conversation-and-how-to-fix-it/