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 Anthony Cole Training Group →

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/

The sales management activities we are performing today are creating the results we are achieving today. Many or few, consistent or irregular, planned or impromptu, the behaviors and activities that we, as sales managers and leaders, use to motivate, train, and hold our producers and relationship managers accountable are at least partly responsible for the success of those we manage.

Now is a good time to assess which activities may be contributing to our current results, especially if those results are unsatisfactory.

The old adage, “If you do what you’ve always done, you will get what you’ve always gotten,” comes to mind. It is up to us as sales leaders to set higher standards for behaviors and activities and hold people accountable so that we get better results. A characteristic of truly effective sales leadership is the desire and commitment to explore and implement new ideas and practices.

1. Hiring

Effective sales leadership starts with understanding how to hire great people. No doubt hiring rainmakers requires a different process than hiring support or administrative personnel. No other role in a company faces the same challenges or deals with the performance pressure as producers and lenders. No other employees are under greater scrutiny or on a shorter leash than those tasked with developing and bringing in new relationships.

The hiring behaviors of effective sales leadership include:

• Utilizing a great job attraction post elaborating on specific skills exhibited by top salespeople

• Utilizing a pre-hire, sales-specific evaluation to identify those who can and will sell

• Having an initial phone interview to discover how good the salesperson is on the phone

• Conducting interviews like auditions, making them as tough as a prospect will

2. Offer and Onboarding

Once the manager selects a candidate, the final step in the hiring process is to conduct a rigorous offer meeting. This is a step we have found many financial services companies do not perfect, but it is critical to effective sales leadership to include the following:

• Make sure the candidate is prepared to make a decision when the offer is made to avoid using the offer to get a better deal from the current employer

• Lay out all the expectations for sales activity, sales goals, sales meetings, use of CRM, and define being a good citizen and how they will be managed and coached

• Gain agreement on all the conditions of taking the role, and then solidify the agreement by asking this question: “Are you sure?” To which the candidate will say yes. Then explain that it’s “going to be hard” and don’t say another word. Let that statement sink in and see what they say. Ask them, “Will you allow me to coach you?” You are setting the expectation from the get-go.

We have observed that many candidates who become “new hires” fail, especially in the execution area of sales activity, including making prospecting calls, securing appointments, hitting goals, attending sales meetings, using your CRM, and responding to their manager’s style and culture.

3. Managing

Effective sales leadership involves understanding what Jim Collins means when he states, “There is no such thing as micromanaging. You are either managing, or you are not managing.”

Effective sales leadership must include managing behavior. The behavior goals must be introduced at the very beginning of the new producer’s career and then regularly throughout the sales year. The following discussions must take place:

• What sales results are attached to the goal-setting levels of extraordinary, excellent, good, poor, and failing results? If done effectively, the lender or producer will establish their own extraordinary goals.

• What activities and success formula will they need to arrive at the outcome they have committed to? (Download our Success Formula here)

• Make sure they are committed to the activity by asking, “Are you sure?” and then stating, “This is going to be hard.”

• Discuss what happens when the data is telling you they are off track. Great managers get permission to coach salespeople when they are failing.

4. Coaching

As stated by Henry Kissinger, “The task of the leader is to get his people from where they are to where they have not been.”

Effective sales leadership is based on achieving success through others and developing them to be their absolute best selves. Coaching hours should be set on the leader’s calendar and communicated to all.

Several critical sales coaching activities include:

• 1-on-1 coaching sessions to improve skill and change behaviors, not just deal-based discussions

• Pre- and post-call strategy sessions to improve the probability of success for each opportunity

• Meeting quarterly to review activity numbers against actual results, discuss success, identify where they are headed, and determine actions to address any activity-to-results gaps

5. Will to Manage

Effective sales leadership begins with the desire, commitment, outlook, responsibility, and motivation to lead others. Those are the five keys that exemplify the will to manage, based on the OMG sales management evaluation that we utilize.

• Desire: Feel urgency to take action, prioritize sales results, and care deeply about achieving sales results

• Commitment: Persevere in helping their people sell to a difficult prospect, push forward despite their own discomfort, and do what is required to achieve sales quota

• Outlook: Feel positive, focused, and appreciative about their career prospects and help foster the same with their salespeople

• Responsibility: Hold themselves and their people accountable for any lack of sales results

• Motivation: Have a compelling dream or goal to drive sales performance

If you and your financial services company need to learn more about effective sales leadership, consider these five behaviors. Download our eBook, The Extraordinary Sales Manager, to learn more.

In the past 30+ years, we have learned a great deal from working with our clients. After we deliver a sales training program, we want to know what successful financial sales organizations do to make sales training live on after the sales trainer has left the building.

The most important component is what we call the “Shadow of the Leader.” For a sales culture to exist and survive, a company must make certain that leaders are involved, engaged, and focused on supporting sales as a priority. Growth strategies must be part of daily activities, tracked, measured, and rewarded. That is our observation from working with hundreds of companies to make sales training stick and be effective. It starts at the top.

We also seek input from our valued banking and insurance clients and have learned what they are doing to build teams of successful, relationship-building salespeople. Certainly, we help them with strategies and tactics within our Sales Managed Environment® and Effective Selling System sales training, but the programs are also flourishing because of strong leadership and a desire to make sales training stick.

Here are some of their key strategies:

1. Sales development is for everyone, even senior producers.

It may be important to treat top producers differently by providing options and flexibility. But greatness is achieved by always learning, so top performers must actively participate in sales training and offer mentorship to other producers.

2. Why be good when you can be great?

Great companies and leaders make sure this is an underlying and consistent theme that drives development efforts and generates engagement from financial services relationship managers. Who does not want to be part of a great team?

3. Sales training must be company-wide.

All lines of business need to be in for a successful sales team. The same language must be spoken, and an easy-to-follow sales process must be used consistently for financial services advisors to leverage opportunities and bring in partners.

4. Sales development is a capital investment and should be positioned and reported as such.

One bank we work with reports quarterly on the number and dollars of deals in the pipeline compared to the prior year, as well as the improved “pull-through rate,” which is the number of sales compared to deals entering the pipeline. Transparency and data reporting are key to making sales training stick.

5. Use Big Math for coaching.

The data does not lie, and it takes the personal out of the conversation. Of course, companies must collect the right sales data, including outreaches, appointments, opportunities, presentations, approvals, average size sales, and deals closed. This data will tell a seasoned coach where their bankers need to improve.

6. Leverage small group training.

Even though it may be more time-intensive or costly, it is worth it to keep it small. Small group training allows bankers to be more comfortable practicing in front of others through role-play. One leader said they practice until the banker no longer feels like “throwing up on their shoes.” That is what gets them to greatness, along with having senior leadership actively present.

7. Clear out the BS in the pipeline with regular 30- and 60-day reviews and personal coaching.

Do not let the pipeline carry dead weight. This helps the pipeline become more predictive of future success and clarifies the potential need for additional prospecting activity on the part of the relationship manager or producer.

8. Require Opportunity Memos for middle- to late-stage pipeline deals.

One way to make the pipeline more real is to require Opportunity Memos for deals that are in the middle to end stages of the pipeline. This memo clarifies the prospect’s qualifications based on the scorecard attributes identified by the bank. Share our Prospect Scorecard tool with your team.

Many clients are reaching out to their banks and insurance agents to ask questions, explore options, get better rates, and feel more secure. These 8 keys to making sales training stick can help your team differentiate, engage clients and prospects in a new way, and build a stronger sales culture.

Download our Relationship Selling eBook to learn how to build stronger client relationships and create more effective sales conversations.

In today’s world of selling, it is increasingly difficult to get the attention of a prospective buyer after only a few outreach attempts.

We know prospects are busy, but let’s face it, we’re all busy. The real question is this: how do you stay consistent and persistent in your outreach while remaining sensitive to your prospect’s time, priorities, and daily distractions?

Sales prospecting has always been a difficult task for salespeople, especially when it comes to reaching the prospects they call and email each day. They call, they email, they follow up, and they wonder if anybody will ever do one of two things:

• Answer the phone.
• Return a voicemail or reply to an email.

While this is certainly not a new challenge in selling, engaging with prospects has become dramatically more difficult. If we go back to 2009, it took around 8-10 outreaches on average to engage with a prospect. Today, that number has risen to 16-18 attempts. Keep in mind that these are averages. Sometimes, it takes even more attempts across multiple channels before a prospect pays attention.

Recently, I was leading a sales training workshop in Dallas, and a high-ranking bank executive asked me why I thought the number of outreaches required has increased so dramatically in the world of sales prospecting. In my judgment, there are three main reasons.

1. Distraction

Prospects are busier than ever before and are constantly battling the distractions that come their way. Their mobile device buzzes, and they have to look. The email notification on their computer sounds, and they can’t resist. Some have estimated that the typical person picks up and puts down their mobile device between 200-300 times each day.

2. Competition

There is more competition than ever before, and it is fiercer than ever before. Online resources, AI options, and apps on every device all contribute to a chaotic, competitive world where prospects have more choices and more noise surrounding them.

3. Commodity

Unfortunately, in some industries, the prospect believes that the vendor calling them and the vendor they currently use are essentially the same. The prospect does not see any meaningful difference.

To them, a bank is a bank. An insurance broker is an insurance broker. A technology provider is a technology provider.

Of these three reasons, the third is the most concerning, or it should be. If you do not differentiate yourself from your competition by providing value, your prospect will do the differentiating for you. But they will not use a measuring stick of value. More often than not, they will use a measuring stick of price.

So, what can you do to improve your sales prospecting success?

Add value.

Giving Instead of Selling

Value does not begin when you present a solution. It begins with how you show up in the sales prospecting process.

The most crucial principle of a value-based selling approach is focused on giving to your clients, not taking or selling. Read the book Go-Givers Sell More. Unlike other methodologies, value-based selling is not about what products and services you offer. It is about what the client wants and how you can help them achieve their goals.

You’ve heard the saying, “It’s about the journey, not the destination.” Value-based selling, especially in financial services, is a relationship-building process. Part of your value is the process you take prospects through as you provide advice, ask questions, and help them think differently about their challenges.

Give a Listening Ear

You may have had this experience before: someone asks you a question, and before you finish answering, they are off to the races with their own stories and thoughts, interrupting you along the way.

That is not a good feeling when it happens, right?

You want others to hear you when you speak. Unfortunately, financial services salespeople are often guilty of doing the same thing. A salesperson might ask, “What do you plan to use these funds for?” and then immediately jump to a product solution without asking any further questions.

Using a value-based sales approach requires you to go deeper in discovery. You must become better at asking good questions and listening first. Skilled salespeople know they can learn almost everything they need through the process of asking and listening, and that is what builds trust.

See how many questions you can ask before proposing a solution. It will become easier with practice.

Spend Time Getting to Know Your Client

In the world of financial services sales, every client is different. The early stages of the sales process should be used to learn as much about them as possible.

Identifying the different relationships with your clients, thinking about what has worked for other similar clients, and sharing relevant examples can help you develop credibility with new relationships.

What do you bring to the table for your prospect that no one else does?

Surely your product can be found elsewhere, so your value must come from more than the product itself. Your experience uncovering issues, asking better questions, and solving similar business challenges is what spotlights your value.

Follow Through Using a Process

Value selling in financial services is not easy. Becoming masterful takes consistent focus, work, and insight.

We know through thousands of evaluations that elite salespeople utilize a consistent sales approach process because it works. Strong value-based salespeople care deeply about the benefits the customer receives, and they are disciplined enough to follow a process that helps uncover the right solution.

That same discipline matters in sales prospecting. If most salespeople give up too soon, then consistency itself becomes a competitive advantage.

Here is another sobering statistic about the world of modern-day sales prospecting. While the average number of attempts has increased to 16-18, most salespeople quit after fewer than 5 attempts.

Maybe they think the prospect is being rude by not replying. Maybe they think that, “in the good old days,” people used to return calls. Regardless, the world has changed.

Prospects are a hard fish to catch. You might need to be out there fishing just a bit longer than in the past, with something much more enticing on your hook.