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Develop Your Sales Coaching Skills with 9 Keys

Posted by Anthony Cole Training Group on Fri, Nov 21, 2025
 
Coaching a sales team is more than managing numbers or reviewing activity reports. It is about knowing how to develop people. Our 9 chapter audio library delivers the short story on what it takes to be a great sales coach and gives sales leaders practical, real world coaching guidance without the fluff. Each audio clip breaks down one core Sales Coaching Skill and provides clear insight into how effective coaches think, behave, and lead. Below is a high level look at the nine skills included in the series.
 

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.

 

Topics: sales coaching skills

3 Rules to Having Powerful Sales Conversations

Posted by Anthony Cole Training Group on Fri, Nov 14, 2025
 
Typically, when a salesperson doesn't win an account, it's due to a few different factors: the prospect didn't have a compelling reason to make a change, the salesperson didn't do enough to uncover their capacity to invest, or the incumbent wasn't properly eliminated from the running.

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.

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

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.

Topics: powerful sales conversations

3 Steps to Building a Successful Sales Environment

Posted by Anthony Cole Training Group on Fri, Nov 07, 2025
 
Every company wants to grow revenue, increase profits, and strengthen its sales team, but few take a hard look at whether their structure truly supports those goals. Building a successful sales environment takes more than setting targets and hiring talented people. It requires systems that identify problems early, conversations that drive accountability, and technology that actually supports selling. Without these elements, even the best intentions can lead to frustration and underperformance.
 

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.

Request Free  Sales Force Performance  Evaluation Samples

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.

Finding & Growing Your Future Leaders

Posted by Anthony Cole Training Group on Fri, Oct 24, 2025
 
Every organization faces the same question: who will lead next? Building a strong bench of future leaders doesn’t happen by chance; it’s the result of continual recruitment, intentional strategy, consistent coaching, and understanding key performance data.

In our recent webinar, Finding & Growing Your Future Leaders, Jack Kasel and Alex Cole-Murphy explored how top-performing financial institutions identify, develop, and retain leadership talent. They discussed the four key components of a strong succession plan and shared insights on how leaders can use data and coaching to prepare their next generation of high performers.


 

Why Leadership Assessments Matter

Jack and Alex emphasized that finding the right people for leadership roles starts with a structured assessment process. Resumes and interviews only tell part of the story. Effective organizations use sales-specific tools, such as Objective Management Group (OMG) assessments, to evaluate candidates on 21 Core Sales Competencies. These tools help uncover the traits and belief systems that drive real performance.

Beyond assessment, leaders must also understand their own biases and blind spots. Recognizing how personal beliefs shape coaching and hiring decisions allows organizations to make better, more objective leadership choices.

Coaching Over Commanding

Great leaders coach; they don't command. Moving from a sales role to a leadership role requires a different skill set. Handling rejection, motivating others, and developing emotional intelligence are crucial for success. As Alex shared, “Positional authority may get short-term results, but personal power inspires long-term growth.”

Leaders who engage in regular coaching conversations, roleplay exercises, and feedback sessions create more resilient teams. Jack added that challenging team members with high standards helps them grow, but it’s the coaching process that keeps them engaged and improving.

Building a Strong Succession Plan

Succession planning should be proactive, not reactive. The best organizations develop leaders before they need them. Jack and Alex discussed how using consistent data, clear accountability, and repeatable hiring processes ensures that leadership transitions happen smoothly. They encouraged companies to think beyond immediate needs and start developing internal talent now because the future of your business depends on it.

Watch the entire webinar above! 

 

FAQs

1. How do I identify future leaders within my team?
Look for team members who take initiative, handle challenges well, and influence others positively — not just your top performers.

2. What’s the best way to develop emerging leaders?
Provide stretch assignments, coaching, and feedback that build both confidence and decision-making skills over time.

3. How can I create a culture that grows leaders at every level?
Model strong leadership behaviors, encourage ownership, and make development a regular part of performance conversations.

 

Contact the Speakers:

Alex Cole-Murphy: alex@anthonycoletraining.com

Jack Kasel: jack@anthonycoletraining.com 

The Power of Relationship Selling: A Sneak Peek at Our New eBook

Posted by Anthony Cole Training Group on Thu, Oct 02, 2025
 
This week on the blog, we’re sharing the first two chapters of our brand-new eBook, The Relationship Selling Guide. Inside, you’ll discover why assertiveness and empathy are critical to winning the right clients, how bold questions can transform your sales conversations, and how to create remarkable client experiences which are the key to long-term loyalty. Our new eBook contains practical, proven strategies that will help you strengthen client trust, shorten your sales cycle, and build lasting relationships.

Chapter 1: Relationship Selling - The Key to Your Sales Challenges

In today’s unpredictable and rapidly shifting markets, one of the most persistent challenges in sales is staying focused on adding value, not just making the sale. That’s where relationship selling comes in. While this concept isn’t new to most of us in sales, applying it effectively and consistently is where the real challenge lies.

Many organizations are striving to become more customer-focused. But how can advisors and sales professionals remain productive and assertive without sounding overly sales-driven?

The Power of Assertive Relationship Selling

Here’s the truth: Assertive salespeople, those who lead with confidence and care, win more business. These professionals are so committed to doing what’s right for their clients that they’re willing to risk the sale to help the customer make the best possible decision.

This is the essence of relationship selling: prioritizing the long-term relationship over the short-term win.

Assertiveness in sales isn’t about pressure, it’s about clarity, curiosity, and courage. When done well, your early conversations help qualify (or disqualify) prospects quickly and respectfully. That means less wasted time chasing people who will never buy, and more energy directed toward solving real problems for real buyers.

The Discovery Process: Ask Better, Sell Smarter

In those initial, assertive conversations, your goal is to uncover the prospect’s real pain:

  • What problems are they facing?
  • What have they done to try and solve them?
  • How is their current provider performing?

These conversations aren’t just about gathering surface-level information. They’re about building insight, so you can determine whether a true, mutually beneficial relationship can form.

In our sales methodology, a qualified prospect must meet three key criteria:

  1. They have a compelling reason to buy or make a change.
  2. They have the resources and willingness to invest (time, money, effort).
  3. They have the authority and readiness to make a decision, including financial decisions.

Bold Questions That Build Relationships

To discover whether a prospect qualifies, you need to ask bold, sometimes uncomfortable questions, questions that require assertiveness and emotional intelligence.

Here are a few examples:

  • “How will you go about telling your current provider that you’re moving in a different direction?”
  • “If funding is limited, how do you plan to address the problem?”
  • “The budget you mentioned won’t achieve your goals. What would you be willing to compromise?”
  • “What will you do if your partner isn’t on board with making this change?”

Imagine having the confidence to ask these questions regularly. What would happen?

You might fear losing opportunities, but in reality, you’d likely gain more meaningful ones. You’d eliminate indecision, shorten your sales cycle, and build trust by helping your prospects face their own obstacles head-on.

Final Thought

Relationship selling, when done with assertiveness and empathy, doesn’t just help you close more deals, it helps you close the right ones.

When you stop making presentations to people who can’t say “yes” and start focusing on those who are ready to move forward, your entire sales process becomes more efficient, more effective, and more rewarding.

So, if you’re facing challenges in your sales process, try this:
Be more assertive. Ask better questions. Focus on building real, lasting relationships. The results will speak for themselves.

 Compass

 

Chapter 2: Build Lasting Relationships in Sales

If your goal is to retain and grow client relationships, you must consistently create a remarkable experience for your customers and prospects. Because if you’re not providing that superior experience, rest assured, your clients may start wondering, “Who else will?”

Ask Yourself These Key Questions:

To evaluate your customer relationship strategy, reflect on the following:

  • What are you doing to keep your clients happy and satisfied?
  • Are your clients referring others to your business?
  • Is your organization delivering an exceptional experience at every touchpoint?
  • Are you learning your clients’ wants, needs, and pain points, every single day?
  • Are you under-promising and over-delivering?

What Can We Learn from Disney?

Think about a place where you wait in long lines, spend a lot of money, and still leave excited to tell others how great your experience was. For many, that’s Disney.

Disney has built decades of success by exceeding expectations and creating passionate brand advocates. In Inside the Magic Kingdom, author Tom Connellan outlines seven keys to Disney’s customer experience strategy. The biggest takeaway? Their “magic” isn’t random, it’s the result of a consistent, intentional process that dazzles.

Dazzling Experiences Aren’t Optional

To truly impress your clients:

  • Your service must be predictable and consistent.
  • Your clients must know what to expect and trust you to deliver.
  • It can’t be a once-in-a-while thing, it must be how you do business, every day.

This doesn’t mean treating everyone the same. Your top 20% of clients should get a different level of attention than your bottom 20%, but everyone should get the basics done right, every time.

If you want to stand out from competitors and earn long-term loyalty, you need to go beyond service, you need to dazzle. Treat your advocates like family. It’s not extreme, it’s what separates memorable companies from forgettable ones.

Because in business, it’s always the little things that matter.

4 Strategies to Retain and Create Loyal Advocates:

  1. Find out what they want
    Don’t guess, ask. Give clients a list of preferences and allow space for them to tell you what really matters.
  2. Prioritize critical areas
    Clients won’t always tell you what’s wrong. Just like saying “It was fine” at a restaurant, they may avoid conflict. Dig deeper to find the real issues.
  3. Identify their performance bar
    Where are they setting expectations? Don’t assume. Find out and then evaluate if you’re meeting or exceeding them.
  4. Negotiate expectations
    If something doesn’t align with your process, say so. Don’t agree out of fear of losing a deal, because if expectations don’t align now, they won’t later either. That client is unlikely to become an advocate anyway.

Final Thought

This all assumes that you already have the business acumen to understand your clients’ industry, goals, and challenges. But even then, never assume you know what they expect, ask them.

That simple conversation can lead to extraordinary results: repeat business, strong referrals, and loyal client relationships that last.

Because when you understand expectations, exceed them, and stay consistent, your clients will not only stay, but they’ll also bring others with them.

Want to keep reading?

Download the entire book for free here!

free download (1000 x 1000 px)-2

 

Topics: Sales Training, relationship selling


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    About our Blog

    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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