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

 

 

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