By Gerhard Gschwandtner, Founder and CEO of Selling Power Magazine

There’s a particular look that some entrepreneurs wear like a tailored suit. A mix of modest confidence and deep-seated grit. John Flannery wore that look when I sat down with him—plus an actual tuxedo, in honor of his company’s 20th anniversary.

Two decades of building a business from scratch. That’s rarefied air in the sales training world, where trends change with every algorithm tweak and buzzwords have shorter half-lives than TikTok memes. But Flannery isn’t a trend chaser. He’s a process guy. A clarity guy. The kind of leader who spotted a systemic flaw in big companies—that the larger the organization, the more cracks you’ll find in the sales process —and built a business to fix it.

“I had a good business once,” Flannery tells me, reflecting on his early ventures in wireless tech. “But the partnership didn’t work out.” That’s the sort of line that sounds easy in hindsight but stings in real-time. What followed was a stint working for someone else—a career detour that, for many entrepreneurs, feels like purgatory. But purgatory, as it turns out, is a great place to study the system. And Flannery noticed something: sales processes in big organizations were bloated, fragmented, and increasingly ineffective.

Then came a spark. A trainer he was working with introduced him to a nimble model for sales development. That moment? That was Flannery’s founding motivation. He didn’t just launch a company—he declared a war on complexity. And he armed himself with simplicity, repeatability, and, most of all, a repeatable, adaptable, highly effective process.

Early success came wrapped in grit. “I was 14 months in, still prospecting,” he recalls. Then, like a plot twist in a feel-good movie, a referral introduced him to the president of a scientific distribution company. What started as a one-year contract for 400 employees bloomed into a six-year partnership impacting over 1,100 people.

“That was the anchor tenant,” Flannery says. You can hear the gratitude in his voice. But also the strategy. He knew how to land a whale and build a processing ship around it.

Then came the pandemic—the great disrupter of handshakes in hotel sales conference rooms. Twenty-one in-person workshops, vaporized in a week. On March 12, Flannery was flying back from Philadelphia. On March 13, the country shut down. The old model—face-to-face training—was dead. Online video technology took off.

It could have been a death knell. Instead, it was a pivot. Flannery adapted quickly, transforming 15 of those 21 sessions into virtual trainings. “We had to get good behind the lights,” he says. And fast.

Now, the next tidal wave looms: artificial intelligence. While some view it as a threat to human touch, Flannery sees opportunity in its algorithmic prowess. “Coaching is where AI will lift us the most,” he tells me. His team is working with developers to embed AI into sales coaching—using machine intelligence to tee up the right questions, identify risk signals early, and accelerate pipeline movement before a human coach ever steps in.

This isn’t about replacing the human touch. It’s about preparing it.

As Flannery gears up for the third decade in his business, he’s not chasing novelty. He’s chasing effectiveness. That’s the difference. And maybe the key lesson.

In the end, John Flannery isn’t just building a better sales process. He’s building something more enduring: trust through structure, clarity through chaos, and momentum through meaningful work.

If you’re wondering what it takes to last 20 years in sales training, don’t just study his methods. Study his mindset.

Watch the video to learn more about what sales leaders need to find out where revenue leaks are and what they should be checking for.

When a business undergoes an acquisition, upselling and cross-selling become essential strategies for integrating product lines and maximizing value. Upselling encourages customers to buy premium or enhanced products, while cross-selling offers complementary products from the newly combined company portfolio. During acquisitions, these tactics help drive immediate revenue by enhancing existing customer relationships with broader offerings. By strategically aligning sales teams and cross-promoting the acquired brand’s products, companies can create a unified customer experience and unlock new growth channels in the expanded business landscape.

Join a select group of 30 director-level peer experts for a breakout discussion on best practices for stopping revenue leaks and driving revenue growth.

You don’t want to miss this opportunity to transform your approach to revenue growth and secure long-term success for your organization.

Session highlights:

  • Equip yourself with tools and strategies to identify and eliminate revenue leaks, ensuring sustained revenue growth.
  • Learn from real-world case studies to develop a robust revenue leak prevention strategy.
  • Discover how to diagnose common revenue loss sources, quantify their financial impact, and implement effective solutions.
  • Engage in a breakout session with peers to share best practices and collaborate on strategies.
  • Walk away with a clear roadmap to optimize your revenue management processes and achieve your financial goals.

Masterclass experts:

John E. Flannery
President
Flannery Sales Systems
Gerhard Gschwandtner
Founder and CEO
Selling Power
Email me if you are interested in signing up:  john@drive-revenue.com

Note: Seating is limited and the organizers reserve the right to deny access to anyone that doesn’t fit the level of qualification required for this Masterclass.

You spent a lot of time building, delivering and coaching your commercial strategy for this year. And soon you’ll find out the results. To meet and exceed on a regular basis requires some fundamental execution. Click above to learn more.

One of the hardest parts of sales is keeping the pipeline filled with qualified opportunities. Nurturing leads is something salespeople put off. Akin to delaying the home maintenance project you perceive as time-consuming or the medical check-up that makes you uneasy – procrastination is a creeper But avoiding necessary actions can make things harder over the long term.

 

We know the importance of sustaining the pipeline and nurturing leads so why do we drag our feet? I’ll explain some reasons why as well as tell you how to prevent procrastination from taking root.”

 

So, what’s hanging us up?

  • Time Constraints: Sales reps often face tight schedules and multiple priorities. Nurturing leads requires time and effort, which can lead to procrastination when other urgent tasks take precedence.
  • Lack of Resources: Limited resources, such as manpower or tools for automation, can make lead generation seem like a daunting task.
  • Focus on Immediate Wins: Low-hanging fruit. Some may prioritize pursuing new leads and immediate sales rather than investing time in nurturing existing leads, especially if they are focused on meeting short-term targets.
  • Unclear Strategy: Without a well-defined strategy, sales teams may struggle to prioritize and execute consistent actions, leading to procrastination.

Being mindful of your circumstances and some of the classic reasons why we procrastinate can help reduce its occurrence. Here are some other ways to bury the tendency and continuously fill (not kill) the pipeline.

 

  • Evaluate Current Customers: It is not uncommon for 60-70 % of new revenue to be generated from an existing customer base. These prospects are more likely to close in a timely, predictable fashion, and forecasting their revenue is typically more accurate.
  • Assess the Lead’s Value: Whether a lead is given to you or organically generated, the most qualified leads are those with a personal connection. We are interconnected like no other time in history – personally and professionally. A quick LinkedIn search can reveal if you know someone within the company you are targeting. A cold lead instantly turns warm with an introduction from a mutual acquaintance.
  • Weigh Progress with a Milestone: The velocity of water through a pipe depends on pressure. Likewise, it’s advantageous for salespeople to have some pressure – or triggers – to determine the pace of a deal from contact to close. This is especially true immediately following an initial customer conversation. Did the customer share any goals? If yes, spend more time pursuing that. A great forecasting tool is a Deal Map. This document identifies by date and responsibility a map of the deal. Buyer and seller agree to the terms and proposed timeline. When both parties are working off the same document, forecasting probability and close date are easy to determine.

 

Regularly evaluating and refining your approach will contribute to a more resilient and effective sales pipeline management strategy – leading to more confidence and less procrastination. As William Butler Yeats, one of the greatest poets of the 20th century, said, “Do not wait to strike till the iron is hot, but make it hot by striking.”

Trust is a crucial aspect of business and relationships. Developing trust over the duration of a customer relationship takes attention and focus. Creating a good first impression can go a long way in establishing trust in business relationships. The initial encounter sets the tone for future interactions and can significantly impact how others perceive you or your company. 

I’ve shared how the concept of trust was uniquely presented to me as I went through airport security on an international trip. After responding to the standard questions, the security agent asked a final question, “Should I trust you?” I answered in the affirmative, of course, but the unconventional question got me thinking!  

Reflecting on the experience – which was used to gauge my response under pressure and assess my overall demeanor – I gained real insight into how trust is perceived and established. In business and personal relationships, trust develops through a combination of communication, consistency and demonstrated reliability. Verbal and non-verbal cues also play a significant role in establishing trust.  

When meeting with a prospect for the first time, how do you establish trust? This is not the same type of trust you have with a family member or friend. It’s the trust that allows someone to have a candid conversation about their business issues. 

Plenty is written about what not to do, such as being pushy, talking too much or just falling into stereotypical selling behavior. But in that critical window of time (which can be as short as a minute) how do you make a connection that allows the prospect to feel comfortable sharing information with you? How do you show that you genuinely care about understanding their business situation? 

Here are three actionable steps to help establish trust during your initial interactions.  

  1. Be prepared with questions about the prospect’s organization and needs, not statements or brochures about your product, service or organization. 
  1. Allow the prospect to set the pace of the meeting. Help the prospect discover their needs by listening to what they say. A few well-constructed questions will help the prospect come to their own conclusion. And only offer suggestions for items to review after they have expressed their priorities. 
  1. Be sincere. Being sincere means doing what you say you are going to do. The first way to establish sincerity is a prompt, written follow-up after that initial meeting that captures the important components for the prospect and their organization. 

You can shape the trajectory of a long-term customer relationship by establishing trust early on. While some think trust takes years to cultivate and develop, the agent at the airport thought it could take one second, a reaction to a question. One thing is certain; establishing trust is a central component of all healthy relationships. Successfully lay the foundation and watch a lasting and fruitful customer relationship unfold.   

zp8497586rq

Have you ever spent several thousand dollars (and then some) on training only to see no change or short-term boosts at best? If your sales training is striking out, it’s probably due to a lack of prep and follow-up. There are ways to achieve long-term positive changes through training but you’ve got to know what you’re signing up for and consider some clear-cut strategies.

For starters, different types of training accomplish different goals. Over the years we’ve been hired by clients for one-hour kick-off motivational keynotes, three-day intensive sales process training and everything in between. We’ve learned a few things along the way including – sales training conducted as an “event” simply doesn’t work.

If your goal is to transform your organization so that it’s achieving goals like increasing sales or increasing profit margin, the training itself is only 10% of the overall process. To make your training investment stick, consider the following before you spend valuable dollars.

You Need an Implementation Plan. Start your transformation with the end in mind. What metrics will be used to measure the success of the salespeople, manager and related team member(s)? Will leadership hold them accountable for achieving these goals? For example, to achieve 10% growth in revenue you’ve calculated that each salesperson needs to meet with one additional qualified prospect per day. The skill being developed is new business development. How will you hold each person accountable for that number? The measure of success could be an email the salesperson sends to the customer that summarizes their meeting. This is an auditable measure that a manager and a manager’s manager can use. The email not only provides quantitative measurement, but the leaders, and even the CEO, can review the email and see the quality of customer interactions. How well was the new skill captured in the follow-up e-mail? Does this contact meet the defined metric of adding one new qualified prospect per day?

Have a Strategy to Reinforce and Coach Learned Skills.

Sales skills that are enhanced or gained in a training session are 80% forgotten after the first 30 days. Why? When not practiced or measured with a 3rd party, there’s often little to no change in behavior. The formula for reinforcement is: a) apply the learned skill b) share results with the coach and then c) reinforce the behavior. For coaching, first get attendees to apply new skills in the field. This could be verbal or written sales skills – but only introduce one skill at a time. Then it’s time to coach. Ask specific questions about the desired outcome. For the example above, did the salesperson meet (or converse) with one new, qualified prospect a day? Frame questions that help them understand what went well and where correction needs to happen. Next, ask them how they can improve their results. Effective coaches help people find their own answers. Finally, ask what would happen if the next time they tried … and then insert a specific recommendation. Reviewing a video of someone good at executing a skill is a way to fine-tune a new sales method. Rehearsing a future conversation with a recording is also a good practice.

When changes are reinforced, salespeople will remember how inspired and motivated they were at training. And with effective measuring, they’ll know these skills and behaviors will be recognized.

When I’m retained by clients to help their sales team, the first thing I do is to ask to interview their top performers. My purpose is to decode their selling DNA and identify the markers that make them successful.  

Invariably, effective salespeople sell value, not solutions or services. They recognize that it’s the ‘why’ that resonates with buyers – the business value. Equally revealing is illustrating how today’s problems impact the overall bottom line. But selling value and the total cost of problems facing a customer is where many sales teams run into trouble.  

Pinpointing and helping customers articulate these positions may not come naturally but it’s a necessary practice if you want to meet or beat your goals. Top performers use the following three tactics to draw out the answers to business value and the cost of challenges.  

  1. Get to the cost of today’s problem. Buyers face a number of problems and challenges.  Great salespeople help buyers define – in totality – all of the costs these problems bring. While costs may be non-monetary, such as frustration or low morale, the numbers that hit the bottom line are those that are heard by every person involved in the buying decision. Great sellers shape and frame conversations around the costs of the buyer’s problems. This is especially important if the solution’s value comes with a higher price tag. Early conversations around costs will help sell more and ensure that the necessary margins are hit in the end. 
  1. Tell stories. Stories help buyers discover for themselves the problems that they are facing and the solutions they need. High achievers have several stories at the ready that they can tailor and share based on the buyer’s situation or desired outcome. When the conversation lulls and the buyer is unable to explain their problem, share a story! Start by framing who the experience is about. Then identify the problem, turning point and resolution. Buyers who hear successes and failures of industry peers become more willing to share details about themselves and have an easier time finding their voice. Stories not only get to problems, they also help describe how others use and derive business value from your products. Stories have purpose and great salespeople use them again and again. 
  1. Summarize conversations in writing. This is a tactic that all sellers tell me they do, but few do it well. I sell my services to many companies in different industries. I constantly refer to follow-up emails I’ve written after conversations. The emails sum up problems a client is facing and the associated costs, the solutions we discussed and their value, and of course, proposed next steps. These emails help the customer and I keep the focus on the problems we are trying to solve. Top performers don’t rely on memory. They simplify, write the plan down, share it with the customer and allow the customer to give feedback. 

If you want to sell the business value your products bring, incorporate these techniques and the process will be habit in no time.