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What An MBA Didn’t Teach You About Sales

The sales profession is challenging. You need to work hard at it to succeed. You need to learn from the best. You need to improve your skills continuously. If you think you can sell since you are a hit at parties and have a lot of friends, you may soon find that you are a failure as a salesperson. Blunt truth:

because the sales profession is so hard, you have to focus on doing everything in sales very well, or you will be considered a failure.

I call this blog, Skinned Knees because I try to relate all of the learning that I have done over the past 4+ decades (while skinning my knees in the learning process).

I hope that you learn from my mistakes so that your business will grow!

Beyond Spell Check: How Grammarly’s AI Can Transform Sales Communication

Clear, professional communication is the foundation of sales success. Yet, in 2025, much of our selling occurs not face-to-face, but through written words, emails, proposals, CRM notes, and social media messages. This shift means your writing is no longer just a form of communication; it’s your personal brand, your first impression, and often the deciding factor in whether a conversation continues or comes to a halt.

Grammarly has evolved far beyond its original purpose as a grammar checker. Today, it’s an artificial intelligence–powered platform that helps sales teams increase efficiency, refine their messaging, and accelerate revenue growth. It works directly within the tools you already use, such as Gmail, LinkedIn, Salesforce, and HubSpot, helping sales professionals write with greater confidence and clarity.

Sales organizations using Grammarly have seen measurable improvements: Databricks saved $1.4 million annually; Smartsheet cut thousands of hours from proposal creation; and Zoom reported higher customer satisfaction thanks to improved written communication. These results aren’t luck; they’re the product of refined sales processes, consistent messaging, and clear communication supported by AI.

For individual salespeople, Grammarly helps improve value selling by ensuring that every message is professional, engaging, and on-brand. Its AI engine not only corrects errors but also suggests stronger phrasing, predicts reader reactions, and even aligns your tone with your business acumen and brand voice. For sales leaders, it standardizes team communication and reinforces a culture of professionalism across departments.

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AI Isn’t Replacing Salespeople, It’s Giving Them a Competitive Edge

AI isn’t replacing salespeople, it’s making them more effective. The real risk isn’t losing your job to AI; it’s losing to a competitor who uses AI better than you do. Sales professionals who integrate AI into their workflow will outperform those who don’t. 

It’s not about technology taking over but about using technology to gain an edge. The market is becoming increasingly competitive, and the most efficient salespeople will emerge victorious.

Time is a salesperson’s most valuable asset. 

Every minute spent on administrative tasks is a minute not spent selling. AI helps reclaim those lost hours. Tools that automate writing, scheduling, and research allow salespeople to focus on what matters: building relationships and closing deals. If you’re not leveraging AI to increase productivity, you’re leaving opportunities on the table.

Sales emails need to be clear and professional. AI-powered writing assistants ensure your messages are polished and effective. A poorly written email can cost you a deal. AI tools catch grammatical mistakes, improve clarity, and even suggest more effective phrasing. This isn’t just about looking professional; it’s about being understood. 

If your message isn’t clear, it won’t convert.

Presentations are another time-consuming task. AI can generate professional decks in minutes. Instead of spending hours designing slides, salespeople can focus on developing effective strategies. AI-powered tools create branded, structured presentations based on simple inputs. This ensures consistency while saving time. Sales professionals who utilize AI for presentations can focus on delivering insights rather than formatting slides.

CRM systems are the backbone of sales operations. AI enhances CRM by automating data entry, tracking customer interactions, and suggesting next steps. Salespeople often struggle with keeping CRM data updated. AI reduces this friction by automatically capturing and organizing information. A well-maintained CRM leads to better forecasting and stronger customer relationships. 

If your CRM doesn’t have AI capabilities, it’s time to upgrade.

AI-driven insights enable sales managers to make more informed decisions, rather than relying on instinct. Managers can use AI to analyze performance trends, identify coaching opportunities, and predict revenue outcomes. AI doesn’t replace leadership; it enhances it. 

Sales managers who adopt AI can build stronger teams and achieve better results. Ignoring AI in sales management is a strategic mistake.

Lead generation is another area where AI adds value. AI-powered tools can analyze vast amounts of data to identify high-potential prospects. Instead of spending hours researching leads, salespeople can receive AI-generated recommendations. This allows for more targeted outreach and higher conversion rates. AI doesn’t just find leads, it finds the right leads.

Sales follow-up is often inconsistent. AI ensures follow-ups happen at the right time with the right message. Automated reminders and AI-generated responses keep deals moving forward. 

A well-timed follow-up can be the difference between closing a deal and losing it. AI helps salespeople stay on top of their pipeline without relying on memory.

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The Power of Personal Branding in Enhancing Sales Productivity

Navigating the world of sales can sometimes feel like traversing a labyrinth. Salespeople, sales managers, and CEOs alike grapple with the challenge of increasing revenue and enhancing productivity in their sales processes. To be successful, you need more than knowledge of products and services; you need to develop trust and a strong personal brand.

Business-to-business (B2B) sales involves transferring trust from ourselves to our prospects. We trust in our products and company, but convincing prospects to share that trust is the real challenge. This trust should encompass the product, the company, and perhaps most crucially, the salesperson. Remember, B2B sales could be defined as helping prospects decide in our favor within the desired timeframe.

The key to B2B sales is developing a personal brand that inspires trust in salespeople. The salesperson’s ability to convey reliability, expertise, and credibility can significantly influence how fast a prospect invests in a product or service.

Developing a strong personal brand begins with creating a presence that signals control and understanding of the business. This can be achieved by showcasing the benefits of your product or service to your customer’s business. A straightforward way to build your brand is by seeking references from your network, former employers, and customers, and showcasing these on professional platforms like LinkedIn.

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Two Tall Guys Talking Sales – Future-Proofing Your Sales with the Right Tech Stack – E115

This episode of Two Tall Guys Talking Sales is a must-listen for anyone looking to future-proof their business. Kevin and Sean offer practical advice and actionable strategies to help you streamline operations, adopt cutting-edge technologies, and align your team for success. Whether you’re planning for 2025 or 2035, the insights shared in this episode will set you on the path to achieving your goals.

Adapting to the New Sales Landscape: The Importance of Omni-Channel Outreach

Are you still relying on trade shows as your primary sales driver? The sales landscape has undergone a seismic shift. Those packed convention halls and endless rows of booths no longer serve as the bedrock of business development they once were.

Let’s talk about what works in today’s sales environment. Building an effective outbound pipeline isn’t just an option anymore – it’s your survival toolkit. But here’s the challenge: how do you stand out in a market where everyone’s fighting for attention?

Your unique value proposition makes all the difference. Yet many sales professionals miss a crucial point: your value proposition isn’t static. What resonates with a manufacturing client might fall flat with a distribution company. Have you tailored your message to address each industry’s pain points?

Think about your last prospecting campaign. Did you give up after four or five attempts? Research shows it takes 12 to 16 touches before prospects typically respond. This gap between persistence and practice often determines success or failure in modern sales.

The game has changed. Your prospects live in an omnichannel world. They check email between Zoom calls, scroll LinkedIn during lunch, and scan their phones throughout the day. How are you showing up in their digital world?

Consider this: every unanswered email or phone call might be a messaging problem. Are you talking about your features when you should be solving your prospects’ problems? Your prospects don’t care about your product specifications. They care about their challenges, their goals, and their bottom line.

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The Secret to Sales Success: Effective Management and Qualification of MQLs and SQLs

The concept of leads is familiar to sales and marketing novices and experts. However, leads are not created equal. There are Marketing Qualified Leads (MQL) and Sales Qualified Leads (SQL). The differences between these two types of leads and the approach to handling them can significantly impact the efficiency and success of your sales pipeline.

The journey of a lead typically begins with the marketing team. They craft messages and campaigns to attract potential customers, drawing them towards the company. These potential customers or leads are known as Marketing Qualified Leads (MQLs). MQLs are individuals who have shown interest in the company’s product or service but have yet to be vetted for sales-readiness. They may have responded positively to the company’s marketing efforts by downloading a case study, signing up for a newsletter, following the company on social media, or a wide variety of other criteria that can be unique to each selling organization.

Unfortunately, just because a lead has shown interest does not mean they are ready to make a purchase. This is where the sales team comes in. Their role is to qualify these leads further, turning them into Sales Qualified Leads (SQLs). SQLs are leads the sales team has determined are ready for direct sales engagement. They have been vetted and have shown a clear interest and willingness to hear about the company’s offering from a sales perspective. 

While marketing messages are designed to attract and engage a broad audience, the sales approach is more personal and more targeted. Sales focuses on building a relationship with the individual, understanding their unique needs, and demonstrating how the product or service can meet those needs.

Miscommunication or differing expectations can result in leads being passed along that are not truly sales-ready. This can waste time and resources and even damage potential customer relationships. It’s important for sales and marketing to work together, communicate effectively, and have a clear understanding of what constitutes a qualified lead.

One way to navigate this challenge is to establish clear criteria for MQLs and SQLs. What actions or behaviors indicate that a lead is ready to move from marketing to sales? This might include downloading certain resources, attending webinars, or requesting a product demo. By defining these criteria, both teams can ensure they’re on the same page and that leads are passed along at the appropriate time.

Salespeople should also understand how a lead became an MQL. What attracted them to the company? What information have they consumed? This understanding can inform the sales approach and help the salesperson build a relationship with the lead.

Communication between sales and marketing doesn’t end when a lead becomes an SQL. Salespeople should provide feedback to their marketing colleagues about the leads they’re receiving. If certain leads aren’t panning out, it’s important to communicate this so that marketing can adjust their strategies accordingly. Similarly, marketing should be open to feedback and willing to collaborate with sales to refine their lead qualification process.

In the end, marketing and sales have the same goal: to generate revenue for the company. By working together to manage and qualify leads effectively, they can ensure they’re both working towards this common goal. 

With clear communication, collaboration, and a shared understanding of what makes a lead sales-ready, marketing and sales can streamline the sales pipeline and drive success. 

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Mastering Sales in the Digital Age: A Case Study on Megan O’Hara

The sales landscape constantly evolves, and the tools and techniques used to reach potential clients are continually refined and reimagined. One such innovative approach to sales and marketing is pioneered by salespeople and sales managers leveraging technology to add value to their client relationships and boost their sales figures. 

Megan O’Hara, an executive solution specialist in Columbus, Ohio, is at the forefront of this movement. She has developed a unique method of reaching out to clients that adds value to their lives, increases her customer access, and builds her credibility. This method is simple yet impactful: Megan sends a weekly tech tip in a short video format every Monday.

This approach is designed to keep her name at the top of her clients’ minds. In a world where attention spans are increasingly limited and competition for customer attention is fierce, being the first person a client thinks of when they need a product or service is vital. By sending out these tech tips, Megan is providing a valuable service to her clients and ensuring that she remains at the forefront of their minds.

The success of this approach is evident in the response Megan has received from her clients. Many have contacted her after receiving her tech tips, expressing appreciation for her added value to their lives and initiating further business conversations. This is a clear testament to the power of this approach in building strong client relationships and driving sales.

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Elevating Your Sales Game in the New Year: The Essential Guide to Social Selling – Video 8 of the New Year Motivation Series

Leveraging social selling is essential in today’s digital-first business environment. This guide offers advice on creating a professional digital persona, engaging with prospects, and setting consistent interaction goals on platforms like LinkedIn. It emphasizes the importance of activities such as updating profiles, sharing relevant content, and attending virtual events to build connections and increase sales success. A focus is placed on using LinkedIn’s Social Selling Index (SSI) to measure and improve social selling effectiveness, aiming to make the New Year a milestone in sales achievement.

Monitoring Client News and Updates: Stay informed about client updates to address their changing needs  – Driving New Sales: Transforming Small Businesses into Sales Powerhouses – Episode 5

The latest episode of “Driving New Sales”, sponsored by “Two Tall Guys Talking Sales”, features sales consultant Sean O’Shaughnessey. He discusses the importance of staying updated with client news and updates for enhancing B2B sales strategies. He elucidates the use of tools like Google Alerts, social media, analyzing client data, and market trends to gain insights, improve sales outreach timing, and align efforts with sales objectives.