Skip to content

schedule

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!

Energize and Motivate: Essential Tips for an Effective Sales Kickoff Meeting

Before the year comes to a close, it’s time for sales teams and their leaders to prepare for the annual kickoff meeting. Don’t wait until December to start this process. If you have 50 or more people to invite, you may have to plan 6-9 months in advance. If your group is smaller (under 50), you should start planning by late September or early October.

This crucial event sets the stage for the upcoming year, establishing goals, strategies, and the motivation necessary to hit the ground running. Whether you are a salesperson, a sales manager, or the CEO of a small company, organizing an effective kickoff meeting is imperative to ensure a successful year ahead.

The first step in planning your annual sales meeting is to choose an appropriate venue. While it may be tempting to hold the meeting in your usual office space, it’s beneficial to opt for a location outside of your daily work environment. This helps to minimize distractions and fosters a creative atmosphere. 

A nearby hotel or a conference center can serve as an excellent venue. The key is to find a place where your team can focus entirely on the meeting without the usual interruptions from their day-to-day responsibilities.

Once the venue is secured, it’s time to think about who should be in attendance. While the primary focus will be on your sales team, consider including key personnel from other departments such as marketing, IT, and customer service. These individuals play a crucial role in supporting the sales process and can provide valuable insights and updates that will help your sales team achieve success. Additionally, involving them in the kickoff meeting promotes a sense of unity and collaboration across the company.

Read the rest of the article…

Transform Your Sales Team: Strategic Compensation Adjustments for Year-End Momentum

Autumn is the time of year for sales leaders, managers, and CEOs to begin laying the groundwork for next year’s success. Have you considered how your current sales compensation plans impact your team’s motivation and productivity? Now is the ideal moment to evaluate, adjust, and deliver these plans, preferably by December 1st. Doing so can significantly influence your team’s drive to close deals in December and build momentum heading into the next fiscal year.

Sales compensation should be motivating and rewarding for employees. It directly shapes your sales team’s behaviors and priorities. An effective plan incentivizes the right actions and deters the wrong ones.

Consider a common pitfall: salespeople holding back deals to inflate their numbers for the following year. Does your current compensation structure inadvertently reward this practice? If so, you’re unintentionally harming your year-end results.

To counter this, strategically incorporate compensation escalators and cliffs into your plan. Escalators progressively reward increased sales performance throughout the year. Higher performance equals higher commission rates, driving your sales team to push forward continually. 

Commission cliffs reset commission rates at the beginning of each year, creating a sense of urgency to close deals before the end of December. Communicating these compensation details clearly by early December ensures your team understands what’s at stake.

Don’t hold your team back!

Another critical compensation consideration is eliminating commission caps. While some organizations cap commissions to control expenses, this practice can backfire dramatically. Caps tell your top-performing salespeople that their exceptional efforts are neither valued nor rewarded appropriately. This demotivates your top talent and encourages them to seek opportunities elsewhere that offer uncapped rewards. 

Removing commission caps signals that the organization fully supports and rewards outstanding performance. Have you considered how much growth your company might achieve if artificial constraints didn’t limit your sales team?

When evaluating compensation, look beyond simple cost containment. Consider the true profitability of incentivizing increased sales volume. Once salespeople reach their targets and enter accelerators, each additional dollar earned typically comes at a lower incremental cost to your organization. 

Sales transactions earlier in the year have already covered the salesperson’s base salary once they have met their annual quota. In fact, at 100% of quota, the salesperson should have covered all their costs and their share of the overall company’s revenue needs. Thus, every extra sale at escalated commission rates still contributes positively to your overall profitability. 

Read the rest of the article…

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.

Read the rest of the article…

Turning Around Sales Performance: Strategies for CEOs and Sales Managers to Foster Internal Alignment

Navigating a sales turnaround isn’t just about fixing numbers; it’s about transforming the business. It’s about realigning expectations, rebuilding internal trust, and creating a structured, sustainable path forward. 

If you’re a CEO, sales manager, or a key salesperson in your organization, the pressure to reverse a sales slump can feel overwhelming. However, the truth is that turnarounds aren’t made in a sprint; they’re built through clarity, consistency, and effective communication.

Too often, sales leaders make the mistake of focusing only on the downward trend. They get caught up in the urgency of the numbers and forget that the real challenge lies in managing upward, setting expectations with executive leadership, and aligning them with reality. 

If your sales team is underperforming, your internal stakeholders are your new audience. Just as with external prospects, you need to manage their expectations with a clear, actionable plan.

The process starts with a shift in mindset. 

Instead of viewing upper management as critics, think of them as clients. What do they need to believe in this turnaround? What information do they need to trust your leadership? Start by building a high-level outline. Avoid over-engineering the details in the early stages. Focus on where you want to go, then reverse-engineer the steps to get there.

Every turnaround starts from a rear position. That means your first job is to stop the downward momentum. Before you can scale revenue, you need to stabilize it. That requires a clear definition of success, agreed upon by everyone involved. 

  • Are you trying to double revenue in 12 months? 
  • Or just return to last year’s baseline? 
  • Is that goal realistic given your market, team, and resources? 

If not, revise it. A stretch goal is fine. A fantasy is not.

Read the rest of the article…

Two Tall Guys Talking Sales – Breaking the Silos: Aligning Sales and Marketing for Real Revenue Growth – Episode 147

In this episode of Two Tall Guys Talking Sales, Kevin Lawson and Sean O’Shaughnessey dive deep into one of the most misunderstood dynamics in business: the relationship between sales and marketing. Pulled directly from a thought-provoking question inside the B2B Sales Lab community, this conversation explores how sales teams can contribute meaningfully to marketing efforts and why that collaboration drives better revenue generation. Whether you lead a sales team, run marketing campaigns, or wear both… Two Tall Guys Talking Sales – Breaking the Silos: Aligning Sales and Marketing for Real Revenue Growth – Episode 147

Two Tall Guys Talking Sales – Patrick O’Donnell Explains How to Hire and Onboard Sales Talent That Actually Performs – Episode 139

In this high-impact episode of Two Tall Guys Talking Sales, hosts Kevin Lawson and Sean O’Shaughnessey welcome sales acceleration expert Patrick O’Donnell to tackle one of the toughest challenges facing small business CEOs: hiring and onboarding top-performing sales talent. Together, they dive deep into proven sales strategies that help CEOs find strong candidates and keep them engaged, successful, and driving revenue. If you’ve ever hired a salesperson who didn’t work out, or you’re planning to… Two Tall Guys Talking Sales – Patrick O’Donnell Explains How to Hire and Onboard Sales Talent That Actually Performs – Episode 139

Validation Events: The Unsung Hero of Sales Process Discipline

In the complex world of B2B selling, trust is built in stages. The challenge in all sales campaigns is ensuring the prospect trusts they are making the best decision for their business.

  1. Do they trust that the salesperson is giving them all of the information?
  2. Do they trust that the company will support them after the sale?
  3. Do they trust that the product will perform as they expect it to perform?

As I have explained in my book, Eliminate Your Competition, as well as the blog for that book and in this blog, the prospect needs to trust all three elements the salesperson is selling:

  1. They need to trust the product.
  2. They need to trust the company behind the product.
  3. They need to trust the salesperson.

Prospects listen to your sales message, review your materials, and hear your claims, but none of that guarantees belief or trust. Trust is validated when your claims are validated. That’s why validation events are crucial to any rigorous sales process.

In The Qualified Sales Leader, John McMahon stresses the importance of customer-driven validation. He cautions sales leaders against relying on internal optimism or anecdotal “good signals” from prospects. Instead, McMahon emphasizes observable proof—real buyer behavior that confirms alignment, commitment, and value. Validation events are when the customer takes action to validate that what you’ve promised is accurate and valuable.

An excellent sample sale process flow looks like this:

  1. Discover
  2. Scoping
  3. Economic Buyer Meeting
  4. Validation Event
  5. Business Case and Final Proposal
  6. Negotiate and Close

As you can see, the Validation Event is the last step before creating the final business case, which will be bundled with your final proposal.

Read the rest of the article…

Two Tall Guys Talking Sales – Scaling Smarter: Building Sales Teams with Steve Caton – Episode 136

What does it take to scale a sales organization in today’s unpredictable business environment? In this dynamic episode of Two Tall Guys Talking Sales, hosts Sean O’Shaughnessey and Kevin Lawson welcome back Steve Caton, CEO of Altezza Solutions, to unpack the nuances of scaling sales teams, especially through the power of fractional sales professionals. Together, they explore the critical role that sales processes, sales management, and business acumen play in enabling organizations to grow without… Two Tall Guys Talking Sales – Scaling Smarter: Building Sales Teams with Steve Caton – Episode 136