Skip to content

guidance

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!

The Future of Prospecting: Using Artificial Intelligence to Read Buyer Intent

The modern salesperson faces two extremes: total blindness or total overload. Some still cold call a list of fifty prospects hoping one will answer, while others drown in dashboards flashing with “intent data.” Both approaches fail because neither interprets what the data truly means.

The future of sales management lies in balance — using artificial intelligence to translate buyer behavior into clear, prioritized action. AI can read digital body language, scoring every click, visit, and download to reveal genuine purchase intent. This isn’t about replacing salespeople. It’s about enabling them with sharper business acumen and faster, more precise decision-making.

When sales leaders align technology with disciplined sales processes, they move from guesswork to guidance. Value selling becomes tangible because messaging is timed to the buyer’s journey, not to the rep’s quota. The best teams build standardized playbooks for each stage — from early curiosity to re-engagement — and rely on revenue management data to decide when to act.

Read the rest of the article…

Two Tall Guys Talking Sales – The First 90 Days as a Sales Leader: Proven Strategies for Sales Management Success – Episode 157

When a company hires or promotes its first sales manager, expectations run high, but clarity can be low. In this episode of Two Tall Guys Talking Sales, hosts Sean O’Shaughnessey and Kevin Lawson unpack what the first 90 days should look like for a new sales leader. Whether you’re a CEO onboarding a new manager or that manager stepping into the role themselves, this discussion provides practical guidance on setting realistic expectations, building trust, and establishing the foundation for long-term sales success and revenue growth.

Key Topics Discussed

  • Setting Realistic Expectations as an Owner (02:00)
    Kevin explores how CEOs should frame success during the first 90 days, emphasizing the importance of patience, trust-building, and understanding that sales management transformation takes time.
  • Avoiding the “Fix This First” Trap (06:30)
    Sean cautions business owners against dumping old personnel problems on new leaders, explaining why cleaning up someone else’s mess undermines early business acumen and trust.
  • Building Relationships and Learning the Business (08:30)
    Sean shares tactical advice for new sales managers: conduct one-on-ones, ride along with reps, and build rapport across departments, marketing, operations, and finance, to master internal sales processes and interdepartmental alignment.
  • Understanding Internal and External Tools (11:12)
    Kevin discusses discovering hidden tools and levers, people, systems, vendor programs, or product configurations that can immediately improve team performance and value-selling opportunities.
  • Repackaging and Aligning Offers to the Market (12:30)
    The hosts outline how sales leaders can rethink product structures and messaging to better serve customer needs, thereby improving revenue management and profitability.

Key Quotes

  • “Trust is a currency. It has to be earned by customers, by salespeople, by peers, and you can’t buy it in the first 30 days.”,  Kevin Lawson (03:00)
  • “Don’t make your new sales leader the bad guy. If there’s a tough personnel decision, handle it before they start.”,  Sean O’Shaughnessey (07:00)
  • “Learn your company inside and out. If you don’t know who runs manufacturing or how the supply chain works, you can’t lead your salespeople effectively.”,  Sean O’Shaughnessey (10:00)
  • “You might have 20 products, but 100 possible solutions. The smart leader finds ways to repackage and sell in ways the customer actually values.”,  Kevin Lawson (13:00)

Additional Resources

  • Episodes on sales onboarding, marketing alignment, and ideal customer profiling (ICP) were referenced throughout the conversation.
  • Explore more insights and tools for sales leaders at b2b-sales-lab.com.

A Significant Actionable Item from this Podcast

Create a 90-Day Integration Plan.
If you’re a new sales manager, spend your first month listening and learning. Conduct one-on-ones with every salesperson, schedule cross-department meetings, and document what each function needs from sales. In the second month, identify process gaps and start designing improvements. By the third month, implement one or two visible wins, such as improving forecasting accuracy or clarifying sales messaging, to demonstrate value and build momentum.

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…

Two Tall Guys Talking Sales – How to Define Sales Territories for Maximum Revenue Generation – Episode 154

Sales leaders and sales professionals: are your territories setting you up for sales success or holding your team back? 

In this episode, hosts Kevin Lawson and Sean O’Shaughnessey tackle the critical role of defining territories, commission plans, and account strategies. From building fair but effective territories to creating actionable plans that drive revenue generation, this conversation blends sales management insight with practical sales strategies to help you win more consistently and grow with intention.

Key Topics Discussed

  • Defining Territories with Purpose (00:23) – Why intentional design matters more than “spray and pray” selling.
  • Fairness vs. Evenness in Territories (01:27) – Sean explains why territories don’t need to be identical, but they must be logical and fair to prevent turnover.
  • How Salespeople Should Approach New Territories (04:53) – Kevin outlines the mindset and business acumen required to succeed under a new commission plan.
  • Planning Ahead for Sales Success (08:21) – Sean breaks down how early planning impacts Q1 results, revenue management, and long-term sales processes.
  • The Power of Written Territory and Account Plans (12:23) – Kevin explains how documenting your strategies in a CRM enhances value selling and accountability.

Key Quotes

  • Sean O’Shaughnessey (01:10): “When you’re driving down the road, you’re not driving with the mirrors—you’re driving with the windshield. Defining your territory is incredibly important to know where you’re going.”
  • Kevin Lawson (06:00): “A new commission plan is not an indictment of past performance; it’s your executives telling you how and where they want the company to grow.”
  • Kevin Lawson (12:42): “When a plan is written, it’s real. You win more often when your goals and account strategies are captured, documented, and revisited.”

A Significant Actionable Item from this Podcast

Write down your territory and account growth plan before the new year begins. Identify 20 accounts to expand, document the cast of characters (champions, blockers, decision-makers), and map a path to increase revenue generation. Then, enter this plan into your CRM to hold yourself accountable and align with your company’s sales strategies.

Read the rest of the article…

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 – Tom Gottlieb of Berkshire Hathaway Explains How Buyers Want Growth- How Sales Leaders Can Increase Company Worth – E131

In this insightful episode of Two Tall Guys Talking Sales, hosts Kevin Lawson and Sean O’Shaughnessey welcome business intermediary Tom Gottlieb of Berkshire Hathaway. Tom brings decades of experience in buying, selling, and valuing businesses across the Midwest. The conversation dives deep into what truly drives the value of a company—and how sales leaders and business owners alike can prepare their organizations for a future transition. Whether you’re a business owner considering a sale or… Two Tall Guys Talking Sales – Tom Gottlieb of Berkshire Hathaway Explains How Buyers Want Growth- How Sales Leaders Can Increase Company Worth – E131

Unlock Revenue Growth with a Fractional VP of Sales

Are you feeling stuck trying to grow your company’s revenue? Do you find yourself juggling too many responsibilities, struggling with outdated sales methods, or unsure how to take your sales team to the next level? You’re not alone. Many business owners face these challenges, and at New Sales Expert, we’re here to help. I’m Sean O’Shaughnessey, founder of New Sales Expert, and we specialize in helping B2B companies accelerate revenue production by implementing proven sales… Unlock Revenue Growth with a Fractional VP of Sales

Unlocking Sales Success: The Power of KPIs in Sales Processes

Are your sales KPIs helping your team succeed? Many sales leaders focus solely on closed deals. This narrow view misses crucial elements of sustainable sales growth.

The journey matters more than the destination. Sales excellence follows a similar path. Your team’s daily actions and behaviors create the foundation for lasting success.

Effective sales measurement requires a comprehensive view of your team’s activities. Top performers consistently execute vital behaviors that drive results. They prospect strategically, nurture relationships, and expand their presence within existing accounts. These leading indicators paint a clearer picture of future performance than lagging metrics alone.

Your KPI framework must evolve beyond historical analysis. Forward-looking metrics help you spot opportunities and challenges before they impact revenue. What’s happening in your pipeline right now? How are your teams finding new prospects? Which accounts show growth potential?

Experience levels significantly impact appropriate performance measures. New salespeople face different challenges than seasoned veterans. A rookie might need help with fundamental sales behaviors while learning your company’s approach. They need clear operational guidance and structured metrics that reinforce proper execution.

Veteran salespeople bring established skills and proven track records. Their KPIs should emphasize continuous improvement and cultural alignment. How are they advancing their capabilities? What value do they add to the broader sales organization?

Read the rest of the article…

From Micro-Manager to Leader: Fostering Growth in Your Sales Team

Are you unknowingly sabotaging your sales team’s success? The answer might surprise you. The actual cost of micromanagement extends far beyond immediate productivity concerns.

Trust forms the bedrock of every high-performing sales organization. Yet many sales leaders unconsciously undermine this foundation through micromanagement. You’ve seen the signs – constant check-ins, questioning every decision, and hovering over your team’s shoulders. The culture you’ve worked so hard to build is slowly eroding.

Your best salespeople are leaving. Team morale is plummeting.

Let’s be clear about what constitutes micromanagement in sales. It’s not about being involved or interested in your team’s work. The real issue emerges when you start dictating every move and creating an atmosphere of constant surveillance.

Consider the cost of replacing top sales talent in today’s market. Beyond the substantial financial investment, you’re losing institutional knowledge and client relationships. Your organization can’t afford this drain on resources, and the impact reverberates throughout your entire sales ecosystem.

Read the rest of the article…