Sales motivation

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

By Sean O'Shaughnessey

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.

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Transforming Quota-Setting: Strategies for Sales Leaders to Optimize Performance and Revenue

By Sean O'Shaughnessey

Quota-setting is one of the most misunderstood elements of sales leadership. Too often, it’s treated as a spreadsheet exercise or a top-down directive, rather than a strategic lever that drives behavior, performance, and growth.

Whether you’re leading a team of 20 or you’re the founder managing three reps, how you define quotas has a direct impact on your revenue trajectory and your team’s motivation.

So, where do you start?

With timing. If you’re not delivering quotas to your team until February or March, you’re already behind. Salespeople need clarity by December. That gives them runway to plan, prioritize, and hit the ground running in January. Delayed quotas create confusion and stall momentum. To achieve a strong Q1, you need to equip your team early.

Quota-setting varies depending on the size of your company. Larger teams offer more flexibility. With 10 or more reps, you can spread risk, balance performance, and model averages. You’ll have top performers who consistently overdeliver, alongside newer reps who are still ramping up. The law of averages works in your favor. You can afford some variance. Smaller teams don’t have that luxury.

When you’re running a small team, maybe two or three reps or founder-led sales, every individual matters. One person missing quota can tank your number.

You can’t rely on averages. You need precision.

That means tying quotas to actual relationships, known opportunities, and real probability. It’s not about slicing up a target evenly. It’s about assigning numbers based on what’s realistically achievable in each territory or account list.

Territory design plays a big role here. Whether it’s geographic, vertical, or named accounts, quota must reflect the market potential. You can’t expect equal performance from unequal opportunity. If Rep A has 500 viable accounts and Rep B has 50, their quotas shouldn’t look the same unless you have data that says Rep B’s accounts are closer to your Ideal Client Profile. Use available market data to inform the number. Don’t assign quotas in a vacuum.

In larger organizations, quotas often originate from the top down, typically from finance. The CEO and CFO commit a growth number to the board, investors, or in public filings to the SEC. They have no choice but to pass it down. It’s not uncommon for the sales team to receive the number without context. That’s a problem. If you’re in a leadership role, you need to pressure test that number. Can your team realistically hit it? If not, what additional resources are required?

More headcount?
Better enablement?
Marketing support?

In large organizations where the quota is driven by investor expectations, the VP of Sales must establish an organization well before the new year that achieves this year’s goal, while also meeting the expectation of growth for the next year. Planning ahead, sometimes years in advance, is part of the job.

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Two Tall Guys Talking Sales – The Motivation Formula: Achieving Big Wins in Sales – E116

By Sean O'Shaughnessey

In this compelling episode of Two Tall Guys Talking Sales, hosts Kevin Lawson and Sean O’Shaughnessey dive deep into the heart of sales motivation and goal setting. They share relatable stories, actionable insights, and practical strategies for salespeople and sales leaders. Using a vivid sports analogy, Sean sets the tone for an episode packed with strategies to stay driven—even when the path isn’t clear. Whether you’re grappling with setting goals or maximizing your commission potential, this episode is a goldmine for actionable advice and personal growth.

Key Topics Discussed

The Athlete Analogy: Personal Motivation Meets Team Success (0:00)
Sean parallels a high school sprinter’s rigorous training and the dedication needed to succeed in sales.
The Importance of Personal “Why” in Sales Motivation (6:00)
Kevin and Sean explore how individual motivations—whether financial goals, family obligations, or personal growth—shape sales performance.
Breaking Down Your Sales Math to Achieve Success (10:00)
Kevin explains how to reverse-engineer your earnings goal, calculate deal requirements, and align your activities with desired outcomes.
Creating Personal Rewards for Milestone Achievements (9:00)
Sean shares a story about a salesperson’s unique approach to celebrating significant deals and how small rewards can drive consistent motivation.
The Art of Setting Goals When None Are Provided (3:30)
Kevin and Sean discuss practical steps for creating your own sales targets when your organization hasn’t assigned any.

Key Quotes

Sean O’Shaughnessey (2:00):
“What motivates you as a salesperson to do incredibly well? What are you doing to achieve your goals, and because you achieve your goals, maybe you’re inspiring someone else on your team to do the same.”
Kevin Lawson (4:29):
“If you’re not given a goal, do the math that gets you to success. It starts with understanding your economic driver and building a plan from there.”
Sean O’Shaughnessey (9:20):
“Choose something unique to reward yourself when something good happens. It’s a motivator for the day and can become the beginning of your career motivation.”

A Significant Actionable Item from this Podcast
Reverse-engineer your sales goals for 2024. Start by defining your desired income, break it down into weekly targets, and calculate how many deals you need to close. Then, analyze your closing rates to determine how many leads and opportunities you need to generate. Finally, track your progress weekly and adjust your strategy to stay on course.

Summary Paragraph
This episode of Two Tall Guys Talking Sales delivers powerful insights into staying motivated and setting actionable sales goals. Sean and Kevin expertly weave relatable analogies with proven strategies to help you master the art of self-motivation and goal achievement. Whether you’re working towards a personal milestone or aiming to inspire your team, this episode provides the tools to elevate your performance. Tune in and take control of your sales journey today!

Overcoming Ghosting and Other Modern Sales Challenges: A Proactive Approach

By Sean O'Shaughnessey

Many salespeople, sales managers, and company CEOs grapple with the unique problem of adapting their sales strategies to ever-changing market dynamics. This problem stems from an old-fashioned practice in which sales leaders tend to offer the same advice that made them successful when they were nascent salespeople. However, to remain competitive and productive, realizing that this traditional advice may no longer hold relevance in today’s sales world is crucial.

Let’s consider a sales leader who made his mark when the internet was still in its infancy, and email and mobile phones were not part of the sales process. If this sales leader continues to advise their team based on those past experiences, they will likely be setting them up for failure. Today, the sales world is no longer about physical gatekeepers but about navigating spam filters and phone blockers. The sales environment has evolved, and it’s time sales strategies do, too.

A typical issue salespeople face today is being ‘ghosted’ by potential clients. Ghosting, a relatively modern term, refers to the situation where the person you’re trying to reach is not returning your calls or emails. It’s a frustrating experience, but it also indicates a salesperson’s failure to be proactive and do the right things earlier in the sales cycle. Modern salespeople need to think ahead, plan better, and ensure they set up the next meeting before leaving the current one. This proactive approach can help prevent ghosting, keep the sales conversation going, and indicate progress.

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Two Tall Guys Talking Sales Podcast – Happy July 4th – E94

By Sean O'Shaughnessey

Welcome to a special edition of Two Tall Guys Talking Sales with your hosts, Kevin Lawson and Sean O’Shaughnessey. As we celebrate Independence Day this week, we’re bringing you a brief yet powerful episode filled with actionable sales insights and heartfelt holiday wishes. Whether you’re relaxing with family or catching up on work, this episode is designed to give you a quick boost of sales motivation and inspiration.

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