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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!

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.

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From Crisis to Control: Managing Expectations in Sales Leadership

The concept of “managing up” emphasizes the importance of aligning a sales team’s objectives with the expectations of upper management. This approach is particularly crucial during periods of sales turnaround, where the usual metrics might falter and innovative, agile responses are required. “Managing up” involves treating higher management as an internal customer whose needs must be understood and met with the same diligence as those of external clients. For sales leaders, this means crafting a… From Crisis to Control: Managing Expectations in Sales Leadership

Segmenting Target Market: Categorize potential clients to tailor strategies effectively – Driving New Sales: Transforming Small Businesses into Sales Powerhouses – Episode 7

In this episode, Sean O’Shaughnessey has provided valuable insights into market segmentation, demonstrating its critical role in a successful sales strategy. Implement these actionable steps and witness a transformative impact on your business. Stay subscribed for more insightful episodes exploring practical strategies to drive new sales and enhance your company’s growth.

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.

Leadership Styles Differ Based on the Situation: Sales Growth vs. Sales Recovery 

By Sean O’Shaughnessey & Kevin Lawson

As B2B-focused businesses navigate the ever-changing landscape of a post-COVID economy, sales leaders must adopt and institute strategies to meet the demands of a business in growth or recovery mode. 

While the goal for a sales organization may be to sustain the growth trajectory aligned with organizational goals, the year-over-year approach to achieving success can vary significantly. Sales leadership styles depend on the current situation, the starting point, and the existing team charged to accomplish the goal. Good sales leaders find a way to achieve the annual goal; great sales leaders find ways to achieve the goal and systemize the process to allow for repeatable growth, pivots, and rapid scale.      

Growth Focused Leadership

Sales leaders focused on growth must proactively identify new market opportunities, verticals, geographies, platforms, or sales talent. They must invest in new sales channels and technologies, along with onboarding and training programs to support the growth of their sales teams and the acquisition of new client relationships.

When sales teams are in a breakout stage of growth, it can be challenging to gain the discipline to systems and alignment on processes and approaches due to the nature of managing client expectations on a wildly rising revenue outlook. This situation demands that all of the skills of a sales leader be applied consistently and strategically across the team and sales practices.  

Seasoned leaders know that hiring for an increased workload and rapidly scaling teams can be tempting. However, this approach can often lead to problems down the line. Further, we must suppress the desire to hire quickly instead of exercising patience in finding the right candidate to continue to scale teams and culture appropriately. That patience means we must endure the short-term challenges of being under-resourced and under a great deal of pressure to keep performing as if we already had the resources on the team.  Instead, it is essential to focus on finding the right candidate who will not only be able to handle the current workload but also contribute to your team’s culture and help your organization achieve long-term success. Take the time to vet candidates carefully and consider not only their skills and experience but also their values and how they fit into your team’s dynamic. By prioritizing quality over speed, you’ll set your team up for success in the long run.

Another important consideration when building a team is to prioritize scalability. It’s easy to get caught up in your organization’s immediate needs and hire for the present moment, but it’s crucial to think about how your team will grow and evolve. Look for candidates with the potential to take on new responsibilities and leadership roles as your organization expands. Consider investing in training and professional development programs to help your team members acquire new skills and stay up-to-date with the latest industry trends. By prioritizing scalability, you’ll be better equipped to adapt to changing business needs and continue to achieve success over the long term.

Discipline to proven systems is essential for leadership and having transparent KPIs and organizational goal communications. The rigor and discipline of a sales leader in a growth cycle are particularly demanding. One primary concern for leaders in this mode is talent loss due to competitive pressures to grab your resources for their growth. It would help if you had experience and discipline for these growth moments.

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Fractional Executives Are Better Than Consultants For Driving Valuable Changes in Small Businesses

Change is inevitable, and small business owners must constantly adapt to stay ahead of their competition. While traditional consultants may offer valuable insights and recommendations, they often lack the hands-on commitment to implement these changes effectively. A consultant will write a report and presentation to advise management of required changes and then count on management to deploy the advice effectively. More than a report or playbook is usually needed to drive tangible results.

Enter the concept of a fractional executive. This innovative solution provides small businesses the strategic guidance and support they need to grow and evolve. In this blog post, we’ll explore the role of a fractional executive, discuss their benefits, and share tips for finding the right fit for your business.

A fractional executive is a seasoned professional who offers expertise and leadership on a part-time or project basis. These individuals often have extensive experience in their respective fields and can fill critical gaps in a company’s leadership team. From acting as a temporary CEO to guiding sales or financial strategies, fractional executives provide services tailored to your business’s unique needs.

The critical difference between a fractional executive and a traditional consultant lies in their level of commitment. While consultants often deliver a one-time report or set of recommendations, fractional executives are actively involved in the day-to-day operations of your business. They work closely with your team to implement changes, monitor progress, and adjust strategies as needed, ensuring that your business thrives in the long term.

Consultants can create beautiful reports using modern tools like Chat GPT. While a report generated by Chat GPT can provide valuable insights and recommendations for a business, it is crucial to recognize that such a report alone is insufficient to drive meaningful changes. To successfully implement and manage the recommended changes, businesses require a more hands-on and personalized approach that addresses their unique challenges and opportunities. A report can serve as an excellent starting point, but companies must invest in dedicated human expertise to ensure that the proposed changes are effectively integrated into their operations.

A Chat GPT report may be insufficient for driving change because it cannot fully account for the intricacies and nuances of each business. While AI-generated reports can be well-researched and informative, they may need a more profound understanding of company culture, team dynamics, and specific market conditions necessary to develop tailored strategies. On the other hand, a human expert can work closely with stakeholders, employees, and customers to gain a comprehensive understanding of the business’s unique needs and challenges, allowing them to develop and implement more effective change initiatives.

Additionally, change management requires ongoing support and guidance, which a Chat GPT report or an absentee consultant cannot provide. Implementing changes often involves overcoming obstacles, refining strategies, and addressing unforeseen issues that arise during the process. A human expert, such as a fractional executive, can provide the necessary support and adaptability to navigate these challenges and ensure the success of the change initiatives. By working closely with the business daily, they can monitor progress, identify areas for improvement, and make real-time adjustments to keep the change process on track.

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Two Tall Guys Talking Sales Podcast – Manage the Expectations of Upper Management for a Sales Turnaround Effort – Episode 18

In this episode, Sean and Kevin discuss the struggle of a sales turnaround.  It is important to define what a turnaround means for your specific sales department, as the definition may vary depending on the nature of the business, the industry, and the competitive landscape. Once you have a clear understanding of what constitutes a successful turnaround for your team, you can start outlining a plan of action that meets or exceeds the expectations of… Two Tall Guys Talking Sales Podcast – Manage the Expectations of Upper Management for a Sales Turnaround Effort – Episode 18