The Power of Retrospection in Sales Strategy

Welcome to the blog! In this post, we're diving deep into a critical yet often overlooked aspect of sales strategy: retrospection. We'll be exploring how taking the time to reflect on past interactions, strategies, and outcomes can lead to significant improvements in performance and ultimately, drive sales success. This post is inspired by my recent conversation with Jonathan Levitt, a top sales performer at InsideTracker, on the Thoughts on Selling podcast. Jonathan shared invaluable insights into his approach to sales, emphasizing the power of curiosity, relationship building, and, most importantly, retrospection. Check out our full conversation on episode 17. Enterprise selling is like running a marathon, and Jonathan Levitt describes why "choosing to do hard things" allows us to be successful in both! to hear more about Jonathan's journey and learn even more about his strategies.

Introduction: The Overlooked Power of Retrospection in Sales

In the fast-paced world of sales, it's easy to get caught up in the day-to-day grind of making calls, sending emails, and chasing leads. Often, we're so focused on the next deal that we fail to take a step back and analyze what's working, what's not, and why. This is where the power of retrospection comes in. Retrospection, or reflective thinking, is the act of critically examining past experiences to gain insights and improve future performance. It's about learning from our mistakes, celebrating our successes, and identifying patterns that can help us refine our sales strategies.

Imagine a sports team that never reviews game footage. They'd likely continue making the same errors, missing opportunities, and ultimately, underperforming. Sales is no different. Without regular retrospection, we risk repeating ineffective strategies, neglecting valuable relationships, and leaving money on the table. The ability to analyze past interactions, understand customer behavior, and adapt our approach accordingly is what separates good salespeople from great ones.

Jonathan Levitt's Journey: From Ultramarathons to Enterprise Sales

Jonathan Levitt's career path is a testament to the power of perseverance, adaptability, and a willingness to embrace challenges. He's not only a top sales performer at InsideTracker, a blood analytics company, but also an accomplished ultramarathon runner. His journey from managing ambassador programs and developing influencer relationships to selling corporate wellness services to government agencies showcases his diverse skillset and ability to excel in different environments.

What's particularly fascinating about Jonathan's story is how he applies the lessons learned from running ultramarathons to his sales career. Both require immense mental fortitude, strategic planning, and the ability to push through obstacles. In his own words, "choosing to do hard things" is a key to success in both realms. He understands that success in sales, like running a marathon, is a long game that requires consistent effort, patience, and a willingness to learn from setbacks.

Before focusing on enterprise and public sector sales, Jonathan worked with leading professional and elite athletes and also focused on direct-to-consumer sales. Along the way, he's sold millions of dollars in blood analytics and has built his own podcast, For the Long Run, into a pretty good sized operation.

The Role of Retrospection: Levitt's Key to Sales Breakthroughs

Retrospection plays a central role in Jonathan Levitt's sales methodology. He emphasizes that taking the time to reflect on past interactions and strategies has led to some of his most significant breakthroughs in awareness and strategy. It's not enough to simply go through the motions; he actively seeks to understand why certain approaches worked while others didn't.

This involves analyzing various aspects of the sales process, such as:

• The effectiveness of different messaging strategies
• The quality of customer interactions
• The impact of specific sales tactics
• The overall alignment of sales efforts with company goals

By critically examining these factors, Jonathan can identify areas for improvement and refine his approach to achieve better results. For example, he might realize that a particular sales pitch resonates better with a certain type of client or that a specific follow-up strategy leads to higher conversion rates. This kind of insight is invaluable for optimizing sales performance and maximizing revenue.

Key Tools for Success: Curiosity, Relationships, and Enthusiasm

While retrospection is a crucial component of Jonathan Levitt's sales approach, it's not the only factor contributing to his success. He also emphasizes the importance of curiosity, relationship building, and enthusiasm.

• Curiosity: A genuine curiosity about the client's needs and challenges is essential for building rapport and understanding their pain points. By asking probing questions and actively listening to their responses, salespeople can tailor their solutions to address the client's specific requirements.
• Relationships: Building strong relationships with clients is crucial for long-term success. This involves establishing trust, providing value, and demonstrating a genuine interest in their success. Nurturing relationships can lead to repeat business, referrals, and a loyal customer base.
• Enthusiasm: Enthusiasm is contagious. When salespeople are passionate about their product or service, it's more likely to resonate with potential clients. Enthusiasm can also help overcome objections and build excitement around the value proposition.

These three qualities, combined with a commitment to retrospection, create a powerful foundation for achieving sales success.

Retrospection in Action: Analyzing Past Interactions for Strategic Insights

Let's delve deeper into how Jonathan Levitt applies retrospection in his day-to-day sales activities. He doesn't just passively reflect on his experiences; he actively analyzes past interactions to identify patterns, trends, and areas for improvement. This involves:

• Reviewing call recordings: Listening to past call recordings can reveal valuable insights into how the conversation flowed, what questions were asked, and how the client responded. This can help identify areas where the salesperson could have been more effective.
• Analyzing email communication: Examining past email exchanges can shed light on the effectiveness of different messaging strategies, the responsiveness of clients, and the overall engagement level.
• Tracking key metrics: Monitoring key sales metrics, such as conversion rates, deal size, and time to close, can help identify areas where the sales process is performing well and areas where it needs improvement.
• Seeking feedback: Asking for feedback from colleagues, managers, and even clients can provide valuable insights into blind spots and areas for growth.

By systematically analyzing these data points, Jonathan can gain a deeper understanding of his sales performance and identify concrete steps to improve his results.

Patience and Persistence: The Long Game in Public Sector Sales

Jonathan Levitt's experience in public sector sales highlights the importance of patience and persistence. Unlike some other industries, public sector sales often involve lengthy sales cycles, complex procurement processes, and bureaucratic hurdles. Success in this arena requires a long-term perspective and a willingness to persevere through challenges.

Jonathan emphasizes that public sector agencies often have their own immutable timelines, which means that salespeople need to be patient and persistent in their efforts. It's crucial to build relationships with key decision-makers, understand their needs, and consistently follow up over time. Even if a deal doesn't close immediately, the relationships and groundwork laid during the initial stages can pay off in the long run.

Reverse Calendaring: An Effective Approach

One of the effective techniques Jonathan Levitt uses is "reverse calendaring." This approach involves working backward from a desired outcome to create a timeline of specific activities and milestones. By identifying the steps required to achieve a goal and assigning deadlines to each step, salespeople can create a clear roadmap for success.

For example, if the goal is to close a deal by the end of the quarter, the salesperson might use reverse calendaring to identify the key milestones, such as scheduling a demo, submitting a proposal, and negotiating terms. By assigning deadlines to each milestone, they can stay on track and ensure that the deal closes on time. This also helps to manage the client's expectations and gain commitment to specific activities and timelines.

Identifying Decision Makers: Asking Direct Questions

Identifying the key decision-makers is crucial for any sales process, but it's particularly important in complex organizations like government agencies. Jonathan Levitt emphasizes the importance of asking direct questions to identify who is ultimately responsible for making purchasing decisions. This requires curiosity and a willingness to challenge assumptions.

Instead of relying on assumptions or hearsay, salespeople should proactively seek to identify the individuals who have the authority to approve deals. This might involve asking questions like:

• "Who will be responsible for making the final decision on this project?"
• "Who needs to be involved in the evaluation process?"
• "Who controls the budget for this type of solution?"

By directly addressing these questions, salespeople can gain a clear understanding of the decision-making process and focus their efforts on influencing the right people.

Taking on Hard Things: Pushing Boundaries and Achieving Success

Throughout his career, Jonathan Levitt has consistently sought out challenges and embraced opportunities to push his boundaries. Whether it's running ultramarathons or selling complex solutions to government agencies, he believes that taking on hard things is essential for personal and professional growth.

He suggests that choosing to do hard things teaches us the limits (or lack thereof) of our capabilities, and this translates across personal and professional boundaries. By stepping outside of our comfort zones, we can develop new skills, build resilience, and ultimately achieve greater success. This willingness to embrace challenges is a key factor in Jonathan's success, and it's a lesson that all salespeople can benefit from.

Conclusion: Embracing Retrospection for Continuous Improvement in Sales

In conclusion, retrospection is a powerful tool that can significantly enhance sales performance. By taking the time to reflect on past interactions, strategies, and outcomes, salespeople can gain valuable insights, identify areas for improvement, and refine their approach to achieve better results. Jonathan Levitt's experiences at InsideTracker demonstrate the transformative potential of retrospection when combined with curiosity, relationship building, and enthusiasm. It's about the small steps you take along the way, just like running a marathon, so that you can plant the seeds for success and see it come to fruition.

As we discussed in this post, retrospection is not a one-time event; it's an ongoing process of continuous improvement. By incorporating regular retrospection into your sales routine, you can stay ahead of the curve, adapt to changing market conditions, and ultimately, achieve greater success. I hope this post has inspired you to embrace the power of retrospection in your own sales strategy. Be sure to listen to the full episode with Jonathan Levitt on the Thoughts on Selling podcast, available here: 17. Enterprise selling is like running a marathon, and Jonathan Levitt describes why "choosing to do hard things" allows us to be successful in both! to learn even more about his approach and gain practical tips for improving your own sales performance. Thanks for reading!