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The Leap: Making the Jump From Sales to Sales Leadership

If you are like me, you’ve always wanted to move your career to the next level. I loved sales, but I always wanted more than managing accounts for a career. I'm not saying that's bad at all. I know several successful sales reps who retired after a very rewarding career doing just that. Maybe we are cut from the same cloth. Even if we aren't, we can find a common thread. Let me give you some background, and you can decide if this article suits you.

My Journey to Sales

After leaving the Marine Corps, I discovered an interest in sales despite my initial doubts about it being a suitable career path. At first, I struggled with reluctance towards making sales calls and lacked confidence. However, I persisted and managed to overcome my perceived weaknesses. Despite not excelling academically, I refused to let those experiences define me. Instead, I used them as motivation to showcase my abilities.

photo by Natalie Savage

Through determination and continuous learning, I excelled as a top salesperson at Zimmer Orthopedics, eventually rising to regional Vice President and Vice President of Sales in an orthopedic company. I also authored two successful books, obtained a pilot's license, and pursued a Ph. D. in leadership philosophy.

As leaders, we have faced and conquered challenges and setbacks, sharing our triumphs and failures. On a journey like this, you can't see the top of the staircase, but having faith and belief in oneself is a driving force to take the next step. My daughter sent me a picture of a hike she was on while I was writing this article, and it is an appropriate metaphor.

Building Self-Confidence

Building self-confidence is crucial for anyone transitioning from sales to sales leadership. Here are some practical steps to boost your confidence:

  • Acknowledge Your Achievements: Keep a journal of your big and small accomplishments. Reflecting on your successes can help reinforce your self-worth.

  • Set Realistic Goals: Break down your career aspirations into smaller, achievable goals. This approach makes progress measurable and less overwhelming.

  • Seek Feedback: Regularly ask for feedback from peers and mentors. Constructive criticism can provide valuable insights and help you improve.

  • Continuous Learning: Invest in your personal and professional development by attending workshops, reading books, and taking courses related to sales and leadership.

Limiting Beliefs

The intricate web of limitations we weave around ourselves often stems from the intricate tapestry of past experiences that have shaped our perceptions and beliefs. Every decision and action contributes to the intricate mosaic that ultimately defines our current selves. In politics, the pervasive discourse surrounding misinformation and disinformation sheds light on the power of deceptive or false information to manipulate and mislead the masses. Over time, the truth unravels such misleading narratives, revealing the fallacies. On a more personal level, we are not immune to deception, especially self-deception. Our minds have a way of convincing us that we are not capable enough, that the unknown is too risky, or that failure is inevitable. These self-imposed limitations often serve as a protective mechanism, shielding us from potential harm or discomfort. However, when we internalize these limiting beliefs rooted in past negative experiences, regrets, or traumas, we inadvertently hinder our own growth and development. Recognizing and challenging these self-imposed limitations is crucial for personal growth and self-empowerment. By acknowledging the source of these beliefs and actively working to reframe our mindset, we can break free from the constraints that hold us back. Embracing the discomfort of venturing into uncharted territories, learning from past mistakes without letting them define us, and seeking healing from past traumas are all essential components of overcoming self-deception and unlocking our full potential.

Overcoming Mental Barriers

In life, we start with a clean slate. As soon as we are born, our minds are filled with everything that surrounds us, including our parents, siblings, friends, and environment. We begin to value things and concepts and start to judge people and the world based on the knowledge our brains accumulate. We are creatures formed around cause and effect, actions, and outcomes. Eventually, that stored information becomes the governor of our lives, often serving to protect us yet sometimes holding us back.

As a young sales rep, I drove three hours to an account but didn't go in. I had created a story in my mind that I would be turned away. A few years later, I faced a similar situation after a long day. This time, I turned left and visited a stoplight near a client’s office. When I arrived, the new prospective client was the only one left in the office. I knocked on the door and greeted this person, and the rest is history. That visit became one of my most successful accounts.

The Salesman's Dilemma

Picture a scenario where a salesperson enters an office only to be met by an unfriendly receptionist who dismisses them. The potential client has had negative encounters with salespeople, leading them to treat every salesperson poorly. Unaware of this history, you bear the brunt of their negativity. Over time, these repeated experiences shape your expectations for future sales calls. If left unaddressed, this negativity cycle can lead to avoiding making calls altogether. Instead, you may procrastinate and only reach out to clients who respond positively. Why? Because it boosts your morale, shielding you from the anticipated pain your mind has conjured up for cold calls. Let's be honest; we've all faced similar situations, whether as accomplished sales professionals or ambitious CEOs who have climbed the corporate ladder. As leaders, we must acknowledge and address these challenges to support our sales team effectively.

Managing Fear

I’ll be the first to say I have often put that fear in the garage, but sometimes it wants to come out for a spin. When it does, sometimes it likes to take an extended drive. When it does, I end up becoming self-deprecating. I look at the success my mind perceives others as having and put up roadblocks to my progress and better outcomes. My mind lets me forget all the good things I have done, all the accomplishments I have made, and won’t let me use them when I need them most—to self-validate, to bring myself out of the valley to begin to climb that next mountain. Your brain does this in the form of self-sabotage. You do things like busy work to tell yourself you are having a productive day, but all you do is spin around the block instead of up the hill. Look up; that’s where progress is. Look ahead and around only to assess where you are, and don’t look down; it will only lure you into complacency and apathy. It’s okay to look back, but only to see how far you have come. The rearview mirror is small because the things behind you are less important than the windshield, which is big because it lets you see the abundance in front of you, lets in the light, and lets you choose where you want to go.

Handling Rejection and Building Resilience

Rejection is a part of sales, but I learned it doesn’t have to derail your progress. Here are some tips for maintaining motivation and handling rejection constructively:

  • Stay Positive: Focus on the positives of each experience, even when things don’t go as planned.

  • Learn from Rejection: Use rejection as a learning opportunity. Analyze what went wrong and how you can improve for next time.

  • Build a Support Network: Surround yourself with supportive colleagues and mentors who can provide guidance and encouragement.

Finding Your Why

This leads to a big question: Why? Why am I doing this? Pursue whatever it is for a reason. The purpose will build on the why and tell you and the world what you aim to achieve. Vision paints a picture of what that looks like, and the mission outlines the plan to achieve purpose and vision.

Embodying Leadership and the Leadership Legacy

As leaders, we need to exemplify this quality. We must have a clear understanding of it to assist others in defining it for themselves. As leaders, we naturally aspire to reach our maximum potential while aiming for our followers to do the same. Empathy plays a crucial role in this process. A leader who has faced similar challenges can appreciate them more and provide strategies for salespeople to overcome these obstacles, drawing from their own experiences. This does not mean doing the work for them but rather being a supportive presence in their lives - someone who lifts them up when they are down and pushes them when necessary. Ultimately, progress depends on the followers' belief in their leadership in leading a team or organization. A key aspect of leadership is ensuring that we do everything possible to bring out the best in our team members.

Transitioning from sales to sales leadership is akin to entrepreneurship and requires courage. Challenges and obstacles are plentiful, but with a genuine interest in people and a commitment to your mission and vision, others will recognize your dedication, believe in you, and allow you to impact more individuals than you ever imagined positively. Successfully transitioning from sales to sales leadership will establish a legacy that makes a lasting difference.

Chart: Sales Rep Failures and Leadership Intervention

The chart shows that 55% of sales rep failures in the first year are related to a lack of confidence and guidance from leadership. These two factors appear to be interconnected. Without confidence, sales reps are less likely to take risks and make bold moves, while a lack of leadership guidance means they do not receive the support and direction needed to build that confidence. As leaders, we can increase the success rate by using our acquired skills to mentor those new to our business or organization.

 Sales Rep Failures in the First Year:

  • Lack of Confidence: 30%

  • Lack of Guidance from Leadership: 25%

  • Other Reasons: 45%

Strategies for Leaders to Counteract Failures:

  • Confidence Building: Implement regular training sessions and workshops to build sales reps' confidence.

  • Mentorship Programs: Establish mentorship programs where experienced sales leaders guide new reps.

  • Continuous Feedback: Provide continuous feedback and constructive criticism to help reps improve.

  • Empathy and Support: Demonstrate empathy and emotional support to help reps overcome challenges.


Transitioning from sales to sales leadership is a significant leap, but it is achievable with the right mindset and strategies. Building self-confidence, overcoming mental barriers, handling rejection, and defining your purpose are crucial steps in this journey.

As leaders, embodying these principles helps personal growth and inspires and uplifts your team. Remember, leadership is about guiding others to achieve their fullest potential while continuously striving to reach your own. Doing so will leave a lasting legacy and meaningful impact on your organization.

At Four Pillars Consulting Group, we focus on sales and sales leadership from the ground up. Please feel free to book a 30-minute discovery call using the link below or just share your story. We are all in this together!


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