Leadership Sales

ATM Unplugged: From Sales Pro to Sales Leader

You’ve been an AE or BDR for some time now; you’ve been brainwashed your entire career to think the next step is naturally becoming the manager. Maybe not. Leadership needs to have solid foundations in one’s desire to help and guide others to improve, make a positive impact, and facilitate change. So, when contemplating this career advancement, you should ask yourself: Why do I want to be a leader?


Don’t Be a Manager, Become a Leader 

I despise the word “manager.” So much so that I try to NEVER use it. Managers are for factories. No one wants someone over their shoulder telling them what to do, and when/how to do it. The transition is viewed as a linear progression from being a business development representative (BDR) to an account executive (AE) and eventually a “manager”, without deeply considering whether one genuinely desires the role of a leader. Merely wanting to control others and dictate their actions is not a good motivation — pursuing such a path will lead to personal dissatisfaction and an unhappy team. Instead, reflecting on what truly matters to you and why you want to make this transition is vital. 


Empathy, Guiding Others, Sharing Best Practices Over Quota 

There are a few important realizations when transitioning from a sales rep to a manager. Firstly, it’s crucial to understand that being the top-performing salesperson doesn’t automatically qualify someone as a manager. These roles require vastly different skill sets. Oftentimes, the top-performing rep will make the worst manager. My personal story may help to illustrate this point.

For years, I was the number one sales rep, and I applied for a manager position not once but twice and was turned down both times. I was frustrated and couldn’t understand the reasons behind it. Then, during a national sales meeting, I had a conversation with the VP of Sales that I will never forget.

She straightforwardly told me that managing involves leadership, helping others, fostering collaboration, and effective communication. These were all things I was failing miserably at. Time to take a long hard look in the mirror.

While an exceptional salesperson, I had the habit of constantly highlighting my accomplishments, being unwilling to share my expertise, and not supporting others. Those qualities didn’t align with being a good leader. It was a truly eye-opening moment. 

If you aspire to a leadership position, you need to make a change. 

While you don’t have to be the top-performing rep to become a manager, you can’t be the worst. Finding yourself in the middle of the pack can be a good starting point. So, what does the transition to a leadership role entail?


Key Considerations for Aspiring Leaders 


  • Adopt a Leadership Mindset from the Start

First and foremost, if you’ve decided to pursue a leadership role, it’s important to start acting as a leader before officially becoming one. 

  • Take the initiative to coach and support your fellow reps. 
  • Proactively seek opportunities to assist those above you and demonstrate your commitment to learning and growth.

The most exceptional leaders I’ve encountered, whether they were promoted internally or hired externally, were the ones who showed leadership qualities even without the title. They willingly assisted struggling reps, not because they had to as a leader, but because they genuinely wanted to help others improve.


  • Embrace the Change from an Individual Contributor to a Leader 

As a sales rep, you operate as an individual contributor responsible for your own success, having control over your performance. However, as a leader, you relinquish that control. Your success depends on the collective performance of your team. You have to be willing to work to make everyone better. The team is only as strong as its weakest link.


  • Get Ready for Difficult Conversations 

Be prepared for a mental shift. As a leader, you must embrace being a team player and take on the responsibility for the success of others. This may involve challenging conversations and holding individuals accountable, even if they were once your friends and colleagues. You’ll experience increased responsibilities and pressure. Your performance will be evaluated based on the performance of your entire team, not just your individual results. You won’t be in the spotlight anymore, so get comfortable being in the background.


  • Connect with the Community of Leaders

To better understand the role, it’s crucial to seek insights from individuals with firsthand experience. Don’t limit yourself to speaking only with your immediate leader or a colleague. Connect with multiple people who currently hold or have held the leadership position. This research and exploration will help you grasp the reality of the role, which may differ significantly from your initial assumptions. 


  • Build Cross-Functional Relationships

Prepare yourself well in advance and start cultivating cross-functional relationships before getting the role. Making a name for yourself and positioning yourself as a leader is crucial. Otherwise, you’ll be isolated, operating as a lone soldier without recognition. You’ll give yourself a competitive advantage by demonstrating your readiness for the role, engaging in conversations, and fostering relationships.


You’ve Landed the Role, What’s Next?

Sad truth? There’s no playbook. You’ve gone through everything we’ve discussed, aced the interview, secured the promotion, and you’re suddenly a manager. Congratulations! The problem is, no one tells you what to do or how to do it.

If you’re lucky, you receive thorough training when you’re hired as a new sales rep in most companies (excluding brand-new startups). You learn about the product, handling objections, conducting demos — you name it. But when you get promoted to manager? No training, no guidance, so where to start? 

There are a ton of great books out there on sales leadership, but in my mind, the single most important thing you can do is to get a coach and a mentor. It’s important to note that these are two very different things. A mentor is someone who is in the role now, who takes you under their wing to provide help and guidance. A coach is likely someone with significantly more experience who you pay for their time. I didn’t hire a coach until 3 years ago. Had I done it sooner, I have no doubt I would be much further along in my career. 


Four Pillars of Management

These pillars form the foundation of successful leadership, and mastering them will set you on the path to becoming an exceptional leader.


It involves ensuring that everyone is handling their day-to-day responsibilities. Are they hitting their targets, making their calls, and taking care of their customers? Are they properly inputting data into the CRM? Most people typically associate this with being a manager, but it’s just a quarter of the role. And if your team respects you, and if you’re working alongside them, this aspect tends to take care of itself. Supervising should only take up a small portion of your time. 


This is where you truly shine as a leader. Leading by example is crucial. There are two types of leaders: the ones who sit and refresh Salesforce all day, checking on their team’s performance, and those who serve as mentors.

People want a leader willing to get in the trenches, lead by example, participate in customer calls, and even role-play to demonstrate how the job is done. This mentoring aspect should take up around 50 to 60% of your time. It’s also the most challenging part of the job. Here’s the tricky part: resisting the urge to step in and preventing your team from making mistakes during sales calls.

Allowing them to make mistakes is essential for their learning and growth. Stepping in too soon hampers their development and damages their credibility with customers, so letting them own their mistakes and addressing them after the call is crucial. To this day I will still sit on my hands on some sales calls to allow my team to make mistakes. 



Take the time to train your team in the art of sales. You’ve been chosen for this role because you demonstrated your sales skills and leadership potential. Now, it’s time to share everything you’ve learned throughout your career and teach your team. This can be done through role-plays, one-on-one sessions, mock discovery meetings, demos, or group training. It’s important to remember that the goal of training is NOT to make everyone a mini version of you. The goal is to make everyone a better version of themselves. 



This is where you provide ongoing feedback and guidance to help your team members excel in their roles. This is primarily done through one-on-one sessions, not in group settings. Coaching allows individuals on your team to overcome their own obstacles or “head trash.” It’s about finding their motivation, understanding how they can succeed, and working with them on skill development and attitude.

Many leaders make the mistake of combining coaching with pipeline reviews and performance conversations. Critiquing someone’s numbers or going through their pipeline is one thing, but coaching is about helping them improve at their job. 


How To Excel in the Leadership Role?


Become an Advocate for Your Team

You must champion your team and ensure they have the necessary tools and training for success. Advocacy also extends to maximizing their compensation plans and closing deals. This changes the more senior you become. As you move from being a front line leader to a second or third line leader, your “team” changes. More on this below.


Ask For a Feedback 

A key element of being a successful leader is actively seeking feedback. Many leaders hesitate to ask for it from their team due to fear of vulnerability or negative perceptions. However, you can gain valuable insights by openly acknowledging your imperfections and inviting input. One of the helpful tools could be a “working with me” doc, which outlines our strengths, weaknesses, and preferred ways of collaboration. Encouraging team members to create similar documents fosters a culture of feedback and continuous improvement.


Time Block Your Calendar

Effective time blocking becomes essential as your managerial responsibilities increase. As a leader, your role is to simplify your team’s work lives by minimizing administrative burdens. For instance, owning the agenda for one-on-one meetings can alleviate your team’s need to come up with discussion topics.


Find a Coach 

More people need to recognize the value of having a coach. Continuous improvement should never cease, and a coach can play a pivotal role in helping you enhance your leadership skills.


Transitioning to a Director

Managing managers brings new nuances and challenges. They have already been placed in their roles because they are leaders and they are competent at what they do. You need to foster a strategic partnership with them. You cannot manage managers the same way you manage individual contributors. 


Focus Shift To Bidirectional Exchange

As a director, your focus shifts towards a bidirectional exchange of ideas and feedback. You work together with the managers, supporting them and their teams. Your role becomes more of a strategic thought partner rather than a frontline leader. 


Advocating for the Executive Team of the Company

As a frontline manager, your advocacy is primarily for your team, their tools, training, and compensation. However, as a director, you must advocate for your first team, which is the company’s executive team. This requires a fundamental mindset shift. For instance, when it comes to a compensation plan, you move from advocating for a plan that benefits your team to one that strikes a balance between fairness for the team and safeguarding the company’s interests. (You can learn more about it from the book: “Five Dysfunctions of a Team”  which delves into the concept of the “first team” versus “your team.”).


Assuming Fiduciary Responsibility for the Company 

Becoming a director entails assuming a fiduciary responsibility to the company. As a result, you may need to make decisions that protect the company’s interests, even if they are not always popular with your team or managers. 


Focusing on Cross-Departmental Communication & Collaboration 

As a director, you must emphasize the importance of cross-departmental collaboration and communication. Building relationships and understanding the perspectives of other departments, such as product and marketing, becomes essential. It’s no longer solely about managing the sales team; it’s about comprehending the decisions made by other departments and effectively communicating them to your leaders and their teams.


Navigating Internal Dynamics with Tact and Empathy 

Being a successful director also requires finesse and tact in navigating internal dynamics. You have to be selective in choosing the battles you fight.

Adopting a leadership mindset, embracing the shift from an individual contributor to a leader, building cross-functional relationships, and following the four pillars of management will help you make the foundation for your new role. Whether you’re contemplating a leadership role or seeking to excel in your current position, these strategies can contribute to your personal and professional growth.

ATM Unplugged is the new content series by Adam Jay where he delves into the art of successful selling. From mastering sales processes to fostering a thriving sales culture, he shares unique learnings that are exclusive to this series. Adam believes in empowering the next generation of sales leaders to set new standards, and he’s here to support you every step of the way.