How to Promote the Sales Leader of the Future (and How Not to)

Even with a steady stream of technological advancements shaping the way that salespeople sell, the way companies operate, and the way buying teams make decisions, there is still one area where almost every organization struggles:  onboarding and retaining qualified sales management talent.  This is one problem that no fancy new phone app has yet managed to solve.

Solving this problem is arguably more important than ever. Why? Because intelligent, adaptive sales leadership is more important than ever. The landscape in which our sales teams operate has changed profoundly. Professionals have evolved in the way they think as sellers, as buyers, and as (formal or informal) members of buying committees.  And the most effective selling teams e now leverage data and analytics tools that didn’t exist even a few years ago; they lean into ChatGPT, and other AI-driven sales enabling technologies, to manage everything from their marketing to their outbound prospecting, from their presentations to their proposal submissions, from account management and buyer history and to trend analysis. Yet we persist in promoting our top salespeople into sales management positions without any meaningful training or preparation. 

This is a flawed practice that has been going on for decades. 

At the surface it seems like it makes sense. We quickly “promote” our top salespeople, believing that they in turn will create a team of top performers “just like them.” How hard could it be to do that? All they have to do is replicate, through others, what they achieved as a top performing seller. 

This approach breaks down in a number of fascinating ways.  First, does the top seller even want a role in sales management? We can’t assume the answer is “Yes,” especially in situations where top sellers have far greater income potential, and far fewer headaches and heartburn problems, than the person who leads their team. Many executives assume that everyone wants to be promoted … but this is not the case. 

Another issue arises when companies rush into the decision to “promote from within,” without committing the time or the resources to train that top-performing salesperson on even the most basic  sales management skills, never mind providing them with the coaching and mentoring skills that could be useful in leading a sales team – or, for that matter, the necessary coaching and mentoring as they themselves navigate a major career transition. And make no mistake: This is a major career transition. In most cases, the skills and competencies that made your top producer successful will not make that person a successful leader.

Yet, repeatedly, we see companies acting as though “scaling revenue” means “promoting top salespeople into management” and expecting them to “hit the ground running.” Sometimes, they do. Most of the time, they don’t. They get frustrated, stressed, and burned out – and they leave.  Or — what’s sometimes far worse – they stay. The business loses productivity from a top producer and gains an inept manager who isn’t equipped to lead a team and does not “hit the ground running” … which means the sales team they’re leading underperforms and experiences higher turnover than it should. We’ve seen this cycle play out more times than we can count. So, that’s the bad news. Hopefully, organizations will start to get it right. I offer what follows here in the hope that it will provide some guidance to leaders who are interested in correcting this common, massive mistake.

The first step is to ask the salesperson whether they are even interested in a management position. Do not paint a false picture for them. Do not tell them it’s a natural or expected career move, because for them, it might not be. Do not tell them they’d be perfect for the job, because that’s statistically unlikely to be true. Help them to understand the good, the bad, and the ugly of what they could be signing up for.  Make it clear that taking this job to get rid of the pressure of carrying an individual sales quota is a mistake. (In a sense, sales leaders carry everyone’s sales quota … because they’re responsible for the entire team making their number.) Tell them about Workload, hours, likely challenges, and compensation – and make sure everything you say is realistic. It may appeal to their ego to make the jump to management, and if they already have management as a career goal, that is great news. Just make sure they have all the facts, then give them space and time to consider the decision. Pressuring them to accept a management role helps no one, even if there is a vacancy that needs filling.  It’s possible – indeed, highly likely – that the best thing for them (and for the company) is to stay in the role they are in now. If you both decide that’s not the case, then yes, you can start the process of preparing them for the daunting role they’re about to take on. That means developing them as a future leader … not assuming they are ready to lead a team first thing tomorrow morning!

Next, check the data. Let’s assume there is interest in a sales leadership role. The next step is to gather relevant data and analytics. There are many great assessments available that determine skills gaps or talents and competencies. Top sellers are likely to score well on a sales assessment … but how do they score on a management assessment? Are they so hard-wired in some areas (competition and personal goal pursuit, for instance) that it would be a challenging task to upskill them to where you need them to be (in areas such as listening and delegation)? Although you may want them to move into a management role, and they may say that they want that role too, the data is going to tell you what the likelihood of success will be. Don’t ignore the data. If the assessment is a sound one, and the evidence is compelling that this salesperson will struggle in a management role … encourage them to stay where they are. 

Finally, leave no bad feelings behind. If the data points toward a mismatch, make the case that the salesperson will be happiest if they avoid that mismatch.  Draw that line and defend it! By the same token, if the salesperson decides on their own, at any point, and for any reason, that a management role is not right for them, accept and support their choice. After all, they’re not letting you or the organization down by choosing to stay in a role where they are currently excelling! Remember: You want this person to stick around and keep contributing, regardless of the role they choose to play.

Assuming we are moving forward in the process, what sales management profile would they fall into? There are six you will want to learn to recognize. Each carries its own unique opportunities and challenges.

The Administrator – This sales manager loves reports, is always on top of their numbers, and is typically maniacal about CRM hygiene. Nothing wrong with any of that. A potential blind spot, though, is their preference to spend more time with the data and the numbers than they do with their people. Administration is a great strong suit, especially if it can remove some of the burden from their salespeople. But administration can only ever be a part of the sales leader’s primary role. Developing top talent, who in turn can help attract more top talent, and identifying what will motivate the individuals on the team to hit their numbers, are ultimately more important goals.

The Trainer – This is the sales manager who knows the products, services, and solutions that the company offers inside and out. They love to spend time in role-play situations and scenarios, and they love proving that they still have that sales muscle and can still flex it, even in their current role. This syndrome is a double-edged sword. Product knowledge is important … but sometimes these folks miss important coaching and mentoring opportunities as they revert to lecturing others about how they used to do things back when they were selling. (Side note: In 2024, how they used to do things may not be as relevant a topic as they imagine.)

The Superhero – One of the most common profiles. This is the sales manager who keeps their red cape close by, so they can jump in at a moment’s notice to help close the sale. Their attention to reporting and administration is typically low. Their deep belief is that by flying in to rescue the deal, they are training their team in how to win business. They’re not. This approach to sales leadership is not scalable, sustainable, or replicable in any way. The false sense of security that it builds for senior leadership (in the short term) arises from the fact that real numbers are coming in. Yet leadership doesn’t realize it’s the same top seller they just promoted to sales manager who is still doing the selling. Typically, this path results in burnout (on the Superhero’s side) and unacceptably high turnover rates (on the team’s side).

The Firefighter – This manager moves from crisis to crisis. Sometimes, people decide this person waits for a crisis to come along! The Firefighter is most comfortable defusing problems and resolving disputes. In many organizations, that’s an approach with its benefits, assuming the sales manager can balance the other roles (such as coaching, mentoring, and keeping track of the relevant numbers). Let’s face it: sometimes you need a Firefighter. There is dysfunction in every organization, and when it comes to sales and ops, sales and marketing, and/or sales and finance, there are all kinds of interdepartmental trouble spots that sales managers sometimes have to sometime navigate – not just to help their sellers sell, but also to make sure the product, service, or solution is delivered to the satisfaction of the client.

The Raging Bull – Recently a sales manager mentioned during a coaching session that his boss had told him that he was being “too nice.” I asked him what he thought that meant. He explained that his boss had insisted that if his salespeople didn’t fear or hate him, then he couldn’t possibly be doing his job right. This is as old-school as it gets; more to the point, it doesn’t work. You can’t attract and retain a great staff this way. The Raging Bull approach has no place in the sales arena today. Personal accountability is absolutely necessary, as is full ownership of all relevant commitments on the part of the salesperson. Those things don’t happen when the manager is consistently making a conscious effort to be a jerk. If proper expectations are established, and everyone is aware of the consequences for nonperformance, there is no need to intimidate anyone using fear tactics. And there’s certainly no advantage in getting the people who report to you to hate your guts.

The Arsonist – This is someone with whom you want to part company as soon as possible. The Arsonist is the manager (or salesperson) who thrives on stirring up problems, and who is always the squeakiest wheel on the team. It should be obvious that if this is the profile of a salesperson on your team, there is nothing to be gained by promoting the individual into a management position. Some (not all) Arsonist managers sell themselves a false narrative: If there are always problems to solve and fires to put out, I will have job security … even if I cause the problem or start the fire. This attitude is terrible for the company culture, and its damaging effects far outweigh any short-term gain associated with this type of team leader 

The Coach/Mentor – These are the sales leaders of the future. These are the ones people will attract, develop, grow, and retain the salespeople of the future. These are the folks who never pretend they know it all, who specialize in asking good questions, and are themselves willing to learn and grow, so that they in turn can grow others. Becoming this kind of sales leader is not as easy as one might imagine. Many leaders we work with feel that they are coaching and mentoring, yet come to discover that they have never really taken the time to learn how to properly and effectively coach and mentor their people. The top-performing salespeople who do want to move up the ladder and into more senior executive sales roles must first become accomplished coaches and mentors. These are the roles that, once mastered, will serve them well throughout their career. And as they continue to build their people through stronger and stronger coaching and mentoring practices, their people will in turn build a better business. (To find out how to get help on ramping up someone’s coaching and mentoring skills, email me.)

Sales managers are arguably the hardest-working people in the company. They are responsible for managing up by interacting with superiors, for managing down by interacting with direct reports, and also for managing side-to-side. Managing side-to-side means they are interacting effectively with all the other interdepartmental teams that support their sales teams, in addition to working side-by-side with their sales managing peers to share best practices so the whole company can succeed. 

Maybe one day we will finally break the cycle of simply promoting our top salespeople into sales management roles, without first setting up a solid development and performance plan that will accelerate and maintain their long-term success in their new role. Management plays a critical role in the success of any organization, and it’s time to get it right for both the selling team and the company.

Written by Michael Norton.

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