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“I Want a Promotion!” 4 Steps to Guide Sales Reps’ Careers


A sales rep knocks on a manager’s office door and asks for a few minutes to chat. And then comes the blindsiding, sledgehammer of a question that many managers fear hearing from their team — simply because they don’t know how to successfully handle this conversation.

“Can we talk about my promotion to a management position?” the sales rep asks. “I believe I’m ready.”

Pick a reaction: a cold sweat, a blank stare, or a defensive posture. The manager’s response is a common one: A lot of reactionary preaching as to why the sales rep can’t get that promotion, and ultimately saying, “It’s just not an option right now.”

This is a typical scenario when it comes to one of the most important things for anyone: career advancement. The problem is that the sales rep (and others on the team) will keep asking for that same promotion because the manager isn’t taking the time to ask the right questions to understand that person’s point of view; explore why the rep even wants to be a manager in the first place; and, most importantly, map out career goals, skills required, and realistic timelines and milestones to achieve that would prepare the rep for this promotion.

What would a successful conversation sound like? Managers need to craft an approach that creates alignment around what it takes to get that promotion, while also being a world-class manager who supports employee career goals.

Here are four surefire steps and the talking points to help you guide employees and answer that age-old promotion question.

Step 1: Start the conversation.

In my book Coaching Salespeople Into Sales Champions, I discuss the importance of an in-depth, authentic conversation with employees about management opportunities. This is important so managers can set and re-set clear expectations, intentions, and understanding around the expected results required prior to a promotion. It’s also imperative to address the professional development and internal organizational changes needed to get promoted into a management position or any senior position that a sales rep wants.

Clarifying this conversation and setting expectations needs to include what a promotion would entail, results that need to be achieved prior to a promotion, skills required, the expectations of a manager, and a realistic timeline for a promotion. Here’s what that could sound like:

“I appreciate your interest and desire to advance in your career and making me aware of your career goals and expectations. I want to support you the best way I can. That includes making sure I’m helping you progress in your career while managing your expectations around your career goals. So what I want for you is to have greater clarity around what the role of a manager truly entails and what it would take to be promoted into a management role. This way, you can assess if it is aligned with your timeline, lifestyle, passion, career goals, values, and expectations. Are you open to discussing this?”

Step 2: This is a coaching moment.

Once you have started the conversation, here are some great questions to facilitate the rest of the discussion based on the expectations you outlined:

  1. Why do you want to be a manager?

  2. What are the benefits of becoming a manager as opposed to staying in the role of an independent contributor?

  3. Can you please share your view around the role and responsibilities of a manager?

  4. What would you want to do less of as a manager? Why?

  5. What would you want to do more of as a manager? Why?

  6. As a manager, what would your priorities be? Why?

  7. Describe what a typical day would look like as a manager.

  8. What challenges would you be faced with in a management position?

  9. What assumptions would you be make about a management role?

  10. How would you go about identifying, developing, and refining the skills you need to be an effective manager?

  11. How does becoming a manager align with your personal and professional goals?

  12. What are the characteristics of an effective, inspirational, and extraordinary leader?

  13. What legacy would you want to leave? How do you want to be known?

  14. What would you have to sacrifice or give up personally and professionally if you become a manager as opposed to an independent contributor?

  15. What is your timeline and expectation around being promoted into a management role?

Step 3: Fill in the gaps and shatter the assumptions.

Once you have an idea of where employees are coming from and the accuracy of their perceptions of what it takes to be a great leader, it’s time for the reality check. While some people may be fairly tuned in to what the role entails, there will be others that, well, quite frankly, have no clue about what it takes to be a successful leader and manager.

Some people are inspired to build, develop, and lead a team, realizing the spotlight is no longer on them but their team.There are others who are seduced by the allure of management, and envision a position of power and success. They may see being a manager as an opportunity to delegate the things they don’t want to do, solve the problems of their team, and make more money.

Many assume they know what it means to be a great manager. For many organizations, this is the farthest thing from the truth. For example, one manager asked a direct report looking for a promotion to shadow him for the day. After the sales rep observed what the manager’s day looked like, how hard the manager worked, and the responsibilities involved, the rep said, “I thought I’d want to be a manager but after watching you for the last day, there’s no way I want your job.”

Step 4: Set expectations and map out a career trajectory.

If your employees are still passionate about becoming a manager, share or create with them the job description and expectations of a manager in your organization. This way, they now have full visibility into exactly what their responsibilities would be. And because they co-created the description with you, they have greater ownership of the role. At this point, they can identify how much of this role aligns with their values, priorities, career vision, and what it means to be a transformational, elite manager and coach.

It’s also essential that employees receive a chronological path and realistic timeline regarding what they would need to accomplish in their current role before getting a promotion. Are they achieving their current business objectives? Are they a good model for their team? Do they have the skills, attitude, and behavior that would make them thrive? Identifying these milestones is critical so your employees can make the best decisions for them and the company based on facts rather than assumptions.

After going through this exercise, you’ll find that some employees may want to stay in their current position or pursue roles other than management. And, of course, there are others who will persevere and make great future leaders. By engaging in the right conversation and coaching your team throughout this process of self-discovery, you can avoid the redundant conversations regarding promotions. Now you can use this strategy to best assess the future leaders of your organization and those that may be a better fit elsewhere.

Managers need to craft an approach that creates alignment around what it takes to get that promotion, while also being a world-class manager who supports employee career goals.”

Keith Rosen | Author of "Coaching Salespeople into Sales Champions"

Learn More

The 7 Sales Skills That CAN’T Be Taught By Dan Ross,
Sr AVP, Commercial Sales, Salesforce
Why It’s Now or Never for Social Selling with LinkedIn’s Mike Derezin Interviewed by Laura Fagan,
Product Marketer, Sales Cloud, Salesforce
Making the Tricky Transition from Sales Peer to Sales Manager By Keith Rosen,
Author of "Coaching Salespeople into Sales Champions"



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