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Dear Quota Team,
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I’ve been in sales since my mid 20’s, and I’m turning 40 in a few weeks. I’ve made sales my career, and it’s given me a lot of things that I probably wouldn’t have been able to have otherwise. I own my own home in a town with a good school district. My wife only works part time, and gets to take care of our two beautiful kids. And we have newer cars and take vacations a few times a year. The point I’m making is that I’m not ungrateful. 
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But after putting in fifteen years into this career, I’m still grinding it out as a sales rep, and am not in management. I’ve worked for four different companies in that time, so I am a fairly loyal employee and don’t hop around when things get difficult. My performance is almost always solid. I’m not at the top of the board every month, but I am the guy that will stay late and work weekends to make sure I hit my goal and deliver. That is, I will do what it takes to pull my weight, unlike many of my coworkers.
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I am getting older, and when I think of the future, it makes me a bit depressed. I don’t want to spend the next twenty-five years doing the same thing (selling). I want to move into management. I will admit that I don’t necessarily have the most assertive personality, but I am honest and professional, and generally have good relationships with my coworkers. How do I set myself up to get into a management role without pretending to be somebody that I’m not? When I think of being an independent contributor ten years from now, it kind of drains the life out of me. Do you have any tips? 
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Concerned in Washington     
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Dear Concerned,
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Here’s a piece of advice that many people learn too late: unless you’re born into a powerful family, almost nothing in life happens unless you make it happen. As a successful sales rep, you know exactly what we mean. Prospects rarely beat down your door, and opportunities almost never do. 
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So what are we saying? Here it is: If you want to become a sales manager, it’s up to you to make it happen. Here are some things you can do:
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Talk to management. Ask them what they look for when hiring and promoting managers. Ask what you could work on to become a prime candidate. Don’t assume you’ll be a sales manager where you work; it might take a few lateral moves before you find the right fit. 
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Learn everything you can about sales management. Read books/blogs/talk to sales managers. Ask questions. Network. Update your LinkedIn to highlight leadership skills. Take on more responsibility. Proceed forward confidently – this is an attainable goal, and if you keep at it, you absolutely will become a sales manager. 
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Dedicate yourself to this next career step. But make sure you keep closing deals in the meantime. You don’t need to change your personality to become a manager. As long as you can take criticism, be professional, and learn from your mistakes, it doesn’t matter if you’re introverted, extroverted, short, tall, loud or quiet. All that matters is that you can produce results. 
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But to get there, you need to do the one thing that all sales reps should never fear: you have to ask for the job!