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Every sales leader has a story of what they’ve learned and what they’ve gone through in their sales careers. From times when they thought they should have gotten a promotion but didn’t get it, to times when they finally got it and then felt they were the worst managers in the world or realized they were better reps than managers.

How can salespeople advance in their careers and become better at their jobs? That is the topic of conversation of this episode of the Modern Selling podcast with my guest, Scott Leese.

Scott is a 6x Sales Leader, 3x Author, 3x Entrepreneur, and 1x Unicorn builder, who serves as a strategic advisor and consultant to dozens of companies around the world. He specializes in building sales processes and salespeople, maximizing new customer growth, increased average contract value, and upselling and retaining customers.

Sales Managers Podcast - From Rep to Manager Book Cover

Scott and his coauthor, Ryan Walker, wrote From Rep to Manager for anybody who wants to improve as a sales leader.

“There’s a lot of books about leadership in general,” Scott says. “There’s actually not that many books about how to be a good sales manager or how to become or get a sales manager job.”

There’s also a gap in the sales training world. There are a lot of virtual sales training courses, but where is the training for sales managers?

“One of the reasons that so many reps complain about their bosses is because there are people who are in sales leadership who got no training whatsoever. Nobody taught me how to be a sales manager. I just figured it out along the way and having done it for nearly 20 years now, I just felt like I got something to give back.”

Listen to this episode to learn how to advance your sales career and some great tips on sales management.

True! There are many virtual #sales training courses for reps, but very few for those in the #SalesLeadership position. This ep of the @GoModernSelling #podcast w/ @thescottleese and @M_3Jr is mind-blowing 🤯. You have to listen to this. Share on X

How do you go from Rep to Manager?

If you want to lead, you need a specific mindset and a plan to get into management. Here are four questions you must ask yourself.

  1. Am I very good at my job? You don’t have to be the number one salesperson in the company, but you must be good, building your sales pipeline and hitting quota consistently.
  2. Do I really want to move into leadership? If you get more satisfaction out of helping your neighbor close the deal than you actually closing one yourself, even if you’re really good at it, that might be an indication that you have the right kind of DNA to be a sales leader.
  3. Do you want to make less money? It’s very important to set the right expectations when going into leadership.
  4. Do you like helping people in mass quantity? Whether managing a remote selling team or in-house SDRs, you will be helping others become better at their jobs.

Other questions you must consider are:

  • Are you ready to lose autonomy?
  • Are you ready for your income to be determined by others?
  • Are you ready to get all the blame?
  • Are you ready to serve?
  • Are you ready to learn a bunch of new things really fast?
  • Are you ready to lose some work-life balance?


Do I like helping people? That is the question most successful #sales managers had to say 'Yes' to before moving up the org chart. Thinking of taking that shift UP? Listen to @GoModernSelling #podcast w/ @M_3Jr feat. @thescottleese. Share on X

How do you go from Good to Great as a Sales Manager?

Very few companies have sales management training that teaches how to be a great sales manager, sales director, or VP of sales. So, how do you become a great sales manager?

Here are Scotts’s top five tips:

1. Become an apprentice

The best way to learn is to align yourself with a mentor, like an apprentice. Find a great VP of Sales or Director that you can learn from.

2. Simplify

“You have to understand that your job is to simplify, simplify, simplify,” Scott says. “That means to simplify the pitch, simplify the rebuttals for your reps, simplify your feedback to them. So if they do ten things wrong at the same time, don’t tell them all ten things. Start with just one thing. Just simplify their lives in general by removing blockers.”

Ask your team members, “What can I do to help you today?” Then follow through and deliver, because the moment you stop delivering on that, the trust is broken and it just sounds hollow.

“But if you deliver on that consistently for your people, they’ll ask you more, which will force you to work a little bit harder and get a little bit better and get a little bit faster at identifying blockers, noticing trends that are blocking more than one rep.”

3. Collaborate with others

Sales managers must interact and have good relationships with other departments in the company. They will need the help of Product, Marketing or Customer Success at some point, so they must nurture those relationships.

4. Teach your sellers what they need to know

As a sales leader, you must train your reps on the best sales messaging techniques, how to use video for sales, and other information that they usually are not aware of.

For example, sellers need to understand the financial metrics that will help them sell, such as how much they can discount before losing money.

“Reps usually just hear, ‘no, you can’t have that discount’, so taking the time to not only explain why they can’t have that discount but walking them through how that metric impacts the whole business, will help them understand and trust that you are not only just looking out for them, but you’re looking out for the business’ best interest as well.”

How do you go from Good to Great as a #SalesManager? @thescottleese shares 5 powerful tips on this episode of the @GoModernSelling #podcast, with Vengreso CEO, @M_3Jr. Go and check it out now! Share on X

5. Make it known that you have a desire to go into leadership

Many reps or managers don’t get promoted because they never tell their bosses they want to have a new leadership role.

“There’s nothing wrong with making your ambitions known,” Scott says. “Say, look I’m interested in moving into leadership. Here are the reasons. Why what do I need to do? What do I need to show you? How can I improve? What are the things I need to work on? Tell me what I need to do.

Give me a list and I’m going to go do all of those things and if I do all of those things, I hope to be considered for this particular role.”

Don’t miss this episode for more great tips on sales management and don’t forget to grab your copy of Scott’s book From Rep to Manager.


Outline of this Sales Managers Episode

  • [10:00] The need for a book for sales managers
  • [14:50] How do you go from rep to manager?
  • [24:42] How do you go from good to great as a sales manager?

Table of Contents
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