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    3 Key Takeaways From “Sometimes You Win Sometimes You Learn” That Apply to Sales Coaching

    by Will Kloefkorn / January 24, 2018

    Editor's Note: This post has been updated for accuracy and comprehensiveness on November 23, 2020. Photo by Hattie Kingsley Photography. 

    Book Review 4/25Losing is hard, but it is especially hard when you unconsciously correlate your loss to your sense of self-worth. Admittedly, this is something I used to struggle with early and often in my business career. I wish that I had read Maxwell’s Sometimes You Win Sometimes You Learn earlier in my career, but as Maxwell’s mentor, the great John Wooden said “It’s what you learn after you know it all that counts”. I guess that is my silver lining, as well as everyone else’s.

    “It’s what you learn after you know it all that counts”. — John Wooden

    The truth inside this book points out the following; there is no such thing as losing so long as you have the right mindset to learn from your mistakes. Maxwell tells numerous stories about how people who have the humility to learn from their failure are destined to achieve elevated levels of success and those who are too headstrong to admit their mistakes, those who choose pride rather than humility, are ultimately destined to fall flat. Even if the prideful person succeeds, Maxwell reminds us that pride always comes before the fall.

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    Perhaps my favorite line in this book was this, “the person that makes a mistake, and then offers an excuse for their mistake, has now made two mistakes”. Taking extreme ownership to achieve ultimate success was the common thread of book # 2 in this challenge, and that theme showed up time and time again in this book as well.

    When you make an excuse for a mistake that you made, regardless if the excuse is true or has merit, it gets in the way of your learning from that said mistake. The hard thing to do is look yourself in the mirror and try to self-analyze what you could have done differently to avoid this mistake and then move forward.

    3 takeaways from Sometimes You Win Sometimes You Learn that apply to Sales Coaching

    1) Learn from your mistakes

    This seems simple and obvious, doesn’t it? Well, sometimes it is the stuff that is so simple that makes it hard. For example, every sales organization knows that being a high-performing sales person and being a high-performing sales coach require two drastically different skill sets. Yet, almost across the board, sales organizations keep promoting their top performing reps into sales management roles.

    Checklist: Find Out if Your Top-Performing Sales Reps are Ready for Management 

    Why does this keep happening? It’s because they fail to learn from their mistakes. As marketing guru Jay Baer once said “it may be the devil, but it’s the devil they know” so they keep repeating the same “worst practice”.

    My advice: Learn from your mistakes and find a new dance partner.

    2) Adopt a beginner’s mindset 

    Simply put, you don’t know it all so stop acting like a finished product. Try something different and pretend that every person you encounter has something that they can teach you. Adopt a mindset that says, “I can learn something new every day” and every time that you learn something new, you grow and thus so does your team.

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    Your experience and talent my well lend itself to an expert’s status, but you are the law of the lid when it comes to your team. If nothing else, keep learning so that they can grow underneath you.

    3) Allow your sales people to fail 

    The only way wisdom is gained is via real life experience and trial and error. Remember, losing can be a powerful teacher so long as you help your sales team learn from their mistakes. Too many sales managers are afraid to let their sales people lose a deal because they don’t want to miss their quota, which I totally understand, but they need to look at the bigger picture. You cannot sell for the 7–8 people that are on your team. One person doing the work of eight may keep you afloat in the short term, but in the long term you are sunk.

    What you need is eight people doing the work of eight strong and confident sales people. Don’t sell for them, teach and develop them, and don’t be afraid to let them fall. If you don’t allow them to fall, you are stifling their development. Just make sure you are there to pick them back up!

    Truth be told this was my least favorite book thus far, albeit we are early in the challenge. A wise sales coach, and client of the EcSell Institute, told me years ago; even if you go to the worst professional development event out there, there is still a nugget or two that you can take away that will make you better.

    This leader had a beginner’s mindset and I think about him every time someone or something is not exceeding my expectations. This book was by no means bad, in fact it was very good, it just wasn’t my personal favorite. That being said, I focused on the positives and I am now a better person and sales person as a result. 

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    In his attempt to help individuals escape “The Matrix”, Tom Bilyeu, founder of Impact Theory, has a reading list of 25 books which he recommends that everyone read to better understand how they can unlock their potential. Others have embarked on this journey and I have decided to join them by dedicating myself to reading a book per week for the next 25 weeks.

    This week’s high-level review, and application to sales coaching, is the book "Sometimes You Win Sometimes You Learn by John C. Maxwell". 

    Next Review: "Start With Why" - Click here to read it.

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    Will Kloefkorn

    Will Kloefkorn

    Serving as a sales manager with the Ecsell Institute team since the company's inception, Will Kloefkorn is responsible for leading Ecsell Institute's worldwide sales growth strategies and business development initiatives as the VP of Sales. Will's background includes business development jobs across the board with recognized organizations such as ESPN and Enterprise.