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Andy Roddick

Former world #1 tennis player
EPISODE 49

Don’t Be Afraid to Ask Questions

Today’s guest is hall of fame and former world #1 tennis player, Andy Roddick. You may remember him destroying opponents with his serve, or winning the 2003 US Open, or even hosting Saturday Night Live! 

But these days, he’s doing all kinds of other fun stuff. He’s the CEO of the Andy Roddick Foundation, which supports kids in low-income communities.

He’s co-founded two companies, one in healthcare and another in commercial real estate. And if all that weren’t enough, he has also launched Sweetens Cove Spirits and is out there making Tennessee bourbon!

Can you imagine pivoting from what you’ve known your whole life and jumping headfirst into one new situation after the other? 

Andy knows what it’s like to feel out of place and uncomfortable doing something new. But he also knows what it takes to get comfortable. He asks lots of questions. He prepares diligently. And he knows how to develop the right relationships. 

Every leader finds themselves in new situations, where we don’t know the lay of the land. This conversation will show you exactly how to navigate those situations.

You’ll also learn:

  • How to overcome the resistance of getting into a new venture you don’t understand
  • A mindset shift that will change the way you think about preparation
  • The power of a simple ritual to stay mentally resilient
  • The surprising benefits of productive conflict and how to lean into it

Take your learning further. Get proven leadership advice from these (free!) resources:

The How Leaders Lead App: A vast library of 90-second leadership lessons to stay sharp on the go 

Daily Insight Emails: One small (but powerful!) leadership principle to focus on each day

Whichever you choose, you can be sure you’ll get the trusted leadership advice you need to advance your career, develop your team, and grow your business.

More from Andy Roddick

Always ask if you don't understand
If you find yourself in a situation outside your expertise, speak up. Most people are more than happy to share what they know when you ask them respectfully.
There's no substitute for putting in time
There’s a lot you can’t control, but your level of preparation isn’t one of them. Prioritize it, because it gives you an edge nothing else can.

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Short (but powerful) leadership advice from entrepreneurs and CEOs of top companies like JPMorgan Chase, Target, Starbucks and more.

Clips

  • Be honest with yourself when it's time to go
    Andy Roddick
    Andy Roddick
    Former world #1 tennis player
  • Always ask if you don't understand
    Andy Roddick
    Andy Roddick
    Former world #1 tennis player
  • There's no substitute for putting in time
    Andy Roddick
    Andy Roddick
    Former world #1 tennis player
  • Be proud as long as you stay self-aware
    Andy Roddick
    Andy Roddick
    Former world #1 tennis player
  • Play to your strengths (but fill in your knowledge gaps)
    Andy Roddick
    Andy Roddick
    Former world #1 tennis player
  • Put in consistent work to be prepared for big moments
    Andy Roddick
    Andy Roddick
    Former world #1 tennis player
  • Create a go-to ritual that grounds you
    Andy Roddick
    Andy Roddick
    Former world #1 tennis player
  • Simplify your coaching sessions to the basics
    Andy Roddick
    Andy Roddick
    Former world #1 tennis player

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