The Coaching Habit

Michael Bungay Stanier

with Michael Bungay Stanier

Coaching Expert

The Coaching Habit

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Moe Abdou is joined by Box of Crayons founder Michael Bungay Stainer to discuss the essence of coaching and why asking better questions are always more impactful than giving advice.

The Startup Checklist

Anyone who has ever built a business — and I mean a real business trying to tackle and solve difficult problems — would agree that it hardly follows a script.  Nothing comes easy, especially during the early days.  Certainly the vision is invigorating, and the camaraderie gets people up in the morning; still it’s the struggle that ultimately separates the winners from the quitters.

In his book, The Hard Thing About The Hard Things, Andreessen Horowitz co-founder Ben Horowitz tells it like it is when he reminds us that “the hard thing isn’t setting a big, hairy, audacious goal.  The hard thing is laying people off when you miss that big goal.  The hard thing isn’t hiring great people.  The hard thing is when those ‘great people’ develop a sense of entitlement and start demanding unreasonable things.  The hard thing isn’t setting up an organizational chart.  The hard thing is getting people to communicate within the organization that you just designed.  The hard thing isn’t dreaming big.  The hard thing is waking up in the middle of the night in a cold sweat when the dream turns into a nightmare.”  That’s the harsh reality of growing a business, and it’s ultimate test for those who dare take on the challenge.

For nearly four decades now, David S. Rose has been on the entrepreneurial roller coaster.  Having founded or funded more than 100 pioneering companies, he’s seen it all – from runaway success stories to failed ventures and missed opportunities, he knows that no one path assures success.  In his latest book, The Startup Checklist, he takes a detour from the traditional strategy conversation to a provide a more concrete approach to understanding the ins and outs of startup execution, management and growth.  He’s confident and humble, and a few minutes into my conversation, you’ll know why Red Herring magazine describes him as the ‘patriarch of Silicon Alley.”

Here’s a small sample of what we discuss:

  • The mental fortitude that has best served him as an entrepreneur
  • The two key skills that no entrepreneur can survive without
  • The most important contribution an investor can make to a founder
  • The three most important responsibilities of an early-stage founder
  • The balance of moving fast and slow
  • The right time for a startup to consider hiring an executive team
  • The one trap that most early-stage founders face & how to overcome it