244: Asking Better Questions and Designing Your Ideal Day with Claire Giovino

Free Time with Jenny Blake

“What am I pretending not to know?” There is tremendous power in asking better questions, whether it comes to ideal day design, creating systems in your business, or teaching someone how to help tame your inboxes.

Today’s conversation with Claire Giovino covers all that ground and more. We talk about what qualities make email so vexing for many business owners, how to reduce fear and friction when delegating replies, and the importance of asking better questions—of yourself and in your business.

More About Claire: After an extensive career in academia, Claire Giovino began optimizing inboxes for industry leaders, launching InboxDone in 2017. She and her cofounder Yaro quickly scaled the business 10X in three years with no startup capital. Her proprietary recruitment, training and onboarding process ensures that each client is matched with a carefully-selected Inbox Manager and represented with a superior level of communication. These clients now check their inbox just once per month — or not at all. Claire has always been a seeker, maneuvering her way through life with constant questioning. She now has the lifestyle freedom to seek out her dream podcast guests and to start conversations at her Better Question Dinners. She cherishes books, quotes and good listeners.

🌟 3 Key Takeaways

• If you’re hesitant to delegate thinking, “But my emails are special!” Claire says the same patterns exist, no matter the industry, the business model. We can systematize and template every single inbox. No one will serve your client like you, but there is plenty that you can train others to do.
• You’re not outsourcing tasks, you’re delegating decisions. Start with the smallest micro-decisions, then move into higher stakes relationships and messages incrementally by drafting.
• Be willing to accept five percent of mistakes in service of your larger vision of lifestyle independence. Each time you give feedback, have that team member update their Role Description document (RD); review that on a monthly or quarterly basis.

📝 Permission

Drop even things that you’re very good at. Ask: is this nourishing me or depleting me?

✅ Do (or Delegate) This Next

Go back to the ideal day drawing board (here’s a template for that!): If you could spend your day however you wanted, what would that look like? Where would the parts of your business show up on a daily basis? For each area ask, “Am I the one who should be doing this?” Create a time budget for a single work week, starting by tracking how you are currently spending time.

🔗 Resources Mentioned

• Claire on the web, LinkedIn, IG: @thebetterquestions
• The Better Questions
• Company: Inbox Done

💬 Quote

"But it's no use now," thought poor Alice, "to pretend to be two people! Why, there's hardly enough of me left to make one respectable person!"

—Lewis Carroll, Alice in Wonderland

📚 Books Mentioned

• Rocket Fuel by Gino Wickman
• Who Not How by Dan Sullivan and Ben Hardy
• The Emyth Revisited by Michael Gerber
• Free Time: Lose the Busywork, Love Your Business
• Pivot: The Only Move That Matters Is Your Next One
• Life After College

🎧 Related Episodes

• The Better Questions with Claire Giovino
• Free Time: 161: Inbox Taming with Yaro Starek
• 002: Eliminate Email with Cal Newport
• Pivot: 061: Virtual Freedom: Overcome Superhero Syndrome and Start Outsourcing with Chris Ducker

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