An Event Apart: “The Art of the Sale”

Jaimee Newberry speaking at An Event Apart Orlando 2016 at Disney’s Contemporary Resort in Walt Disney World on October 4, 2016.

Throughout her career Jaimee has held roles from in-house teams, to agency partner, to independent consultant. Across these roles, she not only had to sell her own design work, but the work of her teams and colleagues, as well. It stands true that the most important skill she ever learned was how to sell design. Through stories of client interactions and learning experiences, Jaimee will share her two rules of design and describe how her “Check Yourself Checkpoints” have helped her sell design and close millions of dollars in deals, across the past seventeen years.


  • Rule 1: Kill your darlings
    • The client can reject your design
    • You can be difficult to work with if you can’t let go
  • Rule 2: Sell your shit
    • The better you are at selling, the fewer darlings you have to kill
  • Communication builds foundation for understanding; understanding brings confidence; confidence establishes trust
    • When you have trust, you have freedom
    • Communication can set you apart and help you move further faster
  • You can’t control others, but you can control yourself
  • 12 check-yourself checkpoints:
    1. Communication design
      • Start with email; break out long paragraphs into bullets; improve scan-ability
    2. Be specific immediately
      • Eliminates back and forth exchanges; when to meet—start with your availability
      • Always include a time and include the format of the meeting
    3. Word choices
      • Use words with active intent
        • Yoda: do the thing or don’t do the thing, don’t think about it
      • Don’t use the word “just”—demeaning, pointless word
      • Give people a positive perception of working with you
    4. Speak with confidence
      • Lack of confidence comes off a wishy washy
      • Words project different things
    5. Don’t be a jerk
      • There’s a really fine line between being confident and being a jerk
      • Find a diplomatic way to say things if you want to be heard
      • But don’t sugar coat
      • Separate the person from the action; “you broke the code” vs. “the code is broken and we need to fix it”
    6. Don’t be “judgey”
      • Don’t label people
      • Give people the space to communicate
      • Listen more, judge less
    7. Accept responsibility
      • Look for opportunities to be proactively responsible (e.g. follow up with someone when it’s not necessarily your responsibility)
    8. Silence will hurt you
      • When you don’t communicate things you create a gap of mystery (e.g. when you will be gone, what time things will be done)
      • When you leave a gap, someone will fill it with stuff, and the stuff they fill it with is never good
      • There can be lots of gaps with remote workers, so be aware when working remotely
      • Set the expectation and follow through
    9. Follow up
      • Following up can be the little difference you need; it can make it seem like you are available
      • Also, can be key to keeping your clients—if you enjoyed working with someone then follow up with them
    10. Meet them where they’re at
      • Example: Client faxing content—why did I not ask more questions?
      • Ask the right questions up front—don’t fail the client
    11. Love what you do
      • Learn to love what you’re making even when everything around you is crazy
      • What we’re feeling comes out in the work we’re doing
      • In today’s world, there are so many opportunities to shift what we do and still love it
      • If you’re going to ooze, ooze good
    12. Be you
      • What really sets us apart?
      • Develop word of mouth for being you
      • What are things that make you stand out? (i.e. gratitude)
      • Find what makes you special and amplify it
  • Using these tips, sometimes people will enjoy working with you but they won’t realize why you are good to work with
  • When you know how to sell your shit, you only need one idea to present to clients
  • Book available in 2 weeks