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Hannah Donovan
Leading Design, 19/06/2019 Brooklyn
E A R N I N G A S E A T A T T H E T A B L E
HOW A CEO
DESIGNS
Who is a leader?
Who wants to lead (more)?
Design like a CEO
*Whether you’re leading a design team, managing products, running
part of or all of a company, or founding your own business…
This is how you become a better
design* leader in business.
Calendar looks like Tetris
New gnarly product problem
What is this expense for !?
Prioritizing bug fixes at lunch
Drowning in emails
Working on the plane, again.
Someone wants a raise
Office WiFi broke
Weekend? What weekend…
Me around senior year, 2003

In case you forgot this time, Nelly
was charting with ‘Hot In Herre’
Three years later I was the first
designer at last.fm, and then I was
leading and scaling the design team.
Lukewarm reaction to concept
Styleguide whack-a-mole
Engineering totally
misinterpreted it!
PM got more recognition
11th hour project…again
No copywriter budget, it me!
How do I teach my CEO why
design matters?
Everyone should be a
leader of themselves.
Focus on what matters.
What has impact.
If I was CEO, what would
I be doing right now?
1. DESIGNER TO FOUNDER

2. WHAT I HAD TO OVERCOME

3. HOW TO DESIGN LIKE A CEO
WHAT’S ON TAP TODAY:
DESIGNER TO FOUNDER
Like all things,
it all started
with a dream.
2014, LONDON
LATE 2014, NEW YORK CITY
I was lucky to
have help, then
the adventure
truly began…
2015 BEGINS…
Challenge after challenge.
It was relentless.
Burning the wick at both ends
to work hard and network
Rapidly adapting to multiple
new workplaces, relationships
Skilling up every night
Endless immigration
paperwork, ~20k in fees
Instability, fear, loneliness,
unfamiliarity, the unknown
“The most powerful form of
learning comes when we're
desperate. When we have no
choice but to learn” 

– Liz Wiseman
Just when it couldn’t have
been worse…
2015 – 2018, New York City / San Francisco
It got worse.
Commuting between New York
and San Francisco
Trying to build a network and
friendships in both cities…
Navigating a large org during a
difficult time
Layoffs
Negative press cycles
More immigration…
But I got through.
And when I did, I was
different, a new person.
I embarked on the last and
most difficult leg of the
journey…



I started a company.
Getting comfortable with
calling myself an entreprenur
Learning how to raise money
Being a woman founder, so
much sexism!
Building a type of company
there isn’t a playbook for
Learning to ignore people who
told me to play it “safer”
Got into an accelerator.
Raised $2M. Built an AI
product. Got my greencard.
About to launch in beta*
*Want access? DM @thetrashapp on Twitter or IG
WHAT I HAD TO OVERCOME
Personal Practical
Being creative and analytical
are not mutually exclusive
Consider feedback, but trust
myself and my opinions

Career/organization “success”
is not the same as self worth
PERSONAL
Care about where the money
comes from, how you deploy it
Every action I take needs to
have ROI (Impact over busyness)
Think long and work quick
PRATICAL
DESIGN LIKE A CEO
CARE ABOUT WHERE THE MONEY COMES FROM AND HOW TO DEPLOY IT
What’s important to the business? 

(Get coffee with your CEO and find out!)
Is this work going to make the business successful? 

(If the business was failing a year from now, would I
feel dumb for having worked on this?)
How do I have more positive impact on users?

(Your CEO cares about users, and your job is users)
BUSY ≠ IMPACT (EVERYTHING YOU DO SHOULD HAVE ROI)
When the design is finished in Sketch etc., you
are only 10% done
Your job is users. If your work is not impacting
users you’re not doing your job.
Do things that are “outside” of your job. Your job
is not just “design”, the title is misleading :D
Plenty to get on with!
Lots to keep me busy!
Do you need help
prioritizing workload?
THINK LONG AND EXECUTE FAST
Use common sense. This is not less than creativity
and uniqueness. Common sense is a design skill.
Measure twice, cut once. Become an excellent
planner because execution time is so limited.
Stop worrying about being good. Worry about being
fast, and always be nice – that’s the easiest!
GOOD
FAST
NICE
NICE
What makes a “great”
design leader?
POSITIVE. 

USER. 

IMPACT.
We’re hiring a product
design (lead)!
@han, han@trash.app
DM @thetrashapp for Creator
Beta Access!

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How a CEO Designs

  • 1. Hannah Donovan Leading Design, 19/06/2019 Brooklyn E A R N I N G A S E A T A T T H E T A B L E HOW A CEO DESIGNS
  • 2. Who is a leader?
  • 3. Who wants to lead (more)?
  • 4. Design like a CEO *Whether you’re leading a design team, managing products, running part of or all of a company, or founding your own business… This is how you become a better design* leader in business.
  • 5.
  • 6. Calendar looks like Tetris New gnarly product problem What is this expense for !? Prioritizing bug fixes at lunch Drowning in emails Working on the plane, again. Someone wants a raise Office WiFi broke Weekend? What weekend…
  • 7. Me around senior year, 2003
 In case you forgot this time, Nelly was charting with ‘Hot In Herre’ Three years later I was the first designer at last.fm, and then I was leading and scaling the design team.
  • 8. Lukewarm reaction to concept Styleguide whack-a-mole Engineering totally misinterpreted it! PM got more recognition 11th hour project…again No copywriter budget, it me! How do I teach my CEO why design matters?
  • 9. Everyone should be a leader of themselves. Focus on what matters. What has impact.
  • 10. If I was CEO, what would I be doing right now?
  • 11. 1. DESIGNER TO FOUNDER
 2. WHAT I HAD TO OVERCOME
 3. HOW TO DESIGN LIKE A CEO WHAT’S ON TAP TODAY:
  • 13. Like all things, it all started with a dream. 2014, LONDON
  • 14. LATE 2014, NEW YORK CITY I was lucky to have help, then the adventure truly began…
  • 16. Challenge after challenge. It was relentless.
  • 17. Burning the wick at both ends to work hard and network Rapidly adapting to multiple new workplaces, relationships Skilling up every night Endless immigration paperwork, ~20k in fees Instability, fear, loneliness, unfamiliarity, the unknown
  • 18. “The most powerful form of learning comes when we're desperate. When we have no choice but to learn” 
 – Liz Wiseman
  • 19. Just when it couldn’t have been worse… 2015 – 2018, New York City / San Francisco It got worse.
  • 20. Commuting between New York and San Francisco Trying to build a network and friendships in both cities… Navigating a large org during a difficult time Layoffs Negative press cycles More immigration…
  • 21. But I got through. And when I did, I was different, a new person.
  • 22. I embarked on the last and most difficult leg of the journey…
 
 I started a company.
  • 23. Getting comfortable with calling myself an entreprenur Learning how to raise money Being a woman founder, so much sexism! Building a type of company there isn’t a playbook for Learning to ignore people who told me to play it “safer”
  • 24. Got into an accelerator. Raised $2M. Built an AI product. Got my greencard. About to launch in beta* *Want access? DM @thetrashapp on Twitter or IG
  • 25.
  • 26.
  • 27.
  • 28. WHAT I HAD TO OVERCOME
  • 30. Being creative and analytical are not mutually exclusive Consider feedback, but trust myself and my opinions
 Career/organization “success” is not the same as self worth PERSONAL
  • 31. Care about where the money comes from, how you deploy it Every action I take needs to have ROI (Impact over busyness) Think long and work quick PRATICAL
  • 33. CARE ABOUT WHERE THE MONEY COMES FROM AND HOW TO DEPLOY IT What’s important to the business? 
 (Get coffee with your CEO and find out!) Is this work going to make the business successful? 
 (If the business was failing a year from now, would I feel dumb for having worked on this?) How do I have more positive impact on users?
 (Your CEO cares about users, and your job is users)
  • 34.
  • 35.
  • 36. BUSY ≠ IMPACT (EVERYTHING YOU DO SHOULD HAVE ROI) When the design is finished in Sketch etc., you are only 10% done Your job is users. If your work is not impacting users you’re not doing your job. Do things that are “outside” of your job. Your job is not just “design”, the title is misleading :D
  • 37. Plenty to get on with! Lots to keep me busy! Do you need help prioritizing workload?
  • 38. THINK LONG AND EXECUTE FAST Use common sense. This is not less than creativity and uniqueness. Common sense is a design skill. Measure twice, cut once. Become an excellent planner because execution time is so limited. Stop worrying about being good. Worry about being fast, and always be nice – that’s the easiest!
  • 40. NICE
  • 41. What makes a “great” design leader?
  • 43. We’re hiring a product design (lead)! @han, han@trash.app DM @thetrashapp for Creator Beta Access!