Per My Last Email

In this episode, Kaila and Kyle are joined by Cherry Miao, CFO of Hightouch, who gets into the art of conducting an effective job interview, how she susses out a job candidate’s mindset, and what she thinks should be changed about the job interview process in general. She also breaks down the skills that are most important to hone in each stage of your career—from your first entry-level job all the way to the C-Suite. 

00:00 Intro

01:06 The art of the interview, and how Cherry identifies top talent in interviews

07:27 The blameless retro

09:26 Mindset vs skillset

11:05 What Cherry would like to see changed about the hiring process

13:25 The anti-sell interview

15:29 The most important skill to develop as an early career professional

18:41 Advice for the transition into mid-career

23:37 What C-suite level professionals should be focused on

Want to get all of Kaila & Kyle’s career resources? Subscribe to Per My Last Email: https://www.permylastemailshow.com/ 

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@PerMYLastEmailShow

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Each week on Per My Last Email, Morning Brew’s resident career experts Kaila and Kyle – whose careers have collectively spanned the corporate, government, nonprofit and startup sectors – debate the trickiest challenges in work life, and share tactics on how to overcome them. Share the show with a friend, and leave us a review on your favorite podcast app!

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In this episode, Kaila and Kyle are debating ambition: do you really need to be super ambitious to have a successful career? What level of ambition is the ideal amount? And can you be ambitious in both work and life in equal measure?

00:00 Intro

01:21 How we’re defining “ambition”

05:42 Can you succeed without ambition?

13:30 What is the opposite of ambition?

17:05 Kaila’s framework for thinking about the qualities necessary for career success

18:18 How ambitious SHOULD you be?

24:04 Can you be ambitious at work and have some level of work life balance?

27:07 Advice if you’re questioning your own level of ambition

31:46 Work Rants

Want to get all of Kaila & Kyle’s career resources? Subscribe to Per My Last Email: https://www.permylastemailshow.com/ 

Watch Per My Last Email on YouTube:  

@PerMYLastEmailShow

Follow Per My Last Email

Instagram: @permylastemailshow

TikTok: @permylastemailshow

Twitter: @permylast_email

Have a question for us? Send us an email or voice note to permylastemail@morningbrew.com

Learn more about your ad choices. Visit megaphone.fm/adchoices

Each week on Per My Last Email, Morning Brew’s resident career experts Kaila and Kyle – whose careers have collectively spanned the corporate, government, nonprofit and startup sectors – debate the trickiest challenges in work life, and share tactics on how to overcome them. Share the show with a friend, and leave us a review on your favorite podcast app!
Learn more about your ad choices. Visit megaphone.fm/adchoices

In this episode, Kaila and Kyle are joined by author David Epstein to discuss the topic of his latest book, Inside the Box: How Constraints Make Us Better. Listen to hear why constraints increase both productivity and creativity, and how to implement them on your own to help you in work and life.

00:00 Intro

02:05 The story of General Magic

06:02 Additive bias

09:14 Brooks’s Law

12:34 How Bell Labs is an example of useful constraints

14:48 Can removing constraints ever be beneficial?

19:31 How do we build a constraint to prevent distraction?

23:49 David’s observations on AI’s impact on human productivity 

27:30 Creativity and the Green Eggs and Ham Effect

31:07 What is the relationship between creativity, expertise, and constraints?

35:08 Is having unlimited professional options actually good career advice?

39:28 Decision-making and Fredkin’s Paradox 

41:00 How David’s two books Range and Inside the Box tie into one another

Want to get all of Kaila & Kyle’s career resources? Subscribe to Per My Last Email: https://www.permylastemailshow.com/ 

Watch Per My Last Email on YouTube:  

@PerMYLastEmailShow

Follow Per My Last Email

Instagram: @permylastemailshow

TikTok: @permylastemailshow

Twitter: @permylast_email

Have a question for us? Send us an email or voice note to permylastemail@morningbrew.com

Learn more about your ad choices. Visit megaphone.fm/adchoices

Each week on Per My Last Email, Morning Brew’s resident career experts Kaila and Kyle – whose careers have collectively spanned the corporate, government, nonprofit and startup sectors – debate the trickiest challenges in work life, and share tactics on how to overcome them. Share the show with a friend, and leave us a review on your favorite podcast app!
Learn more about your ad choices. Visit megaphone.fm/adchoices

In this episode, Kaila and Kyle dig into the unspoken rules of social media at work. When is it okay to follow a colleague on Instagram? When is posting about your company empowering vs. harmful? And is it okay to have no social media presence at all?

00:00 Intro

00:58 Which social platforms you should and should not follow your coworkers on

08:05 A good rule of thumb for deciding whether or not to follow a coworker on Instagram

09:58 The most important thing to keep in mind when it comes to following on social media

18:11 Posting as a form of empowerment

21:32 Finding the balance between posting too much and posting too little

23:50 Should phones be banned from the office?

Want to get all of Kaila & Kyle’s career resources? Subscribe to Per My Last Email: https://www.permylastemailshow.com/ 

Watch Per My Last Email on YouTube:  

@PerMYLastEmailShow

Follow Per My Last Email

Instagram: @permylastemailshow

TikTok: @permylastemailshow

Twitter: @permylast_email

Have a question for us? Send us an email or voice note to permylastemail@morningbrew.com

Learn more about your ad choices. Visit megaphone.fm/adchoices

Each week on Per My Last Email, Morning Brew’s resident career experts Kaila and Kyle – whose careers have collectively spanned the corporate, government, nonprofit and startup sectors – debate the trickiest challenges in work life, and share tactics on how to overcome them. Share the show with a friend, and leave us a review on your favorite podcast app!
Learn more about your ad choices. Visit megaphone.fm/adchoices

In this episode, Kaila and Kyle are joined by Milly Tamati, the founder of generalist.world, to talk about the benefits of being a career generalist (vs. a specialist), what people get wrong about generalists, and how to start building a portfolio career. 

00:00 Intro 

01:29 Defining what a “generalist” is

02:27 What does a long-term generalist career look like?

04:42 What people get wrong about specialists vs generalists

07:39 How do you figure out your strengths and fit as a generalist?

14:52 What is a “portfolio career”?

21:16 Are there certain personalities that are best suited for a portfolio career?

23:06 How Milly is thinking about AI

27:03 Is it more beneficial in the long run to be a generalist given the AI boom?

31:57 Per My Last Policy

Want to get all of Kaila & Kyle’s career resources? Subscribe to Per My Last Email: https://www.permylastemailshow.com/ 

Watch Per My Last Email on YouTube:  

@PerMYLastEmailShow

Follow Per My Last Email

Instagram: @permylastemailshow

TikTok: @permylastemailshow

Twitter: @permylast_email

Have a question for us? Send us an email or voice note to permylastemail@morningbrew.com

Learn more about your ad choices. Visit megaphone.fm/adchoices

Each week on Per My Last Email, Morning Brew’s resident career experts Kaila and Kyle – whose careers have collectively spanned the corporate, government, nonprofit and startup sectors – debate the trickiest challenges in work life, and share tactics on how to overcome them. Share the show with a friend, and leave us a review on your favorite podcast app!

Learn more about your ad choices. Visit megaphone.fm/adchoices