Episodes
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In this episode, Kaila and Kyle talk about how to handle major, distracting life events at work. From wedding planning, to having a baby, to serious illness or injury—major life events happen to all of us. So what’s the best way to handle this without jeopardizing your career?
00:00 Intro
02:43 How Kaila handled planning her wedding while working
07:27 Kyle’s big announcement
10:03 Expectation setting
14:31 Why it might be worth disclosing a negative life event with coworkers
20:05 How Kyle approached telling his colleagues his big life news
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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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This week we’re bringing you another AITA-style episode (since we had so much fun doing it the first time). Listen to hear Kaila and Kyle read and weigh in on your “am I the a**hole?” submissions around your work-specific scenarios.
00:00 Intro
01:00 Scenario #1 - Dishonest Interview
04:11 Scenario #2 - Tattle Tale
10:31 Scenario #3 - Work Bestie Desserted Me
16:03 Scenario #4 - Boss Is Back From Paternity Leave
Want to get all of Kaila & Kyle’s career resources? Subscribe to Per My Last Email: https://www.permylastemailshow.com/
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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!
Learn more about your ad choices. Visit megaphone.fm/adchoices -
Missing episodes?
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In this episode, Kaila and Kyle dig into the real meaning of “Founder Mode” (made famous by Brian Chesky and Paul Graham), and whether or not it’s a good thing. Is it just a rebrand of micromanagement? Then, Kaila and Kyle debate whether or not micromanagement can ever be a good thing.
00:00 Intro
00:35 A brief explanation of “Founder Mode”
04:45 Talking micromanagement
06:43 The instances where being a micromanager is okay
09:49 The Delegation Ladder
14:57 The three buckets of micromanagement
18:50 What to do when you’re being micromanaged
23:30 Morning Brew’s founder on Founder Mode
Want to get all of Kaila & Kyle’s career resources? Subscribe to Per My Last Email: https://www.permylastemailshow.com/
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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!
Learn more about your ad choices. Visit megaphone.fm/adchoices -
In this episode, Kaila and Kyle dive into the implications of going sober in your career with special guest Andrew Yeung, founder and CEO of Fibe. Can you still network and attend work happy hours when you’ve quit alcohol? What does it mean for climbing the ladder?
00:00 Intro
01:05 What prompted Andrew’s sobriety
05:40 What you miss out on when abstaining from alcohol
10:10 On having to explain your sobriety
15:36 How quitting alcohol impacted Andrew’s lifestyle
18:28 How getting sober impacted Andrew’s business
21:08 How alcohol has impacted Kaila and Kyle’s careers
24:26 Tactics for the sober curious
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
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Have a question for us? Send us an email or voice note to [email protected]
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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!
Learn more about your ad choices. Visit megaphone.fm/adchoices -
In this episode, Kaila and Kyle are joined by special guest (and Morning Brew social media star) Macy Gilliam to discuss whether Gen Z gets an unfair reputation at work, and address questions like: Does Gen Z overshare? Do they lack respect for office etiquette? Does Gen Z care less, or MORE about money than other generations?
00:00 Intro
02:38 Gen Z stereotype #1
08:40 Resume Builder stat
09:26 Gen Z stereotype #2
16:18 Gen Z stereotype #3
20:28 Gen Z stereotype #4
26:04 Gen Z stereotype #5
31:36 Advice for working with Gen Z
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
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Instagram: @permylastemailshow
TikTok: @permylastemailshow
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Have a question for us? Send us an email or voice note to [email protected]
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 occupational personality tests—from the Myers-Briggs Type Indicator, to the science-backed Big Five—and debate their legitimacy, when they might be useful in the workplace, and whether or not they should be used at all.
00:00 Intro
01:00 Myers-Briggs (MBTI)
03:57 Criticism of the Myers-Briggs
07:28 The CliftonStrengths Assessment
18:11 The Big Five Personality Test (OCEAN)
25:19 A big critique of personality tests
27:29 Tactics
New York Times article cited in the episode: Personality Tests Are the Astrology of 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
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Have a question for us? Send us an email or voice note to [email protected]
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 tackle the age-old question of: how hard do you have to work to get ahead? Do you ACTUALLY have to put in overtime, or can you have a healthy “work-life balance”?
00:00 Intro
02:54 Stats on workplace boundaries
05:08 Defining what a workplace “boundary” is
06:10 The 60% Rule
08:55 Three things to keep in mind when adopting the 60% rule
16:30 Decoupling number of hours work from impact
18:19 The Eisenhower Matrix
23:27 The “three seasons of work”
29:15 Tactics for developing work-life balance that works for you
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
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Have a question for us? Send us an email or voice note to [email protected]
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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!
Learn more about your ad choices. Visit megaphone.fm/adchoices -
In this episode, Kaila and Kyle debate whether Amazon’s decision to mandate a 5 day in office policy for all employees is a smart move for the tech giant or just a cover for possible impending layoffs.
Amazon CEO letter cited: Message from CEO Andy Jassy: Strengthening our culture and teams
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
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Instagram: @permylastemailshow
TikTok: @permylastemailshow
Twitter: @permylast_email
Have a question for us? Send us an email or voice note to [email protected]
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 dive into the unspoken rules around Slack, Teams, and email. What is proper etiquette when it comes to professional communication these days? When is email actually necessary in a Slack-driven workplace environment?
Plus, award-winning journalist and communication expert Celeste Headlee weighs in on what she thinks the new rules of workplace communication should be.
00:00 Intro
04:30 The issues with instant messaging
10:32 Have Slack and Teams hurt workplace communications?
15:12 How Slack affects workplace culture after a layoff
18:24 Tactics for Slack (or any workplace IM platform)
20:21 How to think about email when your company has Slack or Teams
26:28 An argument for the email before the meeting
31:42 Tactics for in-person communication
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
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Have a question for us? Send us an email or voice note to [email protected]
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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!
Learn more about your ad choices. Visit megaphone.fm/adchoices -
In this episode, Kaila and Kyle discuss the different styles of mentorship, how to find and secure a career mentor, and why mentorship benefits the mentor as well as the mentee.
00:00 Open
00:19 Intro
03:44 Can a boss be a mentor?
05:14 Defining mentorship
06:03 “Mentorship from afar”
11:00 How to get to an informal mentorship
15:00 Kyle’s advice for how to approach cold-emailing a potential mentor
19:03 The benefits of being a mentor
23:35 Mentorship vs sponsorship
28:27 Tactics
Want to get all of Kaila & Kyle’s resources? Subscribe: https://www.permylastemailshow.com/
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Learn more about your ad choices. Visit megaphone.fm/adchoices -
In this episode, Kaila and Kyle discuss the realities and misconceptions around imposter syndrome, why Kyle has never experienced it, and Kaila’s take on when imposter syndrome becomes a humble brag.
00:00 Open
00:22 Intro
01:07 Defining imposter syndrome
07:13 Stats on the prevalence of imposter syndrome
07:32 Why Kyle has never experienced imposter syndrome
12:35 Kaila’s experience with imposter syndrome
20:43 The people who are actually imposters
22:46 How Kaila overcame feeling like an imposter
26:27 Advice for listeners
Want to get all of Kaila & Kyle’s resources? Subscribe: https://www.permylastemailshow.com/
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In this episode, Kaila and Kyle discuss the actual importance of your first 90 days at a new job, what most people get wrong in the first 90 days, and the best tactics for approaching your early days at a new job.
00:00 Open
00:36 Intro
01:36 Kaila and Kyle’s chaotic first 90 days at Morning Brew
06:02 Why the first 90 days are so important at a new job
10:35 Why the first 90 days for managers bringing on a new employee are so important
18:17 Stats on the reasons people leave a job within the first 90 days
23:11 Harvard Business Review’s 5 recommended steps in the first 90 days of a new job
28:19 Tactics
Want to get all of Kaila & Kyle’s resources? Subscribe: https://www.permylastemailshow.com/
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In this episode, Kaila and Kyle discuss whether or not you need to map your career, and what “career mapping” or career planning actually looks like when done effectively.
00:00 Open
00:25 Intro
05:05 How Kaila did a form of “career mapping” early in her career
06:50 What is a productive “career plan”?
13:30 The importance of having a North Star
19:00 How to decide between commitment and optionality
27:01 Tactics
Morning Brew’s Career Mapping Toolkit: https://shop.morningbrew.com/products/career-mapping
Want to get all of Kaila & Kyle’s resources? Subscribe: https://www.permylastemailshow.com/
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In this episode, Kaila and Kyle dive deep into the ways that the interview process is fundamentally flawed, and share tactics for how to succeed as both an interviewee as well as interviewer.
00:00 Open
00:35 Intro
03:30 Interview stats
10:01 A great interview mindset
12:09 What most job descriptions get wrong
14:17 Easy wins for going into the interview process
17:05 What employers should have prepared for an interview
21:11 Culture fit vs culture add
24:48 Game: good interview question or bad interview question
31:01 Tactics
Want to get all of Kaila & Kyle’s resources? Subscribe: https://www.permylastemailshow.com/
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In this episode, Kaila and Kyle discuss the real meaning of burnout, when and why it happens, and what to do about it if you find yourself stuck in a cycle of burnout.
00:00 Open
00:24 Intro
06:00 What “burnout” really means
08:25 Stats on burnout
11:00 Misconceptions about burnout
16:35 Why burnout is an environmental problem
26:41 Tactics for handling burnout
Want to get all of Kaila & Kyle’s resources? Subscribe: https://www.permylastemailshow.com/
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In this episode, Kaila and Kyle discuss the best way to handle different versions of bad managers, and how to evaluate whether you need to manage up, or if it’s you who should be doing something different.
00:00 Open
00:29 Intro
02:10 Why the quality of your boss matters (stats)
05:12 What having a “toxic” boss actually means
10:24 How the quality of your boss impacts your career trajectory
13:55 Bad Boss Scenario #1
17:02 Bad Boss Scenario #2
20:39 Bad Boss Scenario #3
23:22 Bad Boss Scenario #4
25:50 Tactics
Want to get all of Kaila & Kyle’s resources? Subscribe: https://www.permylastemailshow.com/
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In this AITA-style episode, Kaila and Kyle read and weigh in on listener submissions asking “am I the a**hole?” in specific workplace situations.
00:00 Open
00:15 Intro
02:22 Scenario 1
06:14 Scenario 2
11:54 Scenario 3
16:58 Scenario 4
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In this episode, Kaila and Kyle dig into the history of work attire, and what clothing is considered “professional” or “appropriate” for work in 2024.
00:00 Open
00:26 Intro
02:38 How Kaila’s dressing for work mentality has changed
06:25 How Kyle’s mentality around dressing for work has changed
08:22 How the perception of “work professional clothing” has changed since the pandemic
12:38 Stats on how people dress for work now
14:03 Considering the reasons that work attire even “matters”
18:01 Studies on perceptions of how you dress in the workplace
21:21 Professional or Nah game
24:00 Stats form the WSJ on what is acceptable men’s attire
26:16 Tactics
Want to get all of Kaila & Kyle’s resources? Subscribe: https://www.permylastemailshow.com/
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In this episode, Kaila and Kyle break down what it is to be a “generalist” (aka a jack of all trades) or a “specialist” in your career, the pros and cons of each, and whether one is truly more advantageous than the other.
00:00 Open
00:32 Intro
01:34 Kaila and Kyle’s career concerns as a career “generalist”
03:18 Defining a “Generalist” and a “Specialist”
08:40 The pros and cons of being a generalist or a specialist
11:19 Kyle’s “connecting the dots” framework
16:19 The unique place where specialists succeed
21:23 “Wicked” and “Kind” environments
22:18 The wrong way to approach being a generalist
27:18 How the generalist approach can apply to building teams
29:24 Tactics
Want to get all of Kaila & Kyle’s resources? Subscribe: https://www.permylastemailshow.com/
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In this episode, Kaila and Kyle discuss the merits of getting an MBA, and whether or not it’s even worth it anymore in today’s job market.
00:00 Open
00:19 Intro
03:56 History of MBA programs
05:00 MBA program stats
09:19 Why an MBA is looking like a less promising option lately
11:23 Scott Galloway’s take on MBA programs
12:49 What you’re actually getting when you enroll in an MBA program
17:00 What holds Kaila back from applying for an MBA program
23:43 The worst reason to pursue an MBA
29:31 What to do if you’re unsure about pursuing an MBA
33:31 Advice for listeners when considering an MBA
Want to get all of Kaila & Kyle’s resources? Subscribe: https://www.permylastemailshow.com/
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