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Tentative is a podcast about digital product design. Hosted by thoughtbot's Chief Design Officer Kyle Fiedler & Boston Design Director Jaclyn Perrone.

Weekly hand curated podcast episodes for learning

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The best episodes ranked using user listens.

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62: Down With Portfolios

Jaclyn & Kyle discuss the value of in-person meetings, the philosophy of Trello backgrounds, nostalgia for antiquated recording mediums, refining thoughtbot's designer hiring process, and design implementation. Squad Goals Background bikeTunes The ZIP Disk Jaclyn on Awkward Silences Podcast See open positions at thoughtbot!Support Tentative


13 Dec 2018

Rank #1

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73: 11:15 is a Time, Too

Jaclyn puts together a role-playing workshop for consulting your way through difficult conversations, and building empathy for the other parties. Kyle discusses conducting team 1<>1's all on one day vs spreading them throughout the week. Plus, some techniques for dealing with context switching, blocking off time, and calendar hacks. This episode of Tentative is sponsored by Indeed PrimeSupport Tentative


17 Jul 2019

Rank #2

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78: Everyone Can Draw (Skipper Chong Warson)

Skipper Chong Warson, Design Director of thoughtbot San Francisco, joins Kyle to discuss the psychology of podcast recording, overcoming awkwardness in communication & public speaking, and avoiding proxies when engaging with clients.“Steve would really like you to get 5 stars…”Full EpisodeJustice Sonia Sotomayor on Sesame StreetSkipper on TwitterSupport Tentative


25 Oct 2019

Rank #3

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75: Make It Pretty

Kyle has fun with a hiring-promo read, while Jaclyn dislikes the polling system in Slack. Also, presenting visual design to clients for feedback, frameworks for critique, and fostering creativity through constraints. This episode of Tentative is sponsored by Indeed Prime Red Light, Yellow Light, Green Light: A Design Exercise for Getting Feedback From the Team See open positions at thoughtbot! Become a Sponsor of Tentative!Support Tentative


14 Aug 2019

Rank #4

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65: No Tangents Friday

Jaclyn and Kyle discuss remote interview methodology, skillset tracking, Design Sprint 101™️, and Kyle's skills as a Beer Ninja. Zoom Kyle During Usability Tests Plucky Cards Support Tentative


7 Feb 2019

Rank #5

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68: iPod + a Case of Beer

Jaclyn goes on a ski trip, Kyle eats cake on the microphone (sorry). Also, de-stressing techniques, Austin weather (surprise), daylight savings time, the UI of car clocks, making the most of small gaps in your schedule, enriching collaboration with developers, clarifying the title of "designer", and iterating on podcast recording. Plus, the introduction of a new segment "good, bad, and ugly". Press Me The Case of the 500 Mile Email King Cake Support Tentative


28 Mar 2019

Rank #6

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64: I Know, That You Know, That I Know What a Progress Bar Is

Jaclyn & Kyle wish you a (very belated) Happy New Year, and discuss the shortcomings of video-chat during interviews, using GitHub as a project management tool for company policy, the weirdnesses of user-interviews, and de-jargoning the term "prototype".Support Tentative


24 Jan 2019

Rank #7

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61: Zebras Drinking Mint Juleps

Jaclyn & Kyle chat about the new thoughtbot Austin office, designing for Android, feelings on maintaining Sketch file tidiness, trying to make tabular data exciting to present, and commiserate over call-center software workflows. Material Design for Android Abstract- Sketch Version Control Support Tentative


29 Nov 2018

Rank #8

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67: In This Kitchen, We Iterate

Jaclyn hosts a cooking show while Kyle does what his calendar tells him to. Also, being excited by invalidating ideas, devoting more time to synthesizing, taking TL;DR level sprint-notes, how switch interviews can influence your design sprint, and end of week recuperation strategies. Ralph's Kitchen Delicacies Swedish Fish Sandwich Recipe Support Tentative


14 Mar 2019

Rank #9

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69: Stand in Your Emotion

Kyle deals with a "dentist situation" and writes a blog post, while both he & Jaclyn return to IC design work. Also, manager training, partnering with an offshore development team while on a tight deadline, and the "good problems" of a large design sprint. Plucky Manager Training Jennifer Dary, founder of Plucky, on Giant Robots Red Light, Yellow Light, Green Light: A Design Exercise for Getting Feedback From the Team French Fries Support Tentative


18 Apr 2019

Rank #10

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77: A Hop of Faith (Keiran King & Tyson Gach)

Live from New York, it's Keiran King & Tyson Gach! They join Kyle to discuss designing apples, comparing and contrasting jobs-to-be-done to other frameworks, and defining 'customer success'.Jobs-to-be-done Workshop ReplaySolving Real Problems With Design- Keiran KingWhen Coffee and Kale Compete- Alan KlementCompeting Against Luck- Clayton M. ChristensenShape Up- Ryan SingerKeiran on TwitterTyson on TwitterSupport Tentative


4 Oct 2019

Rank #11

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72: Good Crafternoon

Jaclyn designs wristbands for a 5k, fiddles around with CSS Grid, and kicks off a new project. Meanwhile, Kyle attends many serious meetings. We discuss up-front user-research, timeline interviews, and pacing interviews for sustainability. J.P. Morgan Corporate Challenge Wristbands Support Tentative


20 Jun 2019

Rank #12

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74: Commute to the Basement

While Jaclyn gives interview tips (both user and hiring), Kyle does his best Michael Keaton impression. Also, active listening, pizza facts, trying to keep a work / home balance when working remotely, and interview horror stories. This episode of Tentative is sponsored by Indeed Prime Fun 🍕 Facts Redesigning How We Hire Designers at thoughtbot Support Tentative


31 Jul 2019

Rank #13

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70: Down the Doughnut Hole

Jaclyn is frustrated with calendars, and Kyle continues work on the thoughtbot.com redesign. Also skills evaluations, and lots of interviews. Calendly 15Five Put a Bird on It Support Tentative


8 May 2019

Rank #14

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71: Get Back Up Again

This week Kyle follows his calendar, while Jaclyn wraps up a research project and celebrates a fruitful sales-call, and we discuss trying to focus on positive reinforcement, the importance of being able to communicate your design work, and 'clicking' with the sales process. Designers Who Code Meetup Support Tentative


6 Jun 2019

Rank #15

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63: Solutionland™️

Jaclyn sells some art, kicks off a giant design sprint, and prepares a presentation on how to co-facilitate a design sprint. Kyle deals with new-office echoes & internet woes. We share the projects that we worked on for this year's Ralphapalooza; plus, reactions on designing for React Native. Jaclyn's Art Show! Vendela's Ice Cream Blog thoughtmoji CSS Grid Segway Mall Store Support Tentative


9 Jan 2019

Rank #16

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66: Drink Punctuations

Jaclyn starts a new Meetup and wonders about ice-breaking activities & community building. Kyle tries his hand at video editing after filming a skill interview, and starts work planning a thoughtbot.com redesign. Also, stress around social media email / notifications and why we should design them more humanely. Designers Who Code (Boston) Previous thoughtbot.com Redesign on Tentative Why Does McDonald’s Use the Colors Red and Yellow? Blue-plate Special Jobs @ thoughtbot Tropical Storm Jackie Support Tentative


28 Feb 2019

Rank #17

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76: I Can Wait!

Jaclyn is taking a break for a little bit and Kyle sets a course for happiness. We talk about embracing change as an opportunity to define yourself, and having a similar mindset to build good habits between projects. Also, experimenting with and evolving process, and reflecting on the importance of collaboration.The Science of Well-BeingAtomic Habits- James ClearPractical Applications of Jobs-to-be-Done for Designing Successful ProductsSee open positions at thoughtbot!Become a Sponsor of Tentative!Support Tentative


20 Sep 2019

Rank #18

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87: An Homage to Mean Girls

Kyle gets stressed out by grocery shopping, and prepares for a workshop. Jaclyn finishes a draft on a case study and benefits from the value of time-boxing. Also, tricking Zoom, staying productive, the importance of routine, and little things to break up your days. This episode is brought to you by ExpressVPN. Click through to get three months for free. World Famous Abbey Road Crossing Is Repainted During The London Lockdown The Future of Facilitation Procreate App Being Human in the Absence of Humans: A Q&A for Product Teams Become a Sponsor of Tentative!Sponsored By:ExpressVPN: Click through to get three months for free.Support Tentative


24 Apr 2020

Rank #19

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86: Just a Square on a Screen

As thoughtbot transitions to working remotely, we discuss the tools and tips we use when conducting remote design sprints. Enroll in our free online-workshop on going remote Being Human in the Absence of Humans: A Live Q&A for Product Teams Running design sprints and kickoffs remotely MURAL Miro Invision Freehand Play 'Sorry' 'Online Become a Sponsor of Tentative!Support Tentative


27 Mar 2020

Rank #20