About the show

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

Tentative on social media


  • 76: I Can Wait!

    September 20th, 2019  |  32 mins 50 secs

    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.

  • 75: Make It Pretty

    August 14th, 2019  |  24 mins 6 secs

    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.

  • 74: Commute to the Basement

    July 31st, 2019  |  25 mins 23 secs

    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.

  • 73: 11:15 is a Time, Too

    July 17th, 2019  |  27 mins 31 secs

    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.

  • 72: Good Crafternoon

    June 20th, 2019  |  22 mins 55 secs

    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.

  • 71: Get Back Up Again

    June 6th, 2019  |  16 mins 27 secs

    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.

  • 70: Down the Doughnut Hole

    May 8th, 2019  |  24 mins 12 secs

    Jaclyn is frustrated with calendars, and Kyle continues work on the thoughtbot.com redesign. Also skills evaluations, and lots of interviews.

  • 69: Stand in Your Emotion

    April 18th, 2019  |  19 mins 34 secs

    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.

  • 68: iPod + a Case of Beer

    March 28th, 2019  |  35 mins 34 secs

    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".

  • 67: In This Kitchen, We Iterate

    March 14th, 2019  |  28 mins 50 secs

    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.

  • 66: Drink Punctuations

    February 28th, 2019  |  28 mins 20 secs

    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.

  • 65: No Tangents Friday

    February 7th, 2019  |  24 mins 36 secs

    Jaclyn and Kyle discuss remote interview methodology, skillset tracking, Design Sprint 101™️, and Kyle's skills as a Beer Ninja.

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

    January 24th, 2019  |  33 mins 3 secs

    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".

  • 63: Solutionland™️

    January 9th, 2019  |  29 mins 33 secs

    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.

  • 62: Down With Portfolios

    December 13th, 2018  |  31 mins 3 secs

    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.

  • 61: Zebras Drinking Mint Juleps

    November 29th, 2018  |  33 mins 21 secs

    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.