Welcome back.

It’s Config week, I’m flying out today, and we’re deep in party planning mode for Detach.

But I had to hit send on this.

Friday’s leak of Inflight was one of our most opened issues of the year. So today, we’re going deeper - not just on the tool, but the problem it’s trying to solve:

Feedback still sucks in 2025. Even for good teams.

Even for my team, working on the UX Tools redesign and survey right now.

Here’s what we’re learning, and why Ridd’s Inflight is onto something meaningful.

- Tommy (@designertom)

The Wireframe

• Why I'm betting on Ridd
• Design feedback feels like doing my taxes
• Culture eats tooling

I’m Just Betting on Ridd

This is not sponsored.

No ad slot, no affiliate link, no gentlemen’s handshake.

In fact, before I get into this topic, I want to pause and spotlight someone who’s become one of the most quietly inspiring designers in my orbit:

​Michael Riddering.​

Many of you know him as “Ridd”, host of Dive Club, creator of Figma Academy, now co-founder of Inflight. I’ve gotten to know him as a friend.

Over the past two years, I’ve watched him:

• Leave his role as founding designer at Maven - when things were good
• Launch one of the highest-signal design podcasts in the game - from scratch
• Teach one of the most successful Figma courses on the internet
• Earn trust in the design community not by yelling louder, but by doing better work
• And now: Build a tool to solve a problem most of just accepted

Even if Inflight hadn’t won me immediately, I still wouldn’t bet against Ridd.

He cares about design, the process, the teams, the questions. He pays attention to how ideas move through people.

I take notice when people like him start to build, because it usually means we’re about to work differently, and better.

So today’s deep dive isn’t just about a tool.

It’s about backing a design founder (two actually, with co-founder Kyle Barber).

And why I think this one’s about to improve how we build products in the next 12 months.

The Problem He’s Solving

Let’s call it what it is:

Design feedback is still a mess.

Even with all the AI, even with all the new tools, even as teams “flatten the stack.”

Here’s how we’re doing it right now at UX Tools, on both the redesign and the tools survey:

• I bounce between 3–5 teammates across time zones
• Main comms run through Slack + Loom
• Comments are scattered across Figma, Notion, Slack threads, and pinned links / videos
• When I have a new round of thoughts, I literally open Granola, ramble while clicking through a Figma file, and let it turn my thoughts into a list
• I tweak a few bullet points, clean up the tone, and drop it back into Slack for the team

It works. But only because we’ve built shared trust and velocity over time.

What we’re doing is “fine” - but it’s duct tape:

• There’s no real structure.
• No versioning of feedback.
• No smart capture of alignment vs. surface critique.

And it’s not that different from how I worked at bigger orgs in the Valley.

We’ve made designing fast, but feedback is still slow, vague, and scattered.

So when Ridd showed me Inflight, I didn’t just see a cursor-embedded video walking through a design file - I saw a feedback system built for humans doing work together in 2025.

Together with DSCOUT​

Another tool that empowers a strong culture of humans doing work together is Dscout.

They're the professional-grade research lab you actually want to use.

• Live interviews, async studies, card sorts, screen recordings — all in one gorgeous, unified platform.
• Auto-recruit vetted users or bring your own. Use AI to tag transcripts and surface themes fast. Even spin up highlight reels for that one stakeholder who only watches clips.
• Built-in scheduling, incentives, analysis — no more duct-taping workflows across three tools and a spreadsheet.

If research still feels like a bottleneck in 2025… you’re probably not using Dscout yet.

​Check out the new Dscout →​

Design Feedback Feels Like I’m Doing My Taxes

“A very popular designer recently described the whole category as ‘borderline government software’ and ‘like I’m doing my taxes.’ I agree.” — Ridd

Most design feedback tools feel like admin panels - a bunch of scattered comments, vague Slack replies, and Looms lost in threads. It’s collaboration by checkbox.

When I asked Ridd what broke, he didn’t blame UI. He blamed culture.

“I haven’t used Figma comments in years to get meaningful feedback. For anything strategic, it almost always starts in Slack. And Slack is chaos.”

I’ve seen it too: urgent but disorganized is the norm.

Ridd isn’t just creating a better interface. He’s trying to structure how feedback happens by asking better questions, something he’s uniquely good at.

It’s why Dive Club blew up. It’s why Figma Academy became a hit.

Now he’s building that into a tool.

Instead of vague prompts, Inflight injects questions like:

• “How directionally correct does this feel?”
• “Do you agree with the thinking behind this?”
• “Where would you push this further?”

The result feels more like a structured critique than a survey.

The product’s solid. But the taste - the way it guides feedback - is what stands out.

Culture Eats Tooling

Even the best tools won’t help if your team is afraid to share rough work.

Ridd puts it bluntly: “We say ‘share early and often,’ but most teams don’t.”

And he’s right. The blockers usually aren’t technical, they’re emotional. Fear of looking sloppy. Fear of wasting someone’s time. Fear of not having the “why” figured out yet.

That’s why the best teams build rituals around feedback, not just pipelines.

• Duolingo runs “hot trash” sessions - explicitly named to normalize unfinished work.
• Plaid hosts “design jams” - quick, low-stakes feedback rounds that favor speed over polish.

These aren’t performance reviews. They’re permission structures.

And they work because they lower the cost of getting ideas in front of others quickly.

That’s also where tools like Inflight slot in well.

They don’t demand a polished walkthrough. They support early thinking and async critique without the formality tax.

Smart tools matter. But tools that change cultures... that gets me pumped.

The Bottom Line

Design tools are having a moment - but Inflight feels like more than a tool.

It’s a bet on better questions, smarter critique, and faster alignment across async teams.

• Most teams don’t need more feedback. They need clearer feedback.
• Cultural rituals matter more than tool stacks
• Async walkthroughs are only useful if they spark real conversation
• Inflight is closer to how teams actually work in 2025

And if Ridd’s building the infrastructure for that, I’m betting on him.

What’s your current feedback stack? Hit reply and let me know what’s working (and what’s not).

See you at Config,

—Tommy

P.S. Bring me your memes at Config.​

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