Dear diary, who thought this was a good design?

Reflections on gracefully inheriting past design decisions

Dear diary,

It’s Tuesday. The weather has warmed up so we’re spending more time outside.

Today I’m working on a some brand updates with my team, and it has me reflecting on the challenges of being one of the first designers at a startup. More often than not, I inherit design decisions made by non-designers, like founders, early employees, or contractors just trying to get something out the door.

It can be easy to take a victim mindset and think that all my product and brand designs would be usable, delightful, and accessible if not for these past decisions. But it’s not that simple.

Here’s something I didn’t know when I began at my first startup (but I do now starting at my fifth): you owe your role to the people who came before you. The hustle and the sweat of early employees created a business that needed a design expert.

In some unfortunate cases, it was a designer who preceded me that made questionable design decisions. These might be poor foundations for a weakened design system, or bad habits that encourage teams to treat a designer as a ticket-taker rather than a partner. I’ve been in this situation twice, and in both cases I was brought in to undo and reset the design practice. Even so, I felt grateful I was trusted to do that and I was able to see all the other good things that were already working. It’s great to feel needed.

I have nothing but respect for the founders who may endure late nights, endless pitches, and financial distress to see their dream come to life. I’m humbled they would place that dream in my lap and ask me to help them take it to the next level.

When starting in these roles, my knee-jerk reaction used to be to try and start over from scratch — redesign everything from the ground up. But I've learned that's not the smartest approach. Instead, I focus first on building trust.

Here's the thing — someone thought the existing designs were good enough at the time. Maybe it was the founder who poured their heart into that logo, feeling proud of the meaning behind it. Or maybe they paid good money to an agency for what turned out to be a template. Either way, time and effort went into it. There is probably scar tissue here (and maybe a lot of lost money).

I’ve learned this the hard way over my career.

I once redesigned the primary file browsing screen of a web app. Through the duration of the project I talked shit about the old version and touted how much better my new version was. When the new design was released, it successfully won an A/B test against the old version and I showcased it in my portfolio for several years. Guess who designed the old version? It was the engineers who built the new one. I actually got along great with these engineers for many more years, but I imagine their first impression was one of elitism rather than collaboration.

At another company, I flaunted my criticisms of the logo in an attempt to spark interest in a brand update. It wasn't until later that I found out the founder created it themselves and was proud of the significance behind it. If I had been more mindful and sensitive of past decision makers I could have built my reputation as a partner instead of a critic.

I’ve also had many proud moments and wins as a more thoughtful and mindful designer, but I highlight these learning opportunities so others reading this diary don’t have to make the same mistakes.

The way I give feedback about design sets the tone for how I help build up the business and the team. Tearing things down erodes trust. I try to express appreciation for the hard work done so far, and my excitement to contribute.

Instead of criticizing, I focus on the positives — what's working well and how I can do more of that? I look at it objectively — what goals is the design accomplishing or failing at? And I speak to the future, about refining and elevating it together.

I’ve also learned that language matters. Specifically when dealing with brands, I avoid triggering words like "rebrand" which imply a full re-imagination. That's costly and difficult. I distinguish between the “brand identity” which should very rarely change, and instead focus on the brand style. I suggest a "brand refresh" or "audit" — understanding what's working to build on top of it, not start over.

(On that note, I have a whole toolkit of exercises I call a "brand refresh" to help reflect on what's needed. I’m doing my latest iteration of these exercises on my current team and I’m really happy with them. I’d love to write more about them later, so I hope readers will shoot me note if this interests them.)

Ultimately, as a startup designer, I introduce design expertise to the company — sometimes for the first time. I need to serve the company's mission, not pull it off course into unnecessary overhauls.

It’s still my responsibility to elevate products and brands to the highest quality I know how, but I’ve learned many techniques for doing this in a transparent, empowering, and mindful way. Align the design improvements to broader company goals. Gather feedback about where it’s falling short. Create alliances with leaders who feel burdened by underperforming designs. And so on.

I may have caused some unnecessary collateral damage early in my career, but now I feel like I have the tools to elevate startups to design greatness in mindful ways. I’m really happy with the design work I’m doing right now, and I look forward to it staying that way for a long time.

XOXO,

Taylor

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