Practical Design for Founders

Most founders who haven’t built products before (and even some who have) underestimate the importance of design.

And even if you’ve read the book on Johnny Ive or Build by Tony Fadell, you may not have a practical understanding of how to work with designers.

• When should you trade-off aesthetics for functionality and vice versa?

• Should you invest in building custom components?

• What the heck is “breadboarding” anyway?

Phil Hedayatnia is one of my oldest friends in the startup world, we met years ago in SF and he became my first roommate when I moved to NYC.

I’ve seen him grow Airfoil into a full-service creative agency and incubator working with major brands like Solana, with over 40 employees in 12 countries, they were doing a productized service years before it became popular and he was a resident “design guy” at South Park Commons in their early days.

He’s one of the best at working with early stage founders to help them design and build new products.

Practical Design for Founders

Q: When Should Founders Engage a Designer?

Good designers can help with shaping a problem statement if needed, but typically you want to hand things off to a designer once you have a minimum usable solution.

Phil brought up “breadboarding” which is when there’s a functional but ugly product that gets handed over to the designer to, well, design it, the functionality is already there, so the designer has a clear understanding of what the product is meant to do.

Ideally you give them free reign to improve the UX and UI at that point, while maintaining functionality.

The concept originally comes from the team at Basecamp’s free book Shape Up, where they also mention “fat marker sketches”, simplistic versions of your future design that are just drawn with a simple sharpie (or digital equivalent) and only capture the core components and layout.

I love fat marker sketches, here’s an example of an early one we used for Megaphone’s user dashboard:

Even though I’m not a good designer, this took me less than a minute and gave my designer a clear idea of the functionality I wanted on this screen.

Tools like Whimsical are great for fat marker sketches because they severely constrain your options. Needing to make fewer design decisions can lead to clarity.

Q: How Should Founders Evaluate and Hire Designers?

Have them do some work for you. Pay them for a take-home assignment or a work-trial (like Linear):

Remember, the quality of the work you get from them in an interview setting is likely to be as “tidy” as you’ll ever get from them since they want to impress you.

As a result Phil looks for:

• Did they use auto layout with standard spacing values?

• Did they include a Loom video describing their thought process?

• Is it labeled in a way engineering can take it and run with it?

Phil also says to look for taste, that may sound hard to look for but all it means is that you want them to express opinions. Ask them which designers they admire, and why, or what design trends they dislike.

You want them to be honest with you in this setting. That tells you more than anything else.

But most importantly, just like with any other role for a startup, ask them how they evaluate long-term vs short-term tradeoffs in their work. How do they make decisions? If the answer is a long process where they listen to data then they may be a better fit for a big company than a startup.

You need someone who will be opinionated.

Q: How Can Founders Identify Design Problems?

This one is straightforward, use a session playback tool like Fullstory.

Phil recommended them as his #1 tool to see playbacks of exactly how users move interact with a product, including automatically flagging where they try to do the same action over and over.

Think about your user’s interest level like a health bar in a video game. Every problem they run into, they’ll spend some of their health trying to solve it until it becomes too much and they bounce.

Phil advocates for placing “power ups” around the experience to re-energize them, since your early app experience likely won’t be perfect.

For example if your onboarding flow is long then add another screen with a short welcome message that explains for motivation and goals for the product as a founder. When Phil did this for a client it doubled their onboarding flow completion rate.

Q: Can Good Design Compensate for a Janky Product?

If you ask this question to some designers you’d hear them start talking about gamification, but optimizing the UX for engagement only works if users feel genuinely helped rather than manipulated.

Phil suggested a better approach: give first, don’t ask.

Rather than just giving people some reward or points in a gamified system, introduce friction before they get access to those rewards.