Anonymous interview 2


What frustrates you most about your current job?

The same thing that has frustrated me at the majority of my jobs—leadership failing to recognize they have misaligned goals and the emphasis on short-term gains instead of quality.

This company states that it is a premium product, but is fraught with bugs and provides a poor user experience.

Many companies say they care about design and user experience, but their actions don’t reflect that. Deadlines are handed out without knowing the actual scope, forcing us to cut corners to meet arbitrary deadlines, which results in a house of cards product.

You see similar things happening in the housing market. I recently had a conversation with a builder who explained that everyone wants a nice, big house, but they don’t want to pay for what it actually costs. So they end up going with a cheap builder that cuts corners. Unsurprisingly, those houses end up having constant issues and they end up paying for it on the tail end. Ultimately, it allows them to live in a delusion where they finally have their dream home, but the walls are literally crumbling around them.

The other factor is external pressures from those that have incentives that don’t align with creating a quality product. The board, VCs, shareholders, etc demand everything be done fast and cheap to maximize short-term results so they can make as much money as possible. Overcoming this challenge is quite difficult for leaders. Even those who succeed often struggle to maintain their focus on long-term quality as success breeds more people driven by short-term gains. Greed is a killer of quality.

Is there a practical solution to this problem?

Unfortunately, this challenge is really only fully solvable when you have a leader like Steve Jobs who deeply cares about quality and has the discipline to stick to those convictions.

Since that’s a rarity, the next best option is for design to have a seat at the table. That at least gives Design/Product a fighting chance to achieve some quality. I’ve also seen a few leaders who are particularly adept at politics give leadership the optics they’re looking for while still enabling the broader team to focus on long-term efforts.

Can the leaders who take that approach keep it up?

This is largely dependent on their ability to be successful in winning battles.

One must win enough battles to retain hope that they have a fighting chance for the next battle. Quality dies with a loss of hope.

If you founded a software company, how would you approach quality?

Ensure good processes are set in place that help enforce quality. When you remove leadership challenges from the equation, most issues are a result of poor or nonexistent processes.

A lot of companies treat research, user testing, and code testing as optional. If you skip any of those, it introduces risks that you’re building the wrong thing, designing the experience wrong, and/or creating a buggy codebase.

What frustrates you most about the design community?

Obsession over things that don’t matter. I see a lot of wasted time spent on creating numerous design artifacts or making designs pixel perfect and they lose sight of what problem is being solved and what the business needs are.

The goal is to get feedback early and often to make sure you’re solving the problem well so the business can be successful.

Many of these artifacts seem to largely be there for optics to prove how much effort a design took. It’s the equivalent of showing your work in math class. If you can do it in your head, you don’t need to show how you got there unless you’re in a low-trust environment.

Pixel-perfect designs suggest a lack of a code design system or a designer that believes their mockup is the source of truth when the reality is mockups are guidelines, not blueprints.

With all this wasted time, many forgo the most important tools—validating the design through user testing and gathering feedback from users. Instead, they fall to sunk cost and defend their designs as their artifacts “clearly show” that they’re correct and the user is “wrong.”

Do you have any cynical techniques or beliefs that you’d hesitate to share with others?

I wouldn’t say I’m hesitant to share this directly, but hesitant to share openly. I think many are pretty naive about the politics that come into play with design.

Everyone thinks they can design as it’s a very approachable field. Leaders who don’t have any experience in it will have no problem declaring their opinion or even demanding you do something that is user-hostile or just plain bad design.

One of the biggest pieces of advice I give is to learn how to take control and redirect the conversation. The simplest way is to keep asking the question “what problem are we solving?” to keep them focused. And when they inevitably have solutions that don’t align with that, ask them how that solution solves that problem. This changes the conversation from being about “who is right?” to “what is right?”.

But the truly cynical advice I give is to try to keep designs rooted in what can realistically be accomplished. If you design a Ferrari, but you only have the budget for a Toyota, you’re going to be super depressed with the final product. I don’t even design anything that is more than a quarter out anymore. Experience has shown how quickly roadmaps can change, so spending all this time designing a feature that gets shelved can be extremely soul-sucking.

What frustrates you most about job-hunting?

That interviewing largely evaluates how good you are at interviewing and not your actual skills.

In-interview or take-home design tests attempt to solve for that, but in-interview tests end up testing how good you are at making fast decisions (generally not a desirable trait in a designer) and take-home tests optimizes for candidates that have enough free time (read: single and/or unemployed) to do the test well.

I have yet to see anyone truly solve this, but I think giving people choices is helpful. I had one place give me the option of an in-interview test, take-home test, or I could walk them through an existing project in detail. I thought that was an interesting approach that lets people find one that allows them to pick an option that they’re the most comfortable with.

At your hypothetical software company, is that the approach you’d take?

I think so. I would also ensure that it was just as much of a good fit for them as it would be for the company. Most companies come to an interview with a transactional mindset, but if you truly want a good fit, it has to be a good fit for both sides. And that means letting them know all the warts and challenges of the job without sugarcoating it.

Talking shop is the other thing I’ve found to be helpful as an interviewer. You can be good at interviewing and know the right answers to questions, but it’s much harder to fake it when you’re just having a an in-depth conversation about a topic. Once you get past shallow answers, it’s hard to fake depth.