Lessons of a startup product designer

I’ve been working at an ad agency, software houses, a freelancer for startups and large companies and I am now working as an in-house Head of Design at Jerry.ai.

I feel like I was quite fortunate to go through that exact path because I was gradually able to learn new lessons based off working with various companies and people that have different goals in mind and see how organizations actually affect the user experience, design and development depending on which side of the company you are.

I am aiming this article to be some kind of a guide for newer designers — and perhaps a refresher for the more experienced ones, having this constraint allows me to focus on a specific goal and I will be able to actually end this article relatively fast without boring everyone to death.

So, without further ado, here are some of the most important lessons that I have noted down, some of them I have learned by making the mistake myself, some of them are things that I have observed and some of them are things that I have read or was advised about and applied immediately:

1. Talk with everyone, everyone has ideas that might positively influence your work.
2. Know everything about your users — Observe how your users are using your product every day by utilizing hotjar, uxcam etc. become a customer service representative one day a week, listen to calls, setup research meetings, invite users to talk with you or visit the office, you want to know everything about your users and it should have no clear end, you want to learn about the users constantly as they will evolve along with your product, it’s one side of the Data coin — the Qualitative data it’s the whys and hows.
3. Be data-oriented, not pixel oriented — Quantitative data should be your second best friend, it will help you measure whether you’re failing or succeeding, it will help you find the issues and fix them, understand your users better on a much broader and more specific scale.
4. Share your things early and get feedback but do it at the right time through right means — You might want to show that discovery or a new design to your colleague as soon as you’re done with it but you might end up breaking their focus and their feedback will be very vague as they’ll want to get back to whatever they were doing.
   Asking for feedback is an art on its own — make sure that you do it in a smart manner so that you get something valuable.
5. Do not pretend that you know everything, do not be afraid to say “I don’t know” — Do not respond if you don't know the answer, just say that “You will get back later” (and actually do it, don't treat it as a convenient excuse), don't try to sound smart.
6. But when solving issues, do not stop at “I don’t know” — always come up with some solutions. Just saying “I don’t know” without engaging in a discussion that can solve the issue is unproductive. If you can, propose solutions if it makes sense for you to do so.
7. Do get things done — Just thinking about doing something will get you nowhere. Execute and do it efficiently.
8. Come up with an initiative — Do not wait for people to tell you what you are supposed to work on, if you see something that you feel like you can improve and it meets the business goals or improves the experience, come out with an initiative.
9. Think about the big picture when designing — as you work on a project and go deeper and deeper do not get stuck on a small isolated part, try to see the big picture and how it all adds up together. Just like when you are painting a picture, you start with the big shapes and then slowly go into details while still thinking about the entire painting.
10. Pixel perfect designs do not mean great user experience — A pixel-perfect solution will look great on dribbble but this might not be something you should be spending your time on. Instead, make sure that there is a proper design system in place and you can stop being a pixel pusher.
11. Do not get stuck in jargon — Jargon definitely simplifies things but most of the time you will be speaking with non-designers, the worst thing you can do in an organisation is come out as an ostentatious person that no one understands. Adjust the language to your audience.
12. Learn how to work with stakeholders — Understand who cares for what, a marketing director will not care about amazingly written classes in code, so align your messaging for each of the stakeholders on what matters to them.
13. Keep everyone informed.
14. When you are new to a company, try to absorb more instead of trying to change the processes, tools etc. based on your perceived inefficiencies but do not take things as granted — always ask questions why things are this way and not another.
15. Learn to write efficiently, be concise and thorough in your responses — Everyone are in a rush and everyone most of the time wants a TL;DR version of what you have to say, you do not have to explain every detail, focus on the core message, add details where it makes sense. This goes back heavily to the “Learn how to work with stakeholders” point.
16. Care for data but do not be paralysed if you can’t get it.
17. Document decisions, processes, ideas, findings — everything that is useful (I recommend notion.so for that)
18. Make notes for your own self when you are leaving for the day on the unfinished project to pick it up more easily the next day, what was the last thought you had on this, what are you thinking about right now — it will allow you to resume work way faster next day.
19. Never ping someone by just saying “hi” — always ask the full question.
20. Over-communicate with your stakeholders — Avoid getting an email with “Hey what’s up with an X project”. And remember that over-communication is not a bad thing.
21. Learn to work with different cultures.
22. Assume that every meeting is bad and try to justify having it, you’re not only taking up your time but also others — is it worth it?
23. Do not create random meetings in the middle of the day, make sure that you look at the calendar and clutter them with others — it’s hard to get back to work when you’re getting disturbed every 30 minutes, especially applicable to developers.
24. Status meetings are just a waste of time, make sure that everyone provides that information up-front and then discusses any open questions regarding those.
25. Do not create meetings for the sake of meetings and if you create one make it efficient — go into them with clear goals, keep meeting notes and distribute them to everyone afterward, know when to stop talking about the topic that is breaking the meeting and follow-up separately.
26. Prioritise — When joining a startup you’ll have fewer resources, less time, and more things to do than at a larger company.
27. When a decision is made, document what it is and send it to stakeholders; this prevents later finger-pointing and confusion.
28. Always think of the context of whatever you’re designing.
29. Figure out a way to test things before committing major resources and time — if you have an idea that involves multiple months of implementation, the research should be but might not be enough. Try to come up with a way of testing if your idea is good by utilizing an MVP or do something on the front-end to gauge interest.
30. Have fun doing what you do and work hard!

The list is not final, and it doesn’t include all the notes I’ve made over the years, otherwise, this list would have no end and I would never finish writing it. I’ll see you another time with the next set of lessons.

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If you would like to see more of my work, check it out at:
www.dribbble.com/patrickwestwood / www.patrickwestwood.com