More and more designers are making the jump from freelance or agency life into startups. I'm compiling a list of "things every designer should know before joining a startup"—would love to hear your thoughts.

Answering this is tougher than I thought it would be. My first startup experience was pretty smooth actually. Sure it was long hours and the work style was different, but I'd come from an agency (my own) and, honestly, anything would have seemed "easy" after that. I found it a very nice change of pace. The challenges were a bit different, but the feeling of ownership you get working at a startup, feels great after client work. The long hours and hard work didn't feel so much like work, you know?

I guess one thing I wish I'd known--and still wish I knew more about--is compensation and the financial workings of a funded startup. I've worked at three startups, been through two acquisitions and I'm still a bit mystified by everything.

Be careful when claiming you're changing or disrupting ______.

Start-ups get really excited about what they're building, as they should. But through that excitement sometimes comes hyperbolic claims about what their product is achieving. There's nothing wrong with aspiring to do something great that will really affect people. But is the product actually disrupting an industry? Or changing a behavior? If so, shout it from the rooftops! But if it's not, buckle down, set measurable goals, and knock those out of the park. And all the way, be accurate and realistic with what you're affecting.

I wish I had understood the enormous cost of wasting time over decisions that didn’t matter in the long term. I should have looked at every argument through the lens of “Will this matter a year from today?”

I wish I had been much more meticulous about picking the projects that I worked on. Begging forgiveness is a better skill than asking permission.

I wish I had done a better job recruiting people to the company and later retaining them. Software doesn’t make itself.

The design you do in agencies is not the same design as that you do in startups. The work you did to impress your professors (and show off to your pretentious classmates) in design school is not the same design either.

Always be shipping. If you're not constantly delivering customer-facing value then you're not wasting time (and startups are a constant race against time, really).

Having the most perfect vertical rhythm in the world ≠ shipping. Making your design work with one typeface, two weights & three sizes ≠ shipping. Debating whether to use a minor-sixth or major-seventh for your modular typographic-cum-layout scale definitely isn't shipping.

This Dribbble shot epitomises that mistake for me - looking back on it I cringe but at the time I didn't know any better.
dribbble.com

Also, don't spend time reading TechCrunch. Don't worry (within reason) about whether your startup is going to be successful or if a competitor is doing what you're doing. Take an interest in the direction of your startup, but worrying about if you're going to make it is your CEO's job. You're supposed to be shipping, get back to work.

Startups are the ultimate test of prioritising all the things you could possibly do and the things that you have time to do. Learning to realise what actively delivers customer-facing value and what is just blind perfectionism is a skill.

The amount of self-management required in a startup is substantially greater than that I've witnessed in other work environments. Coming from a background of tiered management and consistent workflows, if you aren't careful you end up wasting a lot of time with wishful thinking and internal debate instead of getting things into the hands of your customers to give you actual, useful feedback.

Three things which should be common sense, but I still had to learn:
- Plans can change.
- Nothing just happens by itself.
- Everyone is just making it up as they go.

Know who's leading you. What are they like under pressure? What's their track record? What kind of management do they prefer?

Ask hard questions. What happens if this tanks? What's the financial plan for scaling and growing? What's your philosophy of options/stocks? Ask to see the financials.

If they don't have a job description for you, make one, and get others to agree on it. Startups have a way of sucking the life out of you unless you setup boundaries for yourself.

Understand that the more compensation in salary the less compensation in stock options.

Understand that MOST STARTUPS FAIL, but EVERY STARTUP BELIEVES IT WON'T HAPPEN TO THEM.

When interviewing:

Ask lots of questions. It is typical in an interview to get asked if you have any questions. Take advantage of this! It should be just as much about you interviewing them as it is them interviewing you. Ask lots of questions, and be cautious if they don't answer openly. Do they have a plan if they aren't acquired? (a lot don't) How long is their runway? If they haven't announced their funding, how much do they have? Is this the founder's first startup? If not, why did they fail. It doesn't matter that they failed, but that they learned lessons from it. These are just the beginning, but all questions you want answered, and should be wary if they refuse to.

It's OK to take a break.

Walk.

Get out of the office.

Take an away day if you need to brainstorm.

Breathe.

Startup offices can be hectic. And hectic doesn't always mesh well with design thinking. I found most of my best ideas, my clearest thinking, and ability to suss out solutions efficiently happened outside of the office.

Don't be afraid to becomes buddies with a nearby park.
To get coffee alone with a sketchbook.
To close the laptop.

Some people will look at you funny but chances are you'll be more thoughtful. And more thoughtful will help the company move forward more quickly, better solutions in hand.

Embrace the instantaneous feedback. It will be a huge adjustment to regularly have things you ship picked apart by customers within moments, especially if you are lucky (imo) enough to work in the enterprise space. It's not easy at first, I know I sure wasn't ready for it. People often get defensive about it, but the information is invaluable. These people are paying for your product, they are who you are building for, it's a built in focus group. Take advantage of that, be constantly communicating with your customers, then use your expertise to filter that feedback and ship something even better next time. You will redo things, you will scrap things, you, and your product, will be better for it.

+1 Craig! That applies double to frenetic start ups, but I think it's good advice no matter where you are. :)

Yep — but doubly easy to forget in startup culture, which can sometimes conflate Infinite Crunchtime with Great Work. :) When for many creatives, the two aren't that compatible.

Background: Left Apple for a startup in 2007, left that startup to lead Mint's UX in 2008. I consider both "my first startup."

The Right Fit:
Seconding Brian, interviewing is equally about a match for you. Your gut reaction about personalities/styles you encounter should be trusted. It will only be amplified when you're reporting to/working with them. Caginess, equivocation, lack of transparency...walk away, but openness, debate, curiosity, etc...embrace it!

The Role:
Clarify it. If there's another designer, talk to him/her and learn. If the CEO plans to give you wireframes and dictate features, get samples. Alternatively, if you're on your own, you'll have to be ok working in isolation. You need to be true to yourself before diving in.

Equity/Compensation:
1. Shares are meaningless w/o a %, value, and strike price. If they won't give you that info, walk away. When you do know, make sure you understand the math, company stage, and growth.
2. Decide whether or not your contribution to the company's future is worth that % and $, or if you need more. Have solid reasoning, not ego.

The Product:
Some teams are lean and focus on a janky MVP, some get it perfect and beautiful before releasing to the public. You'll need to be aligned with the founders' views about this.

Life:
Work hard, set boundaries. Take vacations, turn off your phone, don't sacrifice well-being and happiness because someone else can't resource or plan properly. You will never, ever think it was worth it.

You have to believe in each others abilities and trust them. You hired someone for their personality, skills and talent they can bring to the table. As a founder/employer be aware of that, as an employee be aware of that as well. You must show the respect for your coworkers every day with the work you do. You need to talk, ask questions and not sit at your desk all the time doing your thing.

No answer is obvious, no question is obvious. Share your thinking with each other and as a founder make sure you put together an environment that allows for that. You are figuring the product out together.

You need to make sure everybody is running in the same direction, more so if you just start out hiring people.

1) Understand what motivates the founders. People create startups for different reasons. Some people want to make boatloads of cash, some want control, some want massive growth, some want to build amazing things, some want to change the world, and some just want to be in the game. Decide what motivates you and find a team who shares that motivation. There are no "wrong" motivations. Like many designers, I tend to value quality of experience above all else. I want to build the best product possible. One of the first things I try to identify is if the product exists to support the business, or the business exists to support the product? This subtle distinction will have big implications.

2) Understand the lengths the founders are willing to go in order to prioritize design. There's a huge difference between acknowledging design and truly understanding its value. If the founders don't understand design or aren't willing to hire and fire over it, you're probably going to be spending a lot of your time and energy convincing people of its value. That's not necessarily a bad thing but you should be aware of that going in.

3) Make sure you're passionate about the product. This may seem obvious, but you're going to do your best work when you have a deep and nuanced understanding of the problem you're solving. IMHO, you can only truly achieve this level of understanding when you use the product (and I mean truly use it, even if you weren't working on it). Be careful making on a concession on the product just because you want to work with a certain founder, team, A-list board, hot category, etc.

Say no to meetings.