You’re My Favorite Client

Every Time Your Designer Shows You Something, You Understand Why

Context. When the design team shows you something, do they tell you why they’re doing this and what kind of feedback they need? That’s good. It keeps the feedback focused on moving the project along. Which means you’ll get it to them quicker and keep them moving toward the next milestone.

If they send you something with only a “What do you think of this?” attached, you have a problem. The question is too vague. It opens up too many possibilities.

Let me tell you a story that’s happening all over the world between designers and clients. The designer sends something to the client, without any feedback guidelines. The client looks at it. They’re unsure how to respond but want to do a thorough job. So they take a long time to write a longer email. The client hits send. The designer sighs and rolls his eyes. “I just wanted to know about the typeface.” The design director asks, “Did you tell the client that?” The designer says, “Well, no.” I swear to god this didn’t just happen in my office this morning. I’m also not drinking right now.

The Work Slowly Gets Better

The proof is always in the pudding. Although the initial design concepts might’ve been rough and possibly off the mark—we talked about how this was okay, remember?—what you see afterward should be closer to being right with an extra level of refinement. You’ve been giving the team feedback. The team is iterating. Everyone is pushing each other to do something good. And everything is getting closer to the product that you’ll eventually launch. There is no better feeling for a designer and a client to experience together.

People Argue

Arguing is a good sign—in moderation. This means people give a shit. They’re invested in what they’re doing and passionate about the results. People who are disinterested don’t argue. They meander from one task to another, making sure they do just enough so they don’t get noticed. They go into checklist mode. They don’t look for the best solution since any will do, as long as they get to check it off as done.

You don’t want people throwing punches in the office. And you don’t want the arguing to get personal. (“Your solution sucks” is okay. “You suck” is not.) Get them into a room and mediate. Figure out what they’re arguing about and see if you can help them either find common ground or decide who’s right. If they’re arguing because they care about what they’re doing, you’ve got it made.

People Tell You They Fucked Up

People fuck up in all sorts of exciting, interesting, and sometimes terrible ways. How is someone telling you they messed up a good sign? Because they’re telling you. If you think your project is problem-free, it’s because someone is hiding something.

When a designer tells you about something gone wrong, take a deep breath. Count how lucky you are. You’ve hired people who’re willing to approach you about the problems they’re having or causing. This gives you an opportunity to address them. You can fix zero of the problems you don’t know about. You can fix some of the ones you do.

Also, pat yourself on the back for being the kind of person your team isn’t afraid of talking to about the hard stuff.

The Designers Trust You Enough to Show You Unfinished Work

It’s one thing to show presentation-ready work. It’s quite another to send out work that’s broken and messy. Designers show each other unfinished stuff all the time. Usually because we wanna show off something clever we did, or we’re stuck on solving a specific thing. But mostly we keep it to ourselves. Because we share a trade and it takes a certain amount of trust to share unfinished, messy work with a non-designer, especially the person who’s paying you.

If a designer shows you work in progress, it’s a great sign. It means they’ve moved beyond a fear that all you’ll see is the broken stuff to a willingness to collaborate with you. Look at it in the spirit of collaboration. Ask questions about what they’re showing. Talk about where they’re headed with it. Feel free to ask if there’s any feedback they’re looking for at the moment. They’ve accepted you as part of the team that solves the problem.

You are now in the inner sanctum of sausage making. This is good.

You’ve Shown the New Site to Someone You Weren’t Supposed To

Along the same lines, your designers will implore you not to show the site to anyone outside the company until it’s ready. Why? Because a process exists to get this stuff done, and you agreed to follow it when you hired your designer—and look how far it’s gotten you! I guarantee that fielding feedback from your nephew Dick, who took a graphics course in college, isn’t part of that process. But the desire to share the work with Dick—and the rest of the world—because you’re excited and want to show it off, is a good sign. Do it while he’s asleep or something. We’re excited that you’re excited. Just don’t give us Dick’s feedback.

Someone Complains About the Sorry-ass State of Your Legacy Systems

Shit is getting serious. If someone’s complaining about legacy systems, that means they’re deep in the weeds about to start the most heinous job in Web services.

Dealing with legacy systems is like swimming through maple syrup. No one’s legacy systems are in good shape. They’ve been cobbled and duct-taped together for years. The previous redesign probably entailed a quick fix to avoid them altogether. But at some point someone has to descend into the sub-basement of your Web site and pull this stuff out, clean it up, and import it into shiny, new systems.

The people dealing with your legacy systems are like that person in horror movies who’s brave enough to go into the storm cellar by themselves with nothing but a whiffle bat and a box of kitchen matches, while the rest of the team peeks from behind the door at the top of the steps. They’ll root around in databases containing names from the Mayflower expedition. They’ll sift through years of content and delete inline styles. They’ll collapse more tables than the caterers after a royal wedding. Treat them like the heroes they are and make sure they have pizza and beer and big bonuses at the end.

Please, for the love of all that’s holy, don’t farm this out to someone to do in their spare time. This shit is hard and time-consuming, and if you ignore it until the last minute, your project will fail.

Which is why we’re happy that people started early. It’s a very good sign indeed.

Your Team Is Excited About the Next Deliverable

People settle into one of three emotional camps during a design project:

• Hatred
• Indifference
• Excitement

I almost added anxiety as a fourth, but decided you could be anxious no matter what camp you’re in.

If the people in your company are excited about what’s going on and can’t wait to see what happens next, that’s awesome. Even better is if they participate and seek out ways to get involved. This means they’ve taken a stake in the project’s health and will work their butts off to ensure its success.

People Stay Late to Work

I threw this in here to trip you up. I’ve worked in several companies where staying late was viewed as a good sign. If you left at a reasonable time, you were a traitor to the cause. There will always be moments during the project, notably toward the end, where people have to rally to meet a deadline. When this happens, and it should be infrequent, bring them food and stay out of their hair. If it starts happening regularly, something is screwed up. Take a look at your timelines to see if they’re unreasonable. Get a history of deadlines and see how many have been missed. Talk to the project manager. Long working hours aren’t a sign of a project going well or of devotion to the company. They’re a sign that something has gone wrong. Everyone deserves to go home at a reasonable hour.

The Current Site Makes You Sick

You knew the old site had problems, or you wouldn’t have brought in designers to fix it. But as your new site takes shape, you’re going to look at your current site like a box of week-old donuts you can’t wait to trash. If you find yourself debating whether the new site is better than the old site, that’s a problem. But that moment when you pull up the old site and throw up in your mouth a bit? That’s a good sign.

You Didn’t Mind Writing That Last Check

No one likes writing a check if they don’t feel like they’ve gotten that check’s value. But we’re generally happy to exchange money for something we feel is worth it. Same with design projects. When the desire to get more of the project done beats the desire to hang onto your money, the project is going well.

You Want to Poach Someone on the Design Team

Someone on the design team may do such incredible work, get along with everyone on your team, and understand your business so well that you’re inclined to think, “Boy, I sure wish they worked for us.”

Hey, that’s great. We want you to feel that way about everyone on the design team. Our goal is to become indispensable to the point that you couldn’t imagine working with anybody else. We want you to be sad that we’ll eventually leave.

Wanting to poach someone from the design team is a good sign. Actually doing so is a whole different beast. Let’s all agree to dance with the one that brung us.

But we’re honored you’d want to.

Your Boss Is Happy

Let me tell you the happiest type of email I get. It comes from the project lead a few months after the project launches. It’s some variation of: “Hey, wanted to let you know how well the project was received. Our numbers are up and users are overjoyed. Oh, and on a personal note, I got a promotion!”

Nothing makes me happier than finding out the person who put their trust in us and stuck with us through the work’s duration, ended up looking good and getting recognized for that decision.

One of the designer’s goals is making the person who hired them look like a genius. So I do what I can to support that person when their boss is breathing down their neck. Obviously, this starts with doing good work. But it also means keeping to the timeline, staying within budget, communicating clearly, and offering to stand side-by-side with them when they get called upstairs.

When the people upstairs are happy, the project goes better, you have the room to do your work, and everyone’s a little less anxious.

You Have a Clear Path to the Finish Line

At the very beginning of the project, you and your design team should define what done means. Is it launching the site? Turning over a certain set of deliverables? Passing through QA testing without any bugs? Those are all fine and valid, as long as both parties agree.

When you can see the finish line ahead of you with no further obstacles in your path, you’re gold. Take those few extra steps, cross that line, and celebrate. You are now done. Pop the corks, sign the checks, and await the inevitable promotions.

No, you still can’t poach anyone.

Summing It Up

These are all signs the project is going well. No project is perfect, but knowing how to gauge its health will help you catch mistakes early enough to rectify them without losing too much time or momentum.

But what happens when mistakes don’t get caught, or when partnerships go sour, or you find that, despite your best efforts, you made the wrong choices and they’re unrecoverable? Sadly, it happens. (Hopefully reading this book will minimize the odds of it happening.) Let’s talk about what to do in the worst-case scenarios. 

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