6. When Things Go Wrong

Despite everyone’s best efforts, people make mistakes. How do you sort the small ones from the big ones? How do you know when to change course or cut the cord?

How many of you skipped right to this chapter? It’s okay. If you’re knee-deep in a project that isn’t going well, I can help. First, take a deep breath. Let’s do some triage. We’ll cover whether you’re looking at small or big mistakes. If they’re large, we’ll go over whether you can fix them. Sometimes you can.

After thoroughly exhausting our options, we’ll knock some heads.

It happens. Sometimes, despite everyone’s best intentions, projects go wrong. Sometimes, despite everyone doing their due diligence, they hire the wrong people. Sometimes, and you’re gonna like this part, you can fix these things. Sometimes you can’t. Let’s figure out the difference.

Mistakes happen on every single project, at every point during the project. You can’t avoid them. You shouldn’t even try. Okay, you should try a little. But the case I’m trying to make is that you’re better off putting your energy in figuring out how to recover from mistakes than avoiding them altogether.

A small mistake happens when someone gets the number of templates wrong, forgets to add some obscure functionality, or delivers feedback on Thursday morning instead of Wednesday afternoon. Anything you can fix with a few hours or even days of work is a small mistake. No biggie. You settle up and do the extra work, adjust the project timeline, and move on. The person who made the mistake will likely be extra attentive from now on, which is good, because you’ll watch them like a hawk for a bit to make sure they learned their lesson.

The thing that turns a small mistake into a big one is failing to acknowledge it. I hope you’re basketball fans. If you played as a kid, one of the very first things your coach should have taught you is the minute you get whistled for committing a foul, you raise your hand. You own that mistake. The other team takes their free throws and everyone moves on. I have no patience whatsoever for someone who can’t acknowledge making a mistake, especially since I’ve done a pretty good job of letting people know that mistakes are part of the process. People who can’t admit their errors are usually afraid. They’re worried they’ll be judged and thought less of. You need to create an environment where this isn’t the case. Someone who acknowledges their mistakes is a good person to have around. Not only do they own their responsibilities, but you can be fairly sure they’re not hiding anything from you. A small mistake that isn’t uncovered can grow into a large one.

A big mistake is something that puts the project timeline at risk. It’s one thing to forget to add social tools to the site. That’s fixed in a few hours. It’s quite another to revisit a decision made three months ago. That’s major. It means that any decision made after the mistake is up in the air—and may mean losing hours and budget, and putting the final deadline in jeopardy.

Ifyour design team is internal, that extra time is easier to find. If the mistake rests solidly on the design firm’s shoulders, they need to fix it and eat the time and budget. But if the mistake’s on both of you, as is often the case, or if you’re the one with the hand in the air, you may have to deal with the reality that they’ve already booked another project after yours.

Avoid mistakes of this magnitude by frequently checking in, paying attention to details, and taking extra care that sign-off really means sign-off. Cross your t’s and dot your i’s.

I can’t stress this enough: never, ever, ever sign off on work without being absolutely confident in your decision. Make sure that anyone who can undo that decision gives the green light. It’s better to spend a few extra days doing your due diligence than run the risk of having a project undone because someone who needed to be consulted wasn’t.

The levels of project quality expectations, in descending order:

• We’re going to do amazing work

• We’re going to do pretty good work

• We’re going to get this out the door

• We’re going to cover our ass

• We can probably spin this on our résumé

When you get down to those last two, you’re in the middle of an irreversible mistake—the type that needs a project reset. You’re definitely on your way to an unpleasant conversation with your design team and, if you have one, your boss.

How do you know the relationship is unrecoverable? Simple. You no longer trust the designers. If you don’t believe your team is capable of doing good work, you’ve lost trust in them. They have to go. Here’s the sad dark secret. It may not be fair. You may no longer trust your team for reasons that are totally unfair to them. You may be the one who screwed up. You may be scapegoating them. (In which case they no longer trust you either.) The goal is to be able to work together, not assign blame. If you’ve decided you can’t work together anymore, it’s time to part ways. Bear in mind, deciding you need to get rid of a team because you’ve scapegoated them and they no longer trust you may be the right thing to do for the sake of the project. It still makes you a jerk. But a jerk who’s getting the project done.

Let me tell you a story. We were working on this project for a company we (still) admire. Good work. Fun team. It was their first time hiring an outside firm to do their design work. We were doing good work. The problem was, whenever we showed work to their CEO, who fancied himself a designer (biggest red flag in the business), his only reaction was, “This doesn’t feel like us. Why aren’t we doing this work internally?” No matter what we showed him, that was the reaction. We were obviously in a situation where the client didn’t trust us. To be fair, it had nothing to do with us, and the rest of the team trusted us fine. I saw no way past this, other than letting them kill the project and do it internally. And I was very grateful when they fired us at our request. The project never launched, by the way.

One rule: never make people think they have a chance when they don’t. If you’ve decided to get rid of them, just do so. A fake last chance is a bullshit move that costs you more time and money. Not to mention that it’s totally unfair to the people who you obviously don’t trust anymore and need to go get a fresh start somewhere else. Never punish people or cover your ass by making them think they have another chance.

If the team has strayed so far off course that the project is spiraling toward failure, get everyone in a room and let them know. I recommend a direct approach. Something like, “You’ve strayed off course and the project is headed toward failure!”

Don’t beat around the bush. This isn’t one of those “let’s see if they come to the same conclusion” meetings.

Once you have their attention, lay out the severity of the situation, including the consequences. I recommend rewatching the Alec Baldwin “Coffee is for closers” speech from Glengarry Glen Ross to psych yourself up. (Check YouTube.) Once they understand what’s at stake, you either present your plan for moving forward or workshop that plan together, should you still trust them to do so. However you do it, they need to understand that the minute they walk out of this meeting, their job is to execute that plan. No arguments, no bullshit.

Don’t promise anything beyond that. You may not have the power to do so. Even if they manage to pull the project out of the toilet, they’re still the team that dumped it there.

You’re absolutely right. These meetings aren’t fun. You know what’s even less fun? Explaining to your boss, investors, and other employees who aren’t part of this project but are nevertheless affected by it that you failed. This meeting is your last chance to avoid that meeting.

If I’ve failed at something, and that failure has been confirmed by the person who hired me to accomplish the task, I have a decision to make. Either I can be a dick and get defensive about the situation, and claim that I didn’t fail, or I can acknowledge that I failed. If I take the former option, I learn nothing, and I gain a reputation as a terrible person to work with. If I take the latter, I can review my actions, look for where I screwed up, and ask my boss for details or advice. I can use it as an opportunity to get better at what I do by not repeating those mistakes. I also come off as a person who knows how to hop back on a horse after being thrown.

As the person communicating that failure, it’s in your best interest, especially if you have a long-term relationship with this designer, to set the conversation up to get the result you want. I can help you with a few guidelines. The first and most important is to do this in person whenever possible.

Realize that you’re taking it upon yourself to help them through that period. Give them clear goals, set up regular check-ins, and make sure they can come to you when they need to. Their success or failure is now intricately tied to yours.

Getting fired should never come as a surprise. If someone’s not working out, you need to let them know. You should tell them how they need to improve and by when. If they take it as a wake-up call, they’ll be forever grateful that you gave them a chance. If you don’t see any progress, or they do an even worse job after that conversation, cut ‘em loose.

Trust me, someone who’s in above their head knows it. Firing them will not be a surprise. You’re probably doing them the favor of not having to come in and go through the motions. (And, no, this is not a way for you to feel good about firing someone.)

I’ve fired a few designers in my time, and they’ve gone off to have great careers. I’ve been fired myself more than once, and here I am talking to you. Getting fired isn’t the end of the world; it’s the end of a job.

Let’s be clear about this: firing someone sucks. It should suck. The fact that you feel terrible about it is a sign you’re actually a human being. But however much it may suck to fire someone, it doesn’t come close to how much it sucks to get fired.

Doing the right thing doesn’t always feel great. That doesn’t mean it’s not the right thing to do.

I am far from an HR professional, and your company may have its own guidelines for firing people. But I do encourage you to do it with as much clarity and honesty and empathy as possible. Someone who’s getting fired deserves to know why they’re getting fired, no matter what your HR department says.

If you’ve hired a designer from the outside, things get more complicated. Except that they really don’t. You pay people for the work they did. This is exactly the kind of situation that should be addressed in the contract you both signed before you started the project, specifically in the kill fee. But as a general guideline, you most definitely owe people for the work you’ve approved. If they did good work for two-thirds of the project and you signed off on it and paid them, that money is gone.

I can hear you saying, “But it ended up failing.”

I feel your pain. I do. But the fact that you signed off on stuff means that you were satisfied and acknowledged that things were proceeding in a good way. Make sure you are clear about what you are signing off on and the ramifications. It’s going to be very difficult for you to go back and try to convince the design team or your boss that you signed off on work that was headed toward failure. You’re going to have to convince someone that the design team was keeping something from you, that they knew failure was imminent, and that you signed off on work under false pretenses. If you actually believe that to be the case, then by all means proceed. I have no love for design firms that swindle their clients. It makes everyone in the business look bad, and it makes my job harder. It’s just not going to be an easy case to make.

If the design team comes back and says that you owe them for time and work that was in progress, that’s trickier. Once again, this is something that should be addressed in the contract. And once again, I have a very simple guideline: if you’re going to use the work, even after firing them, pay them for it. But if you’re not using the work, well, fuck ’em.

Like I said, I have no patience for design firms that make us all look bad.

The first thing we need to determine is whether we can finish the project without a designer. We’re entering dangerous waters. To do this, the project needs to be pretty far along, with major systems defined, and the site well into implementation. Well into implementation.

Ask yourself: can you finish the project without a designer and preserve the quality of the final project? Don’t make your users pay for the designer’s mistake. Your users deserve the best you can give them. Don’t rush to completion if you’re going to deliver a substandard product. You may win a battle to lose the war.

If you find yourself in need of another designer, some trust-building exercises may be in order. You just went through a shitty experience with a designer and it’s important that you rebuild your trust in design.

FIG 3: Firing someone is never fun. Here’s a unicorn chaser. Photograph by Rob Boudon (http://bkaprt.com/ymfc/7/).

Before searching for someone new, take stock of what you’ve learned. Did you miss a red flag during hiring? Did the problem stem from the quality of the work or the relationship? Do you need someone with more experience? Or did you choose the cheapest option over someone more qualified because you wanted to save money? (Guess what? You didn’t save money. What you save on cost, you take on risk.)

I can always tell when a client comes to us after a bad experience with another designer. They’re still feeling the sting of being ripped off. Rightfully so. Their questions tend to be pointed—a vapor trail to their pain. Which is good, because I can speak to that pain and help them feel at ease about working with a designer again.

What I need you to remember, though, is that the next designer you hire isn’t responsible for what happened with your previous one. Don’t make your new designer pay for your old designer’s sins. Transference is not in scope. A new designer starts with a clean slate. You’re handing them one hell of a hot potato.

Look, anyone you bring in at this point is going to need some time to get acquainted with the project. They’ll be able to assess how much of it needs to be redone and how quickly it can happen. Make sure the designer you’re bringing in isn’t redoing it for the sake of putting their own mark on it. Yes, had they been there from the beginning, they would have made different decisions. But this is where we are now. Don’t forget: design solves a problem within a set of constraints. Tell them one of yours is that you have a half-finished project that needs an honest evaluation of how much is worth keeping. Possibly add an incentive—offer them a bonus if they finish by a certain date. (You’ll be amazed how much of that work is now salvageable!)

Most projects go well if you hire the right person for the job, work collaboratively, and communicate frequently. But even with the best of intentions, projects sometimes go south. Get out of those situations as quickly as possible. Assess the damage. Come up with a plan to move forward. Don’t let one bad experience destroy your confidence in good design and the people who do it.

Remember, saving a few bucks often ends up costing you far more.