Do or Die? Six Secrets for Managing Deadlines

The art director shut the door quietly behind me, waving me into a seat. Out the windows of his office, I could see snarls of traffic waiting at a traffic light. Rain sluiced off our building in rhythmic waves. The gray weather outside lulled me into a sense of serenity. I liked my new job and the people that worked there. This was my first big agency job, and so far everyone I'd met had been quite helpful. I didn't know what this meeting was about, but I assumed it regarded a new, exciting client engagement that I would soon tackle.

The first thing out of my boss's mouth?

"The most important rule here is that you don't miss a deadline."

This meeting was not going to be about me taking on a new project. My first set of comps would not be critiqued for the nonprofit initiative we'd just begun. No, we were going to talk about the agency's expectations for my design work.

Or, more to be more accurate, we were going to talk about deadlines. I had missed one for an internal project due to time mismanagement on my part, and I didn't let the project manager know until the time of the actual deadline that I would miss it. The project manager complained to the account manager, who then called up the creative director, who sent an email to my manager, who now had me in his office.

Apparently, this was a big deal that would not be smoothed over by me saying, "Oops."

"Our schedules here are managed very closely," he continued. "If you miss a deadline, then the account managers don't have time to review the work. If the work goes to the client and a critical detail isn't covered, then the account manager and the project manager both need to take responsibility for not catching it. But in the end, the blame for the error will be on you, because you didn't manage your time wisely."

As we continued the conversation and my defensive hackles began to lower, I realized I hadn't considered the importance of deadlines beyond my domain of control: creating the tangible, designed artifact. I had come from working at a small design firm, where each of us had had direct client contact and could smooth over tight deadlines by calling up the client and sharing our ideas verbally. Besides, we would only be late with a set of deliverables by a few hours...

Now multiply that staff load by ten, then add in a dash of inter-agency politics and a very hefty amount of strategic thinking that was going on before the work even began. Deadlines became more than just gates that stood through the design process for approval, iteration, and refinement. Deadlines were the lifeblood of ensuring large, complex projects remained on the rails. The client experience could not be influenced negatively by missing a deadline, or turning in work that was not on brief. Otherwise, we were risking long-term issues with the client relationship. And it costs more money to bring in a new client instead of retaining your current ones and initiating new projects with them.

In short, my control of my creative process was crashing up against the well-planned business process of the organization—and in the eyes of my cohorts and managers, my creative process would always need to fit into the structure they'd quite intelligently designed.

"Now, here's the trick about deadlines," my art director continued. "Just because you're given a deadline doesn't mean you need to accept it. Everything can be negotiated."

"But I didn't have any more time!" I said back. "By the time I got through the layout edits on the other project, it was too late to warn the other project manager."

"You knew that before you got through the edits," my manager shot back. "You just didn't think in advance exactly what it would take to get the work done, and tell the project manager that you might need to negotiate a new deadline. If you crack the door open a little bit that you might be late or need help, they aren't going to get upset at you for missing the deadline. They're going to want to help you get the work done as quickly as possible within your bandwidth. If other designers are free, they can help you. You aren't alone in this."

"Besides," he added, "They always pad the deadlines by an hour or two so that if you do go over your time, they aren't completely burned. But they're busy people too, and they have to do their QA to make sure the work is great. So gaming them gaming you isn't going to work. Every deadline needs a buffer."

A twenty-story-tall light bulb went off in my head at that very moment—that I was part of a living system, a corporate organism designed to effectively deliver business results to my clients. Design was the reason that our clients hired us, and consistent follow-through was a cost of doing business. The two are inseparable when applying design in a professional context. To wit:

 

If you want to be a design professional—and be seen as professional by your clients as peers—you have to manage your personal design work like you are an agency. This means that you don't just sit down in a chair and design the day away until you deliver the comps. You build into your working process your own time for project management, overseeing the process. You consider what time you'll need to spend on the phone as the account manager. The proofreader looks for typos that sneaked through spell check. And so forth. Without time for those roles budgeted into the process, you will always run right up to deadlines and risk missing key details in delivery.

 

Each person you add to a project team increases the complexity of execution by an order of magnitude—and the risk of missing a deadline. You are responsible for managing this risk. I learned this not only from being a designer, but also playing in a number of rock bands. Power trio: easy to manage. Four-piece: Sometimes a struggle to get together for practice. Five band members: Impossible to get together for practice without everyone's concerted effort. Add a few more people and things get even hairier.

The reason project managers keep their jobs is by managing risk brought about by a high number of moving parts. The same goes for working with a large client team—more clients means more feedback, which is why you always see designers encouraging a single point of contact who serves as triage and final say on all feedback. The cats need to be herded on both the design side and the client side.

 

If you think you are going to be late on a deliverable, you need to warn everyone impacted as soon as possible—not at the last second. If you've got two days to get the comps finished, but the studio is completely overloaded, now is the time for damage control. Either you hire people to help you finish the work, go into crazy overtime, or you have an honest negotiation with your client as to when you'll need to deliver the work and preserve your boundaries.

Yes, you can look bad in the latter situation and risk losing face with regard to your long-term working relationship. You also send a signal to your clients that you don't know how to manage your time, which dilutes your client experience.

If you wait until the day it's due to drop the bomb on Mr. Client, you're doing everyone involved in the process a disservice. Which leads to a further consideration of how you run your design practice...

 

You need to accept the volume of work that you can actually handle—and not fear declining or deferring the start of new work. I have trouble saying no or deferring opportunities, and there are a few outstanding obligations glimmering in my consciousness right now that have to be addressed. It was my fault that I accepted them knowing that I had twelve balls already up in the air. I need to manage my time better to accomplish what's necessary while still eating, sleeping, and having a life outside of the practice of design. Otherwise, I am going to be living in Burnout City for the foreseeable future.

Does this story sound familiar? I think every designer, at some level, doesn't want to turn away a good thing. In many ways, we need strip away the idea of "good" and make evaluating each opportunity more about knowing exactly what your pipeline looks like and knowing how much work you can tolerate without turning into a work machine. Asking to defer work before it's engaged won't make you look unprofessional. It will tell others that you have a stable working process and standards that you live by. Those are good things.

 

You have to continually reassess and re-estimate your time to execute projects accurately to a deadline—or make an educated guess that accommodates multiple failures in a controlled manner. Every designer wrestles with estimating their time, and generally estimates too little of it for every single project they tackle. As a result, they burn extra time up while bringing the work to their level of satisfaction.

How do you break this habit? Set up your billing fees and deadlines to accommodate the proper level of exploration, then add in buffers for project management and account management. If you can't do that, then analyze how you work to find efficiencies. You'd be stunned at how much time opens up in your day if you get very selective over when you answer the phone, check email and your social networks, Twitter, etc. Also, considering what "done" means is a major issue. Depending on the type of deliverable you're creating, showing pencil sketches at first round is completely fair.

 

You have to respect the time of your client, no matter whether it's a paid contract that you're legally bound to deliver or a personal project for a friend for free. Even if your client is treating you in an unprofessional manner, you should hold to your schedule or deadlines. Don't pay back your client for their behavior. If you ever end up going into mediation or some other legal forum to resolve a dispute, missing deadlines or other milestones that are part of your contract can influence how the scale tips in the final judgment.

And to be clear: In situations where the client says they don't have a deadline, that doesn't mean you can take forever to complete the work. It means you need to propose your own realistic deadline and stick to it. Otherwise, you're risking mismatched expectations for timely delivery and creating a contingency that could cause you to lose a friendship, acquaintance, or future business opportunity.

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Going down this path and asserting control over how you manage deadlines is scary for many designers. In doing so, you aren't focused exclusively on conducting the process of making—which is why we chose to participate in this profession in the first place.

I would argue, however, that one's design training is an accumulation of many skills that form a successful repertoire. Managing deadlines is just one of those skills, and if conducted well over the life of a client project, can contribute value to your overall client relationship and increase the perceived value of your services. It also helps you to manage your own time, so projects don't expand to fill your entire life.

Why would you not want to do that?