Demanding Design Deadlines: A Survival Guide

The above scenario is a bit tongue-in-cheek, but it’s not that far off from what many designers face in their day-to-day work. Nearly every designer will encounter moments where they’re pushed to complete a given deliverable or project in less time than may be desired. In some cases, the timelines may not be ideal but are manageable, and in other cases they may be completely unrealistic. These pressures are especially compounded when designers are working on multiple efforts at a time. It’s also very common to be asked how long something will take to complete without having the necessary information needed to give an accurate estimate. Designers frequently feel that moving quickly will result in a lower quality result, causing anxiety, frustration, and feeling not set up for success.

Dealing with timelines and deadlines is a necessary part of being a designer. While it’s often challenging, there are many methods that you can leverage to manage pressures to move quickly while also achieving a quality result.

Become an active participant in timeline setting

It’s clearly challenging for non-designers to create accurate design estimates and in return, set appropriate deadlines for design work. In order to prevent an ill-informed “we need the designs done on Friday” directive, it’s critical to get yourself involved in setting the timelines from the very beginning.

If you’re in a position where you are not currently involved in setting timelines for your own work, start by explaining to your team the benefits of contributing to the conversation, such as:

• It makes other team members’ lives easier by not having to guess how long design will take
• It ensures that tradeoffs are agreed upon prior to setting deadlines
• Having a designer inform timelines doesn’t always mean that design will always take more time, but rather, it may take less time than expected
• It increases the chances that the effort itself can be successful as opposed to rushed out the door without taking into account key considerations

One key thing to keep in mind is that by getting involved in setting timelines, you’re asking the team to trust you. They need to trust that you’re not only looking out for yourself, but for the success of the entire team. They also need to trust that you are willing to compromise, and that you won’t consistently ask for unnecessary time or under deliver on your commitments. As soon as that trust starts to erode, it’s very hard to get it back. Design isn’t the only part of the product development process that needs to happen in order for an effort to succeed, and it’s important to be open to various approaches based on what is needed for each project.

Providing a time estimate for design work

So you have been brought into the fold and are asked to help inform timelines — great! Then you are asked how long your work is going to take, and fear and uncertainty sets in. How are you supposed to provide an accurate estimate when what’s needed during the design process can often be unknown? Estimates are notoriously difficult, and can seem impossible for larger efforts. However, there are several tactics you can use to make this process less overwhelming and more beneficial.

1. Understand expectations for the effort: Is this going to be a quick experimental project with many future iterations? Is it going to be a single large customer launch at a major company event? Agreeing on where the effort falls on this spectrum will help set expectations for how fully fleshed out and validated a design needs to be prior to launch. Knowing something is going to be an MVP that will have dedicated resources to continue working on it may influence the process you choose to follow. This will also spark conversations around potential changes to the approach to reduce risk and validate ideas more iteratively.
2. Understand priorities and available resources: Knowing how important a particular initiative is over others will help determine who on your team needs to be dedicated to the effort. This may require pulling people off of other projects, and so it’s important to communicate these tradeoffs to the team. Knowing resources ahead of time will help you create better estimates by considering how their skillset(s) will impact speed and quality of execution. If you’re the only designer on the team, these conversations would be geared more around your personal time commitments to this project over others.
3. Break “design” into meaningful phases: Instead of providing a single estimate for the end-to-end design process, think about the major phases instead. Consider starting with a timeline for problem definition before committing to any other phase, then add in phases such as exploration, refinement, prototyping, and validation. Then you can propose that the team regroups frequently to evaluate whether things are on track, and to provide more accurate estimates for the next phase.
4. Articulate what you need to know before you can provide an accurate estimate: Depending on which phase you are in, you may need to know certain things before you can even remotely estimate design work. For example, if you don’t have defined objectives or problem statements, you can’t provide estimates for detailed mocks or prototypes. Where possible, help your team come up with this required information instead of pushing it back entirely on them.
5. Leverage a wide toolkit of potential methods and approaches: Design is often negatively seen as a time-consuming part of the product development process because of designers holding strict to a single (and lengthy) process. Think about how you can be successful using the leanest methods possible, as opposed to defaulting to a “textbook” process. Having a wide variety of techniques to leverage will make you more flexible.

Dealing with difficult deadlines

There will be times when, despite your best efforts otherwise, you will need to complete an effort in less time than you think is necessary to produce the best quality work. Instead of getting frustrated when this happens and resigning yourself to throwing something together just to meet a deadline, deal with these scenarios with a different mindset and approach.

1. Understand the reasons behind the defined timeline: Most deadlines are flexible to a degree, but others, such as end-of-quarter launches, may be set in stone. Knowing where the deadline came from can help you understand whether modifying the timeline in order to achieve better results is negotiable or not.
2. Define success: Ensure that you understand and have the team agree on what success means for the effort as a whole. If shipping and shipping alone is success (let’s all hope that’s not the case), expectations for delivery are different than if the end result is expected to increase conversions or increase customer satisfaction scores or any other more specific success metric. When defined success metrics are in place, lead conversations around what is realistically needed in order to achieve those goals, or revisit the metrics if timing is critical and expectations are unrealistic.
3. Agree on scope and risks: It will be difficult or impossible to meet expectations if the scope of an effort is not clear up front. Ensure that your team understands this and accepts that changes may need to happen if the scope changes. Even if a deadline is fixed, curveballs may happen along the way that will require a change in scope, such as team members leaving, changes in priorities, unexpected technical challenges, or additional stakeholder requirements. Knowing those risks may come up will enable the team to better respond to them if/when they happen.
4. Articulate a proposed alternative, if appropriate: Once you know the reasons for the timeline, what you need to do to be successful, and the scope of the effort, you may be faced with an impossible task. If it truly is going to be impossible to succeed, instead of just saying “no”, proactively suggest alternatives that best meet the goals of the team. If you’re not the one suggesting those alternatives, someone else will decide them for you.
5. Drive discussions around tradeoffs: Assuming you will not be able to achieve everything you want to achieve in a given timeline, there will be tradeoffs to consider. Lead discussions with the team around these tradeoffs: “if we focused on [x], we wouldn’t be able to fully solve [y] this release. Alternatively, if we put more time into [y] and deferred [x] to the next release, we would more directly meet the top user needs and business goals.” Document these tradeoffs so that the team agrees upon them and to help plan for future phases.
6. Don’t reinvent the wheel: Not every design solution needs to be completely innovative, or even especially “creative.” Investigate ways in which you can effectively solve design problems by leveraging best practices, past knowledge, and existing patterns. Then you can focus the majority of your limited design time on the areas that will be differentiating or bring particular delight to the experience.
7. Divide and conquer: If you were successful in the initial timeline setting conversations, you may have access to additional resources to help get the work done on time. Discuss early and often how to best divide up the work to get it done more quickly, and how you can best work together to explore options and solve problems.
8. Be comfortable with knowing your work will not be perfect: Set expectations with yourself and your team that the result may not be completely successful on all levels. As long as you have a plan for how to address the gaps (see below), you can usually end up learning more by shipping an imperfect product rather than trying to validate everything in advance.
9. Plan for measurement and iteration: This may be the most important point of all. Lead the team in coming up with a plan for seeing where the solution is working and where it needs further iteration. If the team agreed upon known tradeoffs up-front, ensure that there’s a plan for addressing any known gaps instead of leaving them hanging. It’s also worth conducting a “post-mortem” or review after the project ends and metrics of success are available to identify whether anything could have been done differently to improve the outcome.

Using these techniques will help you not just survive stressful deadlines, but hopefully make them more manageable. Many organizations may not realize that they could improve the timeline setting process, and you can take an active lead in making improvements. However, your reality may be more challenging. If, despite trying the above suggestions, your organization refuses to involve you in setting timelines, can’t come up with measures for success, wavers on expectations, or simply doesn’t respect design as an equal partner, it may be worth considering finding a new organization that understands the benefits of a more collaborative process. It’s not worth the stress or frustration when better options are out there.