How to Manage Expectations When Deadlines Become Tighter

Underpromise and overdeliver—that’s what they always say, right? When you outperform expectations, you stand out and become an invaluable resource for your boss and organization. But what happens when you finish a multi-day task in just a couple of hours and then are held to this standard going forward? How do you “manage up” to ensure the timeline provided for future tasks is sufficient? How do you ensure you are judged fairly against a reasonable timeline and not a past peak performance?

Let’s take a closer look at what it means to “manage up,” how to understand expectations and timelines ahead of time, and most importantly, how to communicate when a deadline is difficult to meet in a way that is reasonable to your boss.

The Importance of Managing Up

There are many things about your work environment you can influence. You may not think your boss is one of them. It’s why 65 percent of workers say they would choose a new boss over a pay raise at their current job. People don’t quit jobs—they quit the people they work for.

With the right approach, however, you can influence your boss and improve your working conditions. Through the concept of “managing up,” you can improve your relationship with your boss, set clear expectations that go both ways and start to manage deadlines before they become tighter. Some of the core components of managing up include:

• Getting Onboard with the Mission – Sure, you were hired for your skills, but it was in pursuit of something greater. Your job is to support what your boss has been tasked with accomplishing. Embrace that role and it will be easier to have future conversations.
• Understanding the Process –Embracing a mission isn’t the same as blindly following orders. Take the time to ask about specific goals your boss has set—both short- and long-term.
• Communicating Constantly – Support your boss by sharing everything they need to know before they need to know it. When something goes wrong, don’t fix it and hope you can hide it. Tell them what happened—whether it’s an angry customer, a broken process, or a fight with a coworker. Better yet, bring a solution with you when you share these problems.
• Guiding Them in Working with You – Make sure they understand what you do best and how they can best utilize your time. What skills do you have outside your core job responsibilities? How do you work under pressure and stress? When do you have issues? Be honest so they can work with you as effectively as possible.

The goal of managing up is to recognize the importance of your role, but also communicate why you are uniquely suited to perform it and how your boss should be managing you.

The Next Step: Setting Expectations

When you take the time to do these things, you set yourself up to have more direct, and at times difficult, conversations about the work you do. Managing deadlines and expectations frequently falls into this bucket.

To start, make sure you fully understand what you can reasonably accomplish. Are the deadlines you’ve been given reasonable? Or are they aggressively short? Have you communicated your work-life boundaries to your boss, and do they respect them? Before having any conversations, these are important questions to ask yourself.

Setting Achievable Deadlines

To start, set hard deadlines that are reasonably spaced out with your boss. One reason that deadlines often end up too short is that there is no conversation about the big picture. Your boss needs something, they know you can get things done quickly (as you have done before), and so they give you a few days.

But in reality, most tasks are part of a greater whole. “Go write a white paper” isn’t a single task. It’s several. And more likely than not, if the deadline is too short, you’ll disappoint because of the number of steps involved.

To manage this, set a timeline that takes into consideration:

• Dependencies – Are other people required to provide insight, feedback, review, or some other part of the task? This can severely delay some task completion. Build it into your timeline.
• Segmentation – Can your task be broken down into smaller chunks of ownership? For example, with a white paper, you might segment it into research, outlining and interviewing, and drafting. Between each step, input is needed from other stakeholders in the company. Some steps might be delegated to others and possibly completed simultaneously.
• Skill set – Your boss may not have the same expertise as you. They may have a sales background or a technical skill unrelated to yours. How often do designers hear, “Can you Photoshop this?” How many developers hear, “Can you code this real quick?” It’s often not that simple. A mutually agreed upon timeline takes into account the specific tasks and time requirements of those tasks for a new project.

Research shows that evenly-spaced deadlines can lead to a higher level of quality and on-time completion of complex tasks. It’s an important way to manage expectations and avoid disappointment.

Communicating Constantly to Illustrate Changing Conditions

A big part of managing up is communication. Done right, it can help with deadline management as well.

Ideally, you are having weekly meetings with your boss during which you can share your current status, any unexpected demands on your time, or outside factors that might influence your productivity. If not, or if these meetings prove insufficient, consider the following:

• Provide Regular Updates – Don’t assume your boss reads the project management task logs or communication between you and other members of the team working on the same project. When you reach a major milestone or roadblock, tell them immediately. This is more than just an “FYI” email—it’s a way to illustrate the process as it happens. Also, as new projects are added to your list this allows you to share the “complete picture” so that your boss can help to prioritize projects and anticipated deadlines as necessary.
• Highlight Jumps in Productivity – There will be times when you are simply more productive than normal. Don’t hinder your performance or hold back a task to avoid heightened expectations. You want your boss to know that you are capable of amazing things. But context can help manage future tasks. If you get something done faster than normal, explain why you were more productive and what a reasonable amount of time would be for the future.
• Communicate Fixes with Problems – Don’t use hiccups in a project to explain away delays. When presenting a problem to your boss, pair it with a potential fix. Even if it’s not the right fix, it shows initiative and buy-in to the overall mission of your team.

Everyone wants to be the rockstar their boss relies on when things get tough. Still, it’s a fine line between an invaluable top performer and an overworked, underappreciated cog in the machine. Manage your boss’s expectations and impression of your work and you will ideally avoid these issues from recurring in the future.