Managing multiple deadlines can be stressful and challenging, especially if you have competing priorities and limited resources. However, with some planning, organization, and strategy, you can decide which one to tackle first and deliver your work on time and with quality. Here are some tips to help you make the best decision for your situation.
The first step is to assess how urgent and important each deadline is. Urgency refers to how soon the task needs to be done, while importance refers to how much impact the task has on your goals, performance, or reputation. You can use the Eisenhower matrix, a simple tool that divides tasks into four categories: do first, schedule, delegate, and eliminate. Tasks that are both urgent and important should be done first, as they are critical and time-sensitive. Tasks that are important but not urgent should be scheduled for later, as they are strategic and valuable. Tasks that are urgent but not important should be delegated to someone else, as they are distracting and low-priority. Tasks that are neither urgent nor important should be eliminated, as they are irrelevant and wasteful.
Prioritizing multiple deadlines involves a strategic blend of urgency, impact, and task interdependencies. Utilizing the Eisenhower Matrix helps in assessing urgency and importance while considering time constraints. Simultaneously, identifying task interdependencies ensures a smoother workflow, addressing tasks that serve as prerequisites for others. Delegation, aligned with team strengths, aids in efficient completion. This comprehensive approach balances immediate needs, long-term goals, and team capabilities, ensuring effective management of deadlines while preventing bottlenecks in project progress.
In my experience, the best first step and most effective way to assess urgency and importance is by speaking directly with your manager or key stakeholders about each deadline. Many times, our deadlines are dedicated by others. When decision support is unavailable, using the Eisenhower matrix is an effective way for you to categorize competing tasks into smaller, more manageable to-do lists.
When juggling multiple deadlines, prioritize tasks based on urgency, importance, and proximity to due dates. Consider dependencies, workload complexity, and the consequences of missing deadlines. Align with client or supervisor priorities, schedule high-energy tasks during peak hours, and tackle quick wins for momentum. Negotiate deadlines when possible, break down larger tasks, and regularly reassess priorities. This approach, combined with effective time management, will help you navigate and meet multiple deadlines successfully.
Many people will recommend the Eisenhower matrix, which is a great tool. However, I feel that people often overlook how to apply the tool in way that allows you to manage your time effectively. When you are overwhelmed with pressing deadlines, it is important to tackle tasks that fall into the urgent/important box in the matrix. But, constantly chasing urgent/important activities can lead to overwhelm and burnout. So, I recommend that you spend most of your time tackling activities in the non urgent/important box. This requires living with intention and actually planning and scheduling your tasks and activities. My mantra is 'plan for the knowns while leaving room for the unknowns.'
Evaluate the urgency and importance of each task. Focus on high-priority tasks that are both urgent and important. Use frameworks like the Eisenhower Matrix to categorize tasks based on urgency and importance.
The second step is to estimate how much time and effort each deadline requires. Time refers to how long the task will take to complete, while effort refers to how difficult, complex, or demanding the task is. You can use the Pareto principle, also known as the 80/20 rule, to identify the tasks that will give you the most results with the least effort. The principle states that 80% of the outcomes come from 20% of the causes, so you should focus on the tasks that will have the most impact on your goals, performance, or reputation. You can also use the Parkinson's law, which states that work expands to fill the time available, to set realistic and specific deadlines for yourself and avoid procrastination.
I usually try to look into similar efforts if they exist. If not then building a Gantt chart usually helps with breaking the effort down and estimating the required workdays to complete. Then I add between 10%-20% of the critical path as a buffer, depending on the innovation level.
The third step is to prioritize and sequence the tasks according to their urgency, importance, time, and effort. Prioritizing means ranking the tasks from the most to the least significant, while sequencing means arranging the tasks in a logical and efficient order. You can use the MoSCoW method, a simple technique that categorizes tasks into four groups: must have, should have, could have, and won't have. Tasks that are must have are essential and non-negotiable, and should be done first. Tasks that are should have are important and beneficial, and should be done next. Tasks that are could have are desirable and optional, and should be done if possible. Tasks that are won't have are unnecessary and irrelevant, and should be avoided or postponed.
Ruthlessly prioritizing is critical to be effective and maximizing your impact. Years ago I learned the post it note trick - write out all the tasks/dependencies you need to do and sequence them in order and execute. Sometimes getting started is the most challenging and this helps figure out what goes first.
Once you listed all your deadlines decide which ones generate the bigger impact. If you are familiar with Parreto Principle (aka 80) you know that 80% of consequences come from 20% of the causes. The whole point of prioritizing your deadlines is to identify and focus on the 20% that will generate the majority of the impact. The other 80% think hard if you can transfer, delegate or eliminate them from your workload altogether. ? Your line manager may not agree with your decision, but it is important to communicate and explain your reasoning to them. Who knows they may realize the benefits and become a strong advocate for the 80/20 rule. At least they will appreciate the fact that you are thinking strategically.
I use a simple 2 X 2 matrix, with effort on one axis (low to high) and impact (low to high) on the other axis. I put everything I need to do as a dot on this matrix. Anything top right gets done first.
Multiple deadlines, doesn't necessarily mean you should tackle one before the other. Understanding the scope of each project is the key to prioritizing each element of each project, as many elements can be conducted simultaneously. All projects should be scheduled with contingencies and completion dates to meet or exceed any deadlines
In step #1 I estimated the expected income as a result of the task, and also the level of effort required for completing it. The higher the impact and the lower the effort will result in a higher prioritization of the task.
The fourth step is to communicate and negotiate with your stakeholders, such as your manager, clients, or colleagues, about your deadlines and expectations. Communication means informing them of your progress, challenges, and achievements, while negotiation means discussing and agreeing on the scope, quality, and resources of your tasks. You can use the RACI matrix, a useful tool that clarifies the roles and responsibilities of each stakeholder in a project or task. The matrix assigns four levels of involvement: responsible, accountable, consulted, and informed. Responsible means doing the work, accountable means making the decision, consulted means giving input, and informed means receiving updates. By communicating and negotiating effectively, you can avoid confusion, conflict, and disappointment, and ensure alignment and satisfaction.
Collaborating with your managers and stakeholders is vital to handling conflicting deadlines. It is best to start that line of communication for negotiation and solution building. Making this your first step will produce a better working experience for yourself and the peers around you.
This is the most important aspect in my opinion, most projects fail due to lack of effective communication which results in double (or triple) efforts, and not having the teams aim at a shared goal.
The fifth step is to review and adjust your plan and actions as you work on your deadlines. Reviewing means evaluating your performance, results, and feedback, while adjusting means making changes or improvements based on your review. You can use the SMART criteria, a well-known framework that defines the characteristics of good goals and objectives. The criteria are: specific, measurable, achievable, relevant, and time-bound. By reviewing and adjusting your plan and actions, you can monitor your progress, identify your strengths and weaknesses, and overcome any obstacles or challenges.
Periodic sync and check-ins are vital. Remember that a plan is just a starting off point for improvements. Being agile is a must in today's environment.
This is critical in today's rapidly changing environment. While it is tempting to make a plan and then "hunker down" to get it done, today's plan may not make sense in a few days. Reassessing priorities often is critical, otherwise you spend time on something that, once delivered, does not add much value.
The final step is to reward and celebrate your achievements and efforts after you meet your deadlines. Rewarding means giving yourself something positive or enjoyable, such as a treat, a break, or a compliment, while celebrating means acknowledging and sharing your success with others, such as your manager, clients, or colleagues. You can use the gratitude journal, a simple practice that involves writing down the things that you are thankful for in your work or life. By rewarding and celebrating yourself, you can boost your motivation, confidence, and happiness, and prepare yourself for the next challenge.
Every Friday, take 5 minutes and try to identify 2 or 3 projects/people that desire recognition for their hard work. Most companies and managers miss the opportunity to celebrate. If we do not stop to celebrate each other's hard work and commitment, we are nothing but grunt workers.
Inspect the items you need to complete from a risk level perspective - items you have done previously and say have minimum dependencies can be left to be done on a shorter timeframe as these are low(er) risk / higher certainty; whereas items you have not done before, or have dependencies (as an example) would benefit from being tackled first to minimize risk of surprises.
I would consider using the Pareto Principle. What action will deliver the biggest impact. 20% of the actions that delivers 80% results.
They're other prioritization systems to consider. I use a prioritization wheel for myself and with clients. You draw a circle and divide it into 8 sections. Then, you break your project into 8 components. From there, you ask yourself which area if you completed would have the most impact. You rank that as 1, and you continue asking the same question until you have ranked each component in the circle.
What about consideration of Risks and dependencies? Some tasks are high risk so may have to be prioritised, while others may derail other important tasks because of the nature of dependencies