You have multiple deadlines to meet. How do you decide which one to tackle first?

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.

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.

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.

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.

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.

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