Leading Projects with Aggressive Timelines

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I’ve often dealt with many projects that require a very aggressive timeline. It’s less a concern about prioritization and more about getting the products out there as quickly as possible. I have learned that there are a right way and a wrong way to tackle this kind of projects, and here are some tips:

Understand motivation behind the timeline (The WHYs and WHEN).

The first thing as a leader you need to figure out is whether the project is truly urgent in the first place or whether it can be spread out even a bit more. This is the first thing the developers will inquire about when you present the project to them, and you must be informed as much as you can to ward off any resentment or second-guessing. Discuss the project in great detail with your stakeholders to get a real sense of what is driving the urgency and timeline. There may be some valid reasons, such as developing a major sales pitch, supporting a marketing event, syncing up with an urgent technology shift, addressing customer pain points, or something else that drives your business forward.

While knowing that a true business need drove the deadline may not make your challenge any easier, understanding that there was a legitimate reason behind the need may further motivate you and your team members to try to achieve it.

Once you understand the motivation for urgency, the first thing you should do is to make your team aware of it. Even if you don’t have all the answers right away. It is extremely important — and I can not stress enough — that the team gets on board as early as possible with the gravity  and urgency behind the timeline in order to smoothly execute the project. You will be asking a lot of them throughout the project, so make sure they buy in and feel in the loop on the decision-making and what steps to expect.

Understand the deliverables (The WHATs)

Once you have the WHYs and WHEN in place, work with the product team and stakeholders to assess and measure the scope, deliverables and acceptance criteria of the project. You can use any project management tools (we use JIRA) to document them and break them into logical milestones. This will help you discover any possible blockers early in the game and help you communicate that to stakeholders ahead of time, rather than midway through the project when obstacles would inevitably turn up. Predict whatever you can and make those realities known to all.

Understand the resources allocation

As a team leader, you are in the best position to weigh the velocity of the team. You are also the best person to coordinate the  Team-Maturity model. This small act upfront will heavily impact the model if you’re planning to add extra resources to the team later on to complete this heavy project. Find out early on if your team possesses the necessary skillsets or if they require some training, coaching, or additional resources to get comfortable with the task at hand.

Optimize for Project Management Triangle

Like any human undertaking, projects need to be performed and delivered under certain constraints. Traditionally, these constraints are “Scope” (features and quality), “Time”, and “Resources (often understood as “Cost”), traditionally known as STR Model*. These considerations are also referred to as the “Project Management Triangle,” where each side represents a constraint. One side of the triangle cannot be changed without impacting the others. A further refinement of the constraints separates product “quality” or “performance” from the scope and turns quality into a fourth constraint. Weighing all of these considerations at once will leave you having to examine closely your priorities and what you’re willing to give on a bit. That’s because projects require some time and cost to create the deliverables agreed to in the project scope. When one of these constraints is out of balance, you can assume one of the others needs to be adjusted to get them back in alignment. For example, if your budget is cut, you need to reduce the scope or to increase the time to deliver.

In this case, The time constraint is not in alignment with the cost and scope. You’ll need to work with your stakeholders to increase the resources that are available for the project. Adding resources to the project makes the cost go up, but may also enable you to hit the deadline. However, it is not always advisable to use this leverage, as it can also have some unexpected side effects related to the existing team dynamic and having to onboard new team members.

Also, if cost is a major consideration, it’s worth thinking about ways to reduce the scope. See if there are features and functionality that they can live without for now, which you can get to in Stage 2 so that you can deliver the project within the deadline specified. It doesn’t have to be perfect to be finished.

Protect your team

As a leader, one of your key responsibility is to protect your team from external distractions. Working within an aggressive timeline, everyone will be feeling mental pressure to perform.  Show your team you have their backs, that you’re keeping all other requests at bay. This will give your team a necessary focus time to execute project rather than worry about what else they might be asked to do. To meet an aggressive timeline, you need focus.

Celebrate small success and have fun!

Success is largely about having a certain state of mind, a success mindset. By celebrating small successes, you begin to communicate a positive attitude of “We have already succeeded” or “We are successful” in everyone’s mind. As a result, your team will build confidence and cohesion and then accelerate the process of achieving the next milestone. A system of recognition and rewards helps foster and maintain a culture of motivation, unity, and satisfaction – and satisfied employees are more loyal and hard-working than their unsatisfied counterparts.

Whenever you hit a milestone, stop for a bit to enjoy that moment. Give yourself and your team a pat on the back.  What might seem like a break from the focus is actually, in these cases, a way to keep your team energized for what’s next on the list. They’ll appreciate you more for treating them with respect and admiration, and in turn to better work.

*STR Model

The STR model is a mathematical model which views the “triangle model” as a graphic abstraction of the relationship:

Scope = Time × Resources

Scope refers to complexity (which can also mean quality).

Resources include humans (workers or engineers), financial, and physical elements of a project.

[citation: https://en.wikipedia.org/wiki/Project_management_triangle]

Note that these values are not considered unbounded. For instance, if one baker can make a loaf of bread in an hour, that doesn’t mean ten bakers could make a loaf in six minutes.