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A Day in the Life of A Project Manager at WillowTree

Shankhamala Choudhury
Program Director
March 2, 2021

Did you know that, according to a KPMG research, 70% of organizations have suffered at least one project failure in the prior 12 months? Additionally, 50% of respondents indicated that their project failed to consistently achieve what they set out to achieve. Companies that don’t have a strong project management discipline end up wasting their resources, time and money. Therefore, organizations with strong project management practices waste 28x less money because they successfully complete their projects.

A project manager (PM) is the anchor for force for a successful delivery of a project. Project managers at WillowTree have the opportunity to collaborate with Fortune 500 clients and help the client to set a product vision while advising and managing scope, risk, and new product opportunities. While a PM at Willowtree wears multiple hats (see blog), good soft skills are the key to success for a PM.

The core of a PM’s role is communication, coordination and control. A project manager has a people-facing role and needs to work alongside team members to achieve the common goal. Every PM at Willowtree has a different routine and schedule and it may vary depending on the type of project, type of team, and type of industry. However, there are some key functions that every PM performs and are critical to a team’s success. Therefore, my typical day might look slightly different from my other peer PMs at WillowTree, but I hope this blog gives you some insights into the PM life.

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Meetings - 55%

With Covid-19 and remote work, PMs are increasingly finding themselves spending more time on video conferencing calls than any other role. Prior to COVID, a lot of meetings could happen face-to-face and in person and helped teams to have more meaningful conversations. According to Workplace Insight, 73% of employees are reporting burnout as a result of COVID-19. However, in the midst of all this, a PM is still responsible to keep the team morale and team engagement high and ensure a successful delivery of the project.

At WillowTree, we encourage most of clients to follow Agile Software Methodology. As a result, many teams within WillowTree can be found to work in Scrum (a type of agile methodology). Scrum is a lightweight framework that helps people, teams and organizations generate value through adaptive solutions for complex problems. For teams following Scrum software development, they need to attend multiple Scrum events (meetings) such as Daily Stand Up, Sprint planning, Sprint grooming, Sprint demo, Sprint retrospective. Oftentimes, it’s the WillowTree PM who facilitates these meetings. While Daily Stand Up (as the name suggests) occurs every day, other events take place based on the cadence of the sprint.

In addition to these, PMs are heavily involved in client meetings which could include daily client syncs, feature/product kick-off meetings, executive briefing meetings and project planning/status meetings. At WillowTree, we also focus heavily on team collaboration and team bonding. So on a typical day, PMs can be found organizing and leading internal and/or external team meetings for improving team health. Last but not the least, at WillowTree, we encourage PMs to conduct regular 1:1 meetings with their team members to provide feedback, improve productivity and strengthen relationships.

Project Documentation - 15%

One of the key responsibilities of a PM is to remove impediments for their team members and help the engineering team focus on the delivery of the project. As a result, it is quite common for WillowTree PMs to gather requirements, follow up with clients to clarify and understand features requests and in turn also write user stories. In addition to this, a PM is also responsible for creating a project plan and updating the project plan regularly. WillowTree PMs often use client syncs to walk the client through the project plan and update them of any changes made to the existing project plan.

One of the key aspects to make a project successful is to create a risk register. Therefore, the PM is responsible for identifying and tracking potential project risks and ensuring that the client is looped in from time to time on these risks. A good PM will always make sure to identify the risks and take action accordingly in order to manage and complete the project successfully. Last, but not the least, during the course of the project, WillowTree PMs creates executive reports to inform the key stakeholders on the client side with the project status, major project updates and key milestones, team performance and health, and any risks associated with the project. The cadence of the executive report varies from project to project but it could be on either a biweekly basis or a monthly basis.

Communication and Collaboration - 20%

According to saaslist, 31% of companies say that miscommunications about project objectives is the number one reason why projects fail. Hence, it cannot be emphasized enough how deeply communication and collaboration is tied to both a project and team’s success. A PM needs to have very clear, crisp and open communication with the client and the team. Oftentimes, WillowTree PMs can be found involved in heavy negotiations regarding feature requests and competing priorities. PMs work closely with the client counterparts to agree on priorities so that both the client and the development team has a clear understanding of the roadmap and the deliverables. Once an agreement has been reached, it is the responsibility of the PM to communicate the project plan, project timeline, key milestones and deliverables both internally and with the clients. At WillowTree, PMs work in partnership with the Engineering Directors (each project within WillowTree is assigned a project manager and an engineering director) and the development team to clarify requirements, identify dependencies, unblock issues, and chase requirements/issues with client teams or stakeholders.

Keeping Momentum of Projects - 5%

While keeping the momentum running on projects seems to be tied to all the above mentioned points, it might be hard to believe that it does take some dedicated time to keep the ball rolling. It is the responsibility of the PM to keep going back and continuing the email correspondence for ongoing issues. Additionally, the PM also needs to review all the notes from the meetings and post-meetings, and may need to invest time either troubleshooting or following up on action items. Furthermore, a good PM will also invest time to learn and plan from these meetings for future actions and prepare accordingly for the rest of the week/upcoming weeks.

Reading and Relaxation - 5%

Though all the above mentioned may seem overwhelming, PMs at WillowTree also get time to relax. There are multiple Slack channels focusing on different interests, where employees engage in meaningful/fun conversations. PMs at WillowTree also spend time on reading new articles, sharing interesting finds on the PM Slack channel, and participating in fun team events. There is enough time during the day to unwind and unplug and spend some time doing what one loves.


No two projects are the same and hence, my experience may differ from another PM within WillowTree. Irrespective of what project you manage, one lesson to remember is staying organized and being efficient in your day-to-day activities. Having good time management and strong communication skills will definitely help you meet the complex demands and manage the unpredictability associated with any project.

If you’re interested in project management roles at Willowtree, please visit our careers page.

Shankhamala Choudhury
Program Director

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