If you’re a project manager – even if not by title, but as a part of your job – you know how difficult and stressful it can be to manage all the minute details of your projects in a way that:

  • Delivers the project on time.
  • Keeps the project on or under budget.
  • Keeps all the project resources and stakeholders HAPPY.

Most projects won’t satisfy all of these requirements – at least, not in a way that doesn’t seriously jeopardize the sanity and well-being of the project manager and her team. Did you know…

  • Only 37% of project teams in the U.K. complete projects on time more often than not. (Wellingtone)
  • Almost half (49.5%) of project managers report that managing costs was their biggest challenge, while 46% are challenged with hitting deadlines. (Liquid Planner)
  • 59% of U.S. workers say communication is their team’s biggest obstacle. (Atlassian)

I asked 7 business leaders for whom project management is a key component of their jobs: What is your biggest project management challenge, and how did you overcome it?  They certainly did not disappoint, and hopefully their solutions will help you overcome your own project hurdles.

Ashley Saliba, Product Manager, TINYpulse

“Our company follows Agile development methodologies. In Agile, scope and resources are variable, but time is fixed. We’ve run into issues in some releases where we’ve cut items in order to stay within a timebox. We de-scoped items that we thought were low in value but turned out to be hugely important to end users. This pain usually presents itself rather quickly after the release, so we know exactly what needs to be done to alleviate the issue and get the customers what they need. We learned a lot out of this problem, so we focus more on quality than the deadline.

“Our Agile teams use Jira for project tracking. We find this tool to be incredibly useful, especially when determining value and priority of individual items. Product Owners use it to list out user stories for each feature and can prioritize them accordingly. And if there are some stories that don’t fit into a sprint, they’re kept in the backlog or re-added back to the backlog for future prioritization.”

Ashley Harper, Director of Strategy and Learning, Overflow Storytelling Lab

“One of the biggest challenges any project manager faces is the urgency of day-to-day responsibilities, requests, and unforeseen “fires.” Trying to keep a project moving while those responsible for the work are struggling to keep their head above water can seem like a losing battle at times.

“To help ensure that teams continue making progress toward their deadline, it is important to give employees tools to help prioritize their time. The easiest way is to ensure that team members have a clear and common understanding of company goals. Managers and project managers can help by working with their team members to understand how their work is important to the achievement of overall company goals.

“However, this is not enough. The adoption of an agile approach provides a framework for open transparent communication, accountability, and real-time course-correction. Involving those doing the work in planning drives high levels of buy-in. And holding regular meetings for teams to make commitments, discuss progress, and troubleshoot challenges keeps individuals focused on top priorities and provides a natural forum for issue escalation.

“I have seen this work when rolling out a strategy execution system built on agile principles. The improved cross-functional communication and cooperation across teams drove new efficiencies, while team accountability drove increased effectiveness – which translated into increased bookings and profits.”

Jerry Haffey, Jr. President of Business Development, Ambrosia Treatment Center

“Launching the HopeTracker.org website was the biggest project we’ve ever taken on.  Things went fairly smoothly throughout the planning, research, writing and design phases, but faced a huge roadblock when we hit development.

“The developer would miss his own deadlines, which frustrated the team and the excitement for the project was diminishing.  I questioned if his skill level wasn’t high enough or if our requirements weren’t clear enough.  However, the real answer was that other departments were giving him unimportant side-tasks that no one was aware of.  Even though these were small, and the developer thought negligible, the side-tasks sucked an hour or two out of his schedule nearly every day.

“I implemented a new company-wide process where all developer requests would come to me.  With me saying “no” and putting things on hold, the project suddenly started to move smoothly.  While it seems like such a simple thing to clearly understand the schedule and priorities of each team member, it would have been easy for us to get sucked into the frustration or implement incorrect solutions that would only make things more complicated.”

Elizabeth Harrin, CEO and Founder, The Otobos Group and Writer, A Girl’s Guide to Project Management

“I was working on a project that impacted almost everyone in the business. It was the launch of new software and required a lot of support from business users. The go-live date was scheduled for a holiday time when we knew the business would be relatively quiet. Unfortunately, for various reasons we had to change the go-live date for the software from that holiday to another holiday period.

“This was an unpopular decision, as many people had made arrangements to be working over the holiday to support the go-live. They had postponed family time to the next holiday time… and we had just messed up all those plans.

“However, as a project manager, I had worked hard at building relationships with the key stakeholders, as had the people in the team. We were well-respected, and we worked with a number of subject matter experts who also held formal and informal positions of authority in the business. The project team also had strong executive support. It was those relationships that helped us in the end. No one wants to make tough decisions, especially when they impact other people’s work and personal plans. But sometimes it needs to be done. Luckily, the good relationships and good communication channels we had built up helped us explain the rationale for the decision, communicate next steps and get the project back on track with little impact to the project’s reputation overall.”

Kathy Washenberger, CIO, FocusPoint Technologies

“With project management, there are a number of challenges for project managers. The one most challenging is usually around influencing without authority. This means that they are responsible for an entire team of individuals selected to do various project tasks, yet they do not directly supervise/manage the resources. In many cases, the resources performing the work have priorities that compete with the project work they are assigned. They will often times focus on the priorities that come directly from their supervisor/manager and let project work slide. This can be extremely frustrating for program/project managers, but many have found solutions.

“Some of the solutions that work for program/project managers when resources are not performing on their tasks include the following:

“Building Solid Relationships Early. Project managers are leaders of teams. They must be strong leaders that will motivate others to follow them in a positive manner. Building relationships with the team early in the project (through team-building activities or other ice-breaker events) is key.

“Setting Expectations and Following Through. Early in the project, the project manager must set expectations with the team. If those expectations are not met, it is critical that the project manager hold the individuals accountable immediately.

“Reporting on Project Progress to Leadership. Regular reporting using metrics on resource performance, task completion, etc., can be a great motivator. No one wants to be on the “naughty list.”

“Knowing When to Escalate. Many project managers struggle with escalating issues, especially related to resources. They feel they can fix the issue itself, it will magically go away, etc.  The reality is the project usually continues to fall behind. The project manager then has to explain why no one was told about the major delay.  On the other hand, a project manager doesn’t want to escalate all the time – that’s not good leadership either. Finding the right balance is key.”

Dr. Celia Szelwach, PMP

“I was managing a major HRIS/Payroll system conversion during a time of significant transition and change with one of my clients. During this time, there was a restructuring, whereby several essential team members transitioned off my project team – including the project sponsor who had not kept the senior-level executive team completely informed about this project. As the project leader, I had to manage the politics of the situation with the senior-level executive team, re-sell the project as we had already signed a contract with the vendor and were already in project execution, and keep the project team positive and hopeful that we could still complete the project successfully. I overcame this challenge by staying positive about the outcomes, engaging my team to help me re-sell the benefits of the project and value to the organization, keeping the new project sponsor updated on any potential concerns, and continuing to manage the project closely with the vendor.”

Seb Dean, Managing Director, Imaginaire Digital

“The most common project management dilemma we used to face as a web design agency was scope creep and the friction associated with adding costs during the project. We realized over time that customers will often sign up to a scope based on their needs there and then, but will often want to add features as the website is being built.

“The two problems we were facing were 1) customers moving the goal posts in terms of what was required and 2) the issue of charging for these changes.

“To counteract this, we moved to our own hybrid agile project management philosophy, explaining to customers that changing their needs and adding features was absolutely fine and encouraged, but there would be additional charges and a timescale impact to facilitate these changes. We now add clients to our project management software and allow them to request features, then quote for them and require approval before we begin working on them. This added transparency has helped us make projects run much more smoothly.”