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A Project Manager’s 4 Greatest Challenges

Challenges are an ever-present fact of life for project managers. Nothing you will read here changes that. However, by adjusting the approach to these challenges provides the possibility of making them less daunting.

As everyone in the game knows, the issues one faces day-to- day are many and varied. No one can address them all because we don’t have any idea what they all are. Most of the problems we face are unanticipated and only reveal themselves as the project progresses. That said, there are core problems inherent in the life-cycle of every project, such as:

  • Managing expectations
  • Maintaining focus
  • Overcoming team biases
  • Closing the vision gap with executive management

Managing Expectations

Roadmapping is the mechanism by which product managers communicate where the project stands, where the project is going and how the project will arrive. In short, a roadmap is the vehicle for managing expectations.

Challenges usually arise when arbitrary deadlines are not met. To overcome this challenge, we need to abandon some of the preconceived notions we embrace about roadmapping. Hard dates should be eliminated and replaced with less rigid time brackets. Make the roadmap accessible to colleagues and stakeholders, which will integrate them into the product loop. Finally, treat the roadmap as a flexible document rather than an unyielding one by using a format that can demonstrate changes and be updated easily to reflect new decisions brought about by new or better innovations.

Maintaining Focus

Too many of us allow day-to-day demands to overshadow our truly important objectives. Instead, we allow ourselves to be distracted by urgent, although less important matters. Bogged down with emails and derailed by meetings, we are unable to concentrate on strategy. 

This problem can be overcome by breaking down larger strategic goals into more manageable parts. These smaller components will be easier to integrate into your daily routine. It is also helpful to keep your product vision front-of-mind by keeping it visually prominent through printouts posted around the office. It is also helpful to weigh the cost versus benefit for each decision before committing to a product change. This analysis can spare you from paying twice for the same real estate.

Team Biases

Most project managers would concur that their primary focus should be on the needs of their customer, but meeting those needs requires input from everyone in the organization with a customer-facing role. Unfortunately, the sales department, marketing department and other stakeholders are biased in favor of their objectives, and these will not necessarily align with the product direction. 

Meet this challenge by being the definitive link that brings these disparate team views together. Encourage everyone to see the big picture and how their views relate. By doing so, a large part of your mediation work is already accomplished. Additionally, it is paramount that all team input be recorded. If a team’s concern can’t be addressed by the current project, you can point out ways in which it may be addressed in future projects or how it is being addressed elsewhere.

Closing the Gap

How deeply the executive team gets into the weeds will vary with your business, its size, and the personalities involved. Nonetheless, these are the people you need to convince, not only of your vision but the path you have chosen to achieve it. Keeping the daylight between you and the executive team to a minimum can be your greatest challenge. 

The best way to achieve the management nexus is by creating a rigorous and demonstrably equitable process to qualify new ideas and evaluate inputs. This gives you the ability to defend all your decisions, pro or con, with logical arguments grounded in sound business practice.

When the executive team is satisfied that your approach to all ideas, including their own, is fair, consistent, and well reasoned, you will see push back and daylight reduced to a minimum.


Of course, these challenges only scratch the surface, but, they are among the most significant. Following these suggestions are not guaranteed to make your life as a project manager easier, however, they are an excellent starting point.

Imagine having greater flexibility with your roadmap and an easier time maintaining focus. Think about how much further along you would be if you implemented a solution for team bias. More to the point, how much less stressful would your job be if you were able to win the support of your executive team?

I can’t guarantee success even if you implement all these suggestions. However, I can guarantee you that they are worth putting to the test.