101 Project Management Problems and How to Solve Them

Practical Advice for Handling Real-World Project Challenges

Tom Kendrick

• Publisher: AMACOM
• Year: 2025
• eBook ISBN: 9780814415757
• Topic: Business
• Subtopic: Decision Making
• Index: Business

In this helpful how-to, author Tom Kendrick reveals field-proven principles for navigating high-pressure situations, so you can overcome any obstacle.

Even with a terrific project management program in place, problems can arise to derail your team's hard work. This book explores a wide range of challenging scenarios and practical solutions and is packed with insightful answers to over 100 of your most urgent project management questions.

In  101 Project Management Problems and How to Solve Them, you'll learn how to:

• keep a project on track despite unavoidable interruptions;
• how to prevent unreliable outside collaborators from jeopardizing the entire project;
• how to manage project teams who have little or no project management experience;
• how to make up for lost time without cutting corners;
• and how to succeed--even in the face of threatened budget cuts.

The last thing you need in the heat of battle is to dive into project management theories. While there's no one right answer to the challenges you face as a project manager,  101 Project Management Problems and How to Solve Them has a plethora of actionable guidelines that help you troubleshoot quickly so you can get back to doing what you do best.

PART 1: GENERAL

1. What personality type fits best into project management?

Depends on:

The type and scale of the project

Experience of the project team

Understanding Personality Types

There are a large number of models used to describe personalities. One of the most prevalent is the Myers-Briggs Type Indicator (MBTI). One of its factors describes a spectrum between introversion and extroversion. Projects are about people and teams, so good project leaders tend to be at least somewhat extroverted. Introverted project managers may find their projects wandering out of control because they are insufficiently engaged with the people responsible for the work.

A second factor is the dichotomy between a preference for observable data and a preference for intuitive information. Projects are best managed using measurable facts that can be verified and tested. A third factor relates to whether decisions are based on logical objective analysis or on feelings and values. Projects, especially technical projects, proceed most smoothly when decisions are based on consistent, analytical criteria.

The fourth MBTI factor is the one most strongly aligned with project management, and it describes how individuals conduct their affairs. On one extreme is the individual who plans and organizes what must be done, which is what project management is mostly about. On the other extreme is the individual who prefers to be spontaneous and flexible. Projects run by this sort of free spirit tend to be chaotic nightmares, and may never complete.

Considering Other Factors

Project managers need to be “technical enough.” For small, technical projects, it is common for the project leader to be a highly technical subject matter expert. For larger programs, project managers are seldom masters of every technical detail, but generally they are knowledgeable enough to ensure that communications are clear and status can be verified. On small, technical projects, the project manager may be a technical guru, but that becomes much less important as the work grows. Large-scale projects require an effective leader who can motivate people and delegate the work to those who understand the details.

Good project managers are detail oriented, able to organize and keep straight many disparate activities at a time. They are also pragmatic; project management is more about “good enough” than it is about striving for perfection. All of this relates to delivering business value—understanding the trade-offs between time, scope, and cost while delivering the expected value of the project to the organization.

Finally, good project managers are upbeat and optimistic. They need to be liked and trusted by sponsors and upper management to be successful. They communicate progress honestly, even when a project runs into trouble. Retaining the confidence of your stakeholders in times of trouble also requires communicating credible strategies for recovery. Effective leaders meet challenges with an assumption that there is a solution. With a positive attitude, more often than not, they find one.

2. What are the habits of successful project managers?

Effective project leaders have a lot in common with all good managers. In particular, good project managers are people oriented and quickly establish effective working relationships with their team members.

Defining Your Working Style

One of the biggest differences between a project manager and an individual contributor is time fragmentation. People who lead projects must be willing to deal with frequent interruptions. Project problems, requests, and other imperatives never wait for you to become unbusy, so you need to learn how to drop whatever you are doing, good-naturedly, and refocus your attention. Project leaders who hide behind “do not disturb” signs and lock their doors run the risk of seeing trivial, easily addressed situations escalate into unrecoverable crises. Between urgent e-mails, phone calls, frequent meetings, and people dropping in, project managers don’t generally have a lot of uninterrupted time. You may need to schedule work that demands your focus and concentration before the workday begins, or do it after everyone has left for the day.

This is a crucial part of being people oriented. Project leaders who find that they are not naturally comfortable dealing with others tend to avoid this part of the job and as a consequence may not stick with project management very long, by either their own choice or someone else’s. Being people oriented means enjoying interaction with others (while being sensitive to the reality that some of your team members may not relish interaction as much as you do) and having an aptitude for effective written communication and conversations.

Referring to an Old List

As part of a workshop on project management some time ago, I challenged the participants in small groups to brainstorm what they thought made a good project leader. The lists from each group were remarkably similar, and quite familiar. In summary, what they came up with is that good project managers:

Can be counted on to follow through

Take care of their teams

Willingly assist and mentor others

Are sociable and get along with nearly everyone

Are respectful and polite

Remain even tempered, understanding, and sympathetic

Can follow instructions and processes

Stay positive and upbeat

Understand and manage costs

Are willing to “speak truth to power”

Act and dress appropriately

Reviewing the results, I realized that the items from the brainstorming closely mirrored those of another list, one familiar to lots of eleven-year-old boys for about a century; that list is “the Scout Law.” The version I’m most familiar with is the one used by the Boy Scouts of America, but worldwide other variants (for Girl Scouts, too) are essentially the same.

Effective project leaders are trustworthy; they are honest, can be relied upon, and tell the truth. They are loyal, especially to the members of their team. Project managers are helpful, pitching in to ensure progress and working to build up favors with others against the inevitable need that they will need a favor in return some time soon. Wise project leaders remain friendly even to those who don’t cooperate, and they value diversity. They are also courteous, because the cooperation that projects require is built on respect. Project managers are generally kind, treating others as they would like to be treated. We are also obedient, following rules and abiding by organizational standards. Good project managers are cheerful; when we are grumpy no one cooperates or wants to work with us. We are thrifty, managing our project budgets. Effective project leaders also need to be brave, confronting our management when necessary. Good project managers are also “clean.” It is always a lot easier to engender respect and lead people when we are not seen as sloppy or having low standards. (Actually, there is a twelfth item on the Boy Scout list: Reverent. Although it did not come up in the brainstorm, praying for miracles is not uncommon on most projects.)

3. I’m an experienced individual contributor but very new to project management. How do I get my new project up and going?

Depends on:

Availability of mentoring, training, and other developmental assistance in your organization

Your aptitude for leading a team and any applicable previous experience you have

The experience of the team you are planning to lead

Getting Started

Initiation into project management often involves becoming an “accidental project manager.” Most of us get into it unexpectedly. One day you are minding our own business and doing a great job as a project contributor. Suddenly, without warning, someone taps you on the shoulder and says, “Surprise! You are now a project manager.”

Working on a project and leading a project would seem to have a lot in common, so selecting the most competent contributors to lead new projects seems fairly logical. Unfortunately, the two jobs are in fact quite different. Project contributors focus on tangible things and their own personal work. Project managers focus primarily on coordinating the work of others. The next two problems discuss the responsibilities and personality traits of an effective project manager, but if you are entirely new to project leadership you will first also need to set up a foundation for project management. Novice project managers will need to invest time gaining the confidence of the team, determining their approach, and then delegating work to others.

Engaging Your Team

Gaining the confidence of your contributors can be a bit of a challenge if you are inexperienced with team leadership. Some people fear dogs,

and dogs seem to know this and unerringly single out those people to bother. Similarly, a project manager who is uncomfortable is instantly obvious to the project team members, who can quickly destroy the confidence of their team leader at the first signs of indecision, hesitancy, or weakness. Although you may have some coverage from any explicit backing and support of sponsors, managers, and influential stakeholders, you need to at least appear to know what you are doing. It’s always best to actually know what you are doing, but in a pinch you can get away with a veneer of competence. Your strongest asset for building the needed confidence of your team as a novice project manager is generally your subject matter expertise. You were asked to lead the project, and that was probably a result of someone thinking, probably correctly, that you are very good at something that is important to the project. Work with what you know well, and always lead with your strengths. Remember that “knowledge is power.”

Seek a few early wins with your team, doing things like defining requirements, setting up processes, or initial planning. Once the pump is primed, people will start to take for granted that you know what you are doing (and you might also). Establishing and maintaining teamwork is essential to good project management, and there are lots of pointers on this throughout the book.

Choosing Your Approach

For small projects, a stack of yellow sticky notes, a whiteboard to scatter them on, and bravado may get you through. For most projects, though, a more formalized structure will serve you better. If possible, consult with an experienced project manager whom you respect and ask for mentoring and guidance. If training on project management is available, take advantage of it. Even if you are unable to schedule project management training in time for your first project, do it as soon as you can. This training, whenever you can s...

Table of contents

• Cover Page
• Title Page
• Copyright Page
• Dedication
• Contents
• Introduction: Explanations
• Part 1: General
• Part 2: Initiation
• Part 3: Teamwork
• Part 4: Planning
• Part 5: Execution
• Part 6: Control
• Part 7: Tools
• Part 8: Closing
• Index