3 Project Management Challenges Faced by Project Leaders at Small Businesses (and How to Solve Them!)

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Being a project manager isn’t easy.

You have to overcome significant challenges in your efforts to deliver project value—including scope creep, time management, keeping teams on the same page, and more.

Controlling and managing these issues can feel like a full-time job. And for project managers at large organizations, it often is.

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If you’re in charge of projects at a small or midsize business (SMB), however, “project manager” is often just one of your many hats and a mantle you’ve assumed without any formal project management training or certification.

This means that you have to work that much harder to keep all the plates spinning—a balancing act that makes it difficult to spot and correct project management challenges.

Left unchecked, these issues can snowball, risking not only your capacity to deliver project value but also your ability to achieve business goals.

As Mark Langley—president and CEO of Project Management Institute—states in the 2018 Pulse of the Profession report:

“If your organization is not good at project management, you’re putting too much at risk in terms of ultimately delivering on strategy.”

If you’re simply getting by, from a project management perspective, or worse (are actively bad at keeping all those plates spinning), you’re compromising your business’ ability to achieve strategic goals.

Before those plates go crashing to the floor, read on to learn from three of your peers who identified and overcame their own project management challenges.


Project management challenge #1: Balancing PM responsibilities with other job duties

Liz Theresa—founder of LizTheresa.com, an online marketing and design firm—is a big advocate of hiring smart people who can challenge you to work better, not harder. But it wasn’t always so.

In the beginning, she ran her agency by herself. But after four years spent doing 100% of the work, she reached a breaking point:

“I was trying to go to sleep after working like crazy, only to realize I needed to hit ‘publish’ on a page in WordPress because I had a client launching a sale at midnight.”

So she resolved to make a change, beginning with hiring a team to help shoulder the load.

 The solution:  Like many entrepreneurs going from a team of one to a team of more than one, Theresa learned that balancing her workload wasn’t just about hiring more team members, but also about learning to trust her team enough to delegate tasks.

“It was hard for me to let go of 100% control, but when I did, the quality of what we produced improved dramatically.”

After auditing her responsibilities, she discovered several action items that were better delegated to a team member, despite her initial resistance to hand things off.

“Development tasks that took me six hours now take six minutes, because [the developer] is in their zone—which reminds me to stay in mine,” Theresa says.

Because her team is distributed, they use a variety of tools to stay connected:

  • Monthly conference calls
  • Slack: Day-to-day communication
  • Basecamp: Centralized task management

A to-do list in Basecamp, a project management tool

To-dos in Basecamp (Source)

 The results:  Theresa’s task-time audit saved her up to nine hours each week. In other words, she got an entire workday back by delegating tasks that didn’t require her specific oversight.

The big takeaway for SMBs


People have finite bandwidth to devote to work, and when they reach their limit, the result is increased stress (often leading to burnout) and degraded work performance. And when this negatively impacts project outcomes, you compromise your ability to achieve strategic goals.

Remember that “balance” doesn’t mean “layer on top of.” If you (or other project leaders) are taking on project responsibilities in addition to your regular job duties, offset the added load by delegating tasks that don’t require project manager oversight.

Prioritization at this level requires forethought, level-of-effort (LoE) tracking, and a structured schedule. Start using a task management tool, ideally with time tracking functionality so you can monitor LoE for different tasks, and diligently maintain your calendar.

Project management challenge #2: Keeping teams on the same page, and not missing tasks

Flynn Zaiger—CEO of Online Optimism, a digital marketing agency—knows that a shared understanding of what’s considered a priority is fundamental for success. But sometimes it takes a catalyst—such as your business going through a period of fast growth—to realize that you need different and/or additional tools to ensure this same degree of transparency.

When Zaiger founded the agency in 2012, they relied on email and in-person discussions to communicate—as many startups and small businesses do.

But then the company started growing, and fast. The more employees that were hired and departments that were formed, the harder it became for Zaiger to keep track of what was going on, and for employees to keep track of what he wanted them to do.

“When my entire team isn’t on the same page, it’s not only frustrating, but it causes us to fall behind, redo tasks, and forget to do things altogether… I realized there was a problem when we missed deadlines when onboarding a new client due to all the work we had going on, leading to a lack of initial trust—a major issue.”

 The solution:  After researching solutions, Zaiger and his team decided to invest in Slack to streamline communication and Asana to improve workload management.

Here’s a breakdown of how his team uses these tools:

  • Slack: Create channels for different projects and topics and loop in team members that need to be involved in the conversation. Share files, have real-time conversations, and reach conclusions. As an added bonus, conversations are laid out in a familiar format and are easier to follow than long email chains.
  • Asana: Assign projects, tasks, and due dates, making it easy for employees to keep up with action items and check them off when complete. The tool will automatically compile tasks into a to-do list based on deadlines to help users prioritize their work.

Additionally, these tools integrate with each other so users can get notifications in Slack when a task in Asana is created or completed.

Zaiger and his team also created specific “rules” to help govern tool use. For example, all tasks that take longer than one minute are assigned in Asana, and larger projects prompt an email from the team in addition to the assignment.

As the project leader, Zaiger also uses the dashboard in Asana to oversee the work being done that day and/or week, and monitor employee workloads to avoid bottlenecks.

“I like to make sure that everyone has their fair share of projects on hand without one person being too busy.”

A project dashboard showing the status of different projects in Asana, a project management tool

Project dashboard in Asana (Source)

 The results:  Zaiger’s agency tripled their full-time staff in under two years, and Zaiger credits their project management software for the company’s ability to handle that kind of growth by keeping everyone on task and ensuring action items weren’t overlooked.

Additionally, he notes that the day-to-day time savings these tools provide has been a huge positive.

“We still have meetings,” Zaiger says. “But we don’t have to schedule as many meetings when everyone on my team is able to ask and answer questions right away.”

The big takeaway for SMBs


Know when to change, particularly when it comes to saying goodbye to outdated processes and tools. When either (or both) of these are outdated, they impede productivity rather than enable it.

If you’re a first-time PM software buyer, look for tools that will increase transparency into employee workloads and maintain open lines of communication.

If you’re replacing your current system, find out your employees’ pain points (e.g., the current tool lacks functionality, or isn’t a good fit for workflows), and then involve those employees in product demos to ensure the new solution is a better fit for their needs.

Project management challenge #3: Ensuring projects align with and help execute your business strategy

Anders Thomsen—CEO of NoMore, an agency that provides PowerPoint services for management consultants—recognizes that having sufficient time is the most significant challenge faced by businesses every day. A related challenge? Wasting time on projects that deliver little value.

Six months after launching the agency, Thomsen says they found themselves running more than 20 parallel business development efforts. And despite being sound ideas, there was very limited impact coming from these projects.

During an advisory board session, one of the members asked: “How are you spending your time and what is driving the most impact?,” Thomsen remembers.

“I realized I couldn’t give a short precise answer—we were simply running too many things and not focusing on either impact or completion.”

 The solution:  To ensure teams are executing projects that align with and help drive business strategy, Thomsen conducts biannual strategy sessions with the agency’s COO and CMO to discuss their overall business priorities for the following six months.

Then, they set overall targets and choose specific projects to execute in that time. When selecting initiatives to execute on, they consider the following:

  • Expected impact on six-month focus area
  • Feasibility
  • Time to execute
  • Risk

During those six months, they closely monitor each initiative in a spreadsheet and track the above variables as well as project status, who owns what, and any next steps.

During project execution, Thomas says all departments have daily scrum meetings to discuss bottlenecks and check in on overall progress. Additionally, they hold weekly company meetings to discuss last week’s outcomes and next week’s goals.

His teams use a variety of tools to stay on top of task and project progress:

  • Email: For non-urgent one-off communication.
  • Slack: Anything urgent (anything client-related, or things that block you from being productive).
  • Trello: For ideas, bugs, etc.
  • Zendesk Guide: For any information that might be relevant for future employees (non one-offs), e.g. “how to deal with new customers requesting an NDA”.

Setting up a Zendesk integration in Slack

Setting up a Zendesk integration in Slack (Source)

 The results:  After implementing these tools and processes, Thomas’ agency significantly increased their revenue and achieved “break-even” after 18 months with a team of only ten people. Since then, the team and the business have continued to grow.

NoMore has also seen a substantial increase in their net promoter score among customers—going from around 20% to 80% over the last year, while keeping 100% growth in their business.

The big takeaway for SMBs


Strategy is delivered, and business goals are achieved, through projects. Which is why it’s essential to evaluate initiatives against specific criteria before projects get the green light—e.g., expected tangible outcome, unique value-add, risk return profile, etc.

Additionally, conduct project-and-strategy alignment meetings at least twice a year to ensure the right work is prioritized, and employees have a clear idea of how projects align with business goals.

Then, track performance in a project management tool so you can draw on historical project data to make more informed future investment decisions.

Additional resources for project leaders

Whether you’re a full-time project manager or a business leader taking on project manager responsibilities, we can all use a little help in overcoming key project management challenges.

The solutions outlined above are three examples of how your peers learned to balance workloads, stop tasks from falling through the cracks, and align projects with business strategy.

But there are many issues project professionals face every day. Tell me in the comments below what your biggest project management struggles are, and we can ideate solutions together.

We publish new research every week, so don’t forget to subscribe to our project management blog to stay up-to-date on the latest project management technology trends.


Note: The information contained in this article has been obtained from sources believed to be reliable. The applications selected are examples to show a feature in context, and are not intended as endorsements or recommendations.

Looking for Project Management software? Check out Capterra's list of the best Project Management software solutions.

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About the Author

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Eileen O'Loughlin

Eileen O’Loughlin is a Senior Project Management Analyst for Capterra. Her research helps small businesses leverage the latest technology and trends to solve key business challenges and achieve strategic goals. Her work has been cited in various publications, including CIO.com, ProjectManagement.com, ProjectsAtWork and DevOps Digest.

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