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Are you familiar with these struggles: manual work, clunky reporting, lack of tools, overwhelming data, and constant competition over your attention? If so, I’m willing to bet you’re a program manager or portfolio manager.

And these are just some of the issues that keep portfolio managers up at night.

Our team partnered with monday.com to learn more about the main challenges facing program and portfolio managers. We spoke with a variety of portfolio managers about their most significant pain points, which included scoring, prioritizing, tracking, risk management, and reporting.

We dive deep into each pain point and offer practical advice and solutions to help you save time, increase efficiency, and regain some order.

Scoring

How do you decide which project is more important and what resources it should require? Scoring is a complicated issue and is influenced by stakeholders and clients, and has a lot of variants to take into consideration. 

“Scoring is crucial not just for decision-making transparency and support from upper management,” says Doron Eliezer, a PMP-certified Regional Director of Customer Success at monday.com, “but also for linking ground-level efforts to the company's broader objectives. When executed correctly, it serves as an excellent means to clarify the rationale behind our actions.”

There are numerous scoring methods portfolio managers use, but most of them feel the ones they use do not answer their needs. Some portfolio managers create specific and personal matrixes and calculations, and some focus on time frames, budgets, and due dates. 

But the most important thing to understand here is how crucial a suitable scoring method is. We can't stress this enough—it is the foundation of the portfolio, and if done carelessly, could affect efficiency in a big way. An accurate, thoughtful scoring method will help prioritize projects and help decide what to focus on when conditions shift, as they tend to do.

If a portfolio manager can create a clear, transparent scoring system that everybody can understand, their decisions are accepted easier and faster, and they can get broad agreement and cooperation from higher management as well as lower management, stakeholders, and employees.

Prioritizing

During the "ongoing phase" of a project, priorities are always changing, and portfolio managers are constantly struggling with it. When a new project starts or a customer asks for a change, you need to re-evaluate the whole situation and understand what can be deprioritized or moved around. Portfolio and program managers need to figure out how each change affects timelines and budgets—fast. 

At the moment, this is a grueling task for most portfolio managers. And remember that it's not enough to figure this out for yourself—part of the challenge of prioritizing is conveying these changes and their possible consequences to stakeholders and clients. Every decision has a price, and you must make it clear to everybody. 

Tom Evansen, Program Manager at Vaco, agrees: “Our biggest pain point is prioritization. Not being able to enter your financial waterline, your resource waterline, and maybe even a benefit waterline. I need something that will tell me, okay, you prioritize these three things, now you have this much money left. When you're doing the whole prioritization process, it's great to force rank things one through 10, for example. But it could be that you could do … 1, 2, 3, then you only have enough money left for 7. So it makes sense to jump down and include seven even though that means four, five, and six don't get done…” 

Sarah M. Hoban, Senior Director, Program Management Office at Aura says that part of this struggle has to be dealt with at the organization level. “A lot of organizations will say that they want to get better at prioritizing, but in practice, I don't often see it,” she says, “there's this fear of making the wrong decision, and so sometimes that leads to no decision at all.”

In order to reduce the strain of prioritization, “program managers need to ask those tough questions to force an environment or a culture around decision-making, like what do we want to do here? What are our next steps? What's our path forward? How does this fit into the bigger strategy?” Hoban says. 

“The other piece of it is working with the leadership at the organization to create a culture where it's okay for people to make mistakes and to have stretch goals and objectives,” she continues, “we're in a business environment where the priorities may change a lot and that's okay, but leadership has to message that…and then you have to take something off the plate too, as opposed to just adding and kind of keeping things on the back burner. That is the thing that kills productivity, that context switching in the background.”

Something else to consider when prioritizing is the organization’s big picture goals. According to Hoban, a lot of organizations “have a goal-setting process, but it's just checking the box. They make their goals at the quarter, but some of them never look at the goals again till the next quarter.” 

Related to that, organizations might “have this set of goals, but it really turns into like a laundry list of everything you're doing because you're not actually prioritizing,” Hoban says.

There also needs to be cross-functional collaboration. 

“Each department may set their goals and they're supposed to tie to whatever a company goal would be, and maybe it does,” Hoban says, “but maybe two departments have the same piece of a problem. I think goal setting is a way to force them to work together on that problem and understand that it's a common problem, but it takes a while before people learn that. So doing goal setting is a way of driving collaboration, but it takes a couple quarters to have a return.”

Tracking

Tracking is significant because program managers and portfolio managers are always looking for a simple way to understand the right moment to step in and intervene in a project. They can't be in the details—that is the project manager’s job. 

They need to figure out where they are most needed, but there is constant competition over the portfolio manager's attention and every team and each project manager thinks they are the most important. 

Some portfolio and program managers receive hundreds of daily notifications from their many projects, and it's hard to filter out the not urgent or less important ones. They waste precious time on endless syncs trying to figure out what’s important, and they get worn out because they keep switching contexts between platforms and projects. 

Usha Bhovan, a Managing Test Consultant at IBM explains this challenge when it comes to Microsoft Project (MSP). “With … MSP, it's really good at being able to show the interlock between each task or action item, any dependencies, et cetera,” she says, “but it can become a bit of a monster if you are not careful. It is really good because it allows you to track things. But, I know very few program managers who actually do track it [in] MSP, it's almost like they ask their test leads or program leads or project leads or project managers to create spreadsheets, which gives them a summary view of what tasks are going to be performed[,] when they'll be fulfilled by[,] when they'll be delivered, identify any risks, issues, et cetera at that level.”

Sarah M. Hoban talks about what can be standardized across the organization to help with this. “The role that a portfolio manager plays is to bring together all the salient data across different teams. People have a tendency to operate in their little world. And a lot of the incentive structures in a company unwittingly reinforce that it's about you and your performance as opposed to rewarding collaboration,” she says, “the role that a program manager can play is to connect the dots between the different groups, but also figure out how to document.” 

Hoban also sees increasingly large tech stacks as a challenge. “Another challenge is also more technology,” she says, “so how would you solve this? Having someone in the role is great, and having some sort of enterprise software system is also great. But the challenge then becomes: which tool do you use to do that? Because everybody has their own tool or preferred way of working. So I think that's again, where program management could come in and say it's okay that everybody's using all these different tools, but here's how you should go about using it, and here's how you should use each one, and here's what each one is.”

Risk management

Identifying risk demands clarity and precision, as it has a profound impact on future actions and outcomes. The problem is that there is enough data for each project that portfolio managers are drowning in it, and they lack the tools to zoom in on a specific part of a project to help them mitigate risks. 

When they need to filter out the noise and get a fresh look, most of them just switch to different, simpler tools, or even manual tools to help them focus only on what's relevant to the risk at hand. These actions take a lot of time and energy, and they can also be limiting.  

Risk registers are one example of a manual tool. 

“Using a risk register is good practice for planning and thinking ahead, but it's limiting for a couple of reasons,” says Hoban, “one is you're only thinking about your known unknowns … there's going to be something you don't think of that's going to go wrong. The other thing that I see happen is you make it at the beginning of a project, then you kind of like never look at it again. You have to [be] … reviewing that document regularly … In that sense, it drives accountability.”

Hoban continues: “The other thing that's related to risks that I think organizations are universally terrible at doing is keeping track of lessons learned and figuring out how you can use that to inform risk planning for your next projects. Sometimes it's even system-level problems that you can identify that are related to ways of working internally or even working with that client … But there's no template. I mean, there's a template you could fill out to an extent, but there's always going to be stuff that falls outside of that.” 

As Eliezer says, “... the need to share and learn from others' experiences is vital. Program managers can enhance their learning and adopt effective risk mitigation strategies from one project to another, ensuring greater success. There is no need to wait for a grand lessons learned session at the end of the project. Nowadays, each project sync serves as a platform for exchanging experiences and discussing challenges.”

Reporting

It's astonishing to realize how complicated and clunky reporting is for most portfolio and program managers—the ones we talked to said that for them, reporting requires a lot of manual work—they use screenshots from several different tools, which they later insert into their presentations. 

If that's not frustrating enough, they need to present to both higher management and clients, who each want to see a different part of the picture, which means double the work. One portfolio manager told our researchers she manually updates data on a specific tool just for the slim chance that upper management might want to take a look (they never do, by the way). 

Another challenge is that most platforms are visually overloaded with data, and if you're not in the details, it's nearly impossible to understand anything from looking at the projects. This means that portfolio managers must spend time "translating" the data for higher management. 

Aggregating data is also difficult. There is no real standardization, and reports come in different formats, which makes portfolio managers spend a lot of time aggregating the data rather than analyzing it. This also leaves room for possible human errors. 

Evansen describes a scenario where he ran into this challenge.

“One of the portfolios that I managed at the local energy company was an enterprise portfolio, so I had to have a view of every project and program that was going on at the company,” he says, “and at one point there were 62 of them. So you need a tool that could report on all that and … give me some graphs and dashboards that I could use, and not only for myself, but for the C-suite that I reported to… [to] take it to a high enough level … so that they're getting useful information but not, you know, a whole bunch of graphs with 90 data points on them that they're like: ‘I don't know what this means.’

Hoban agrees: “Executive reporting is always really difficult. Organizations either don’t do it, or people don't necessarily want the executive to know this much level of detail and it's really difficult to make a high-level view. Figuring out how to structure the tech stack can really help with this, and tracking should be done in such a way that it's reportable to everybody.”

Where Do Program & Portfolio Managers Go From Here?

Although portfolio and program managers are in dire need of tools that can save them time reporting, tracking, and mitigating risks, they find themselves in a daily, frustrating struggle, manually copying data from one platform to another, taking screenshots, and putting them on PowerPoint slides, and making unnecessary mistakes in the process. 

Project portfolio management tools (PPM tools) are a great starting point. They have key features that specifically address these pain points—risk management and reporting—as well as features that address other challenges like resource management and financial administration. If you’re totally new to PPM, start with our complete guide to project portfolio management here.

Consider the advice here as well—implement what you can immediately, or take it to your upper management. Rest assured that you can bring about change in your organization, even if only by starting small. 

About The DPM

The Digital Project Manager is the definitive resource for professionals looking to deliver impactful projects ahead of the digital curve. We’re on a mission to help the people leading these projects get skilled, confident, and connected so we can amplify the value of responsible project management in a digital world.

About Monday.com

Monday.com is a customizable work and project management software that helps project teams and organizations run more efficient projects through tracking workflows and projects, visualizing project data, and effective collaboration and communication. 

Contributors

Contributors from both monday.com and The Digital Project Manager worked on this report.

photo of nadav hachamov

Nadav Hachamov

UX Researcher

photo of Galen low

Galen Low

Co-Founder & General Manager

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Nuala Turner

Lead Editor

By Galen Low

Galen is a digital project manager with over 10 years of experience shaping and delivering human-centered digital transformation initiatives in government, healthcare, transit, and retail. He is a digital project management nerd, a cultivator of highly collaborative teams, and an impulsive sharer of knowledge. He's also the co-founder of The Digital Project Manager and host of The DPM Podcast.