8 PMO Challenges to Prepare You for Your Next Run-in with the CEO

8 PMO Challenges to Prepare You for Your Next Run-in with the CEO
project portfolio struggles

You’re the Project Portfolio Manager in the organization. Selecting the projects to work on and administering the chosen project portfolio management (PPM) tool is critical to organizational success – especially in a project-centric organization. Choose the wrong projects to engage on and you may be supporting legacy technology or committing to legacy technology for the long term that you will no longer be supporting 2-3 years down the road. Or the projects you support and the clients you go after may not be part of the organization strategy and competitive landscape that the C-level individuals have put in place for the goals and mission and long-term strategy for the organization.

So let’s imagine you are stuck on an elevator with the CEO of the company and he says “Hey Jim, what are the biggest challenges you’re facing right now in your role of Project Portfolio Manager?” What are your key challenges? This is your big chance! If you’re stuck on an elevator and he asks you what five things worry you the most or would be on your wish list to fix or find the right tool for, how would you reply? My guess is that it would be some subset of the following list.

#1 Staying aligned with the business strategies

A solid PPM requires that you be able to break any business strategy down into multiple portfolios and organizations. Flexibility and user-friendliness are key and most offerings fail miserably in this area. These two concepts should be at the forefront of a PPM’s software design and that’s where most fall short.

#2 Prioritization

Prioritization is a key functionality of most wish lists for PPM users. A good PPM should also be able to fund and staff initiatives and actions according to strategic targets, as well as available budgets and resources. This functionality should be expected out of the box in order to make PPM everything you need it to be, but in general, it just isn’t there most tools can’t handle the financial piece or contribute much to that need.

#3 Waterfall vs Agile

The right PPM should allow you to plan work and schedule your resources in a standard or agile mode without being locked into either. Ideally, PPM offering should fit flexibility your organization will obviously need over your entire project portfolio.

#4 Provide high-level and wide-angle views of the project landscape

A full featured PM should also be able to dynamically control execution and progress on several axes and identify the potential gaps with the original targets. High-level views and wide-angle views of your projects at a glance mean you have access to better decision-making for the full portfolio of projects you’re handling at any given moment… and this is what the right PPM solution is all about. Sadly, this again is another key failing point for most of the leading PPM offerings.

#5 Flexibility and scaling

Back to flexibility – the PPM needs to be able to re-align… periodically… with the changing directions, goals, and missions of the organization. It’s how it handles these changes with the growing and changing portfolio quickly and efficiently without lots of redesigns, re-configuration, or re-work that is a sign of “will it really work for your needs?”. In most cases, the answer turns out to be “no” with 95% of the PPM offerings on the table now. 

#6 Keep teams aligned

Keeping teams and project managers aligned with the goals and mission of the organization is another challenge for the portfolio project manager and PPM tool. Solving this is tied into good, customized reporting so all are aware of what each project is about and which ones are coming up next on the project management horizon as well as an understanding of what’s available from the project management resource pool for each project that needs roles filled. When will the right resources and skill sets be available for each project qued up in a PM’s assigned project workload?

#7 Considering the risks project by project

Risks are going to come up on every single project. It is up to the project manager and team – and often the project customer and team to come up with the detailed challenges for each project during the planning phase of the initiative. But prior to that, a high-level list for each project needs to be in place to aid the portfolio manager and the PPM tool in making the proper decision as to which projects are ready, which need more time, and which are just too risky to take on.

#8 Figuring out which projects are the best fit for the organization’s short and long-term goals

As mentioned already – a key challenge for every portfolio manager is to ensure the right projects are being qued up to work on in the right timeframe and priority based on the fit for the project with the resource constraints as well and short and long term goals of the organization. This will always be a key challenge and needs to be a key element of the right PPM tool for the manager and organization.


The bottom line is this – it’s a challenge to be choosing, prioritizing, and executing the right projects at the right time. Going out of order or moving forward with a project that isn’t on the radar for the organization can be a waste of thousands of dollars and unhappy project clients as well as frustrated senior-level managers in the delivery organization as resources are being expended on the wrong work. Keeping aligned with the goals and roadmap of the organization is critical and is – no doubt – one of the key challenges for every project portfolio manager on the planet.

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