8 hurdles that stall transitions to an enterprise portfolio

8 hurdles that can stall your transition to an enterprise portfolio

While many organizations have inspiring mission statements, I’ve noticed that agile Portfolios are often born from struggles rather than dreams. People across the enterprise are noticing one or more of these signs. Miscommunications and delays are becoming difficult to bear. Important goals haven’t been achieved or there’s a need for a massive transformation. So they try something different.

After putting an initial portfolio process in place, some immediate pain points disappear and everyone’s excited about the new direction. However, around three to six months later, confidence falters and attention wanes. Things are slipping back to the status quo.

These are a handful of reasons I’ve seen for why this occurs. I call them “hurdles” because they can be intimidating, but with the right techniques, you can overcome them gracefully.


Hurdle #1) Different visions of what portfolio is and should be in your own organization

Portfolio stakeholders come in with their assumptions and past experiences. They have a mental picture of what portfolio management is, how it’s helpful and how it’s not. They have an idea of the outcomes they’re looking for and the work they’re willing to put in to achieve those results. Misaligned expectations can lead to resentment or frustration.

Jump the hurdle: Creating a shared mental model of what you’re building, who’s involved, how, and why helps to draw out those differences so you can address them. Discuss the portfolio essentials and the scope your portfolio will cover.


Hurdle #2) Different viewpoints of the purpose of your enterprise

Discussing the portfolio design, like how you’ll define value, prioritize, sequence work, and who should participate, can reveal strategic disconnects. Executives might not agree on what the enterprise exists for. Where it should go over the next 5 to 10 years. How much the organization should invest in the existing business model compared to preparing for future evolutions. Without a unifying enterprise vision, the portfolio design that is adopted will likely be what team members can agree on. Which is often a reactive model that handles incoming requests well but doesn’t drive the portfolio in a particular direction.

Jump the hurdle: Revisit or define your organization’s vision, goals, and investment themes.


Hurdle #3) Treating all items in the portfolio backlog as discrete projects

Individual sets of work with few dependencies are great for speeding up the flow of delivery. But how does the enterprise define those discrete projects? How do we know that implementing this one piece won’t adversely impact the broader system and the context it operates in? That this problem is the one we should be solving? Ideas don’t always arrive neatly packaged and pre-vetted.

By assuming that all items are discrete, individual projects, with closely defined boundaries, we are accepting the risk that this change won’t integrate well with the existing system and other items in the backlog.

Creation can happen anywhere on the spectrum from engineering technology to designing experiences, to also crafting marketing, delivery channels, and entire business models. Leading companies re-design markets and industries. Any backlog item is embedded in a broader technical and social system. Portfolios that can handle complexity, interconnections, and ambiguity will have more tools to identify and act on opportunities.

Jump the hurdle: Use tools like a business model playbook, roadmapping, root cause analysis, system maps, process models, and Enterprise Design Sprints to explore and break down more complex problems with a lot of interconnections. If people don’t see the issue with the current set up, pick a topic and build a diagram around it to show where the dependencies are. Don’t forget to include the customer, business, technical, and policy perspectives. A problem might appear discrete from one perspective but interconnected from another.


Hurdle #4) Treating portfolio as the domain of one particular role or business unit

Treating portfolio management as an IT function or the job of the COO or VP of Product limits its impact. For a portfolio management system that better utilizes resources and propels your company to “success” at all layers, it needs to ultimately be an enterprise function. IT, the COO, and product management will probably play a strong leadership role but other people aren’t exempt.

Another mistake is having a team with a lot of managers but no analysts or architects. Treating portfolio as only a management function cuts out a lot of its value. It’s a way to keep track of what you’re working on, make decisions, and verify that you have enough resources and money to complete the work. That’s definitely valuable. But the quality of what goes into your portfolio requires panning for gold and polishing rocks. It requires root cause analysis, exploring opportunities, and designing the structures to support a business that’s evolving. That calls for the skill set of analysts, designers, and architects.

Jump the hurdle: Tackling the other hurdles on this list will help the group realize that changes don’t just impact IT and a variety of viewpoints are helpful for filling, balancing, and executing the portfolio. Check for these signs you need a systems engineer and look for a great fit within or bring in an outside viewpoint.


Hurdle #5) Getting out of firefighting mode long enough to devote energy to strategic planning

Companies shifting to portfolio might be energized for a while, and then as soon as execution projects hit a rough patch, portfolio meetings start getting canceled or taken over by progress updates and risk discussions. Another flavor of this is always scrambling to fill up the backlog in time for the next release, a version of “strategic firefighting.”

Talking about details that impact the probability of a successful launch is important. Plans are only useful if you can get something out into the real world. But the scale of the impact you want in the world merits sometimes stepping away from the short-term treadmill.

It can be challenging to break out of the firefighting/short-term cycle in order to carve out the resources on a regular basis to look up at the broader picture. This relates back to hurdles #1 and #2. If there’s no clear vision and people think the purpose of portfolio management is to manage short-term projects, then protecting space for longer-term and more strategic work will be a tougher fight.

Jump the hurdle: Plan out your strategic routines to effectively allocate energy to both short-term and long-term initiatives.


Hurdle #6) Lack of focus and constantly shifting priorities

While teams and programs can see progress in a matter of hours or months, projects at the portfolio level are usually very ambitious. They often take longer to complete and probably even longer to see the full result of your effort. Staying patient and focused can be a challenge for organizations, especially for those with vocal stakeholders. Reactive portfolios without a strong vision or value framework suffer more from this because they don’t have a core goal to compare shifting requests to.

Jump the hurdle: Map your projects back up to the broader investment themes and goals. Break down large portfolio investments into time-boxed experiments and pilots. Or try out these other tips for staying impatiently patient during long projects.


Hurdle #7) Confusion about who has the authority to prioritize work and allocate resources

In general, people like the idea of autonomy. They like being able to make choices or delegate decision making. That becomes an issue when they don’t also clarify what kinds of choices each level can and should make. So individuals on the ground make choices based on what they can see, executives interfere and question how this fits into broader priorities and the system. Individuals feel like they don’t have autonomy or direction. Executives feel like their employees don’t have the knowledge or are side-stepping responsibility. Delays occur while people wait for someone else to make a decision. Or when someone steps in to overturn previous decisions.

Jump the hurdle: Conduct stakeholder analysis of the people in your organization to map out who has the interests, knowledge, skills, and “authority” to decide what. Consider how it varies depending on the scope, cost, or risk associated with the decision. Discuss the results and address any gaps with training or hiring.


Hurdle #8) Constructing effective channels between the groups

Once you’ve overcome Hurdle #7, things should be humming along more smoothly. But occasionally, autonomous groups need to work together to share information and align plans. The communication and coordination piece is sometimes a hurdle for organizations, especially if they’re used to ad hoc conversations or formal chains of command. Cross-functional teams know they should “collaborate” but sometimes that’s easier said than done. They may not realize when or who they should be collaborating with. They might struggle to coordinate schedules. Or in an attempt to be inclusive, the number of stakeholders invited to work sessions balloons beyond productive levels. This issue needs to be addressed both to help deliver the work you prioritized in the portfolio and to make sure other valuable work is surfaced.

Jump the hurdle: Build on your chart from #7 and plan out effective meetings or asynchronous checkpoints via wiki pages or Slack channels.


If you’re struggling with any of these hurdles, you’re not alone. I hope that some of the advice here will help. The earlier these patterns are spotted and addressed, the sooner you can focus on maximizing the value of your portfolio, but you can apply these changes at any time.

If you’d like someone to brainstorm with, Recharted Territory also helps clients work through all of these hurdles to build a successful portfolio management process. Check out our services to learn more and book a free session to discuss the specifics of your project.

What other hurdles have you encountered?



  • These are highly accurate in terms of the issues I’ve seen with organizations hitting their ceiling in terms of becoming a lean portfolio-driven enterprise. I love the fact that you outline strategies to overcome those blockers. How do you suggest communicating the constraints on their progress to executives in a way that garners their support to overcome those constraints?

    • There are a couple of techniques that I’ve found to be effective.

      For executives who are motivated by having and showcasing a new process, you could directly show them where they are compared to where they could be and a path to get from A->B.
      Ex. All of the companies you admire operate from a vision, and here’s what we can do to create one.

      For those who are motivated by achieving a result, but think the current setup already gets them there, then what if scenarios can help. If you come at it from an angle of stress testing the design together, the stakeholder will feel less defensive and see you as a collaborator instead of a threat questioning her decisions as a leader. Together, pick real examples of cases in their business and talk about how they were handled in the past or could have been handled differently. If the stakeholder recognizes the gap on her own, she’ll be more willing to take action.
      Ex. Our goal is to deliver value to our customers quickly. How well are individual teams doing? How quickly can they deliver? How much value are they creating? How do they figure out what’s valuable? What if a change requires more than one team? How do those teams work together? When are they successful and when do they run into integration issues or delays? What could we change and test to see if it makes a difference?

      Verbal support and active support can be two different things. Once either type of person sees the gap, if they’re not moving forward it’s usually because the perceived value they’ll get isn’t high enough to overcome the perceived effort required to make the change. Effort could be the time, energy, money, or political clout they personally have to put on the line to make it happen. Value could be a mix of individual benefits and organizational benefits. One-on-one conversations here can be helpful to draw out their thoughts, feelings, and assumptions about the required changes. If you can’t meet one on one you could try it in a group session or by reviewing what they’ve written or said in other forums. Uncovering their objections and goals can help you adjust your messaging or the order of changes. Clearing up misconceptions, co-creating the transformation roadmap, and finding ways to lower the initial risk can be helpful for gaining momentum.
      Ex. If you find out that executives are hesitant to move forward on defining a vision because they’re not sure how to go about incorporating diverse viewpoints, then you could offer to facilitate.

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