What my three kids' schedules taught me about strategic portfolio management, competing priorities, and making better decisions when plans change.
There was a time when managing my three kids' schedules felt like a part-time job. Actually, who am I kidding? It still does.
Between club soccer, rec soccer, travel softball, school activities, doctor's appointments, and the occasional commitment I'd completely forgotten about, keeping our family organized was becoming an exercise in logistics. The bigger problem was that none of these commitments lived in the same place. Club soccer had its own team app, softball had another, rec soccer updates arrived by email, and appointments were scattered across various scheduling portals. Everything else lived somewhere in my head, which, as any parent of three can tell you, isn't always the most reliable system.
Eventually, I did what any organization-loving parent would do: I created one very organized, color-coded calendar. Every practice, game, appointment, and commitment finally had a home. For the first time, I could open one calendar and see exactly what our family had going on.
I thought I'd solved the problem. As it turns out, I'd only solved half of it.
The calendar could tell me that three kids needed to be in three different places at 5:30 p.m., but it couldn't tell me which commitment was non-negotiable, which one could move, or which grandparent we'd need to recruit to make the evening possible. When a practice got rescheduled or someone needed an after-hours doctor's appointment, I still had to mentally reconstruct the entire week to figure out what else would be affected.
And when everything felt equally important, deciding what to change became its own challenge. I could see all our commitments, but I couldn't immediately see their dependencies, understand the tradeoffs, or determine which adjustment would cause the least disruption.
I'd solved the visibility problem, but I hadn't solved the decision-making problem.
The more I thought about it, the more familiar that distinction became. Because while my family's scheduling challenges might seem worlds apart from managing an enterprise portfolio, the underlying problem is remarkably similar.
Imagine my family's scheduling chaos multiplied across hundreds of projects, thousands of employees, and millions of dollars in investments. Instead of three kids competing for two parents' time, you have departments competing for the same resources, initiatives pursuing different priorities, and leadership teams trying to understand how everything fits together.
In many organizations, individual project managers maintain their own trackers, departments operate in different systems, and teams have their own ways of defining progress and success. Somewhere in the middle, someone in the Project Management Office (PMO) is responsible for pulling all that information together into a portfolio view leadership can actually use.
Every month, updates are requested, spreadsheets are consolidated, and status reports are reconciled. By the time leadership receives what appears to be a complete picture, something has inevitably changed. A critical resource has been reassigned, a project has slipped, or a new initiative has entered the picture and disrupted the original plan.
Resource conflicts often surface only after they've become a problem. The same senior engineer might be committed to three different high-priority initiatives, with each project manager assuming that person's availability. Nobody necessarily made a bad decision; they simply didn't have a complete understanding of how their individual decisions affected everything else.
In my house, that's usually when I realize I've promised the same grandparent to two different kids. In an enterprise, the consequences are a little more expensive.
This challenge isn't hypothetical. According to a customer story published by Planisware, pharmaceutical company Teva was operating across 17 different systems to manage its generic product pipeline in 2013. Different departments had their own processes, terminology, and ways of managing work, making it difficult to align priorities and resources across the organization.
Bringing that information onto a shared platform wasn't simply about consolidating systems. It was about creating a foundation for more consistent prioritization, resource planning, and decision-making across a global enterprise.
And as organizations become more complex, the stakes only get higher. The Project Management Institute's 2026 Pulse of the Profession found that 97% of project professionals managed at least one complex project in the previous year. Nearly a third (31%) of complex projects failed to deliver the full scope of their intended benefits, while four in five experienced negative consequences, including strategic drift and delivery disruptions.
The report describes an important shift: moving from navigating tasks to navigating systems. In other words, organizations need to understand more than whether individual projects are progressing according to plan. They need to understand how those projects interact, compete for resources, and collectively advance the outcomes the business is trying to achieve.
Here's something I've learned from managing our family's schedule: saying yes is usually the easy part.
Every activity has a reason for being on the calendar. Every kid has something important happening, and every commitment made sense when we agreed to it. But when three activities overlap, the fact that they're all important doesn't magically create another parent or add two hours to the day.
Something has to give, and the difficult part is deciding what that something should be.
Organizations face a similar challenge. Most have established processes for proposing, evaluating, and approving new initiatives. A business case gets presented, an investment is justified, and another project gets added to the portfolio. Over time, the number of commitments grows, often without an equally disciplined process for determining which initiatives should be paused, deprioritized, or stopped altogether.
That becomes particularly problematic when business conditions change. A new strategic priority emerges, budgets tighten, or a critical resource becomes unavailable. Suddenly, leadership must decide which commitments deserve protection and which can no longer be justified.
Consider this question: If your organization's budget were cut by 15% tomorrow, could your leadership team confidently identify which initiatives to stop, which to protect, and why?
Could you explain which investments are delivering the greatest strategic value, which projects depend on the same resources, and which initiatives are consuming significant budget without meaningfully supporting the organization's current priorities?
For many organizations, producing those answers would require days of gathering information, reconciling spreadsheets, and consulting project owners. It's not necessarily because the information doesn't exist. It's because the information isn't connected in a way that makes the tradeoffs immediately clear.
Without that clarity, prioritization can become influenced by whichever initiative has the most vocal sponsor, the most recent presentation, or the greatest perceived urgency. Meanwhile, work that no longer supports the strategy can continue consuming resources simply because nobody has formally challenged whether it still belongs in the portfolio.
Effective portfolio management isn't about finding a way to say yes to everything. It's about having the information and discipline to make intentional decisions about what deserves investment, including when to say no.
Sometimes the smartest decision isn't launching the next initiative. It's creating the capacity to deliver the ones that matter most. Deciding what to stop is exactly what we’re digging into in our upcoming webinar with Planisware, “Fund the experiment, not the plan,” on November 5. Save your seat.
This is where the conversation moves beyond traditional project and portfolio management and into Strategic Portfolio Management (SPM).
There's a meaningful difference between managing a collection of projects and managing the investments an organization makes to achieve its strategy. Traditional project management focuses on whether work is being delivered successfully, while Strategic Portfolio Management takes a broader view, connecting investments, resources, and execution to the business outcomes leadership wants to achieve.
It's the difference between asking whether we're getting the work done and asking whether we're doing the right work in the first place.
And perhaps more importantly, whether it's still the right work.
Think about how much can change between annual planning cycles. Market conditions shift, budgets fluctuate, new technologies create opportunities, and customer expectations evolve. An initiative that made perfect sense six months ago might no longer deserve the same level of investment today.
Yet many organizations continue allocating people and funding based on decisions made when the circumstances were entirely different. The portfolio might look healthy from a project reporting perspective, even as the connection between those projects and the organization's strategic priorities begins to weaken.
It's a little like insisting that our family follow the original Saturday schedule after the soccer tournament moves, the weather changes, and someone wakes up with a fever. The plan might have been perfectly reasonable when we made it, but that doesn't mean it's still the right plan.
Strategic Portfolio Management creates a more continuous connection between strategy and execution. Rather than treating portfolio decisions as something that happens once or twice a year, organizations can regularly evaluate whether their investments remain aligned with business priorities, whether they have the resources to deliver, and how changes in one area affect the rest of the portfolio.
That shift changes the nature of leadership conversations. Instead of simply reviewing project status, leaders can evaluate whether their investments are producing the intended value, understand the consequences of shifting resources, and make more informed decisions about where to focus next.
The goal isn't to eliminate uncertainty or predict every disruption. It's to build the ability to respond intelligently when circumstances change, without having to reconstruct the entire portfolio every time something moves.
This is also where artificial intelligence is beginning to create some interesting opportunities.
And no, I'm not talking about asking ChatGPT to magically solve my family's Thursday night transportation situation. Although, if someone has figured that out, I'm all ears.
I'm talking about using AI to help organizations understand complex, interconnected portfolios and evaluate decisions that would otherwise require significant manual analysis.
Imagine identifying potential resource conflicts before they derail an important initiative, rather than discovering them after a deadline has been missed. Or modeling the impact of a proposed 15% budget reduction across the entire portfolio, with a clearer understanding of which projects, dependencies, and strategic outcomes would be affected.
Instead of spending weeks collecting information to compare investment scenarios, organizations can increasingly use AI-enabled capabilities to accelerate analysis, identify patterns, and evaluate potential tradeoffs. Portfolio management platforms, including Planisware, are incorporating these capabilities to help organizations make more informed decisions.
And adoption is already gaining momentum.
A 2025 global study of 870 professionals across 97 countries, led by Antonio Nieto-Rodriguez and Ricardo Viana Vargas, found that more than two-thirds were using AI tools. However, Planisware's summary of the research noted that only 12% described their AI use as extensive and structured. Planning and resource allocation were among the use cases respondents considered most valuable.
To me, that highlights an important distinction between experimenting with AI and using it to meaningfully improve how organizations operate.
The opportunity isn't simply giving teams access to another technology. It's applying that technology to the decisions that determine whether strategic investments succeed.
Of course, AI isn't going to replace leadership judgment. It doesn't inherently understand the importance of a long-standing client relationship, an organization's appetite for risk, or why one initiative might deserve protection even when the financial analysis suggests otherwise.
Those decisions still require human experience, context, and accountability.
What AI can do is help leaders better understand their options and the potential consequences of each decision. Instead of relying on fragmented reports, outdated information, or someone's ability to mentally connect all the moving pieces, they can evaluate scenarios with a more complete understanding of the portfolio.
The value isn't in letting AI make the decisions. It's in helping people make better ones.
At The Select Group, we're investing in Strategic Portfolio Management as a practice area and partnering with Planisware to help organizations move beyond simply tracking projects toward making more informed, strategy-driven portfolio decisions.
But there's something I think is important to emphasize: the solution doesn't begin with a platform. It begins with understanding what the portfolio is supposed to accomplish.
Before organizations can make better investment decisions, they need alignment around a few fundamental questions. What are our strategic priorities? How do we define and measure value? Who has the authority to make tradeoffs when priorities compete? And how do we ensure those decisions translate into the work teams are actually delivering?
Technology can help bring information together, but it can't establish those answers on its own.
That's why TSG's approach focuses on connecting the technology, processes, and governance needed to translate strategic priorities into execution. We help organizations bring initiatives, investments, and resources into a more complete, current view while establishing the decision-making frameworks that make that information actionable.
Through our partnership with Planisware, we're helping clients strengthen portfolio visibility, understand dependencies, evaluate competing resource demands, and model scenarios before committing to significant changes. Just as importantly, we focus on establishing a consistent cadence for reviewing priorities and adapting the portfolio as business conditions evolve.
This work doesn't end when a platform goes live. Sustainable value comes from helping organizations embed these capabilities into how they plan, prioritize, allocate resources, and make decisions over time.
Because having a complete picture of your portfolio is valuable, but knowing what to do with that information is what ultimately makes the difference.
You don't need to wait for a major disruption to evaluate whether your organization has a portfolio management challenge. In fact, some of the most revealing questions are relatively straightforward.
If your budget were cut by 15% tomorrow, could you confidently explain what to stop and why? This isn't simply a financial planning exercise. It's a test of whether your investments are clearly connected to strategic priorities and whether leadership understands the relative value of the work underway.
When one major program gets delayed, how quickly can you identify the impact on everything else? Dependencies between projects, resources, and timelines can create consequences far beyond the initiative experiencing the delay. Understanding those relationships is essential to making informed adjustments.
How many of your current initiatives can you directly connect to a strategic priority and a measurable business outcome? Activity and progress aren't necessarily the same as value. A portfolio can contain dozens of projects that are technically on track without collectively moving the organization closer to its goals.
If answering these questions requires multiple spreadsheets, several rounds of meetings, or days of reconciliation, there's likely an opportunity to rethink how your portfolio is managed.
And that doesn't necessarily mean starting over. Sometimes the most important first step is recognizing that having visibility into the work and having the ability to make informed decisions about that work are two very different things.
For the record, our household is still chaotic. The calendar is still color-coded, the kids still have competing commitments, and I'm still regularly trying to figure out how three people can be in three different places when there are only two parents available to drive.
The difference is that I've come to appreciate what the calendar can and can't do. It gives me a complete view of our commitments, but I'm still the one evaluating what's fixed, what's flexible, what depends on something else, and which adjustment will create the fewest headaches for everyone involved.
Apparently, I'm the Strategic Portfolio Manager of our household, whether I signed up for the job or not. Nobody gave me the title, and I'm still waiting to hear about the compensation package.
I haven't found an AI-powered solution for our family just yet. (Seriously, if you have one, please call me.) But for organizations managing complex investments, competing priorities, and limited resources, there are better ways to approach the challenge than keeping all those scenarios in someone's head.
That's ultimately what we're helping clients accomplish at TSG: connecting the moving pieces so leadership teams can see the bigger picture, understand the tradeoffs, and make decisions with greater confidence.
Because the most important question isn't just "What's on the calendar?" It's "What happens when something moves?”
If the 15% budget question made you think of a specific program, I’d love for you to join us. In our upcoming webinar with Planisware, my colleague Adam Mattis and Planisware’s Olivier Fleischmann will share a different way to fund work: in smaller rounds, each tied to a claim you can test and a date when someone reviews the evidence.
They’ll walk through how to write a stop condition before a bet is funded, how to run funding gates where stopping is a normal outcome rather than a failure, and how AI and scenario planning can help leaders compare their options at each gate. In other words, how to decide what happens when something moves before it actually does.
The webinar is November 5, 2026, from 12 to 1 PM ET. Save your seat here.