This week we turned our calendars to September. School is back, and so are pumpkin spice and the existential dread of watching the standings every day as a Cubs fan (4 wins in their last 10 as of the time of writing, 8 games out of the division, wild card trimmed but holding at +5)
It also means that you’re thinking about, or probably even start planning, 2027. Last fall we wrote about five questions to ask yourself and your team as you begin planning.
Those essential questions are still a great roadmap for the planning process, but something I read this week caused me to think about them differently.
I was working on some PDU for a project management certification and came across the definitions of a project, program and portfolio.
Projects are the easiest to define, and we all know one when we see it. It’s a task or group of tasks with a defined goal and a clear start and finish. A process improvement, software conversion, and an acquisition are all examples of a project.
A program is a group of related projects that are grouped for extra benefits. The whole of a program is greater than the sum of the individual projects. A program to improve speed to fulfilment may include projects to streamline facility layouts, implement new software for enterprise planning, inventory, or vendor management, and worker training.
Finally, a portfolio is focused on choosing and prioritizing the projects and programs to align with strategy and capacity.
What struck me was this definition of the difference between a portfolio and a program:
Programs ask “are we doing our projects right?” Portfolios ask “are we doing the right projects?”
Our daily and weekly plans should be about doing the work right, answering questions like “what do I need to do today to advance goal x?” But, when it comes to annual planning like you’re probably starting now, focus should be on doing the right things.
Let’s look at those five questions again, and propose some changes.
#1: Which business objective does this advance?
This question is first for a reason, and it holds up. Tying each plan to a business objective is the first step in building a portfolio instead of a pile of plans or work.
#2: What does success look like in one sentence?
This is a “doing projects right” question. It’s necessary for the success of each project, but a clear definition of doing it correctly does mean that the work earns its place in your 2027 plans.
#3: Who needs to be aligned for this to work?
Same here. Once we make a decision, we need to decide who is carrying it out. But, this is a project-level question. We’ll identify a better question to ask to reveal capacity later.
#4: What is the next smallest step we can take?
Ask this question over and over to keep your work manageable and aligned with its original purpose. But this question is too small in scope to build a portfolio around.
#5: What do we need to stop doing in order to make space?
This is one of the most important questions to ask about everything you are considering for your portfolio in 2027. This is the question that keeps you from having a list of a dozen priorities with no chance of finishing more than two.
Cutting your portfolio down to three-five realistic items may seem like shortening your reach. The world talks about stretch and Big Hairy Audacious Goals but building a portfolio of ten initiatives when you only have capacity for two isn’t being ambitious. It’s being structurally dishonest.
You have your proposed dozen. Here are the questions to ask, in order, to build your realistic portfolio:
#1: Which business objective does this advance?
This one stays. Ask it first and every time. If the work isn’t closely and easily tied to an objective, it doesn’t earn its place.
#2: What do we need to stop doing in order to make space?
If we think this initiative belongs on the list, what do we need to drop to make room? After all, you probably haven’t finished everything you set out to do in 2026.
#3 What are we structurally stopping, not just deprioritizing?
This may even be question #2A. Unclear answers to this question are how you end up with a list of twelve in the first place. Deprioritizing something doesn’t mean moving it down the list in case there is time. It means deciding that it doesn’t earn a place.
#4 Who loses a task, a meeting, or a responsibility because of this plan?
Don’t just consider clearing capacity for the organization as you plan. To earn its place, any new initiative must come with space for your teams.
#5 Which three priorities would still be true if you only had a third of the time you're assuming you'll have?
You probably already know which of your priorities would survive this cut. The hardest part is admitting the other nine were never really priorities to begin with.