This is Johanna Rothman's July 2025 Pragmatic Manager newsletter. The Unsubscribe link is at the bottom of this email.
Mike, a new senior leader, wants to know when Engineering will deliver specific projects. He would prefer more accurate estimates, but he's okay with relative sizing, such as:
- Small projects: Not more than a quarter (12 weeks).
- Medium projects: Somewhere between one and three quarters. (12 – 36 weeks).
- Large projects: About a year (52 weeks).
He's looking for a year's worth of certainty.
However, none of the teams were willing to “commit” to their answers. Then, as he reflected, he said, “The Small projects often go past a quarter. A few of the Medium projects sort-of finish inside three quarters. Worse, the Large projects often go past a year.”
I asked if that mattered.
He said, “Of course it does. The longer the project, the fewer we can do. We have too much pressure to deliver something.”
We discussed several ideas:
- The issue of initial estimates being off when people have too much interrupting work. (See Little’s Law for Any Kind of Product Development: How to Learn How Long Your Work Will Take)
- Accurate estimation requires much more information than the teams have. How to Predict When the Team Will Complete a Specific Backlog Item, Part 1.
- Extensive backlogs often mask the few, valuable outcomes the customers need. Why We Have Too Much Pressure and Planning & Too Little Delivery.
He shook his head. “If estimation doesn't work, what's my alternative? I have a business to run.”
I said, “Ask about value and investment. That's much more accurate than cost, and you can choose how frequently to decide again.”
Start with an Investment Question
I often start with this one:
Question 1: How much do we want to invest in this project before we decide on the portfolio again?
Because we do not know how much any effort will cost, we can manage costs by choosing our investment time. This works as long as the portfolio team assigns each project team one and only one project. Then, the team can learn its cycle time. If the management team decides to re-evaluate the portfolio every three months, they might default to a three-month investment.
But this question works even better when the portfolio team has an appetite for too many projects. Instead of investing three months in each project, the portfolio team can choose to invest a smaller time, such as 4, 6, or even 8 weeks. (You might like different options.) That helps the team ask this question:
Question 1A: What are the most valuable outcomes for the customers in this backlog?
Once the project team understands, they can focus on those most valuable outcomes.
Sometimes, organizations realize they need to run some experiments to see how their projects might affect their product or corporate strategy.
That's why I sometimes start with this question:
Question 2: How little can we invest in a team doing this work before we discover what we need to make a better decision later?
This question helps everyone realize that each project deserves a ranked backlog or short roadmap. That also helps the managers make better decisions.
Sometimes, the investment questions are not enough to help the portfolio team decide. That's when the value questions help them make better choices.
Ask Value Questions
Investment means we will decide how much time or money to invest. What will we get for that investment? That's the value. I often use Cost of Delay to explain the possible value. Sometimes, I combine that with the tangible, intangible, and peripheral value to describe all the value better.
Ask any of these value questions:
- How does this project add to the value we offer our customers? Can we increase our revenue or reduce other risks with this project? How early can we tell?
- Will this work make it easier for the employees to do their work? This is often the case with infrastructure or tools projects that companies too often postpone for too long.
- How will this project enhance our desired strategy? (I often use this question when people want to do apparently easy or small projects that do not appear to offer a lot of value.)
When people realize how much more value they can get for a smaller investment, they often choose the project portfolio (or features in a roadmap) differently.
Start with an Overarching Goal
Mike and his leadership team first discussed their strategy. That helped them describe their overarching goal in more concrete terms. Also, that goal helped everyone optimize up for the company's success, not their own department's success.
Then, they learned:
- If they divided one of the Large projects into three parts, they could choose to limit their initial investment. In effect, they could take that Large project and make it a Small project and then decide what to do next.
- Some of the Small projects offered much more value to the customers and employees than any of their current Medium projects.
- The reason their Medium projects were so “random” (their word, not mine) was that no one had any insight into the value of that work.
Once everyone focused on an overarching goal, plus the investment and value questions, people changed how they thought about all the work. That made their portfolio meetings take less time. While they did not have a year's worth of the project portfolio, they had a three-month plan. That was good enough for now.
Investment and Value Questions Matter More than Cost Questions
Many of us have been on projects or programs where the cost question was irrelevant. Instead, the only thing that mattered was how fast the team could deliver an outcome that mattered to the customers. Just imagine if that was the question all senior leaders asked.
Cost questions rarely work. Instead, focus on the few problems you want to solve for customers now, and how fast you can support the teams to deliver those outcomes.
While Mike does not have his yearly plan, he has a more reliable plan that allows him to manage the inevitable uncertainties as they arise.
Start with investment and value questions. That will help you start valuable work sooner. And, stop with the less valuable work.
Read More:
This newsletter touches on several of my books:
- The Modern Management Made Easy books
- Predicting the Unpredictable: Pragmatic Approaches to Estimating Cost or Schedule
- Manage Your Project Portfolio: Increase Your Capacity and Finish More Projects
- Project Lifecycles: How to Reduce Risks, Release Successful Products, and Increase Agility
Learn With Johanna
Effective Public Speaking is with my copyeditor! Then, I'll be able to finish the book and offer my Kickstarter. I'll send you the link so you can decide if you want to back it.
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Links of Interest
New to the newsletter? See previous issues. (I post these newsletters to my YouTube Channel a few days after I send them.)
Here are other links you might find useful:
- Managing Product Development Blog. (Yes, I offer an RSS feed so you can read everything in a newsreader.)
- Create an Adaptable Life Blog to see the weekly question of the week.
- My Books. You can also buy my self-published ebooks and audiobooks on my store.
- My Workshops
- Johanna’s Fiction
See you next month,
Johanna
© 2025 Johanna Rothman
Pragmatic Manager: Vol 22, #7, ISSN: 2164-1196