Too often we solve the wrong problems, wasting time and money. Use a framework to solve the right problem the first time.
by Janet Ply, PhD · The Practical Leadership Newsletter · August 18, 2026
One of my clients, frustrated after yet another project delay, told me, “I’d like you to teach my project leaders how to estimate.”
It sounded reasonable. Sort of.
After years of leading and recovering large programs, I’ve learned not to assume a missed date is an estimating problem.
“Let me take a look at your business case and requirements before we look at estimating practices,” I told him.
It didn’t take long to see that the requirements were incomplete and poorly written.
“How long would it take and how much would it cost to build a three-bedroom house?” I asked.
“How would I know without more information? I’d need a lot more information than that.”
“Exactly. And so do your business analysts, software developers, testers, and operations teams. How are they supposed to estimate the work when they barely have bits and pieces of what is needed?”
Better estimating techniques weren’t going to solve the problem.
We conducted a broader assessment, uncovered problems in multiple areas, and developed a prioritized roadmap to address them.
Had we simply delivered the requested estimating training, we would have spent time and money on a solution while many of the conditions causing the project delays (and frustrations) remained unchanged.
How many times have you sat in a meeting, discussing a problem and people start talking about solutions? Seems reasonable but it’s a little too soon for solutioning.
I can’t count the number of times I’ve stopped conversations and said, “We need to raise this up a few levels.”
Everyone needs to understand:
what we’re trying to accomplish,
what is actually happening,
why it is happening, and
what may be causing it.
We make the mistake of collapsing three different things into one: What we observe. What we think is causing it. What we decide to do about it.
Projects are missing dates - that’s just an observation.
Our project leaders aren’t good at estimating - that’s an assumption.
Let’s give them estimating training - that’s a solution, but unlikely to be the best one.
The assumption may be right. But it isn’t the right diagnosis until we’ve done the work to understand what is actually causing the problem.
I see the same problem in leadership development. An executive says:
“Our leaders need to do a better job of holding people accountable.”
Maybe. Maybe not.
What are we actually observing? Missed commitments? Poor quality? Deadlines slipping? People not following through?
Then we need to understand why.
Expectations may be unclear. People may not understand who is responsible for what. The leader may not know how to address missed commitments, or may know how and avoid the conversation. Workloads may be unrealistic. Priorities may keep changing.
Gallup recently reported that only 23% of employees strongly agree they have a clear definition of what exceptional performance looks like in their role.
If the standard itself isn’t clear, accountability becomes much harder to diagnose.
I’ve learned not to assume the accountability problem starts with the person who appears to be unaccountable.
“We need accountability training” is a proposed solution. We still need the diagnosis.
This is one of the things that is easily overlooked.
The leader may be capable and have the right skills and understand what is expected.
And they may be working in an environment that makes succeeding unnecessarily difficult.
I’ve seen leaders held accountable for dates that were unrealistic from the beginning.
I’ve seen executives change scope without changing the schedule or resources.
I’ve seen people assigned to multiple high-priority initiatives and expected to somehow figure out which one comes first.
Several of these conditions can exist at the same time.
All the analysis, training, and coaching in the world won’t create additional capacity, resolve conflicting priorities, fix broken dependencies, or turn an unrealistic deadline into a realistic one.
Sometimes improving leadership performance requires changing the conditions in which people are being asked to lead.
And even when training is part of the right solution, determining that someone needs development isn’t the end of the diagnosis.
We also need to ask:
Are we putting leaders in an environment where they can use what we’re teaching them?
Poor diagnosis can waste money on training, consulting, technology, or something else that doesn’t address the problem.
I’m more concerned about what happens afterward: the same problem still exists.
Projects continue to miss dates. Decisions continue to escalate. People continue to avoid accountability. Good leaders become frustrated trying to deliver inside systems working against them. Senior executives continue to be involved in problems they thought they had already addressed.
Then the organization may conclude that its leadership development didn’t work.
The cost of solving the wrong problem is much larger than the cost of the solution itself.
There’s an interesting version of this problem emerging with AI.
A leader can ask an AI tool:
“One of my employees isn’t accountable. Help me prepare for a conversation to help them be more accountable.”
Within seconds, they can have a reasonable conversation plan.
But what if accountability isn’t actually the problem?
Speed isn’t particularly valuable when we’re moving quickly in the wrong direction.
That’s one reason I’ve built a robust AI toolkit within the Leadarity Leadership Operating System to help leaders think through situations before deciding what action to take.
Knowing what to explore and what questions to ask before acting is part of leadership judgment.
Organizations need leaders who solve problems well.
Sometimes solving a problem well means resisting the urge to solve it immediately.
So when a meeting starts moving quickly from “Here’s what’s happening” to “Here’s what we’re going to do,” raise the conversation a few levels.
Make sure you understand what you’re trying to accomplish, what is actually happening, why it is happening, and what may be causing it.
Then ask: Am I sure I’m solving the right problem?
The hardest part of leadership development has never been learning the framework. It's applying it, in real time, under pressure, when the stakes are high and no one is watching.
That's exactly why I created the Leadarity (short for leadership clarity) Leadership Operating System built on the same system behind my book, Practical Leadership. Every concept in the book, from building trust and developing awareness to goal setting, leading projects, and building high-performing teams, is embedded in the AI Toolkit that questions you, challenges you, and helps you think more deeping.
Dr. Marshall Goldsmith, Thinkers50 #1 executive coach and bestselling author of What Got You Here Won't Get You There, called Practical Leadership "a practical and actionable guide, grounded in real-world experience - not just theory, but a road map for real transformation."
Leadarity is what makes that road map available to you at 9pm on a Tuesday, when a real leadership challenge lands in your lap and you need to think it through before tomorrow morning.
If you're interested in bringing Leadarity into your organization or your own leadership practice, let's have a conversation. Schedule a call at janetply.me
And if you don't yet have the road map itself, pick up a copy of Practical Leadership on Amazon or your favorite local book store.
Janet Ply, PhD
Author, Practical Leadership ~ Creator, Leadarity AI Thinking Partner and the Practical Leadership System