Why Your “Simple” Project Fails — and the One Question That Can Fix It

When most people hear “project management,” they picture massive enterprise projects, complex charts, and entire teams of specialists.

But many managers today are quietly running small, high-stakes projects on the side of their desk — often without realizing it.

It might be an AI-driven report for leadership, a new workflow automation in Power Automate, or a data cleanup project.

And without structure, these “quick tasks” can turn into sources of frustration, missed deadlines, or disappointment — not because the manager isn’t capable, but because no one ever stopped to define success.

The Problem

According to the Standish Group Chaos Report, only 35% of projects are completed successfully — regardless of size or industry.

That means two-thirds of projects, even small ones, miss expectations. But when basic project management structure is applied — clear scope, ownership, and expectations — success rates jump 2.5× higher.

The First Step: Define “Done”

The simplest and most powerful action you can take at the start of any project is to get agreement on what “done” means.

This conversation might take 15 minutes — but it saves weeks of confusion later.

Think of it like grocery shopping on a budget: you start with essentials. You decide what’s vital, what’s nice-to-have, and what can wait. Everyone understands trade-offs.

When you define “done” in your project:

  • Priorities become clear

  • Budgets make sense

  • Your stakeholders are aligne

Why It’s Crucial in AI Projects

AI projects, especially early ones, are full of hype and confusion.

Example: your boss asks for a Power BI dashboard with automatic AI commentary. Sounds simple — but now you’re managing data access, formatting, refresh cycles, and stakeholder expectations about what “automatic” really means.

If you don’t get everyone’s definition of success out in the open, someone will be disappointed, no matter how much you deliver.

And when you’re not in the room, those expectations grow. Suddenly, you’re “behind” on goals you never agreed to.

The Fix: Structure in Minutes

You don’t need to be certified or use enterprise tools.

A simple one-page project charter can get you started. It captures:

  • What the project will and won’t deliver

  • Who’s involved

  • What “done” looks like

  • How success will be measured

This one document transforms vague ideas into concrete outcomes and helps you manage upwards, sideways, and with your team — without friction.

The Payoff

Getting this right early:

✅ Builds stakeholder trust

✅ Prevents burnout

✅ Boosts your credibility as a leader

✅ Opens doors to new career opportunities

And best of all, it takes less than an hour to do.

Call to Action

Start your project by defining what “done” looks like:

  • Get it simple and in high-level terms.

  • Get this “done” perspective from everyone who is involved on your project.

  • If your project is in flight then attempt to do it to ensure you’re not surprised at the end.

  • Do it as a habit for each of your projects from now on.

In a few posts, I’ll share a link to a simple how-to to get started on a 1-page charter.

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