The Silence Before the Storm
It’s the quiet moments that get you. The day before kickoff. The night after the first board review. That long weekend when the vendor hasn’t delivered, and no one’s answering emails.
In those moments, I’ve learned to ask myself a few hard questions. Not because I enjoy self-flagellation. But because projects will eventually force you to answer them—when it’s too late to do anything about it.
Here are the five questions I ask before every major project engagement. If the answers aren’t clear, I know I’m not ready. And if I don’t ask, the project will.
1. “What is the real goal of this project?”
Not the charter. Not the scope doc. The real goal.
Is it compliance? Is it cost reduction? Is it executive visibility? Is it political?
If you don’t know the why behind the what, you’re managing in the dark.
PM Tip: Write the goal in plain language. Say it aloud. If it sounds like marketing fluff, dig deeper.
2. “Where is the constraint?”
Every project has a bottleneck. Might be a resource. Might be a decision gate. Might be you.
Have I mapped dependencies? Who or what sets the pace? What happens if that part fails?
Identifying the constraint early lets you shape the plan around reality—not optimism.
Don’s Rule: The thing that makes you nervous? That’s probably the constraint.
3. “Do I have air cover?”
You can’t go to war without a general. Who’s going to back you up when things go sideways?
Does your sponsor really understand the risks? Do you have support from legal, finance, IT, etc.? If you raise a flag, will they act—or ask for another report?
PM Tip: If you don’t have air cover, your job isn’t delivery—it’s lobbying. Start there.
4. “What does success look like?”
And I don’t mean KPIs. I mean the scene, the setting, the people in the room.
Who will shake your hand? What will be said in the debrief? What email will go out to the company?
Paint that picture. Share it. Let the team visualize the win.
PM Tip: If your version of success doesn’t excite anyone, expect low energy—and low accountability.
5. “Am I leading or reporting?”
Project managers fall into this trap all the time: churning reports, updating trackers, managing optics. Meanwhile, the team’s confused, vendors are drifting, and momentum dies.
Are you solving problems or documenting them? Are you influencing outcomes or explaining delays? Are you respected—or tolerated?
Don’s Rule: If you’re not changing the outcome, you’re not managing the project—you’re just watching it fail in real time.
Final Thought
Good PMs ask questions. Great PMs ask the right questions—early and often. Projects don’t care if you’re caught off guard. They just keep moving.
So ask yourself before the project does. You’ll sleep better, fight smarter, and lead clearer.
