Clarity is key to momentum. But what do you do when the project itself is unclear?
Through life, and especially in careers in CRE Brokerage or starting your own software company, you’re undoubtedly going to have tons of ambiguous moments and projects. No defined scope, no clear deliverables, very little direction.
In the past, I’ve intentionally given some of our team members some ambiguous project with little direction to see how they would manage it. After guiding our team through a few of these, I documented a process that works.
The goal isn’t to avoid ambiguity altogether, it’s to manage through it with structure and communication. Ambiguous projects lack structure, it’s our job to create it. But how?
Here’s how we navigate the grey.
Start with 5 Questions
When you’re starting something ambiguous, do your best to get the clarity you need to at least get started.
These questions will help clarify expectations, risks, and outcomes:
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“What do I need to know in order for this project to be a success?”
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“What’s the worst-case scenario? What am I worried about, so I can take steps to make sure that doesn’t happen?”
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“What’s the best-case scenario? What should I be working toward?”
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“What’s the criteria for success? What standards do I have to hit to earn confidence?”
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“What micro-deadlines and deliverables should we set to keep things moving?”
These questions help uncover the “why”. They also align expectations early, lowering the risk of completely missing the point.
Build in Feedback Loops
The worst case scenario for everyone is you work tirelessly on a project, in a silo, without outside feedback, and completely miss the mark. We call this the ‘Over the Wall’ approach. The end result gets tossed “over the wall” and the person on the other end often is confused, underwhelmed, or unsatisfied.
Instead, set up iterative cycles, quick check-ins or touch points. Each interaction becomes a chance to realign and make sure everyone is on the right path. These cycles create velocity, Craig’s favorite word.
Don’t wait until it’s “DONE!” to share. Involve your manager or client early and often. It reduces the risk of missing the mark and builds shared confidence in the path forward.
One lesson I’ve learned in my own experience working on grey projects is this: breakthroughs don’t happen if you aren’t spending time working on it. Sometimes, there may not be a clear next step or clear end result. But you aren’t going to get the clarity you need by NOT working on it. Sometimes, on ambiguous projects, velocity looks like just scheduling time to sit down and immerse yourself in it.
Reflect
After any project, especially an ambiguous one, spend 20 minutes on this:
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What worked?
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What didn’t?
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What would I do differently next time?
Even better? Share this with your team, manager, or client. It not only reinforces your own learning but positions you as someone who’s committed to growth.
The most successful people in any organization aren’t just “good at getting things done.” They’re great at creating clarity when there is none.
They ask better questions. They create structure when there is none. Then, they move the ball, every single day.
And in doing so, they turn ambiguity into achievement. They turn grey projects into clear results.
Check out the visual we created: From Grey to Clear – Managing Ambiguous Project
Charlie Coppola
