Why Projects Derail From the Inside Out
Not every project collapses from a headline crisis. Sometimes, it’s the slow internal leaks — the vague expectations, the power plays, the “just say yes” culture — that sink the ship.
Take the time I worked on a massive project with multiple moving parts. We were losing $15,000 a day waiting on a finance sign-off. Everyone pointed to the execs — but the real blocker? Joe Bloggs (yes, that was his name well not really), buried in the finance team, quietly refusing to move things forward. Why? Because he was left out of a meeting and wanted to make a point.
Joe wasn’t on the org chart as a key player. But he held the power. He’s why you build a proper internal stakeholder list — and check it twice.
I’ve seen this pattern too many times as well: leaders trying to avoid conflict, saying yes to everything, and pushing their teams to deliver the impossible. When it all goes sideways? It’s staff left to clean up the reputational and/or operational mess.
After 25+ years (okay, longer — but who's counting after 50+?) working on everything from emergency management to billion-dollar infrastructure, I’ve found one ancient method that still works: Sun Tzu’s The Art of War.
Yep, a 5th-century Chinese general still has something to teach us. Thanks to Karen McCreadie’s brilliant, plain-English version, I’ve pulled together 10 battle-tested tactics — each paired with a modern lens (mine) to help navigate your next stakeholder standoff.
________________________________________
1. Act Fast
"Cleverness has never been associated with long delays." — Sun Tzu, ancient Chinese military strategist
Prolonged in-fighting, endless debate, passive-aggressive silence — it burns budget, morale, and time.
Ask yourself: What niggling issue has been sitting on your to-do list gathering dust? Fix it before it festers to an expensive big burning issue down the road.
________________________________________
2. Pick Your Battles
"Pick battles big enough to matter, small enough to win." — Jonathan Kozol, American education activist
Don’t fight everything. Fight smart. Map out your internal politics and your external alliances. Know what’s worth burning capital on — and what’s better left alone.
Try this: Before your next stakeholder meeting, ask: Why should this person care? And what am I willing to negotiate?
________________________________________
3. Run with Opportunities
“Luck is what happens when preparation meets opportunity.” — Seneca, Ancient Roman Stoic philosopher
Change doesn’t send a calendar invite. Stay nimble. If an advantage shows up, grab it — even if it wasn’t in your plan.
Look around: Can you leverage a connection, a gap in the timeline, or an unspent budget to boost your impact?
________________________________________
4. Turn Misfortune into Gain
“In the middle of difficulty lies opportunity.” — Albert Einstein, physicist and creative problem-solver
Bad stuff happens. The secret sauce? Turning a roadblock into a detour that works in your favour.
Shift perspective: What in this mess could be repurposed, reframed, or used to your project’s (and your project community’s) advantage?
________________________________________
5. Size (and Speed) Matters
"Speed is the new currency of business." — Marc Benioff, CEO of Salesforce and pioneer of cloud computing
You can’t always outspend your competition, but you can often outpace them. Speed builds credibility, trust, and momentum.
Forecast wisely: Could your own internal advocates become blockers if timelines slip or expectations drift?
________________________________________
6. Check the Big Picture (Not Just Yours)
"The belief that one’s own view of reality is the only reality is the most dangerous of all delusions." — Paul Watzlawick, Austrian-American communication theorist and psychologist
We’ve all seen it: A leader makes a grand promise without checking if it’s actually possible. Cue chaos.
Reality check: Who’s your in-house sense-checker? Every project needs a thoughtful pessimist — someone who can tactfully say, “Hold up, that’s not going to fly.”
________________________________________
7. Stay Humble
"The best leaders are the ones who admit they don’t know everything and build a team that fills the gaps." — Simon Sinek, leadership author and eternal optimist
Stuff up? Own it. Apologise if needed. Then move on. Denying reality won’t make the issue disappear — it just breeds resentment.
Gut check: Ever worked with a leader who pretended nothing went wrong? Yeah. How did that feel?
________________________________________
8. Employ the Right People (Not Just Who’s Around)
"First who, then what. Get the right people on the bus, and the wrong people off the bus, before you figure out where to drive it." — Jim Collins, author of 'Good to Great'
Titles and tenure don’t equal capability. If the person can’t handle complexity or conflict, they shouldn’t be in charge of delivery.
Try this:
• Can this person manage messy, high-pressure conversations?
• Are you tolerating skill gaps that are costing your project time and credibility?
________________________________________
9. Build Strength and Agility Through Systems
"Strength comes from people. Agility comes from systems. Long-term success needs both working together." — Mary Todorov, Stakeholder Decision & Execution Specialist (that’s me)
Systems aren’t sexy, but they are what keep things standing when things get bumpy. That means shared protocols, agreed escalation paths, and handover plans that aren’t sitting in someone’s inbox.
Reality check:
• If someone key left tomorrow, would you have chaos or continuity?
• Do your stakeholders know who does what — and how to get help without drama?
________________________________________
10. Talk to Each Other
"You can have brilliant ideas, but if you can’t get them across, your ideas won’t get you anywhere." — Lee Iacocca, legendary American auto executive and turnaround expert
Emails aren’t strategy. Dashboards aren’t conversations. And “we’re too busy to meet” is a red flag.
Quick fix: What feedback loops do you have in place? Can people speak up without fear or fuss? Sometimes just one clear number or channel is all it takes.
________________________________________
In the end, leading complex projects isn’t about being the smartest person in the room — it’s about navigating the politics, power dynamics, and people problems with clarity, calm, and a bit of grit.
Old-school strategies still work. Because no matter how modern our tools get, we’re still dealing with humans. And humans? Well — we’re predictably unpredictable.
When in doubt, channel Sun Tzu. Or call someone who’s been through the fire and knows how to keep the wheels on.
(That’d be me.)
