How I Turned the 'Scary' Executive Into My Project Sponsor
Why leading with risks instead of promises transforms difficult relationships.
Dear Future Leaders,
Your boss just pulled you aside with a warning: "That stakeholder is intimidating. They've been here forever and have strong opinions about how things should work."
Now you have to present a critical project to them, and you're probably planning your approach: polished slides, confident promises, and hope that your enthusiasm wins them over.
Here's why that strategy backfires with experienced stakeholders and what works instead.
The Executive Everyone Feared
My hiring manager's warning was blunt: "One of the major business stakeholders is scary. He is loud and has been with the company for 50 years."
This wasn't just workplace gossip. This executive had legitimate concerns. Previous deliverables weren't on time, quality wasn't good, and Distribution Center operators wanted to revert to the old systems. He had every reason to be skeptical of another technology initiative.
But he was also leading a project to stand up a brand new Distribution Center, and I needed his approval for a complex implementation with an aggressive timeline.
Most people would have walked into that room with confidence and promises. I did something different.
I started with everything that could go wrong.
"You are business, and we are tech. This program is a big one—building a new facility. There are as many business parts to manage as there are tech parts. Now, here are the risks I see and how I am going to mitigate them. I'm a tech advisor here to give you the best advice."
I presented the program, the risk analysis, the mitigations, and the likelihood of those mitigations succeeding.
Then I did something most presenters avoid: I made it his decision whether to proceed.
Instead of challenging my proposal, something remarkable happened. He started problem-solving with me.
By the end of our conversation, he wasn't just approving the project. He was offering resources to ensure its success.
"I checked with Finance and I do have a headcount I can shift to your group," he messaged afterward.
The "scary" executive had become my project sponsor, saying “When Ruchi said, ‘Don’t give them a reason to go back to the old system,’ I was bought in.”
Why Transparency Wins
Here's what I learned about working with experienced, skeptical stakeholders:
They've been burned by overconfident promises before. They can spot overselling from across the room. They respect preparation more than optimism.
When you acknowledge risks upfront, you're treating them like a partner in solving problems rather than an audience you need to convince.
The relationship didn't end with just project approval. I started having regular biweekly calls to maintain transparency and address emerging challenges.
When sensitive topics came up, I approached them with the same honesty - automation issues and vendor frustrations.
These conversations turned potential conflicts into collaborative problem-solving sessions.
What Makes This Work
Difficult stakeholders aren't unreasonable. They're protective because they've seen too many confident presentations followed by disappointing results.
When you lead with risks instead of promises, you demonstrate that you understand real challenges, you've prepared for what could go wrong, and you respect their experience enough to be honest.
The Five Steps That Change Everything
Based on this experience, here's how to transform intimidating stakeholders into allies:
Say what they want to hear, but truthfully.
Shape your words around what matters to them. And don't beat yourself up over bloopers. Jackie Chan once yelled "Cheese!" instead of "Freeze." If you're navigating a different country, culture, and language, you're already winning.Stay consistent.
Keep regular touchpoints. Miss one shot? Take the next. Don't get demotivated. Step up, you'll only get better.Stop procrastinating.
One uncomfortable step beats months of delay. Reality: You just need to start.Prepare.
Get help. Practice. Someone told me, "If you've done it 10 times, the 11th time you'll kill it."Get a coach.
Don't try to win alone. Even elite athletes have coaches. The right coach changes the game.
Your most intimidating stakeholders often become your strongest advocates once they trust that you understand what they're genuinely worried about.
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Your technical skills got you here. Strategic visibility gets you promoted.
Remember:
Your difficult stakeholders don't need another confident pitch. They need proof that you understand what they're actually worried about.
Until next time,
Great piece 👏🏻👏🏻👏🏻