Why Stakeholders Push Boundaries (and How to Respond)

The year was 2003, and I was sitting in the editing closet of a small-town television station, watching an early version of Adobe Premiere slowly render my latest edit. Next to me sat Herb, the station's owner, enthusiastically describing the spinning transitions and sepia-toned effects he imagined for our next commercial. The fact that these effects were either impossible with our software or irrelevant to what our advertisers needed was beside the point – Herb was thinking out loud, throwing ideas at the wall to see what might stick.

Twenty-two years later, as a digital product consultant working with teams of strategists, designers, and engineers, I recognize this same dynamic playing out in boardrooms and client meetings across the technology industry. Non-technical stakeholders often push for features or capabilities that seem either technically impossible or strategically questionable. But I've learned that the key isn't to focus on what's impossible – it's to understand why they're asking for it in the first place.

Beyond the Surface Request

When stakeholders rattle off creative ideas or push for seemingly impossible features, they're rarely just being difficult. More often, they're:

• Brainstorming out loud, hoping their ideas might spark better solutions
• Trying to solve a real business problem, even if their proposed solution isn't quite right
• Expressing a vision of what they want to achieve, even if the specifics aren't feasible
• Drawing from things they've seen elsewhere, without understanding the underlying complexity

Back in that editing closet, Herb wasn't really asking for spinning transitions – he was looking for ways to make our local commercials more engaging and professional-looking. Understanding this underlying motivation was far more valuable than fixating on the technical ability of his specific requests.

Shifting the Conversation

The natural instinct of many technical leaders is to immediately push back on feasibility. "That's not possible with our current stack" or "That would take six months to implement" are common responses. But this creates an adversarial dynamic that misses the real opportunity.

Instead, the key is to:

1. Listen to understand the underlying need or goal
2. Explore why they think their suggested solution would help
3. Redirect the conversation toward pragmatic solutions that address the core problem
4. Then consider technical feasibility as part of the solution design

Today, when a client suggests implementing some complex AI feature or a complete platform overhaul, my first response isn't to explain why it's challenging or impossible. Instead, I ask questions: What problem are you trying to solve? What outcome are you hoping to achieve? How would this change things for your users?

The Value of the "Yes, And" Approach

This doesn't mean saying yes to everything. It means engaging with the spirit of the request rather than its literal implementation. When Herb asked for impossible video effects, a better response than my teenage "that's not possible" would have been: "Tell me more about how you want these commercials to feel to viewers."

However, this approach requires careful balance. You can't just be an endless yes-person, or you risk setting unrealistic expectations and undermining your own expertise. The goal is to:

• Acknowledge the underlying need or vision.
• Guide the conversation toward practical solutions.
• Don't write off wildly imaginative ideas. Engage with them in a sprit of genuine curiosity.
• Set clear boundaries about what's actually achievable over different time horizons.
• Keep the focus on user value and business outcomes.

The Takeaway

In today's technology landscape, where AI and other emerging technologies are constantly expanding the realm of possibility, this skill becomes even more critical. The gap between what people imagine technology can do and what it actually can do (or should do) is growing wider.

The lesson I learned in that small-town TV station wasn't really about video editing software – it was about how to work with people who have big ideas but limited technical understanding. Sometimes they're just thinking out loud. Sometimes they're pushing boundaries to see what's possible. And sometimes, buried in their seemingly impossible requests, is the seed of a genuinely valuable solution.

The key isn't to jump to a technical assessment – it's to understand the underlying need and guide the conversation toward pragmatic solutions that solve the real problems. That's true whether you're making local TV commercials or building enterprise software solutions.