Jessica Best on the POV Paradox and How to Win Stakeholder Buy-In

Editor’s Note 
This article is part of a Digital Summit Collective series where we’re turning standout live sessions from recent Digital Summit events into actionable, on-demand insights for our community. Each piece is adapted from a real stage presentation—capturing the ideas, examples, and strategic thinking that resonated most with attendees. 

Jessica Best has been in enough cross-functional meetings to recognize the pattern immediately. Marketing walks in confident about what needs to change. IT arrives focused on risk and stability. Finance is thinking about cost and long-term impact. Everyone believes they’re being rational—and the conversation still goes nowhere. 

At Digital Summit Tampa, Best unpacked why these conversations break down so consistently, even when everyone at the table has good intentions.

Her central argument was not that marketing lacks the right ideas, but that most buy-in fails because teams enter decisions with solutions instead of shared understanding. 

She calls this disconnect the POV paradox: everyone is right, but only from their own seat. 

The Problem with Starting at the Solution 

Best opened her session with a familiar scenario. Marketing is using an outdated platform that’s slowing performance. The team knows it needs something better, so they research tools, compare pricing, and identify a preferred solution before looping anyone else in. 

By the time IT or finance joins the conversation, marketing is already emotionally invested in a specific outcome. Predictably, the response is resistance. IT raises security concerns. Finance questions ROI. Sales worries about disruption. 

What feels like obstruction is often something else entirely: a reaction to being handed a conclusion instead of being invited into the problem. 

 Why Pitching Creates Pushback 

One of Best’s most resonant insights is that pitching is often the fastest way to create rebuttals. When marketing leads with a solution, other teams respond by defending their own priorities. 

Marketing is rewarded for growth and speed. IT is rewarded for uptime and risk reduction. Finance is rewarded for margin and predictability. None of those incentives are wrong, but they are different. 

Without alignment on the problem, disagreement becomes inevitable. Not because the idea is flawed, but because each team is optimizing for a different definition of success. 

Here’s how to better align teams across the organization and win stakeholder buy-in.

1. Begin Alignment with Shared Language 

Best argues that buy-in doesn’t start with persuasion. It starts with clarity. 

Before tools, timelines, or budgets enter the conversation, teams need shared language. What does “transformation” actually mean in this context? What problems are truly unsustainable today? What constraints cannot be compromised? 

She shared an example where a cross-functional group spent a significant portion of a meeting simply defining terms like data ownership, integration, and risk. While it felt slow in the moment, it eliminated weeks of confusion later. 

When people feel heard early, resistance tends to soften downstream. 

2. Speak to Impact, Not Just Outcomes 

Another common misstep Best highlighted is framing proposals solely around marketing metrics. While revenue growth and efficiency matter, they are not the only measures leadership uses to evaluate success. 

IT cares about system integrity and security. Finance cares about total cost of ownership and long-term payback. Customer-facing teams care about workflow and service continuity. 

Best encourages marketers to ask a broader question: What does success look like for each stakeholder involved? When proposals address those perspectives explicitly, buy-in becomes a shared goal rather than a negotiation.  

3. Prioritize Together to Build Trust

Technology decisions rarely involve a single change. They are a series of interconnected choices with varying levels of impact and complexity. 

Best recommends prioritizing initiatives collaboratively, using frameworks that make trade-offs visible. When teams can see which initiatives are high-impact but low-effort—and which ones require deeper investment—it changes the tone of the conversation. 

Instead of lobbying for individual priorities, teams begin advocating for sequencing, realism, and shared accountability. Just as importantly, silence disappears—and silence, Best reminds us, is never the same thing as agreement. 

The Real Shift Is Empathy 

The most important takeaway from Best’s session wasn’t a process or framework. It was a mindset shift. 

If you walk into a cross-functional meeting convinced you already have the answer, alignment is unlikely. Real buy-in requires curiosity—about how others define risk, success, and responsibility. 

Best closed with a reminder that trust is built in small, human moments. Sometimes alignment starts not with a deck, but with a conversation that acknowledges different pressures and priorities. 

When marketing stops trying to sell solutions and starts building shared understanding, decisions move faster, and with far less friction. 

 Watch the Full Session 

This article was adapted from the live session POV: A Paradigm Shift, presented by Jessica Best at Digital Summit Tampa 2025. 

Watch the full video: 
https://resource.digitalsummit.com/resources/material/pov-paradigm-shift-tam25/