[RBM+E] “D” - Engaging decision-makers at the early stage of proposal.

In this partially free post, I'll share my battle-tested approach for engaging C-level executives during the critical early stages of enterprise proposals. After years working with technology leaders—CTOs, CIOs, and increasingly, Chief Transformation Officers—I've developed a methodology that turns initial conversations into powerful partnerships.

The challenge is clear: today's executives recognize the need for transformation but often struggle to map the journey from the current state to desired outcomes. This creates a perfect opportunity for strategic partners who can bridge this gap with clarity and vision.

Through my work with dozens of enterprise organizations, I've identified these essential elements for successful executive engagement:

• Identifying the right decision-makers

• Creating personalized outreach that resonates

• Positioning early concepts effectively

• 🔐 Building collaborative narratives that extend their thinking

• 🔐 Engaging cross-functional stakeholders before final decisions

• 🔐 Transforming from vendor to trusted advisor

In this guide, I'll walk you through the journey of finding your champions of change and making that first meaningful connection. You'll discover strategies for gathering internal intelligence and crafting messages that cut through the noise of busy executive schedules.

Photo by Paul Hanaoka on Unsplash

I'll then reveal my proven frameworks for managing complex stakeholder relationships, developing proposals collaboratively, and the subtle art of positioning your ideas as natural extensions of executive thinking. Through real-world case studies where these approaches secured million dollar transformation initiatives, you'll gain practical templates and tactics you can immediately apply to your next executive engagement.

Let's begin with the fundamentals of identifying and connecting with the right decision-makers—a skill that separates successful change agents from those whose brilliant ideas never see implementation.

Identifying the right decision-makers

In enterprise environments, not all decision-makers carry the same weight. I've watched truly innovative solutions crash and burn simply because they landed on the wrong executive's desk at the wrong time.

When you're trying to navigate the C-suite, looking beyond someone's title is absolutely critical. Through my years working on major transformation projects, I've noticed three dimensions that really determine how valuable an executive will be to your proposal journey:

First, there's what I call their Sphere of Influence. Have you ever noticed how some executives seem to have tentacles reaching across the entire organization, while others stay in their lane? That CTO who regularly grabs coffee with business unit leaders will open far more doors than the one who's primarily focused on server infrastructure.

Then there's Appetite for Innovation—and this varies wildly. I remember one project where we were spinning our wheels with a risk-averse CIO until we pivoted to the newly appointed Chief Digital Officer. Not only did our timeline shrink dramatically, but our budget actually expanded. The difference in mindset was night and day.

The third dimension—and I can't stress this enough—is actual Budget Authority. There's a world of difference between influencing budgets and controlling them. I learned this lesson painfully with a telecommunications client when our carefully cultivated CIO champion ultimately needed four additional signatures, stretching our timeline by months. That's time none of us can get back.

Before you make your first move, I'd strongly suggest creating what I call a stakeholder influence map. This isn't complicated, but it's incredibly valuable:

• Look at recent transformation initiatives—who actually championed the successful ones? Who has a strong opinion over that?

• Spend some time on LinkedIn, understanding reporting relationships and career backgrounds. Sometime if someone has kids or not can be a critical risk management factor, it works both for your clients but as well your colleagues if you work on internal transformation

• If you have access to industry analysts, they often have insights into who drives decisions, there is a lot of information's like that also available sometime in public reports, but it requires a lot of time

I remember working with a manufacturing client where conventional wisdom suggested targeting the CIO. But after some digging, we discovered the VP of Supply Chain Operations had emerged as the real innovation catalyst. We approached them as a pair, and it made all the difference—enthusiastic support and a much faster approval process.

Photo by Mahdi Bafande on Unsplash

In my experience, the executives most likely to champion your proposal are those facing immediate challenges that align with your solution. I use a simple framework to prioritize my outreach:

1. High Priority:
   When: Publicly committed to relevant transformation. Do: Position as enabler of stated vision.

2. Medium Priority:
   When: Facing industry pressure in your solution area. Do: Educate on competitive advantages.

3. Low Priority:
   When: No visible connection to your value proposition. Do: Build longer-term relationship before proposing.

One thing worth remembering—timing really is everything. That executive who brushed off your proposal in Q1? They might become your biggest advocate in Q3 when their priorities shift. I've personally revived seemingly dead opportunities multiple times just by staying aware of these business cycles and being patient.

When you thoughtfully select your executive entry point, you're not just starting a pivotal conversation—you're designing the path of least resistance for your proposal's journey. Have you mapped out who might be your ideal champion in your current target organization?

Creating personalized outreach that resonates

Once you've identified your executive champions, crafting outreach that genuinely resonates becomes your next critical challenge. I've found that truly personalized communication requires tailoring not just to the organization, but to the specific individual and their unique perspective.

For customer-facing projects, I always research the executive's public statements about their strategic priorities. When approaching a CFO about a financial transformation, I focus on efficiency metrics and ROI. That same proposal to a COO shifts toward operational resilience and scalability. The CIO? They're typically most engaged by discussions of technical debt reduction and integration capabilities.

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Internal initiatives require an equally nuanced approach, but with the added dimension of organizational politics. When seeking executive sponsorship for our internal data governance program, I crafted dramatically different pitches for each leader:

• For our CTO, I emphasized the technical architecture benefits

• Our Chief Risk Officer responded to compliance and security angles

• The CMO engaged when I framed it around customer experience improvements

The perspective gap between roles can be striking. I recall an enterprise resource planning implementation where the CFO was laser-focused on consolidating financial reporting, while the CHRO saw it primarily as a workforce analytics opportunity. Same project, completely different value propositions.

What's worked consistently for me is creating what I call "perspective maps" for each stakeholder. I document their:

• Primary business objectives (both stated and implied)

• Key performance metrics they're evaluated on

• Recent wins and challenges they've faced

• Communication preferences (data-driven, narrative, visual)

This approach paid dividends with a healthcare client where we initially struggled to gain traction. By recalibrating our message for each executive—clinical outcomes for the CMO, cost reduction for the CFO, and competitive differentiation for the CEO—we transformed polite interest into enthusiastic championship.

Positioning early concepts effectively

The earliest stages of engagement are often where the most critical strategic decisions are made. I've found that starting with a targeted approach rather than a broad one yields significantly better results. Three principles have consistently served me well:

Firstly: Identify your ideal champion before crafting your message

Not all executive sponsors are created equal. The most effective champions typically:

• Have direct authority over the problem space you're addressing

• Command respect across departmental boundaries

• Are experiencing active pain that your solution addresses

• Have a track record of successfully sponsoring similar initiatives

I once wasted months courting a CIO who seemed enthusiastic but lacked the organizational capital to drive adoption. Meanwhile, the COO—who rarely attended technology discussions—was actually the decision-maker with the most aligned incentives.

Second: Concentrate resources on securing your champion first

It's tempting to spread your efforts across multiple stakeholders, but this often dilutes your impact. Instead:

• Invest disproportionate time understanding your champion's specific challenges

• Customize early demonstrations to address their particular pain points

• Provide them with materials they can use to socialize concepts internally

• Be responsive to their feedback with rapid iterations

With a manufacturing client, we focused exclusively on the VP of Operations for six weeks before approaching anyone else. By the time we expanded our engagement, he had already become our internal advocate, opening doors we couldn't have accessed directly.

Third: Enable your champion to look visionary

The most powerful champions aren't just solving problems—they're advancing their own strategic narrative. Help them by:

• Connecting your solution to their publicly stated objectives

• Providing insights they can share to demonstrate thought leadership

• Creating metrics that showcase their impact beyond the immediate project

• Anticipating questions they'll face and arming them with compelling answers

Your goal isn't just to win their support but to make them feel ownership of the vision. When they start describing your solution in their own words to their peers, you've succeeded in positioning your early concept effectively.