How I Turned a Cold CIO into a Client by Building Trust and Finding a Win-Win Solution
When all roads to a critical decision-maker feel blocked, do you press on or pull back? Sometimes, success doesn’t mean finding a new door but having the courage to knock harder on the ones already in front of you.
What is holding back your biggest opportunities?
Once upon a time, I faced a situation where I’d been told repeatedly, “You won’t get a meeting with the CIO.” This CIO had become a dead-end for projects, with initiatives routinely stalling on their desk. He said he didn’t like nor meet with vendors.
Instead of accepting defeat, I sought out relationships with the Board, CEO and CFO. They forced him to take a meeting with me, which was painful at first, but the deal happened.
Key Strategies That Made This a Win:
Identify Organizational Values and Synergies
When roadblocks arise, the first step is understanding what matters most to the organization. I worked with my team to pinpoint synergies that aligned with their goals and explored every angle for mutual benefit.
Leverage Influential Networks
I reached out to a contact who was connected to a board member of this organization, litmus testing ideas to uncover where we might bridge gaps. The board’s perspective added new insights and momentum.
Build Relationships Through LinkedIn
From there, I connected with the CEO and CFO on LinkedIn, solidifying a strategic approach to secure the conversation we needed with the CIO.
Face the Objections Head-On
When the CIO, visibly unimpressed, confronted me with “You forced me to say no in person,” I responded with empathy and purpose. I acknowledged their perspective, pivoting to show how we could turn this into a win. “Give us the trust of arming us with your pain points and allow us the chance to address them,” I said, emphasizing a partnership, not a sales pitch.
Demonstrate Value Immediately
The CIO’s guarded trust led to some initial projects—a chance to prove ourselves. We executed them with precision, establishing credibility and showing real value, one step at a time.
What if your next big opportunity isn’t a new lead or account but an existing relationship just waiting for a fresh approach?
When faced with resistance, don’t pull back; push forward with purpose, empathy, and a genuine desire to create value.
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