Geoff Taylor
Technology
From Chasing Opportunities to Choosing the Right One
Geoff Taylor had every reason to be satisfied. He had built a successful career selling innovative technology for companies like Oracle, Salesforce, Quip, and Airtable. From the outside, everything looked right.
Inside, something felt off.
The remote-first environment no longer energized him. Every week another AI startup appeared, creating a constant fear of missing the “next big thing.” He found himself reacting to opportunities rather than evaluating them strategically. And he realized he had become focused on his résumé instead of the unique value he brought.
Geoff and I had worked together years earlier, when he landed a career-defining opportunity at Salesforce. He reached out again, not because he was in crisis, but because he wanted clarity.
The Challenge
Like many high performers, Geoff wasn’t struggling because he lacked opportunities. He was struggling because he had too many. His real questions weren’t “Which company should I join?” or “How do I interview better?”
They were:
Those questions required much more than interview coaching. They required clarity.
My Coaching Approach
Our work moved through four phases: Discover, Define, Differentiate, and Deliver. Then we kept going after the offer.
Discover: Understanding Where He Thrives
Rather than starting with résumés, I started by helping Geoff understand himself. We used the Everything DiSC® assessment, a comprehensive Personal Inventory, career reflection exercises, and coaching conversations. His DiSC® profile revealed a natural catalyst: high energy, persuasive, someone who creates momentum and clarity where neither existed. Looking back across Oracle, Quip, and Airtable, we found the same through-line. He builds things other people don’t think to build, and he sells ideas before there’s a playbook for them. He had lived that strength for years but had never put it into words. The question shifted from “What job should I pursue?” to “What environments allow me to do my best work?”
That shift became the foundation for every decision that followed.
Define: A Framework for Choosing
Together we built a framework for evaluating opportunities on far more than compensation or company reputation:
Leadership quality
Organizational culture
Growth potential
Decision-making style
Work-life integration
Values alignment
Long-term career aspirations
We also named what drains him. For Geoff, it isn’t structure itself; its structure imposed without trust and respect. Knowing that helped him read each company honestly. Instead of reacting to every opportunity, he became intentional about pursuing organizations where he could make his greatest contribution.
Differentiate: From Résumé to Leadership Story
One of the biggest breakthroughs came when Geoff stopped describing himself by where he had worked and started communicating who he is. I challenged him with questions like:
If someone remembered only one thing about you after a conversation, what would you want it to be?
Beyond your accomplishments, what unique value do you create?
What role do you naturally play on every successful team?
Can someone picture you being successful here?
From those answers we built a story bank. Each story led with its one-sentence takeaway and was matched to the room: builder stories for early-stage companies, scaled-deal stories for growth-stage ones. We reconciled every number he cited, choosing one figure per claim and retiring the rest, so his story would hold up under any reference check. And I encouraged him to use AI only to fine-tune, never to write his stories. Interviewers can tell the difference.
Instead of selling his résumé, he learned to communicate his value.
Deliver: Pressure-Tested, Not Rehearsed
Only after that foundation was in place did we turn to interviews, and even then I didn’t hand Geoff answers to memorize.
His DiSC® profile also showed his growth edge. Like many high-energy communicators, he tended to over-explain. So, we built a discipline: lead with the takeaway, land it in one sentence, and stop. I coached him to open with a real win, then volunteer a loss and what he learned. Leaders who own their misses read as more secure, not less.
Before key interviews, we dry-ran the conversation, including the questions he would ask. After each round, Geoff sent me a debrief, and we drilled exactly what slipped. When a familiar gap resurfaced in a new form, we practiced until the right answer was available on any version of the question, not just the one we had rehearsed.
In one final round, the discovery questions we built together turned the interview into a two-way strategy session about the hiring manager’s biggest open problem. That’s the moment a candidate stops being evaluated and starts being seen as a partner.
Along the way we refined his executive presence, storytelling, networking conversations, compensation discussions, and decision-making under pressure. The result wasn’t someone who sounded rehearsed. It was someone who communicated with clarity, confidence, and authenticity.
Beyond the Offer: A Strong Start
Landing the role wasn’t the finish line. Before Geoff started, we worked through my Career Transition Reflection Guide to design his first 90 days. He decided which relationships to invest in first, which requests he’d say yes to, and what he would deliberately not take on too quickly.
For a natural quick-win seeker, his commitment was striking: listen more, earn credibility carefully, and take more time with big decisions.
The Outcome
Over the course of our engagement, Geoff thoughtfully evaluated more than twenty opportunities before accepting a role aligned with both his strengths and the life he wants to build.
More importantly, he left with capabilities that will serve him for the rest of his career:
A repeatable career strategy. He evaluates opportunities through a clear framework rooted in his values, strengths, and long-term goals.
A compelling story. He can articulate not only what he has accomplished, but who he is, how he works, and the value he brings.
Greater executive presence. He enters interviews and leadership conversations with confidence grounded in self-awareness, not just preparation.
A plan for day one. He started his new role with intention instead of trying to prove himself all at once.
A trusted process for future transitions. Whatever comes next, he has a proven way to make thoughtful career decisions.
In Geoff's Words
“Everyone has to learn how to sell themselves. Kristi helps you understand who you are, what you bring to the table, and how to operate at your best.” — Geoff Taylor
Why It Worked -
We started with clarity, not the résumé. Knowing where he does his best work made every later decision easier.
We built judgment, not scripts. A framework for choosing and a discipline for answering work in any room.
We stayed in the loop. Debriefing every round meant he got sharper with each conversation.
We planned past the offer. A strong start protects the decision you worked so hard to make.