Executive Career Coach in Sarasota for Leaders in Transition
Two people find this page. One can't decide whether to leave. The other already did and is now three weeks into a seat that's bigger than the last one.
I'm Christina Carey, an executive career coach in Sarasota, Florida, and I work on both, because they're the same problem at different points on the clock. A transition isn't really a logistics event. It's a period where the story you've been telling about yourself stops matching the situation, and what you do in that gap determines how the next two years go.
What I'm not: I don't write résumés, optimize LinkedIn profiles, run interview drills, or have recruiters to introduce you to. Those are real services and there are people who do them well. This is the other thing: the decision itself, and whether you show up in the new seat as the person the role actually requires.
Three transitions I see constantly
You've been about to leave for eighteen months. The résumé gets updated every few months. You take the recruiter's call. You get to a second conversation and then something intervenes: the counteroffer, the reorg that might change things, the bonus that vests in March.
From the outside it looks like bad timing four times running. It isn't. You're not short of options; you're avoiding a decision about who you are without this title on the badge, and every stall costs you a year you don't get back.
You're ninety days into the bigger job and quietly overwhelmed. You got it, which means they believe you can do it. So you're running the play that worked before: being the most prepared person in the room, out-working the gap, personally handling the things you're best at.
Meanwhile the parts that are actually the new job sit untouched, because they're unfamiliar and you'd rather be excellent at the old thing than mediocre at the new one. Nobody will tell you this for six months. By then it's a pattern people have opinions about.
You were pushed, not pulled. A restructure, a new CEO with their own people, a role that got “redefined” until it wasn't yours.
Now you're running a search from a position that feels like recovery, and it leaks into how you describe the last company, how fast you'd take less than you're worth, how much you're trying to prove in a first conversation. The market reads that instantly, and the harder you work to hide it the more visible it gets.
The part most career coaching skips
First: is it the job, or is it the pattern? This is the question I'd want answered before anyone resigns. Some situations are genuinely bad and leaving is right. But a meaningful share of executive moves are attempts to escape something that turns out to be portable: the conflict avoidance, the over-functioning, the inability to be disliked.
It's waiting at the new company inside a quarter. Nobody wants to hear this in the middle of an exit fantasy, which is exactly why it's worth the conversation. The pattern travels. If it's the pattern, changing companies costs you eighteen months and teaches you nothing.
Then: the identity the new seat requires. Every step up asks you to stop doing something you were rewarded for. That's the actual difficulty, not the skills, which you'll pick up. It's that your sense of being valuable is welded to work the new role needs you to hand away.
Naming that is what makes it possible to let go, rather than white-knuckling it and drifting back within a month. More on that inner work →
Then: accountability through the part where it gets real. A search or a first ninety days is precisely when good intentions decay, because there's no boss checking and the feedback loop is long. We set commitments specific enough to evaluate: conversations to have, people to meet, things to stop doing.
We meet every other week for six months, check in by text or email between, and talk directly when something slips. How the accountability works →
Six months is the right length for this. Long enough to cover a decision, a move, and the first stretch in the new seat, which is the arc where a transition is actually won or lost.
What it looks like when a stalled decision finally moves
A client of mine spent months circling a move she knew she wanted. Then came the week the doubt arrived properly: the pull of the security she was preparing to leave, the excuses, the slowing down. She brought it to coaching instead of hiding it, which is what the structure is for.
“My caveman brain kicked in. Doubting myself, craving security, making excuses to slow down. One accountability conversation later, I was back in motion: five outreach calls done before lunch, and a hard deadline on the calendar. It scares me and excites me to proclaim it.”
The transition didn't turn on motivation. She had plenty and it evaporated on cue. It turned on a coach who expected the truth about the wobble, a commitment with a date attached, and a next action small enough to finish before lunch on a Monday.
Common questions about executive career coaching
- Do you help with résumés, LinkedIn, or interview prep?
- No. I don't write résumés, rewrite profiles, run mock interviews, or make recruiter introductions. Those are legitimate services. Hire someone who does them well, and do it alongside this if you're in an active search. My work is the decision underneath the search and the person who shows up in the new role. Different problem, different specialist.
- How is this different from working with a recruiter?
- A recruiter is paid by the company to fill a role, which makes them useful and means their interests aren't yours. Outplacement is paid by your former employer. I'm paid by you, which is the whole difference. It also means I'll tell you when I think the move you're describing is a mistake.
- I'm not sure I want to leave. Is that too vague to coach?
- That's the best possible starting point, and it's when this is most valuable. Once you've resigned, the decision is made and we're just managing consequences. Ambivalence is workable material. Usually the ambivalence itself is the information, and it's pointing at something specific.
- I just got promoted and things are going fine. Why would I need this?
- Because the first ninety days set expectations you'll live with for years, and the failure mode is invisible while it's happening. Coaching arranged after a new executive struggles is remediation and everyone knows it. Coaching in month one is just competence, and it moves faster.
- What if I'm leaving to start something of my own?
- That's a large share of my work. The transition from operator to owner is mostly a mindset transition. The income drop is survivable and the identity change usually isn't planned for at all. It's the move I've coached more than any other.
- How long is an engagement, and how often do we meet?
- Six months, every other week, in person in Sarasota or over Zoom, with check-ins by text or email between sessions. I don't do single sessions. A transition decision made in one conversation is a decision made under pressure.
- What does it cost?
- $2,000–$3,000 per month depending on scope, billed monthly. Detail on the coaching fees page.
- Do you work with leaders outside Sarasota?
- Yes. I meet clients in person across Sarasota, Bradenton, Lakewood Ranch, and Venice, and work with executives nationally over Zoom.
Before you decide, have one honest conversation
Thirty minutes, free. Bring the move you've been turning over: whether to make it, or the one you just made and are quietly white-knuckling. You'll leave with a clearer read on whether it's the job or the pattern, which is worth knowing either way.