(read to the tune of Green Eggs and Ham)
I do not want just any role.
I want the one that fits my soul.
Could you help me? Yes, you could!
Hey, would you? Yes, you would.
I've led a team. I've run a board.
I've cut the costs the CFO deplored.
I've launched the product, closed the sale,
I've steadied ships about to fail.
But now I'm here and I'm unsure.
Is corporate really my next tour?
Or should I found? Or should I buy?
Or go fractional and multiply?
Would you take a founder's leap?
Would you buy a franchise cheap?
Would you consult from nine to three?
Would you chase the C-suite fee?
I could go tech. I could go health.
I could chase impact, chase the wealth.
I could go finance, lean and sharp,
or nonprofit and pluck that harp.
A VP here? A chief out there?
A fractional seat? A founder's chair?
The titles blur, the options grow,
and you ask, "What do you know?"
I know supply. I know the chain.
I know how to explain the plain.
I know the pitch, the deck, the room.
I know the market's bust and boom.
I speak in data. I speak in teams.
I turn the mess to workable dreams.
I read the P&L with ease,
I calm the storm, I steer the seas.
"But here's the thing," you say to me,
"the pay is not the whole story.
The two-fifty base can look just fine
and hollow out your one true line."
Would you take it for the check?
Would you wreck your health, your neck?
Would you climb a ladder tall
that leans against no wall at all?
I would not take it for the pay.
I would not lose myself that way.
Not for the title. Not the perks.
Not for a role that never works.
So you sat me down to see
not just the market, but the ME.
The skills I have, the ones I've grown,
the kind of work that feels my own.
And here's the thing I did not know:
the clearest people move and grow.
Not fastest first, but truest aimed,
they land the roles that feel unshamed.
Would you found? You just might.
Would you go fractional? That's right.
Would you take the corporate seat?
If it's the one that makes you complete.
I do not want just any role.
I want the one that fits the whole
of who I've been and who I'll be.
And now, at last, I think I see.
I'll take the path that fits my soul.
Thank you, coach.
You helped me find my role.
So, that was fun with Claude and Doctor Seuss. All of which leads to the following: there are important questions to be answered by leaders contemplating hiring a career advisor (aka Coach).
A few years ago, when a leader found themselves between roles, what came nex was fairly simple. Where is my next corporate job, and how fast can I land it? The whole search pointed in one direction, and the only real variables were speed, title, and compensation.
That isn't the whole conversation anymore. For many accomplished professionals, a layoff, or even a career that has simply run its course, has become the first real permission they've had in decades to stop chasing the next title and start designing a career that truly fits who they are today.
In 2026, more of the executives, founders, and professionals I speak with are slowing down before they sprint toward the next opportunity. They're asking: What do I actually want this next chapter to look like? Is another corporate leadership role the right fit? Is this the moment to build something of my own? Should I acquire a business, invest in a franchise, or leverage my experience as a fractional executive across several organizations instead of dedicating it all to one?
As I am sure you can tell, those paths are not variations on the same search. Founding a company, buying a franchise, going fractional, and taking another executive role are four genuinely different lives. They demand different risk tolerances, different financial runways, and different daily realities.
Before you hire anyone to help you, you have to get honest about which direction you are even heading and whether the person you are considering as your career counselor is equipped to help you get there. A resume expert cannot help you pressure-test a franchise model. A job-search coach is not the right partner for deciding whether you have the temperament to found something.
So before you interview anyone, interview yourself. People ask me all the time who the best career coach is, and I always give the same answer. The best advisor for someone else might be exactly wrong for you, because the right help depends entirely on the path (or paths) you are choosing.
To me, this is advisory rather than coaching, and the distinction is not just semantics. A coach helps you run a play. An advisor helps you decide which game you are playing in the first place. When the question on the table is founder versus fractional versus franchise versus corporate, you need a thinking partner, not a coach.
Here are the questions worth sitting with before you choose anyone.
Do you actually know which direction you are heading?
Be honest about whether you have really decided, or whether you are defaulting to another corporate role because it is familiar and the bills are real. There is no wrong answer here. Another executive seat can be exactly right. But so can founding, buying, or going fractional, and each one asks something different of you. Ask yourself:
- If money were not the immediate pressure, which of these paths actually excites me?
- What am I moving toward, versus just moving away from?
- Have I ever run my own thing, and did I love it or resent it?
- Whose life, among people I know, do I actually envy right now?
Do you want to learn how to run a search, get an education, and grow your network as you research, or do you want someone to lead you every step?
Some professionals want to genuinely understand the terrain, whether that is today's hiring market, the economics of a franchise, or how to structure fractional engagements, so they never feel lost again. Others are simply exhausted and want someone to say, "Here is what we are doing this week; follow me." Neither is wrong, but the fit breaks down when your expectations and their style do not match.
Ask:
- Will you teach me why we are doing something, or mostly just tell me what to do?
- How much of this is educational versus done for me?
- By the end, how independent should I expect to be?
- Have you helped people pursue paths other than a traditional job search?
What kind of accountability actually helps you?
Some people need encouragement. Some need someone willing to challenge them. After years of working with executives, founders, and professionals in transition, I can tell you both approaches work. The only thing that matters is knowing which one moves you. If you were just blindsided by a layoff, rebuilding confidence probably comes first. If you have been circling the same decision for eight months without acting, you may need someone who will lovingly refuse to let you hide.
Ask them:
- How do you handle someone who stalls out?
- Tell me about a time you had to challenge a client.
- Tell me about a time you helped someone rebuild their confidence.
- How would the people you work with now describe your style?
Are you choosing a person, or buying a product?
This is the one I wish more people slowed down for. Never invest thousands of dollars before you have met the actual person you will be working with. Not the salesperson. Not the founder who ran the webinar. The person who will be in the room with you week after week. Chemistry matters. Trust matters. The way someone communicates matters enormously when you are about to be honest with them about your fears, your finances, and your future. If a company assigns you to someone without letting you decide whether it fits, ask why. You deserve a say.
Does the engagement actually make sense?
I believe this work should build momentum, not dependence. I would be cautious about signing a six or twelve-month commitment before you have ever worked together. Three months is usually enough to know whether the relationship is productive. If things run longer, look for arrangements that let you extend month to month rather than locking you in from day one. The right advisor wants you to stay because you are seeing results, not because you are trapped in a contract.
A few more worth asking before you sign anything
- Who, specifically, will I be working with?
- Can I switch to someone else if it is not clicking?
- How reachable are you between sessions?
- What kinds of professionals and paths do you help with most often?
- What does success look like in the first thirty days?
- What happens if this takes longer than expected?
Be careful with anyone who guarantees the outcome
Be cautious of anyone who promises to get you hired by a certain date or guarantees a specific salary, and be just as cautious of anyone who promises your business idea will work. No one can control the market, the timing, or the hiring manager, and certainly no one can guarantee a venture. What a good advisor can control is the quality of your strategy, the strength of your positioning, the depth of your preparation, and the honesty of your thinking. Those are the things that reliably improve outcomes. Anyone selling you certainty is selling you something that does not exist.
One last thing
This next chapter is one of the biggest investments you will ever make, and not just financially. It is emotional, and it asks a lot of you. The right advisor does not just polish your resume. They help you decide which direction is genuinely yours, think more clearly once you have chosen it, describe your value accurately, and keep moving when it gets hard.
But even the most accomplished advisor will not be right for everyone. So do the quiet work first. Get honest about the direction. Understand yourself. Then choose someone whose experience and process fit both the path you are on and the way you actually work.
That is the whole reason we built ReflectionPoint Advisors the way we did. Not as a coaching program with one fixed script for one fixed outcome, but as an advisory partnership for leaders standing at a genuine fork, trying to choose well. If that is the kind of thinking partner you are looking for, a Clarity Call is a good place to start. It is complimentary and a real conversation, not a pitch.
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