How to Find and Choose the Perfect Advisor for You and Your Business

Theodore Georgedakis
2 days ago
4 min read

Most Leaders Hire Advisors for the Wrong Reasons

Let's be uncomfortably honest.

Most entrepreneurs hire advisors because:

They want validation, not challenge
They need a name on their deck, not wisdom in their ear
They're buying credibility by proximity
They hope delegation equals transformation

And here's what happens: six months in, the advisor becomes a quarterly Zoom call, a signature on an email, and a line item that drains budget without driving momentum.

The problem isn't the advisor. It's the selection criteria.

After 22 years building, advising, and occasionally being the wrong advisor for the wrong client, I've learned this:

The right advisor doesn't give you answers. They upgrade the questions you're asking.

So if you're about to hire an advisor—for growth, strategy, operations, or positioning—here's the system that actually works.

1. Diagnose Before You Recruit

What You Actually Need (Not What You Think You Need)

Most founders skip the diagnostic and jump straight to the Rolodex. Bad move.

Ask yourself:

Energy Question:Do I need someone to ignite momentum, or sustain momentum?

Friction Question:Is my bottleneck strategic (direction), operational (execution), or psychological (courage)?

Alignment Question:Do I need an advisor who challenges me, or one who translates my vision to the team?

The 3 Advisor Archetypes:

Type	Best For	Red Flag
The Strategist	Founders who know how to execute but lack clarity on what to build	If they can't simplify complexity into one sentence
The Operator	Founders who have vision but weak systems	If they've never built what they're advising on
The Connector	Founders who need doors opened, not plans written	If their network is their only value

Most businesses need one type—but hire all three, creating noise instead of momentum.

2. Test for Fit, Not Pedigree

Credentials Are Overrated. Chemistry Is Underrated.

A Harvard MBA who scaled three SaaS companies is impressive.

But if they:

Don't understand your market
Can't communicate in your language
Aren't emotionally aligned with your pace

...they're the wrong advisor.

The Fit Test (Run This in Your First Conversation):

Do they ask more questions than they give answers?Great advisors diagnose before they prescribe.
Can they name the one thing you should stop doing?Weak advisors add complexity. Great advisors create clarity through subtraction.
Do they challenge your assumptions without dismissing your intuition?You need tension, not validation. But you also need respect, not arrogance.
Would you want to have a drink with them after a brutal quarter?Advisors aren't spreadsheets. They're humans. If the chemistry feels transactional, it will become transactional.

3. Structure the Engagement Like You Mean It

Vague Mandates Create Vague Results

If your advisor relationship is "we'll meet quarterly and see what comes up," you've already lost.

The Ignition Agreement (What to Define Up Front):

The Strategic Mandate:

What is the one outcome this advisor must help you achieve in the next 90 days?

Not "growth." Not "strategy."Try: "Clarify our ICP and kill three underperforming initiatives."

The Rhythm:

Weekly 30-min strategy calls? Monthly deep-dives? Async Loom reviews?
Don't default to "whatever works." Momentum needs cadence.

The Boundaries:

What decisions do they influence vs. make?
When should they challenge you publicly vs. privately?
What does "success" look like in 6 months?

The Escape Hatch:

Great relationships have exit clauses. If it's not working after 90 days, both parties should be able to walk without drama.

4. Avoid the 5 Advisor Traps

Trap 1: The "Trophy Advisor"

Big name. Zero time. Great for your LinkedIn. Useless for your business.

Trap 2: The "Theorist"

Brilliant frameworks. Has never executed one under real-world pressure.

Trap 3: The "Yes Person"

Validates every decision you make. You hired a cheerleader, not a strategist.

Trap 4: The "Empire Builder"

More interested in building their brand through your success than your momentum.

Trap 5: The "Fixer"

Steps in to solve every problem. You become dependent. They become indispensable. You never learn to lead without them.

The antidote?Hire advisors who make themselves obsolete by making you better.

5. The Questions You Should Ask (That Most Founders Don't)

In your vetting conversations, skip the resume tour.

Ask these instead:

"What's a decision you got spectacularly wrong, and what did you learn?"
If they can't name one, they're either lying or haven't taken enough risk.
"What would you do in my position if you had six months and limited budget?"
Tests for strategic clarity and prioritization under constraint.
"What do you think I'm avoiding right now?"
Great advisors sense what you're not saying.
"How do you define success in an advisory relationship?"
If their answer is vague, the relationship will be too.
"What would make you walk away from this engagement?"
Reveals their standards and boundaries.

6. Pay Them Like You Mean It

Equity, Retainer, or Hybrid?

Cheap advisors give cheap advice. Expensive advisors aren't always worth it.

The Compensation Matrix:

Model	Best For	Risk
Equity Only	Early-stage, cash-light, long-term play	Advisor has no urgency
Retainer Only	Established business needing consistent strategic input	Advisor may lack skin in the game
Hybrid (Retainer + Equity)	High-growth phase where both cash and upside matter	Balance complexity

Controversial take:If an advisor isn't willing to take some equity, they don't believe in your business. If they only want equity and no retainer, they're not committed to the next 90 days.

The Real Test: Do They Increase Your Momentum?

Here's the only KPI that matters:

After three months with this advisor, has your business accelerated?

Not "learned more."Not "feels good about strategy."Not "has better slide decks."

Accelerated.

Meaning:

Clearer priorities
Faster decisions
Reduced friction
Increased alignment
Measurable forward motion

If the answer is no, the advisor is either wrong for you, or you're wrong for them.

Final Provocation: Maybe You Don't Need an Advisor

Here's what no one tells you:

Most businesses that think they need an advisor actually need:

✔ A decision they're avoiding

✔ A system they haven't built

✔ A conversation they haven't had

✔ A priority they haven't clarified

Advisors are force multipliers—but only if you're already moving.

If you're stuck, an advisor won't ignite you.

You have to ignite yourself first.

And once you do?

The right advisor will help you turn that spark into a system.The wrong advisor will make you feel productive while you stay stuck.

Choose accordingly.

Theodore Georgedakis

Growth Igniter