Most business mentorship is just older people telling younger people what worked in a world that doesn’t exist anymore.
I’ve sat through enough mentorship sessions—both as the person asking and the person answering—to see the pattern. Someone comes in with a real problem. The mentor listens for about ninety seconds, nods knowingly, and launches into a story about what they did in a similar situation.
Except it’s never actually similar.
The market’s different. The tools are different. The expectations are different. The entire economic reality is different.
But the mentor feels useful, the mentee takes notes they’ll never use, and everyone pretends something valuable just happened.
It’s theater.
Here’s what actually happened in most of those conversations: someone with a 2025 problem got a 2010 solution delivered with 2025 confidence.
The Advice Reflex
We’re wired to give advice. It feels helpful. It positions us as competent. It’s faster than actually thinking through someone else’s specific situation.
Picture this scenario: A junior team member is trying to decide between two job offers. One’s at a stable company with predictable growth. The other’s at a startup with equity and chaos.
The advice reflex kicks in immediately:
- “Take the stable job, build your foundation first.”
- “Go for the startup while you’re young and can take risks.”
- “Negotiate the salary at the corporate job.”
- “Equity is a lottery ticket, take the cash.”
All of this might be reasonable. None of it might be right.
Because advice is general. Problems are specific.
The mentor giving that advice is projecting their own risk tolerance, their own career trajectory, their own definition of success onto someone else’s life.
What if the person asking doesn’t care about traditional success metrics? What if they’re trying to buy time to figure out what they actually want? What if the real question isn’t about the job at all, but about whether they’re even in the right field?
You can’t advice your way out of that. You have to question your way into it.
The Question Framework
Good questions do something advice can’t: they force clarity.
When someone comes to you with a problem, they’ve usually already thought through the surface layer. They know the obvious options. What they haven’t done is interrogate their own assumptions.
That’s where questions become useful.
Instead of “Here’s what I would do,” try:
- “What would success look like in this scenario if everything went perfectly?”
- “What’s the worst realistic outcome, and could you recover from it?”
- “What are you optimizing for—money, learning, optionality, stability?”
- “If you knew you’d be doing something completely different in three years, would this decision still matter?”
These aren’t rhetorical. They’re diagnostic.
The goal isn’t to lead someone to your answer. It’s to help them find their own answer using their own criteria.
Why This Matters More Now
The world changes faster than advice expires.
A career strategy that worked in 2018 might be irrelevant in 2025. The skills that made you valuable ten years ago might be commoditized or automated now. The industries that felt stable last year might be collapsing this year.
Gen Z hasn’t lived through a stable decade. They’ve seen:
- The 2008 financial crisis (even if they were kids)
- The gig economy replace entry-level jobs
- A pandemic collapse the office-based work model
- AI tools emerge that can do in seconds what used to take hours
- Entire career paths appear and disappear within a few years
They’re not looking for a map. They’re looking for a compass.
Advice is a map. “Go here, do this, follow these steps.”
Questions are a compass. “What direction matters to you? What trade-offs can you live with? What does north even mean in your situation?”
Maps go out of date. A compass still works.
What Bad Mentorship Sounds Like
“When I was your age, I worked eighty-hour weeks to prove myself.”
Okay. And? That was when face time mattered and remote work wasn’t an option. It was when showing up early and leaving late signaled commitment. Now it might just signal poor time management.
“You need to stay at a company for at least three years or your resume looks flaky.”
Maybe in 2005. Now, staying too long at one place might signal lack of ambition or fear of change. The entire context has shifted.
“Don’t job-hop for money. Build relationships and loyalty.”
Great advice—if companies still rewarded loyalty with anything other than a pizza party and a 2% raise. But most people get their biggest salary increases by leaving, not by staying.
This isn’t to say experience is worthless. It’s to say that experience without context is just nostalgia.
What Good Mentorship Sounds Like
- “What are you actually trying to solve for?”
- “What assumptions are you making that might not be true?”
- “What would you need to believe for option A to be the right choice?”
- “Who’s already done something close to what you’re trying to do, and what can you learn from their path?”
- “What’s the smallest version of this you could test before committing fully?”
Notice the difference: these questions don’t assume the mentor knows better. They assume the person asking has information the mentor doesn’t have—about their own priorities, their own constraints, their own vision of what matters.
The Socratic Shift
Socrates didn’t lecture. He questioned.
He’d take a confident statement and pull at its threads until the person realized they didn’t actually know what they were talking about. Not because Socrates wanted to humiliate them, but because clarity comes from interrogation, not assertion.
Modern mentorship needs more of that energy.
Not the arrogance—Socrates could be insufferable—but the method. The willingness to say “I don’t know your situation well enough to tell you what to do, but I can help you think through it.”
That’s harder. It takes more time. It requires you to actually listen instead of waiting for your turn to talk.
But it’s also the only kind of mentorship that scales across contexts. Because the questions work even when the answers change.
When Advice Actually Works
There are times when advice is useful:
- Tactical execution: “Here’s how to structure a pitch deck.”
- Procedural knowledge: “Here’s how equity vesting typically works.”
- Pattern recognition: “I’ve seen this exact scenario three times, and here’s what usually breaks.”
These are transferable. They’re not context-dependent in the same way.
But even then, the best mentors frame it as information, not instruction.
“Here’s what I’ve seen work” is different from “Here’s what you should do.”
One leaves room for judgment. The other assumes your situation maps perfectly onto someone else’s experience.
The Uncomfortable Truth
Most people who offer mentorship are doing it to feel useful, not to be useful.
It’s ego disguised as generosity. “Let me tell you about my journey” is often just “Let me talk about myself while you take notes.”
Real mentorship is uncomfortable. It means admitting you don’t have all the answers. It means sitting with someone else’s uncertainty instead of rushing to resolve it. It means asking questions you don’t know the answer to and trusting that the other person can figure it out.
That’s not satisfying in the moment. You don’t walk away feeling like you dropped wisdom. You walk away feeling like you just had a good conversation.
But six months later, the person you talked to has made a decision that actually fits their life. They didn’t follow your advice—they followed their own logic, sharpened by your questions.
That’s what mentorship should feel like.
The Real Value of Experience
Experience isn’t worthless. But its value isn’t in the conclusions you reached. It’s in the process you used to get there.
The frameworks you built for evaluating trade-offs. The mistakes you made that taught you what to watch for. The moments when conventional wisdom turned out to be wrong and you had to adjust.
Those are transferable. The specific decisions you made are not.
So when someone asks for your advice, don’t tell them what you did. Tell them how you thought about it. Share the questions you asked yourself. Describe the variables you weighed.
Then let them run that same process on their own situation.
What This Looks Like in Practice
Someone asks: “Should I take this job?”
Bad response: “Yes, that company has great culture and the role will teach you a lot.”
Better response: “What would make this job a success for you personally? Not in general—what specifically are you hoping to get out of it?”
They might say: learning, money, network, resume credibility, work-life balance, creative freedom.
Then you ask: “Which of those is non-negotiable? Which could you get elsewhere? What’s the downside if this doesn’t deliver on the thing you care most about?”
Now they’re thinking in terms of their own priorities, not yours.
Someone asks: “How do I get promoted?”
Bad response: “Work hard, take initiative, make yourself indispensable.”
Better response: “What does your company actually promote people for? Is it tenure, results, visibility, relationships, or something else? And do you know anyone who got promoted recently—what did their path look like?”
Now they’re investigating the real system, not following generic advice.
Someone asks: “Should I start a business or stay in my job?”
Bad response: “Follow your passion” or “Stay safe and build security first.”
Better response: “What would starting a business give you that staying in your job doesn’t? And is there a way to test that hypothesis before you fully commit?”
Now they’re designing an experiment, not making an all-or-nothing bet based on someone else’s risk tolerance.
The Shift
Stop positioning yourself as the person with answers.
Start positioning yourself as the person who asks better questions than the other person has asked themselves.
That’s the mentorship that really matters.
Because in a world where everything changes every three years, the only sustainable skill is knowing how to think, not what to think.
And you can’t teach someone how to think by telling them what to do.
You teach them by making them defend their assumptions, clarify their goals, and confront the trade-offs they’ve been avoiding.
That’s uncomfortable. It’s slow. It doesn’t feel like you’re helping in the moment.
But it’s the only thing that actually works.
The Bottom Line
If you’re mentoring someone and you spend more time talking than they do, you’re doing it wrong.
If you’re mentoring someone and they leave with your answer instead of their own, you’re doing it wrong.
If you’re mentoring someone and you feel like you just gave a great performance, you’re doing it wrong.
Good mentorship is awkward, uncertain, and collaborative.
It doesn’t feel like wisdom being passed down.
It feels like two people trying to figure something out together, except one of them has seen more patterns and knows which questions usually lead somewhere useful.
That’s it. That’s the whole thing.
Start asking better questions.
The people you’re trying to help will thank you for it… and ultimately, you will thank yourself.
Want to Learn How to Ask Better Questions?
Whether you’re leading a team, building a business, or navigating your own career—the right questions change everything.