When the mentor is wrong

by Kat Shepherd | Leadership, Strategy

BizFlixTalk cover illustration: Kat Shepherd at a boardroom table with six advisors, beside books labelled strategy, finance, legal, marketing, operations, people and culture, and industry insights

It is a good thing to seek advice.

As founders, owners and leaders, we can get stuck inside our own thinking. We know the business. We know what we want. We have instincts that got us this far, and sometimes those instincts are exactly right: go for it, keep going, trust yourself.

But sometimes we build a wall around our own ideas without realizing it. That’s when an outside voice can be incredibly valuable.

A mentor can expand your thinking. An advisor can see a risk you missed. Someone who has already lived through what you’re facing can save you from learning every lesson the expensive way.

I believe in mentors. I believe in advisors. I also believe you should never hand either one the steering wheel to your business.

Advice comes with a backstory

Stories tend to give us mentors who are reliably right. They walk into the scene, say something profound, and somehow know exactly what the protagonist needs to do. Real life doesn’t work quite like that.

Real advisors are often very good at advising us about situations they understand deeply—and considerably less reliable when they move outside that experience.

Because advice isn’t just information. Advice is a compressed account of somebody else’s experiences, mistakes, knowledge, circumstances and results.

“This worked for me.” Great. But where did it work? When? At what size? With what customer? With how much money? With what team? Under what market conditions? And what happened that didn’t make it into the success story?

Advice can be excellent and still not be right for your business.

Experience creates wisdom. Context determines whether that wisdom applies.

The more confident the advice, the more questions I ask

Have you ever had somebody tell you: “Oh, you absolutely need to do this.” Maybe I do. But before I rearrange my business around somebody else’s certainty, I want to understand the conditions behind that advice.

Questions to ask before you act on advice

  • What was true about your situation that may not be true about mine?
  • What would have to be true for this advice to be wrong?
  • What did this decision cost you that you didn’t expect?
  • Who would this advice not work for?
  • What resources did you have that made this possible?
  • What would you do differently if you had to make the decision again?

Those questions aren’t disrespectful. They’re due diligence.

Take advice seriously. Take it conditionally.

Build a panel, not a guru

This is where I think entrepreneurs sometimes get into trouble. We find one smart person we trust and suddenly start asking them about everything. Strategy. Taxes. Contracts. Marketing. Hiring. Financing. Insurance. Investments.

Hold on. Nobody knows everything.

When I’m mentoring or coaching someone, I may tell them what I see from a business perspective. But there are also times when I say: “Now you need to talk to an attorney.” Or an accountant. Or a banker. Or another professional whose expertise actually matches the decision.

I don’t want one guru. I want a dream team. And here’s something else I want on that dream team: disagreement.

If five smart people around your table always agree with one another — and with you — you may not have an advisory panel. You may have an echo chamber.

One advisor may see the opportunity. Another sees the financial risk. Another sees the legal issue. Another asks whether you have the capacity to execute it. Another says, “Wait. Why are we doing this in the first place?”

Good. Now we have something to think about. Disagreement can expose assumptions that one trusted voice might leave buried.

Different perspectives. Stronger decisions.

Know who should be sitting at your table

Think about your business right now. Who is on your dream team?

Who is at your table, and which chairs are empty?

  • Who helps you think strategically?
  • Who understands your numbers?
  • Who understands taxes?
  • Who understands contracts and legal risk?
  • Who understands banking and financing?
  • Who understands insurance and risk?
  • Who understands your industry?
  • Who has actually traveled the road you’re trying to travel?

You don’t necessarily need all these people on payroll. Some relationships may be professional engagements, mentors, industry colleagues, coaches or people you consult when a particular decision requires their expertise.

And sometimes relationships can be reciprocal. You may have knowledge, connections or resources that help someone who is helping you.

The point isn’t to collect advisors. It’s to build access to the right expertise when the business needs it.

The time I didn’t take the advice

I remember very clearly someone telling me not to pursue a particular dream.

I listened to what they had to say, but I couldn’t follow their advice because they were making that recommendation without information I had. I knew things about the opportunity, the situation and what I was capable of that they simply didn’t know. And even when I tried to explain it, they couldn’t fully see what I could see.

So I had a decision to make: abandon something I believed in because someone I respected told me not to do it, or trust the knowledge and evidence I had and move forward anyway.

I pursued the dream—not because I ignored advice, but because I understood its limitations. And in the end, I was victorious because I made the decision based on what I knew.

Sometimes good leadership means listening carefully to advice and then having the courage to say, “Thank you. But this decision is still mine.”

Listen, then remember who owns the business

After all the conversations, meetings, recommendations and opinions, something important hasn’t changed. You’re still the owner.

Your advisors see pieces of the business. You have the responsibility for the whole thing.

That doesn’t mean your instincts are always right. Mine aren’t. That’s why we ask for help in the first place. But an advisor’s confidence does not transfer the consequences of the decision to them. If it works, your business lives with the result. If it doesn’t, your business lives with that result too.

Trusted advisors support decisions. They do not make decisions.

Five things you can do today

1. Draw your advisory table.
Write down the expertise your business needs: strategy, accounting, tax, legal, banking, insurance, marketing, operations, technology or industry knowledge.

2. Identify the empty chairs.
Where are you currently making important decisions without enough expertise?

3. Pressure-test one piece of advice.
Take a recommendation you’re considering and ask: what assumptions have to be true for this to work in my business?

4. Get a second perspective on significant decisions.
Especially when the decision crosses disciplines. A growth opportunity can simultaneously be a strategy decision, cash-flow decision, legal decision and capacity decision.

5. Make the final decision yourself.
Gather the evidence. Listen to the experts. Let them disagree. Ask better questions. Then decide.

The decision stays yours

Outside advice should not replace your thinking. It should expand it.

Build your dream team. Find people generous enough to share what they know and experienced enough to tell you what they don’t know. Listen carefully. Ask questions. Let smart people disagree.

Then gather all of that information and remember: the decision stays yours. And so does the consequence.

Watch it. Learn it. Apply it. Grow.

These ideas come out of real conversations with business owners. Join the next one.