If you’re building a business, your relationship with money isn’t theoretical. It’s tied to cash flow, payroll, vendor terms, expansion plans, and the occasional 3 a.m. panic about liquidity. So when it comes to finding someone to help manage that reality, it’s worth slowing down and asking better questions than “Who’s available?”
Understand the Role
Not every advisor understands how to work with business owners. Some specialize in retirement accounts or high-net-worth individuals with passive income. You want someone who can look at your P&L and immediately understand what keeps you up at night.
Think of the advisor less like a vendor and more like a long-term collaborator—someone who can talk about capital structure, forecast scenarios, and succession planning without skipping a beat.
A few prompts to start with:
Have they worked with businesses similar in size and sector to yours?
Can they help you navigate both personal and company finances without blending the two carelessly?
Are they charging based on assets, a flat fee, or something else? Does that model create any pressure on their recommendations?
Don’t Confuse Credentials for Compatibility
Plenty of advisors hold impressive certifications, but that doesn’t mean they’re aligned with your needs. Big-name firms often come with baked-in incentives—products they’re expected to push, quotas to hit. That can subtly shift the focus away from your business and toward theirs.
Independent advisors often have more latitude. They may not have the same corporate backing, but they’re usually more agile, especially when it comes to crafting custom solutions instead of relying on one-size-fits-all portfolios.
Neither path is automatically better. What matters is who listens more than they pitch, who asks better questions, and who seems actually to understand your business model.
Even the sharpest advisor doesn’t get a crystal ball. They work from data, trends, and years of context, but at the end of the day, they’re drawing maps based on historical weather. That doesn’t mean they’re useless—it means their real value shows when the conditions change.
Watch how they handle uncertainty. Do they freeze, deflect, or overexplain? Or do they adjust, talk through contingencies, and stay proactive without selling panic?
That kind of mental flexibility matters more than hitting every target.
Questioning Isn’t Rude (It’s Responsible!)
A good advisor won’t flinch when you press them for clarity. “Can you explain why this allocation makes sense right now?” or “How does this strategy reflect my risk tolerance and business stage?” are not accusations. They’re signs you’re paying attention.
Pushback, within reason, creates better decisions. And if your advisor seems more irritated than engaged when challenged, that tells you everything you need to know.
You’re Allowed to Fire Them
Sometimes an advisor relationship starts strong and loses its way. That doesn’t mean you failed at picking one—it means your needs changed, or their priorities did.
Look for these signs:
They don’t adapt strategies as your business grows or pivots.
They focus on products more than plans.
They go radio silent until quarterly meetings.
Their fee structure no longer matches the value they provide.
Advisors work for you. If the relationship starts feeling like a burden, treat it like any other professional hire: review, replace, move on.
Choose With Longevity in Mind
This isn’t just about better investing—it’s about building financial infrastructure that can weather bad quarters, fund new divisions, and support exits when the timing’s right.
If done right, the advisor you choose will help turn intention into action and uncertainty into something a little more manageable.
But none of that happens unless you start by choosing with clarity, not just convenience.