I see the same pattern over and over again: business owners trying to make a strategic decision but starting with the wrong question entirely. It’s easy to think that the decision you need to make is the right question, but that fails to account for some critical assumptions and doesn’t connect this decision to the bigger picture.
Many business owners assume there is a checklist that ensures taking the right action at the right time. For example, when I reach X revenue, I should take X action. The reality is that the decision needs to be tied to the context that fits that business. And when you start with the wrong question, decision paralysis is the likely result.
Additionally, it is important to ask bigger-picture questions before taking action. Questions like “What is the end result I’d like to achieve?” help business owners put the decision into the proper context. This helps you ask the right next questions and make decisions aligned with your future goals.
Why Business Owners Get Stuck Making Decisions
When business owners have difficulty making decisions it usually means they have failed to define the bigger picture and have assumptions driving them towards what they think they should do. If your starting point is off-center, your options will be too.
The HVAC Example: Right Topic, Wrong Question
In a blue-collar business group, an HVAC owner recently asked whether he should hire a general manager. He gave information about his company’s revenue. The thread exploded. People argued yes, definitely. People argued absolutely not. And most of the responses hinged on revenue thresholds or what worked in their own businesses. He had 107 opinions but no real direction for what action to take.
But the real issue wasn’t whether a general manager was the “next logical step.”
The issue was that he didn’t start with:
What end result am I actually trying to create?
Without that question, no answer — not mine, not yours, not Facebook’s — was ever going to fit.
In his situation, the deeper layer might eventually lead to questions about his own role. But that only becomes relevant after he defines the outcome he’s building toward. When you skip that step, you end up with advice that’s generic at best and a distraction at worst.
The Myth of the Revenue Checklist
People love rules of thumb:
– “At $500K you should hire a GM.”
– “At $1M you should stop doing X.”
– “At this size, you should operate like this kind of company.”
But businesses aren’t assembly lines. Business owners aren’t all the same. Growth does not follow a template. For every company where hiring a general manager is absolutely the right next move, there are ten where doing so would stall growth or solve the wrong problem entirely.
This is why “should” is dangerous. “Should” belongs to someone else’s business, not yours.
The Real Strategic Work: Anchor to the Outcome
If you want to make better business decisions, anchor everything to the outcome you’re trying to create. Once you define that, most decisions become surprisingly straightforward. Not easy — but no longer ambiguous.
You know whether you’re aiming to:
– step back from daily operations,
– scale capacity,
– increase margin,
– change your role,
– stabilize chaos,
– or prepare for sale.
Each of those desired outcomes leads to a different strategic move. If you don’t define the outcome, every option looks equally plausible — and equally risky.
Who You Ask Matters as Much as What You Ask
Here’s the part people forget: even smart, well-meaning people will answer the wrong question if that’s the one you hand them.
If you ask Facebook whether something is tax-deductible, they’ll answer that question — even though the real question should be:
Does this deduction make sense in my business according to someone who actually knows my books?
Your tax professional will help you frame the right question before they ever give you an answer. Your friends online can’t. They don’t have your context, and they don’t carry any liability for being wrong.
This isn’t about dismissing crowdsourced wisdom. It’s about recognizing its limits.
The Through-Line of Good Strategy
Better decisions don’t come from gathering more opinions. They come from clarifying the right question and bringing it to the right person at the right moment. Everything else is noise.
