Why Allison Cannella Believes the Best Business Decisions Start With Better Questions
In business, we tend to celebrate quick, confident decisions. The leader who knows exactly what to do and does it right away makes a great story. But many of the most expensive mistakes I’ve seen didn’t come from a lack of confidence. They came from answering the wrong question very confidently
Start by Asking What Problem You’re Really Solving
It’s surprisingly easy to jump into solutions before clearly defining the problem. A team asks how to cut costs when the real issue is that a product isn’t meeting customer needs. A leader asks which vendor to hire when the better question is whether the work should be outsourced at all.
Before weighing options, I like to step back and ask what we’re actually trying to achieve. A clear problem statement often makes the right answer far more obvious, and it keeps everyone from solving different problems at the same time.
Ask What You Might Be Missing
Most of us are naturally drawn to information that supports what we already believe. That’s human, but it’s also risky. One of the most valuable questions in any decision is simply asking what you might not be seeing.
It can help to imagine that the decision has already gone wrong and ask what most likely caused it. That small exercise tends to surface risks, assumptions, and blind spots that optimism tends to hide.
Ask Who Else Should Weigh In
Big decisions affect many parts of a business, including finance, operations, people, technology, and customers. The people closest to the work often see practical issues that leaders miss.
Asking who else should weigh in, and actually listening to their answers, can prevent costly surprises. It also builds buy-in, since people are more committed to decisions they helped shape.
Ask Whether Urgency Is Real
Deadlines create pressure, and pressure can quietly push people toward choices they wouldn’t otherwise make. Some deadlines are real. Others are self-imposed or exaggerated.
I find it useful to ask whether we’d make the same decision if the deadline disappeared. If the answer is yes, great. If it’s no, that’s a sign urgency might be shaping judgment more than it should.
Ask What the Alternatives Are
Decisions often get framed as yes or no, when there are usually more than two options. Doing nothing, doing a smaller version, delaying, partnering, or trying a pilot are all choices worth considering.
Asking what the alternatives are expands the field and often reveals a better path than the one first presented. Even if you end up with the original option, you’ll choose it with more confidence.
Ask What Happens If You’re Wrong
Every decision carries risk, and it helps to understand the downside clearly. What would it cost if this doesn’t work? How easily could it be reversed? Who would be affected?
Some decisions are easy to undo, so they can be made quickly. Others are hard to reverse and deserve more care. Knowing which kind you’re facing helps you decide how much time and analysis it truly needs.
Ask How You’ll Know It’s Working
Good decisions include a plan for measuring results. Defining what success looks like before you begin makes it much easier to tell whether the choice is paying off or needs adjusting.
Without that clarity, teams can spend months defending a decision instead of evaluating it honestly.
Create a Culture That Welcomes Questions
All of this works best when people feel comfortable asking hard questions. In some organizations, raising doubts is seen as negativity or a lack of commitment. That’s a mistake.
Leaders can set the tone by asking questions themselves, thanking people who raise concerns, and treating disagreement as useful information rather than a challenge to authority. The goal isn’t endless debate. It’s making sure the important questions get asked before the decision, not after.
Know When to Stop Asking
Questions are powerful, but they can also become a way to avoid deciding. At some point, you’ll never have perfect information, and waiting too long carries its own costs.
The aim is to ask enough of the right questions to make a sound decision, then commit and move forward with clarity.
Deciding With Clarity
Better questions don’t slow good leaders down. They point them in the right direction from the start. By defining the real problem, looking for blind spots, hearing from the right people, and understanding the downside, you give every decision a much stronger foundation.
The next time you face a big call, write down three questions you haven’t asked yet, and make sure you have answers before you commit.
Key Takeaways
- Define the real problem before evaluating solutions.
- Ask what you might be missing and who else should weigh in.
- Check whether urgency is real or just pressure.
- Consider alternatives beyond a simple yes or no.
- Decide how you’ll measure success before you begin.
