Why Strong Companies Ask Better Questions, Not Faster Ones
- Brittney Simpson
- 3 days ago
- 20 min read
Speed is the business world's favorite drug.
Move faster. Decide faster. Execute faster. Fail fast, learn fast, grow fast.
In the rush to move quickly, many companies stop asking good questions. They stop looking into why things happen, stop challenging assumptions, and stop thinking things through.
They just react. Quickly.
And they call it decisive leadership.
From my experience working with founders who are always busy but not making progress, I notice they ask plenty of questions, just not the right ones.
They're asking "How do we fix this?" before they've asked "What's actually broken?"
They're asking "Who can we hire?" before they've asked "What do we actually need someone to do?"
They're asking "What's the fastest solution?" before they've asked "What's the right solution?"
Speed can feel productive, but without direction, it often leads to chaos with a deadline.
Strong companies succeed not by asking questions faster, but by asking better questions.
These are the questions that get to the root of the problem instead of just addressing the symptoms.
In a world that values speed above all, this way of thinking can seem unusual.
It shouldn't be.
The trap of fast questions
Let me give you an example of what fast questions look like in real situations.
A founder calls me: "I need to hire someone immediately. My operations manager just quit, and everything's falling apart. Can you help me find someone fast?"
That's a fast question. It's urgent. It demands immediate action.
But it's also the wrong question.
Because before we talk about who to hire, we need to ask:
Why did the operations manager quit?
What were they actually doing? Is that one role or three roles smashed together?
Are we replacing a person or rebuilding a function?
What broke when they left, and what's working fine?
These questions take time and require discussion. They may not feel as productive as quickly posting a job opening.
But they're the questions that determine whether you hire someone who actually solves the problem or just becomes another person drowning in the same dysfunction that burned out the last person.
Fast questions might seem efficient, but they skip the deeper thinking that makes answers meaningful.
Here's another example:
A CEO tells their team: "Revenue is down. What can we do to boost sales this quarter?"
Fast question. Action-oriented. Gets everyone moving.
But these questions only scratch the surface.
Because revenue being down is a symptom, not a diagnosis.
Are you losing deals you used to win?
Are clients buying less? Is your pipeline weaker?
Are conversion rates dropping?
Is retention suffering?
"Boost sales" might be the wrong answer entirely if the real problem is that you're churning clients faster than you're acquiring them.
Fast questions lead to quick answers, but those answers are often incomplete.
What better questions actually sound like
Better questions don't have to be complicated. They just require you to slow down and think. Can you fix this problem?" Ask: "What's causing this problem?"
Instead of: "Who should own this?" Ask: "What actually needs to happen here, and who's best positioned to do it?"
Instead of: "Why isn't this person performing?" Ask: "What's preventing this person from performing?"
Instead of: "How do we grow faster?" Ask: "What's limiting our growth right now?"
Instead of: "What's our biggest priority?" Ask: "What happens if we don't do this?"
See the difference?
Can you see the difference? You need to find solutions quickly, while better questions help you understand the real issue.
Understanding is what allows you to solve the real problem, not just the one you can see.
Why founders default to fast questions
If better questions lead to better answers, why don't more founders ask them?
Slowing down can feel irresponsible.
When revenue drops, someone quits, a client is upset, or a deadline is near, taking time to think can feel like wasting time. It can seem passive, as if you're not doing your job.
Your brain screams: Don't just sit there, do something!
And so you do. You make a decision. You take action. You solve the surface problem.
Then, a few months later, you find yourself dealing with the same problem because you never fixed the real cause.
I see this pattern constantly with founders:
They confuse activity with being busy. They often mistake being busy for making progress. Moving quickly can feel like progress, even if it's in the wrong direction. cisiveness, not thoughtfulness. Boards, investors, teams—everyone wants leaders who act quickly. No one gives you credit for the problem you avoided by asking better questions up front.
They're afraid of looking. Many fear appearing indecisive. If you don't answer right away, people might think you don't know what you're doing. So you give an answer, even if it's not the best one, instantly. When you're always in crisis mode, you don't have the luxury of deep thinking. You just react to whatever's burning hottest.
All of this is understandable, but it's also why so many companies get stuck in the same cycles, solving the same problems again and again.
Because they never slow down long enough to ask why the problems keep happening.
The cost of skipping the thinking
Here's what happens when you focus on speed instead of substance in your questions.
You hire the wrong people. Because you rushed to fill a role without understanding what the role actually needs to be. So you hire someone who looks good on paper but doesn't solve the underlying problem.
You build the wrong processes. Because you implemented the first solution that seemed workable instead of the one that actually fits how your business operates.
You chase the wrong goals. Because you set targets based on what sounds ambitious instead of what would actually move the business forward.
You lose good people. Because when someone raises a concern, you jump to fixing the symptom without asking what's really wrong. And they leave because the real problem never got addressed.
You waste time and money on solutions that don't work. Because you were solving for speed, not accuracy. The worst part is, you might not even notice you're doing it. You're busy, always moving, always taking action. But in the end, you have little to show for all that effort. for it.
What's asking better questions actually reAsking better questions isn't about intelligence; it's about discipline.
It means pausing when you want to act, sitting with the discomfort of not having an immediate answer, and resisting the urge to solve before you understand.
Here's what that discipline looks like in real life: This is what that discipline looks like in real life: When someone brings you an issue, your first instinct is to solve it. Resist that. Instead, ask: "Why is this happening?" Then ask it again. And again. Until you get past the surface explanation to the actual root cause.
Question your assumptions. You think you know why revenue is down, or why someone's struggling, or why a process isn't working. But do you actually know, or are you assuming? Test your assumptions before building solutions on them.
Involve the people closest to the problem. The people doing the work usually understand the problem better than you do. Ask them what they're seeing. What's actually broken? What would actually help? Their answers will surprise you.
Be open to finding out you were wrong. Sometimes, better questions show that the real problem is different from what you thought. That can be uncomfortable, but it's valuable.
Make time for thinking. You can't ask better questions if you're always rushing from one crisis to another. Set aside real time to think, protect it, and treat it as seriously as any other meeting.
None of this is complicated, but it does require you to value understanding more than speed.
Most founders don't do this—at least not until they've spent enough time on quick, wrong answers and are finally ready to slow down.
Real examples of better questions in action
Let me show you. Let me share some real situations I've seen founders go through.
The turnover problem
A founder came to me frustrated. High turnover in one department. People kept quitting. He wanted help hiring better people faster.
Fast question: "How do we hire people who will actually stay?"
Better question: "Why are people leaving?"
We asked the better question and found out it wasn't a hiring issue—it was a management issue. The department head was a micromanager who burned people out. They were great at technical work but struggled with leading people.r" People wouldn't have fixed anything. They would have quit, too.
The real solution? Address the management issue. Either develop the manager or replace them. But we only got there by asking why people were leaving instead of jumping straight to how to hire better.
Example two: The capacity problem
Another founder: "We're overwhelmed. We need to hire more people."
Fast question: "Who should we hire first?"
Better question: "What's actually? " When we looked closer, the problem wasn't a lack of people—it was a lack of clarity. People were working on the wrong tasks, priorities kept changing, and no one knew what was truly urgent. That just felt urgent.
Adding more people to that chaos would have made it worse, not better.
The real solution? Get clear on priorities. Stop saying yes to everything. Give people permission to focus.
Hiring came later. But only after they'd fixed the underlying lack of direction.
Example three: The performance problem
A founder struggling with an underperforming employee: "Should I put them on a performance plan or just let them go?"
Fast question: "How do I manage this person out?"
Better question: "What's preventing theIt turned out the employee was in the wrong role. They were promoted because they did well in their old job, but the new position required skills they hadn't yet learned. A quick answer would have been to let them go. The better answer was to move them back to a role where they could succeed and hire someone else for the position they had been struggling in.
The result is the same—a new person in the role—, but you keep a good employee instead of losing them.
This only happens if you ask why someone is struggling, not just how to let them go.
The questions that matter most
If you take nothing else from this, take these questions. They're the ones I see the strongest companies asking consistently:
"What are we optimizing for?" Before making any decision, be clear about what success means. Are you aiming for speed, quality, cost, growth, or stability? You can't have everything, so pick one. Would this look like if it were easy?" Most problems are overcomplicated. This question forces you to strip away the noise and find the simple solution you're probably avoiding because it seems too obvious.
"What's the smallest version of this that would tell us if we're right?" Rather than betting on one big solution, test your ideas with the smallest experiment possible. Learn quickly, then build on what works. preventing this from happening?" When something isn't working, the instinct is to push harder. But often, the problem isn't effort—it's an obstacle you haven't identified yet. Find the obstacle first.
"What would need to be true for this to work?" This question brings out your assumptions. If you can't answer it, you may not understand the problem well enough yet. I'm not seeing?"
This is the most important question of all. It acknowledges that you don't have complete information. It creates space for perspectives you're missing. It keeps you humble.
Ask these questions before you jump to solutions. Not every time, not for every decision. But for the ones that matter? Absolutely.
When fast is actually the right answer, I'm not saying speed is never important. Sometimes it is.
In a true crisis—when something's on fire, when a client is about to leave, when you're about to miss payroll—you don't have time for deep existential inquiry. But the truth is, most situations that feel like crises are just urgent, not true emergencies. There's a difference.
Crises require immediate action to prevent catastrophic damage.
Urgent issues feel pressing, but won't cause catastrophic damage if you take an extra day to think. Most things founders treat as crises are really just urgent issues. Treating them like emergencies means you keep making quick decisions when you should be making thoughtful ones.
So yes, when the building is actually on fire, move fast.
But the rest of the time? Slow down. Ask better questions. Make sure you're solving the right problem. Solving the wrong problem quickly usually costs more than taking a little extra time to solve the right one.
If you want your company to ask better questions, you need to set the example. You have to model it.
That means reward thoughtfulness, not just speed. If someone brings you a rushed solution, don't praise how fast they worked. Encourage them to think more deeply.
Ask "why" more often than "how." When your team brings you problems, don't jump to solutions. Ask why it's happening and what they think is causing it. Let them do the thinking. Make time for questions in meetings. Don't just present information and expect agreement. Allow space for real questions, not just ones for show.
Be willing to say "I don't know yet." Leaders who always have quick answers teach their teams to value speed. Leaders who say "I need to think about that" show that thoughtfulness is important.
Celebrate when someone changes their mind after asking better questions. That's not a weakness—it's learning. Make it safe for people to admit mistakes and adjust. Your team will reflect what you value. If you value speed, they'll focus on speed. If you value insight, they'll focus on insight. Choose carefully.
The shift
Here's what happens when you start putting better questions ahead of faster ones: You stop repeating the same mistakes. Because you're actually understanding what went wrong instead of just fixing the surface symptom.
Your team gets smarter. Because they're learning to think, not just execute.
Your decisions get better. Because they're based on understanding, not urgency.
You waste less time because you're solving the right problems the first time, instead of fixing the wrong ones over and over.
You build a more resilient business. Because you're addressing root causes, not just managing symptoms.
This change doesn't happen overnight. It takes effort to resist the urge to act immediately. But it's worth it.
In the end, the companies that succeed aren't the ones that move the fastest.at move in the right direction.
And you only find the right direction by asking better questions. You should be asking right now.
If you're reading this and feel pressure to move faster, decide quicker, or have all the answers right away, take a moment to pause. What problem am I actually trying to solve?
Not the surface problem. Not the urgent thing that's demanding attention right now. The actual, underlying problem.
Sit with that question for a while. It could be a minute, an hour, or even a day. Don't start planning action items. Just think.
What's really going on here?
Once you have the real answer—not just the quick one—you'll know what to do. will actually matter.
That's the difference between strong companies and busy companies.
Strong companies ask better questions.
Busy companies just ask faster ones.
Which one are you building?
Why Strong Companies Ask Better Questions, Not Faster Ones
Speed is the business world's favorite drug.
Move faster. Decide faster. Execute faster. Fail fast, learn fast, grow fast.
And somewhere in that relentless pursuit of velocity, most companies stop asking good questions. They stop digging into why things are happening. They stop challenging assumptions. They stop thinking.
They just react. Quickly.
And they call it decisive leadership.
But here's what I see when I work with founders who are constantly in motion but never gaining traction: they ask a lot of questions, but the wrong ones.
They're asking "How do we fix this?" before they've asked "What's actually broken?"
They're asking "Who can we hire?" before they've asked "What do we actually need someone to do?"
They're asking "What's the fastest solution?" before they've asked "What's the right solution?"
Speed feels productive. But speed without direction is just chaos with a deadline.
Strong companies don't win because they ask questions faster than everyone else. They win because they ask better questions. The kind that actually gets to the root of the problem instead of just treating symptoms.
And in a world that rewards speed above everything else, that kind of thinking feels radical.
It shouldn't be.
The trap of fast questions
Let me show you what fast questions look like in practice.
A founder calls me: "I need to hire someone immediately. My operations manager just quit, and everything's falling apart. Can you help me find someone fast?"
That's a fast question. It's urgent. It demands immediate action.
But it's also the wrong question.
Because before we talk about who to hire, we need to ask:
Why did the operations manager quit?
What were they actually doing?
Is that one role or three roles smashed together?
Are we replacing a person or rebuilding a function?
What broke when they left, and what's working fine?
Those questions take time. They require conversation. They don't feel as productive as posting a job description immediately.
But they're the questions that determine whether you hire someone who actually solves the problem or just becomes another person drowning in the same dysfunction that burned out the last person.
Fast questions feel efficient. But they skip the thinking that makes the answer actually matter.
Here's another example:
A CEO tells their team: "Revenue is down. What can we do to boost sales this quarter?"
Fast question. Action-oriented. Gets everyone moving.
But also: totally surface-level.
Because revenue being down is a symptom, not a diagnosis.
Are you losing deals you used to win?
Are clients buying less? Is your pipeline weaker?
Are conversion rates dropping? Is retention suffering?
"Boost sales" might be the wrong answer entirely if the real problem is that you're churning clients faster than you're acquiring them.
Fast questions push you toward fast answers. And fast answers are almost always incomplete.
What better questions actually sound like
Better questions aren't fancy. They're not complicated. They just require you to slow down long enough to think.
Instead of: "How do we fix this problem?" Ask: "What's causing this problem?"
Instead of: "Who should own this?" Ask: "What actually needs to happen here, and who's best positioned to do it?"
Instead of: "Why isn't this person performing?" Ask: "What's preventing this person from performing?"
Instead of: "How do we grow faster?" Ask: "What's limiting our growth right now?"
Instead of: "What's our biggest priority?" Ask: "What happens if we don't do this?"
See the difference?
Fast questions push you toward solutions. Better questions push you toward understanding.
Understanding is what lets you solve the actual problem, not just the visible one.
Why founders default to fast questions
If better questions lead to better answers, why don't more founders ask them?
Because slowing down feels irresponsible.
When revenue is down, when someone quits, when a client is angry, when a deadline is looming—sitting in the question feels like wasting time. It feels passive. Like you're not doing your job.
Your brain screams: Don't just sit there, do something!
And so you do. You make a decision. You take action. You solve the surface problem.
And three months later, you're solving the same problem again because you never addressed what was actually causing it.
I see this pattern constantly with founders:
They confuse activity with progress. Moving fast feels like progress even when you're moving in the wrong direction.
They're rewarded for decisiveness, not thoughtfulness. Boards, investors, teams—everyone wants leaders who act quickly. No one gives you credit for the problem you avoided by asking better questions up front.
They're afraid of looking indecisive. If you don't have an immediate answer, people assume you don't know what you're doing. So you give an answer, even if it's not a good one.
They're firefighting constantly. When you're always in crisis mode, you don't have the luxury of deep thinking. You just react to whatever's burning hottest.
All of that is understandable. But it's also exactly why so many companies stay stuck in the same cycles, solving the same problems over and over.
Because they never slow down long enough to ask why the problems keep happening.
The cost of skipping the thinking
Let me tell you what happens when you prioritize speed over substance in your questions.
You hire the wrong people. Because you rushed to fill a role without understanding what the role actually needs to be. So you hire someone who looks good on paper but doesn't solve the underlying problem.
You build the wrong processes. Because you implemented the first solution that seemed workable instead of the one that actually fits how your business operates.
You chase the wrong goals. Because you set targets based on what sounds ambitious instead of what would actually move the business forward.
You lose good people. Because when someone raises a concern, you jump to fixing the symptom without asking what's really wrong. And they leave because the real problem never got addressed.
You waste time and money on solutions that don't work. Because you were solving for speed, not accuracy.
And the worst part? You don't even realize you're doing it. Because you're busy. You're moving. You're taking action.
You just don't have anything to show for it.
What does asking better questions actually require?
Asking better questions isn't about being smarter. It's about being more disciplined.
It requires you to pause when everything in you wants to move. To sit in the discomfort of not having an immediate answer. To resist the urge to solve before you understand.
Here's what that discipline looks like in practice:
Stop accepting the first version of the problem. When someone brings you an issue, your first instinct is to solve it. Resist that. Instead, ask: "Why is this happening?" Then ask it again. And again. Until you get past the surface explanation to the actual root cause.
Question your assumptions. You think you know why revenue is down, or why someone's struggling, or why a process isn't working. But do you actually know, or are you assuming? Test your assumptions before building solutions on them.
Involve the people closest to the problem. The people doing the work usually understand the problem better than you do. Ask them what they're seeing. What's actually broken? What would actually help? Their answers will surprise you.
Be willing to discover you're wrong. Sometimes better questions reveal that the problem you thought you had isn't the problem at all. That's uncomfortable. It's also valuable.
Create space for thinking. You can't ask better questions when you're sprinting from one crisis to the next. You need actual time to think. Block it. Protect it. Treat it as seriously as any other meeting.
None of this is complicated. But all of it requires you to value understanding over speed.
And most founders don't. At least not until they've wasted enough time on fast, wrong answers that they're finally ready to slow down.
Real examples of better questions in action
Let me show you what this looks like with real situations I've seen founders navigate.
Example one: The turnover problem
A founder came to me frustrated. High turnover in one department. People kept quitting. He wanted help hiring better people faster.
Fast question: "How do we hire people who will actually stay?"
Better question: "Why are people leaving?"
We asked the better question. Turns out it wasn't a hiring problem. It was a manager's problem. The department head was a micromanager who burned people out. Great at the technical work, terrible at leading people.
Hiring "better" people wouldn't have fixed anything. They would have quit, too.
The real solution? Address the management issue. Either develop the manager or replace them. But we only got there by asking why people were leaving instead of jumping straight to how to hire better.
Example two: The capacity problem
Another founder: "We're overwhelmed. We need to hire more people."
Fast question: "Who should we hire first?"
Better question: "What's actually overwhelming us?"
When we dug in, the problem wasn't a lack of people. It was a lack of clarity. People were working on the wrong things. Priorities were constantly shifting. No one knew what was actually urgent versus what just felt urgent.
Adding more people to that chaos would have made it worse, not better.
The real solution? Get clear on priorities. Stop saying yes to everything. Give people permission to focus.
Hiring came later. But only after they'd fixed the underlying lack of direction.
Example three: The performance problem
A founder struggling with an underperforming employee: "Should I put them on a performance plan or just let them go?"
Fast question: "How do I manage this person out?"
Better question: "What's preventing them from performing?"
Turns out the person was in the wrong role. They'd been promoted because they were good at their old job, but the new job required completely different skills they didn't have and hadn't been trained in.
The fast answer would have been to fire them. The better answer was to move them back to a role where they could succeed and hire differently for the position they'd been struggling in.
Same outcome—new person in that role. But you keep a good employee rather than lose them.
That only happens if you ask why they're struggling, not just how to exit them.
The questions that matter most
If you take nothing else from this, take these questions. They're the ones I see the strongest companies asking consistently:
"What are we optimizing for?" Before you make any decision, get clear on what success looks like. Are you optimizing for speed, quality, cost, growth, or stability? You can't have all of them. Choose.
"What would this look like if it were easy?" Most problems are overcomplicated. This question forces you to strip away the noise and find the simple solution you're probably avoiding because it seems too obvious.
"What's the smallest version of this that would tell us if we're right?" Instead of betting everything on one big solution, test your assumptions with the smallest possible experiment. Learn fast, then scale what works.
"What's preventing this from happening?" When something isn't working, the instinct is to push harder. But often, the problem isn't effort—it's an obstacle you haven't identified yet. Find the obstacle first.
"What would need to be true for this to work?" This question surfaces your assumptions. If you can't answer it, you don't understand the problem well enough to solve it yet.
"What am I not seeing?" This is the most important question of all. It acknowledges that you don't have complete information. It creates space for perspectives you're missing. It keeps you humble.
Ask these questions before you jump to solutions. Not every time, not for every decision. But for the ones that matter? Absolutely.
When fast is actually the right answer
I'm not saying speed never matters. Sometimes it does.
In a true crisis—when something's on fire, when a client is about to leave, when you're about to miss payroll—you don't have time for deep existential inquiry. You act.
But here's the thing: most situations that feel like crises aren't actually crises. They're just urgent. And there's a difference.
Crises require immediate action to prevent catastrophic damage.
Urgent issues feel pressing, but won't cause catastrophic damage if you take an extra day to think.
Most of what founders treat as crises is actually just urgent issues in disguise. And treating urgent issues like crises means you're constantly making fast decisions when you should be making good ones.
So yes, when the building is actually on fire, move fast.
But the rest of the time? Slow down. Ask better questions. Make sure you're solving the right problem.
Because the cost of solving the wrong problem quickly is almost always higher than the cost of taking an extra week to solve the right problem.
How to build a culture of better questions
If you want your company to ask better questions, you have to model it.
That means:
Rewarding thoughtfulness, not just speed. When someone comes to you with a half-baked solution they threw together quickly, don't praise the speed. Ask them to think deeper.
Asking "why" more than "how." When your team brings you problems, resist the urge to solve them immediately. Ask why it's happening. Ask what they think is causing it. Make them do the thinking.
Creating space for questions in meetings. Don't just present information and expect people to nod along. Build in time for questions. Real ones, not performative ones.
Being willing to say "I don't know yet." Leaders who always have immediate answers train their teams to value speed over substance. Leaders who say "I need to think about that" train their teams that thoughtfulness matters.
Celebrating when someone changes their mind after asking better questions. That's not a weakness. That's learning. Make it safe to realize you were wrong and adjust.
Your team will mirror what you value. If you value speed, they'll optimize for speed. If you value insight, they'll optimize for insight.
Choose carefully.
The shift
Here's what changes when you start prioritizing better questions over faster ones:
You stop repeating the same mistakes. Because you're actually understanding what went wrong instead of just fixing the surface symptom.
Your team gets smarter. Because they're learning to think, not just execute.
Your decisions get better. Because they're based on understanding, not urgency.
You waste less time. Because you're solving the right problems the first time instead of solving the wrong problems repeatedly.
You build a more resilient business. Because you're addressing root causes, not just managing symptoms.
It doesn't happen overnight. And it requires you to fight against every instinct that tells you to just move, do something, act now.
But it's worth it.
Because at the end of the day, the companies that win aren't the ones that move fastest.
They're the ones that move in the right direction.
And you only find the right direction by asking better questions.
The question you should be asking right now
If you're reading this and feeling the pressure to move faster, to decide quicker, to have all the answers immediately—pause.
Ask yourself this: What problem am I actually trying to solve?
Not the surface problem. Not the urgent thing that's demanding attention right now. The actual, underlying problem.
Sit with that question for a minute. Maybe an hour. Maybe a day.
Don't jump to solutions. Don't start planning action items. Just think.
What's really going on here?
Once you have that answer—the real answer, not the fast answer—you'll know what to do.
And whatever you do will actually matter.
That's the difference between strong companies and busy companies.
Strong companies ask better questions.
Busy companies just ask faster ones.
Which one are you building?
Visit us at savvyhrpartner.com and follow us on social media @savvyhrpartner for expert tips, resources, and solutions to support your business and your people. Let’s bring savvy thinking to your people strategy!
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