21 Questions To Improve Any Business

I’ve been collecting questions in Moleskine notebooks for years. They fill the margins of my journals and populate random notes on my phone. Why? Because I’ve learned that the right question can unlock more value than a hundred answers.

Questions are the skeleton keys of innovation. They open doors we didn’t even know existed. They challenge our assumptions, reveal our blind spots, and force us to think beyond our usual patterns. The best questions aren’t just about getting answers – they’re about shifting perspectives. They make us uncomfortable in exactly the right way. They force us to confront the gaps between where we are and where we could be.

I’ve gathered some of the most powerful business questions I’ve encountered. Each one is designed to illuminate a different corner of your business and spark meaningful change. Some might make you uncomfortable. That’s good – it means they’re working.

Here are some thought-provoking questions to help improve any business:

What can we stop doing that won’t hurt the company? Targets unnecessary activities that continue purely from habit or inertia. Perfect for identifying time-wasting meetings, redundant reports, or outdated processes that no one questions but adds no value. The key is it makes it safe to identify things to eliminate by focusing on non-essential activities.
What do our customers ask for and our answer is always no? Reveals potential opportunities we’re missing and challenges our default assumptions. These consistent “no’s” often hide outdated thinking or artificial limitations that could be profitable to overcome. Sometimes there are good reasons for the “no,” but often it’s just organizational inertia.
What’s one thing, if you were me, you’d be doing differently? Gets honest feedback by combining role reversal with psychological safety. The hypothetical nature makes people more comfortable suggesting bold changes, while “one thing” forces them to prioritize their most important insight.
Where are we wasting the most time, money, or resources? This forces an honest look at inefficiencies that have become normalized. Often the biggest waste isn’t in obvious places, but in seemingly necessary processes that could be streamlined or eliminated.
What processes feel unnecessarily complicated, and how can we simplify them? This targets bureaucracy and over-engineering that typically develops as companies grow. It’s particularly powerful because it encourages input from people doing the work, who often see simpler solutions.
What is our biggest bottleneck, and what’s the first step to removing it? This combines problem identification with immediate action. Breaking it down to the “first step” makes it feel more manageable and likely to happen.
What frustrates our customers the most? This cuts through internal assumptions to focus on actual customer pain points. It’s especially valuable because frustrated customers often don’t complain – they just leave.
If a competitor wanted to take us down, what weak spot would they attack? This encourages brutal honesty about vulnerabilities by shifting perspective. It helps identify weaknesses before they’re exploited.
What’s one thing our competitors do better than us? This pushes past defensive thinking to acknowledge specific areas for improvement. The focus on “one thing” makes it more likely to get an honest, actionable answer.
What’s the biggest risk we’re ignoring? This surfaces unspoken concerns and blind spots, particularly useful for identifying slow-moving problems that could become critical.
Where are we undercharging or leaving money on the table? This reveals missed revenue opportunities, often in areas where value delivery has improved but pricing hasn’t kept pace.
If we had to double our revenue in the next year without increasing costs, how would we do it? This constraint forces creative thinking about leverage points in the business model. It often reveals opportunities hidden by incremental thinking.
What are we doing just because “we’ve always done it this way”? This challenges inherited practices that may no longer serve their original purpose. It’s particularly effective at identifying outdated policies and procedures.
If we had to 10x our efficiency with half the team, what would we change? This radical constraint forces a fundamental rethinking of how work gets done, often revealing major efficiency opportunities masked by current staffing levels.
Which customers are costing us more than they are worth? This acknowledges that not all revenue is good revenue. It helps identify where customer service costs or complexity are eating into profitability.
What’s the #1 complaint we get that we haven’t solved yet? This focuses attention on known problems that have been normalized or deprioritized. It often reveals institutional resistance to important changes.
If we started this business from scratch today, what would we do differently? This mental reset helps identify legacy systems, products, or approaches that wouldn’t be chosen in today’s environment.
What’s working so well that we’ve stopped paying attention to it? This highlights successful areas that might be taken for granted and need protection or investment to maintain their performance.
Which tasks should we automate, delegate, or eliminate? This creates three clear paths for efficiency improvement, making it easier to categorize and act on opportunities.
What would make our employees twice as engaged and productive? This focuses on multiplicative improvements in human capital, often revealing systemic issues that limit performance across the organization.
If we had to double our goal in the next 30 days, what would be our first three moves? This question forces rapid prioritization and bold thinking by creating an artificial crisis. The “had to” framing pushes past incremental improvements to identify major leverage points in the business. The focus on the “first three moves” cuts through analysis paralysis and gets to concrete, immediate actions. Combining urgency with specificity reveals opportunities that might be overlooked during normal planning.