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20 Questions Every Business Owner Must Ask Themselves To Achieve More


Barnaby Lashbrooke

Founder and CEO of Time etc, author of The Hard Work Myth

10 minute read

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In the world of business, success doesn't just come down to having the right amount of capital, effective marketing strategies, or even the perfect product.

It takes a deep understanding of yourself and your organization—from strengths and weaknesses to how you operate on a daily basis—to make each and every critical decision that will steer your company in the right direction.

To make sure your small business continues to thrive, it pays to take regular stock of your processes so you can question, evaluate, and, ultimately, improve how things are done.

Start by asking yourself these 20 questions to gain some much-needed clarity on where your business is now, what might be holding you back, and what could take you further.

Questions about you

1. When do I work at my best?

Unlocking your business's growth begins with understanding yourself—since you are the driving force behind it.

While there's no shortage of advice and best practices to help us boost our focus, energy, and productivity, it's crucial to remember that what works for one person doesn’t always work for another.

For example, Apple CEO Tim Cook wakes up at 3:45 a.m., while Reddit co-founder Alexis Ohanian starts his day at around 10:00 a.m.

Do you find yourself energized in the morning, refreshed in the evening, or at your peak around midday? How does your mood and behavior shift throughout the day? What are you doing when you feel the most energized and motivated?

Knowing the answers to these questions will allow you to build a routine that is fully optimized for you and help you make the most out of every hour in your day.

See: How To Manage Your Energy Effectively To Achieve More In Your Business

2. What are my biggest interruptions?

According to experts, it takes around 23 minutes to get back on track after an interruption. So whether it's an unexpected phone call, a sudden knock on the door, or the constant pinging of notifications on your phone, even the most seemingly insignificant interruptions can add up.

Once you've identified the biggest distractions in your day, you can take steps to create an environment or a routine that allows you to get into the zone—and stay there!

See: 10 Ways To Overcome Distractions And Stay Focused As An Entrepreneur

3. Where do I excel?

This question isn't just about recognizing what you're good at, it's about understanding your unique talents and how they can help you succeed.

When you have plenty of opportunities to leverage your specific skills and talents, it's easier to stay motivated, produce outstanding results, and explore innovative new ideas and approaches.

See: Why Focusing On Your Unique Ability Is Crucial For Business Success

4. What is the next skill I need to develop?

Often, what sets successful entrepreneurs apart from others is their commitment to continual learning and skill development.

Investing in yourself is key to staying ahead of the game and staying on top of the latest trends, technologies, and innovations in the market. By expanding your knowledge and refining your skills, you will be better equipped to identify opportunities, anticipate and adapt to changes, and develop effective strategies for long-term success.


5. Does my work routine allow me to maintain healthy habits?

When you're battling against a mountain of tasks or you're racing against the clock to meet a deadline, it's easy to ignore your own needs in favor of getting things done.

Missing out on a meal, a workout, or a good night's sleep can feel like a small price to pay, but it's a slippery slope. Regularly neglecting your own well-being in the name of productivity is neither sustainable nor effective.

If your current routine makes it difficult to maintain these vital habits, then it's time for a reshuffle. Investing in your own well-being now will lead to greater success in the future.

Questions about your goals

6. What short- and long-term goals do I want to achieve?

Having a vague idea of what you want to accomplish isn't enough, you need a crystal-clear understanding of what you want to achieve.

I find setting and achieving goals to be much like planning a vacation. For starters, you choose your destination first. If you didn't know where you wanted to end up, you'd risk wasting a lot of time, energy, and resources wandering around aimlessly.

7. Do I have a strategy in place?

Once you know your destination, you’ll have a much better idea of the steps you’ll need to take to get there.

What would need to happen for your goal to become a reality?

Without a well-defined strategy, all goals—big and small—will stay just wishful thinking. Your strategy serves as your roadmap, outlining the steps you need to take, the resources you'll require, and any potential obstacles you might encounter.

8. How will I know when these goals are met?

While it may sound obvious, no strategy is complete without establishing your criteria for success.

Use quantifiable metrics or indicators to clearly track your progress and stay accountable during the process.

9. Do my short-term actions support my long-term goals?

When we think about our long-term goals and the success we want to achieve in the future, it can feel a lot less tangible and less pressing than the things that we have to deal with on a daily basis, especially when the results are more immediate. As a result, the important work we need to achieve our goals often falls to the bottom of our priorities.

To avoid 'spinning your wheels' and losing sight of the big picture, make sure you have enough time in your schedule for activities that are directly related to, add value to, or move you closer to your goals.

10. What motivates me?

Understanding what motivates you is essential for fuelling your perseverance, especially during challenging times.

Whether it's wanting to make a difference for others, striving for self-improvement, or chasing financial freedom, knowing your "why" will give you the strength and drive needed to keep you on track.

See: Why Motivation Matters: The Key To Success For Entrepreneurs


Questions about your workload

11. What do I want to accomplish today?

This isn't merely devising a list of tasks to tick off, rather, it's figuring out how you can make your day count.

Setting clear daily goals creates a focused path for the day, ensuring you're not merely reacting to situations but proactively shaping your journey.

"When you make a conscious effort each morning to focus on specific goals, your afternoon is less likely to be derailed by distractions or unplanned matters," says bestselling author and FutureThink founder and CEO Lisa Bodell.

12. How do my current responsibilities make me feel?

Does the thought of doing certain tasks fill you with dread? Do you find yourself constantly putting these tasks off, to then be plagued with nagging guilt?

Is your workload so overwhelming that you feel like you're fighting a losing battle?

How you feel about your responsibilities can significantly affect your performance and productivity—not to mention your well-being. If you answered "Yes" to any of those questions, it's time to switch things up.

13. In an ideal world, what would I spend my day doing that I’m not currently able to do?

This question can give you some much-needed clarity and perspective on what matters most to you, as well as which areas in your business should be prioritized.

From there, you can start putting together a plan to fit them into your current strategies. Not only could this help you take your business to the next level, but you'll also benefit from more fulfilling and meaningful work days.

14. If I could clone myself today, what would be the first task I would assign to my clone?

No matter how passionate you are as a business owner, there's bound to be at least one thing that you wish could magically disappear from your to-do list.

Bonus question: What’s stopping you from delegating it?

If it doesn't require your specific knowledge or expertise to complete, and anyone could do it with the right instructions, you should seriously consider taking it off your hands.

See: Four Reasons Why You're Struggling To Delegate As An Entrepreneur

15. How much time do I spend working in the business instead of on the business?

In other words, how much of your time is spent on routine, day-to-day operations and putting out fires and how much is spent on strategic planning and revenue-generating activities that lead to increased growth in your business?

While there's a lot to be said for being a hands-on leader, you should be spending the vast majority of your time working on your business if you want to unlock its full potential.


Questions about your business

16. Am I aware of my business’s financial health?

When was the last time you reviewed your sales, profits, overheads, and expenses?

As a business owner, the decisions you make will be greatly impacted by your company’s financial situation, and vice versa. Maintaining a solid awareness of your business’s finances will help make sure you're making sound decisions.

17. Do I know who my clients/customers are?

Chances are, you'll have already spent some time narrowing down your target market, creating buyer personas, or delving into demographics.

But in this ever-changing world, it's important to make sure that the customers or clients you are targeting are still the ones who are buying your products and services. Regular customer analysis is key to making sure you're always meeting their needs and reaching the right people at the right time, so your marketing efforts don't go to waste.

18. Do I know who my biggest competitors are?

Similar to your customers, understanding the competitive landscape of your industry is essential.

Knowing which companies and similar products are currently available in the market, and how they differ from yours in terms of pricing, services offered, quality, and any other factors will enable you to spot gaps in the market, refine your value proposition, and stay up-to-date with industry trends.

19. Do I know what’s working and what isn’t working?

Consider this a little health check-up for your operations.

No matter how satisfied you are with the status quo, there’s almost always something that can be done to take things from 'good' to 'great'. But it'll be tough to make those improvements if you don't know what needs to change.

Pinpointing your shortcomings is the first step to planning an effective strategy to overcome them, and recognizing your successes allows you to capitalize on them further.

20. Can the business function day-to-day without me?

If you've put in the hard work and dedication to build your business from the ground up, it's natural to want to stay completely involved and in control at every level.

But this question isn’t about handing over the reins or absolving yourself of all responsibility. You are still leading the company and remain in charge of its growth, vision, goals, and values. It's about whether you have robust systems, reliable processes, and a competent team in place that can handle daily operations even in your absence. This frees you up to focus on growth, strategy, and other high-level concerns, safe in the knowledge that everything is ticking over nicely in the background.

What’s the bottom line?

Entrepreneurs and small business owners should not forget the importance of taking a step back to reflect. Taking time to ask yourself critical questions gives you the power to be more strategic in how you run your business, making sure that every decision you make is informed, meaningful, and in line with your goals.

During your reflection, you may find that your days are filled with the same low-impact tasks, and your time, energy, and skills could be put to much better use elsewhere.

What happens now?

If you’re ready to start getting more done each day without compromising on the things that matter, Time etc is here for you. Our mission is to help hardworking business owners take back control of their time and unlock their full potential by matching them with the best virtual assistants for their needs.

Speak to our expert team to get started and we’ll set you up with a dedicated professional based on the skills and experience you need.

Or try us out for free!

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About the author

Barnaby Lashbrooke is the founder and CEO of Virtual Assistant service Time etc as well as the author of The Hard Work Myth, recently recommended by Sir Richard Branson. Barnaby is a Forbes Columnist on productivity and is also an accomplished entrepreneur, selling more than $35 million worth of services.

Psssst...want a free copy of my book The Hard Work Myth?

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