Top 15 questions business owners should ask themselves
– if they want to grow their business – by Douwe Hoogstra

As small business owners, we don’t ask ourselves enough questions that really make us think. What questions would make you squirm and want to avoid answering? These are the questions that every business owner should ask themselves, and questions we routinely ask.

It will help to show you where you’re at, and in which direction you should make some changes to allow your business to grow. Here’s the Top 15 questions to ask yourself:

1. Why did you start your business? What’s the driver behind it?

First on our list of questions to ask a business owner is all about their ‘why’.

If your answer is “to make a profit”, think again. Making a profit is a result of your ‘why’.

Your ‘why’ is the reason your business exists in the first place – it’s the purpose and belief that sits behind it. Thinking about your business from this perspective inevitably translates into your marketing and how you sell, meaning people are more likely to invest in your offering if they resonate with your cause. Here’s a video by Simon Sinek demonstrating that the ‘why’ of your business comes first.

2. What are you passionate about in business and life?

As a business owner, it’s easy for the day-to-day stresses of running your business to drain your energy, until eventually you’re left feeling burnt out and unsure of how to progress.

Reminding yourself what you’re passionate about in your business is really a big key to success.

Start with identifying your personal motivators, or core values. These will help drive your personal ‘why’ and  it’s likely that you can also bring these values into your business.

Once found, you’ll have the motivation to take the necessary action to improve your business and bring balance to your life.

3. How’s your mindset?

Growing your business requires a growth mindset. This means a mindset where change is welcomed in an environment of continuous improvement.

A growth mindset is based on high levels of self-awareness, and taking responsibility for your ‘operating state’. In our Be Bold curriculum, we call this operating from the green.

This blog by Martine Pierhagen from Sweet Orange explains why mindset is so important.

4. What keeps you awake at night?

Got that niggling feeling that something in your business isn’t quite where it needs to be? Don’t ignore it. If there are worries keeping you awake at night, they’re probably there for a reason. The only way to get rid of them is to solve the issues at hand.

However, when you’re so close to a problem, it can be difficult to understand what needs to be done to fix it. We often find that the concerns of most business owners can be boiled down to certain problems with their processes, which cause knock-on issues when they’re poorly organised.

If you’re struggling to get your processes in order, it could be time to look for some external help.

5. If you had unlimited resources, what would be the one thing that you would do to improve your business?

No business is perfect. There will always be things that can be improved on – but that’s not a bad thing. It simply means that you have the opportunity to continually work on your business.

Identifying the things you would do if you had unlimited resources is a great exercise to follow. You’ll understand where your priorities lie and what kind of developments you hope to see in the future as you continue to grow. From here, you can start outlining a plan to get your business where you want it to be.

6. What’s stopping you from growing?

This question is an important one – and it’s where you’ll need to weigh the pros and cons of pursuing business growth. Usually, it will be a lack of resources that are preventing you from growing your business in a sustainable way- whether that’s cash or people. However, a lack of resources shouldn’t stop your business development altogether.

For example, in order to grow your business you’ll need marketing. Your  target audience needs  a way to find out about you and why they should buy from you. If you don’t have the resources to do this internally, outsourcing is an option. For those on limited budgets, there are flexible solutions out there where you can have a dedicated team to help you with your marketing.

Ultimately, if your return on investment justifies the costs – take the plunge. A lack of resources shouldn’t be the thing that stops you.

In my experience, more often than not what’s stopping you from growth is not actually the lack of resources, but rather the growth mindset required.

7. What’s your 5-year goal?

If you’re running a business, you’re no stranger to setting goals. They’re invaluable for outlining what kind of progress you’re aiming for and provide you with the direction you need to plan so that you can achieve those goals.

5 years might seem too far ahead to set goals for, but it’s well worth your time to consider the question.

While you can’t really predict what will happen over the course of the next 5 years (after all, which businesses foresaw the disruption of things like the Covid pandemic), it allows you to think big and start making plans that will see your business become more secure and sustainable over time.

Of course, a big 10-year goal will need to be broken down into smaller chunks so that you can gradually work towards making it happen, but with a solid wireframe to follow, you’ll be thinking steps ahead of most of your competitors and have a greater chance of success.

8. What part of the job would you happily give up?

The more you enjoy what you do, the more you’re likely to thrive doing it. This is why it’s important to assess the responsibilities you take on day-to-day and consider which ones you’d gladly stop if they didn’t have to be done. The chances are there’s at least a couple of tasks that you can identify.

As well as recognising the parts of your job that are your least favourite, think about how you could repurpose your time without them. This could be a new task that would benefit your business, or even time to rest and recuperate so you can put more energy into the parts of your job that you enjoy.

If you have responsibilities that you don’t enjoy, it could be time to hire someone to take on the work or outsource the task completely. Life’s too short to simply ignore it and try to power through, and the extra effort you make doing things that you don’t enjoy could be sapping the energy it takes to succeed at the parts of your job that you really love.

9. If you couldn’t work in your business through injury or sickness, how would your business survive?

If you are a sole trader, there may not be a lot you can really do if you are injured or sick. Ideally, you would have key person insurance in place to compensate you for the loss of business. Hopefully, your regular customers will be able to accommodate you and come back when you are back at work.

As a business owner with employees, you will have built a team around you who can take care of things in your absence. You will have put processes and systems in place to make sure the work still gets done in the way you designed it. This should be the goal of any business owner, that the business can continue even when a key team member becomes unexpectedly unavailable, and that includes you.

10. What’s your exit plan?

No one builds a business without hoping it’s going to stand the test of time. However, planning for your exit is one of those things that many business owners put off. If left too late, the process of ensuring your business’s future and retiring when you want to can become tricky.

It needs a bit of thinking, and the exit plan needs to be put into effect early enough.

If you want your business to continue to thrive once it has left your hands, you need to start thinking about who’s going to take over the reins. This process can be more straightforward for a family business but for others, finding a suitable replacement can be a mammoth task.

Whether you want a solid succession plan in place or simply want to sell your business when the time comes, it’s never too early to start outlining the finer details.

Find more tips in our publication The SME Business Owner’s Guide to Succession Planning and Exit.

11. If you were less involved in the day-to-day running, what would you do?

For business owners, the day-to-day of running a business means that we have to deal with a whole range of responsibilities, and it’s easy to lose sight of what areas of the job and skills you should be prioritising and developing. So while this might not jump to the top of the list on questions to ask a business owner, it’s important to consider.

Asking yourself what else you would be doing if you weren’t so involved in the operational side of your business assists with identifying most suitable roles, and also priorities to do the important tasks in order to grow your business.

12. Is your business profitable?

Business owners know that profit is essential for business growth, but they don’t always know what steps to take to generate more of it.

There’s a common saying: “Sales are vanity, profits are sanity”.  In order to generate spare cash to reinvest into growing the business, we first need to make some decent profits.

There are four areas in business that assist in increasing profits:

  • Increase sales
  • Increase price
  • Reduce direct costs
  • Reduce expenses

Incremental steps in all four areas will result in substantial profit increase. All these can be analysed, and change effects modelled and compared to benchmark industry statistics.

Businesses that have good financial management perform substantially better than the average. This includes budgeting, forecasting and regularly monitoring their financial performance. Gone are the days of waiting for your accounts half a year (or more) after the end of the financial year. That’s historical tax accounting, and definitely not suitable for a growing business. Have you seen pro-level rugby, or netball, competition played without a plan and without a scoreboard? Of course not!

13. Can your business survive for 3 months without any sales?

Very few people saw the pandemic coming, or if they did, little was done in the way of preparation which is why this is one of the most relevant questions to ask a business owner.

Fact is, there will always be external threats to your business, and the only way to deal with them is to plan for them, even if you’re not sure what they are yet. Ideally, your business needs to be in a position where it could survive at least 3 months of little to no sales.

If you’re not sure what other external factors could be affecting your business, it’s worth taking the time to complete a PEST analysis where you look at what political, economic, social and technological issues are influencing your business or market to help you identify the ‘bigger picture’ threats and opportunities in your market.

14. What would happen if your business had a cyber-attack?

There are lots of challenges to running a business, much of which is about keeping control over the reins, so the last thing you need is an attack on your business IT systems.

We increasingly rely on technology to assist in running our business. Have a think about all your systems and technology that is in use in your business, and how your business be impacted if the systems went down and discuss with an IT expert to protect your systems as much as possible.

15.How much time do you spend working on the business?

Many business owners spend most of their time working IN their business, but few spend enough time working ON their business, which brings us onto the last of the questions to ask a business owner.

To really help your business to thrive, you need to look at the bigger picture as well as dealing with your day-to-day responsibilities. Spending time reviewing, planning and preparing for a number of eventualities is the only way to secure your business and head down the road to success.

However, if you’re swamped with the everyday duties with little time to plan for the practicalities of the direction you want to take your business in, it could be worth investing in a good business coach to keep you on track.

Final thoughts

So, which of these questions to ask a business owner resonates with you? Which gave you the most insight?

If you work through these questions systematically, you will get greater insights into why you are running your business and help to give you a better sense of direction.

If you would like some help asking these questions of yourself contact me for a free strategy session.


#loveyourbusiness #itsyourchoice #beboldinbusiness




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