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17 Reflective Questions That Will Take Your Small business to A Whole New Level

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Last updated 14th October 2022

reflective questions

Let’s face it, growing a business from the ground up can sometimes feel like you’re trying to drag a boulder up a mountain backward! Starting a business in any industry is challenging, even for those with heaps of experience in their back pocket, but entering the wellness, lifestyle, and beauty space is crowded, and bustling with entrepreneurs who ‘Just ‘seem to have it all together. The truth is that’s not always the case. Like you, they have been through their fair share of ups and downs, feelings of frustration, and are ready to pack it all in.

But I want to show you that with a few simple questions, and a smidge of consistency you can reach your goals, build a brand people love, and grow your business with confidence, and clarity.

Read more: How to Create a Vision Board for Life, Love, and Work

How reflection has helped my businesses success rate

These questions helped me stay focused, consistent and clear on what matters in my business. I learn things about myself as both a business owner and a designer. Just like my health, family, and finances, I make sure to dedicate time to nurture my business with what it needs by listening and reflecting. It’s like business therapy.

From frustration to simplification

When I started my business 4 years ago I was always on the hunt for quick smart ways to improve my small business, yet I found myself at a loss with what direction to take and what I needed to do in terms of creating content, day-to-day admin, and finances. I decided to shift my focus, ‘was I asking the right questions?’. I don’t know, what I don’t know. Right…?

After another morning of feeling defeated, I decided to take my dog on a walk and I remembered my dad was an NLP practitioner way back when, and I remember him going on about the art of questioning (I was only half-listening at the time, sorry dad). So while walking around my park I gave him a ring. We had the usual catch-up chat and after I asked him “Hey dad, do you remember when you did NLP? What did you mean by the ‘art of questioning’?”, in short, he replied:

“The idea of reflective questions is that we are the only ones with answers to our own questions. That’s why successful people ask better questions and as a result they get better answers.”

He then told me to get a journal and everyday answer these 5 simple questions. Over time you’ll start to notice patterns and a shift in your mindset, growth, and development.

5 Daily reflective questions

So here are the 5 reflective questions I ask at the end of every day which I believe has helped me grow my business, maintain a strong mindset and learn to develop my skills. Do this every day and I promise you’ll see results!

  1. What went well?

  2. What could have gone better?

  3. What do you need to do more of?

  4. How do you feel?

  5. What are you grateful for?

Other growth-worthy questions to ask monthly/quarterly

To keep your business and brand on point throughout the year you could also ask yourself these questions at the end of every month to see what worked and what didn’t and where to focus your attention.

  1. Was my business memorable? Did people recognise my brand?

  2. What positive feedback have I received?

  3. More importantly, what negative feedback have I received?

  4. Where is my brand positioned among all my competitors?

  5. Which areas of my business do I need to improve on to become irresistible to my ideal audience?

  6. Was my identity consistent across all touchpoints of my business? 

  7. Did I gain a clear understanding of my target audience and what they want?

  8. Which social platforms did I see the most engagement/action on?

  9. Which posts worked super well? What should I post more of?

  10. When did I feel most exhausted and drained last year? (How can I avoid that again?)

  11. Did I stay true to my business plan?

  12. What did I say ‘yes’ to that I wish I said ‘no’ to?

I usually dedicate the last Friday of every month to giving my business an audit. This is also an opportunity for me to create my content for socials, do maintenance on my website, and little read up on the latest trends in both the design, and what’s new in the wellness and beauty industry.


Kate Male Brand Designer & Creative Director based in London

About Kate

Kate is a brand designer and creative director based in London. She works with wellness, lifestyle, and beauty brands who want to tell their story with depth, and style.

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