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Coaching for Female Entrepreneurs: 6 questions for success

You took the first step and decided to get your idea down on paper or off the ground. Now you have everyone telling you how you should do it and who you need to be to make it work.

Enough. Let’s take a step back and remember why you chose this path and did this in the first place.


Here are 6 self coaching questions for female entrepreneurs to start exploring (or re-exploring) what their OWN version of success is; not just what the world tells you it should be!


As a female entrepreneur and business coach myself, I experience, daily and first hand, the challenges with feeling successful as a woman.

And after 10 years in the advertising industry, I had absorbed a pretty solid idea of what I needed to change about myself in order to be a ‘successful woman’. (Hello new personality implant, power suit, and a new voice box!).


I worked with my own female business coach to sort and work through how these ideas showed up for me, how I could honour how they served me for a while, and how I wanted to move through them.


I have also been a business coach for women a-plenty now. Women starting their own small business, women who have been running a business for years and now want to change how they do it, women who are dreaming of quitting their jobs to become entrepreneurs.


I observe the same patterns, similar thoughts and challenges over and over again.

One that strikes me most is this idea of what a successful female entrepreneur is.

If I asked you, what would you say?


There are many external factors that feed in to our ideas of success. These come from society, culture, upbringing, conditioning, history, etc.

If you’ve never thought about it before, it can take time to sift through it all before you get down to the actual things it means for YOU. Then, you also have the challenge of potentially being surprised by it, or uncomfortable with it. It's a process!


This is all work that we do and explore in business coaching.

If you fancy dipping your toes, then here are 6 questions you can ask yourself as jumping off points.


If it brings up anything you’d like to work on - I am here for you.

You can always book a free consultation call [here] to discuss it and see if business coaching or career coaching is something you’d like to invest in for yourself or your business ideas.


Grab a pen and notepad, and let’s go!



1. If you asked your most important people to say something about you as a female entrepreneur, what would you love to hear?


This is one of the first questions I’d ask you as your business coach. It invites you to come back to your intention and the energy you are putting behind your business. It also pulls apart the external and internal driving forces behind why you do what you do.

E.g. Do you want to be accepted by someone or a group of people? Do you want to prove that you can do something you feel other people don’t think you can? (External)

Or, do you want to finally give yourself the gift of doing what you really want? Do you want to do it because it means you could have more control over your time and energy? (Internal).


Once you’ve gone through it all and made a list, consider what female entrepreneur stereotypes might be influencing your answers, and what you might say if you knew gender was not an issue.

It’s important to say that this is not about changing any of your drivers, but becoming aware of them, where they come from, and being mindful of what you do with that information.



2. If you knew you could never fail, and had all the self-belief and money in the world, what would you work on?


Women are more likely to have to deal with imposter syndrome. I see this as a symptom of working in a culture that is not built for women to easily succeed, or more importantly, thrive.

We grow up in a world that paints our life path a certain way, and therefore, there is more conditioning that we women have to untangle, unscramble, and work through to get level.

Ultimately, this gets in the way of us believing that our dreams, wants, or objectives are possible, or that we deserve them.


In a business coaching capacity, we can explore what is behind this, and what is holding you back. By putting yourself in to the mind space that failure is not possible, and nothing could get in your way, you open your perspective to what is possible, and therefore, what you would choose if anything was possible.



3. What do you secretly not actually care that much about, but would never tell anyone because it might make you look ‘bad’?


Because women often have to work harder to be seen as ‘successful’, we sometimes get caught up in chasing things that are not necessarily what we actually want. This is fully normal and understandable, given our position.

I coach women who get to a point in their career where they realise that what they are doing is not in line with who they are anymore. They feel disconnected from the success they have, and out of alignment with their personal or professional values.

Sometimes, they feel guilty for this. That they should be grateful and happy about where they have gotten to.

By removing this sense of judgement or expectation from the shoulds, and making it safe to say that you actually might not care as much about what you currently have, you can start to paint a new picture of success for yourself.



4. Make a timeline of the past 5 years. Plot the things you are most proud of/happy about/satisfied with/most enjoyed/most glad of from the past 10 years.


This, personally, was a huge one for me. It showed me how skewed my perspective was.

It highlighted how my brain was focusing on everything I wasn’t or hadn’t done yet, instead of focusing on honouring and building on where I had been (which was lots of great things!)


My best tip is to keep this exercise intuitive and unjudged. Let whatever comes out, come out. Plot it on the timeline. Go with what feels good and what you, personally, feel proud of yourself for.

The moments don’t always have to be tangible things either - it could be a moment of realisation or an energetic step change you had.


Then, when you’ve finished, step back and take a moment of appreciation to bask in your glory!



5. What advice would you now give yourself when you started your career?


Looking back at the start of your career is a helpful way to understand some of the pressures and influences that affected you most. This can indicate where you may have felt you had to direct your energy and adjust your ideas of success.

It’s also a great way to look back and see what you were doing well; to see what skills were going unused. Perhaps no-one had noticed yet, perhaps you hadn’t given yourself permission to blow your own trumpet, perhaps you hadn’t had the opportunity.


By zooming out and elevating your perspective, you can see things you hadn’t seen or given time to before. It helps you take a more objective stance on your career so far, and offer some more useful insights to yourself.



6. What made you start your own business?


This is a simple one. Come back to your original why.


When was the first time you thought about starting your own business and what was so exciting about it? What made you dream of doing this? What were you fed up of? What change did you want to make in the world?


Revisiting those ideas and feelings will keep you connected to your ‘own version of success’ goals. The things that really make you tick. The things that you love doing and know you are great at. The things you would wish for yourself.

These are the things we can come back to when coaching for your success.



So, how does it feel now? What perspectives or insights have you gotten out of the questions? What are your key takeaways? And therefore, what’s your next step?


These exercises can start to uncover the tip of the iceberg. I promise you there is a lot more juicy stuff going on under there, and I promise you that you will never regret uncovering it!


Just remember that whatever success looks like for you, it’s ok. Actually, it’s great. Because the more accepting of and aligned with yourself you are, the more your own success can start to flow for you.


And again, if you are ready for some coaching support in your journey as a female entrepreneur, I am here to help, so always feel free to book in and say hello!