• Coach Kate

10 Crucial Career Questions to Ask Yourself.

As a career coach and specialist I spend a lot of my life asking clients deep and insightful questions to help them understand what they really want from their work and their careers.


When I start to work with anyone we always start with what they want their life to look like and involve - yes your career can be a vital and important part of your life, however, we must remember that is is just that - a part of it. For so many people they allow their role to define who they are, their work to rule their life and then wonder why it has taken over.

This was me a few years ago - so there is no judgement here! It was only until I burnt out at work that I realised I needed to fully understand what would make me happy - at and outside of work.


In this article I will unpick the reasons behind 10 of the crucial career questions I ask clients when we start coaching together.

Have a go at answering them yourself too - remember that there are no wrong answers, initially clients often tend to respond with answers they think a career coach wants to hear - NO!

Answer truly for yourself - this is all about you.


  1. What energises you? This centres on motivation and enjoyment as one of the main career complaints I hear is that "I feel so demotivated" If you are working doing something that you enjoy then chances are you will continue to do it, make more of an effort whilst doing so and will reap greater feelings of satisfaction from it

  2. What 3 activities or responsibilities from your daily life make you truly happy? These may be when you experience a state of flow, as in ‘time just flies by' and it feels effortless. Why 3 though? Well - we all know that 3 is a magic number, but really we are honing in on the essential things that drive and excite you.

  3. What are you really good at? This question identifies your strengths, skills, expertise, unique talents - the stuff that people ask you to help with time and again. For many of the people I work with this is the hardest question for them to answer due to low self-esteem or just not willing to talk about themselves positively. We are much more used to talking to and about ourselves with a negative focus. This question allows my clients to identify and realise how talented they are, recognise all that they are capable of and therefore the career opportunities open to them.

  4. If you won £10 million, what would you do with your time? Similar to "if money were no object what would you do?" however with a limit it enables people to consider what is top of their list of priorities. No surprises for guessing that for most of us it is ensuring we have some stability and security for us and our families - the number one answer is "pay off the mortgage / buy a house" The reason behind asking this one is to begin to uncover what success means for my clients and what their fears are around job loss or financial concerns. There is no point going down a new career route if it will leave you penniless of in severe debt - we have to be realistic.

  5. What would you most like to develop and improve in yourself? Full disclosure here - if a prospective client doesn't elaborate much here then chances are they are not the right client for me and I won't work with them. Unless you are prepared to delve deep, develop, grow and learn through coaching then I wouldn't waste your or your coach's time. If all you are looking for is a larger pay packet then consider going on a negotiating course. If you want to genuinely progress in your career or start something new then come on down!

  6. What would you like to contribute to the world? Note that this is not about reinventing the wheel or changing the world - this is about your purpose and what you can do to help or benefit others, your local community, the environment, your place of work, your family, your friends - whatever it may be this question uncovers your higher purpose.

  7. What beliefs do you need to let go of in order to be even more successful? Ah - one of my least favourite words 'success', however, it resonates so deeply. We are engineered to see success as high achievement and to work to attain it in everything we do. What if we swapped that word out to 'happy' or 'content'? Well guess what? We do! I lead with successful to understand what this means for my clients - if they want to be at C-Suite level then our work towards this will be very different to our work towards a successful life - work balance. (Yes - life comes before work!) This question also uncovers some of the limiting beliefs my clients have held onto and continue to invest in - the scripts they were imprinted with as a child or things they have been told by teachers, lecturers, bosses, colleagues which have instilled themselves as facts but are mere opinions.

  8. What will the world pay you for? This is our reality check question where we explore what are the job opportunities like at the moment, would the pay be enough and do these jobs work practically for your life in terms of location, working hours, package etc. If there are limited job openings for an opera singing lion tamer then we might want to re-look at the opportunities available to you.

  9. Who do you love spending time with? We have a tendency to get caught up in our careers and working lives so much that we forget other aspects of our lives which bring us joy - family, friends, partners etc. This question not only reminds us of that and how important they are in our lives but it also highlights the types of people we want in our work tribe - colleagues, managers, leaders, those we lead. Work culture is invariably made and enforced by the people who work there and we often remain at an organisation because of the people - make sure they are the right people for you.

  10. What physical environments light you up and bring you alive? Work from home may not last forever and chances are many will opt for a hybrid of in office and at home working so let's now take a look at what working environments empower you to do your best work. This may mean converting a spare room, garage or shed into a full working office. It may mean requesting to go to the office you will be working in before accepting the role. Why am I making such big deal out of this one? We spend a third of our life at work which is a hell of a long time to be at a dingy, uncomfortable, uninspiring office with crap coffee. It's not merely about the aesthetics - you may notice a toll on your physical, mental and emotional health if the majority of your day is spent with limited natural light, an uncomfortable chair and desk set up, little to no nature - the list goes on. The other hugely important factor is you feeling safe at work - safe and secure to be yourself and do your best work.

If you found these questions helpful, inspiring and insightful then don't hesitate to get in touch to see how career coaching can help you find fulfilment in your work.


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