The Disenfranchised Podcast – Don’t ever have a Plan B

In the Disenfranchised podcast series, Ed talks with entrepreneurs, experts and leaders from across the franchise community discovering their life stories and their tips for success away from the typical 9-to-5 grind.

The #Disenfranchised was created to showcase a community that offers a different career path and lifestyle for people who have become disenfranchised with the world of employment, inspiring them to take control of their lives and start earning more for themselves.

About this podcast episode

Kate Chastey, our franchisor, was delighted to be asked to talk with Ed Purnell on his renowned podcast.

Making the decision to leave employment is one of the toughest decisions you can make in your career, but you need to commit to it fully! A plan to return to employment if it all “goes wrong” might seem like a good idea, but it could determine the outcome before you’ve even got the business off the ground.

In this episode Ed speaks with Kate Chastey of The Passionate PA and learns how, despite the odds, she repeatedly committed to her plan A and created the career she desired. We enjoy a fun conversation that also included:

  • How she found work experience with a TV celebrity
  • The fear of stepping off the corporate ladder
  • Kate’s dedication to helping people to build great careers
  • The common misconceptions of the franchise industry
  • Strange requests from clients
  • And of course much, much more!

Click here to listen to the podcast

Or watch the recording below!


Further blogs from The Passionate PA: 

How to find the right business support for you

Freelancers, or business support professionals, can be the solution to many modern business problems. There is no shortage of skills and experience available to businesses large and small, through the army of freelancers available in the UK and further afield.

However, a question we hear so often is “how do I find the right business support for me?”

The blog below has been created to give you an insight into finding the right solution for your needs. However, if you’d prefer to listen to a podcast, our director Kate Chastey was recently interviewed by Karen Murray and they discussed all of the below, and more!


Or to Karen Murray’s website to listen there


Ok, on to the blog…

First things first

As the business owner, you need to determine what ‘right’ looks like to you.

What problem do you need to solve?
Be clear on the challenge you are facing and your desired solution. Is this challenge the result of an immediate or ongoing resource shortage? What skills and expertise are required?

How do you want your freelancer to work/deliver services?
Are you needing to physically meet with your freelancer or will briefing/communication all be done via technology? If you are looking for a long-term business relationship, consider how you want this to take shape.

When do you need work completed?
What are your timescales/deadlines and what working routines are you hoping for?

Who is the person you are looking for?
Or, more to the point, what characteristics and personality traits matter to you?

Why is a freelancer the best option?
Are you looking for flexibility or a skill you don’t have in your team?

With all that clear in your mind, finish this sentence; the perfect scenario is…

Check this is realistic by discussing it with trusted business colleagues or a seasoned freelancer (we are always happy to talk 😊).


Then comes the research

The next step is to start looking for the freelancer you need. The best places to do this are:

  • Your personal business network – ask for recommendations and referrals from people that know you best
  • Social media (particularly LinkedIn if you are keen to find a professional)
  • Internet search using key words (skills and location)
  • Then there are, of course, some big listing websites that will introduce clients to freelancers. These have their plusses and their minuses – but that’s probably a different blog altogether!

7 brilliant questions to ask your potential freelancer

So, after you have made it clear what you’re looking for – preferably by email so the potential freelancer has time to digest and you both save 15 mins on the next step… a Zoom call – then, it’s time to really get to know each other.

Here are 7 questions, with talking points, that will sort the wheat from the chaff. Remember, the beautiful, valuable, amazing thing about freelancers is that each one is unique. It’s hard to find the perfect fit but, once you do, that’ll be partnership power like you’ve never known before.

1. Tell me about your background and your skills and experience as a freelancer

  • Ask how long they have been freelancing – just starting out or seasoned pro
  • Discuss why they choose to freelance
  • Talk about what skills and experience they have to share

2. How could you add tangible value to my business?

  • Discuss what they know that you don’t
  • Ask what efficiencies they could introduce
  • Talk about the software/tools they are confident with
  • Ask whether they are an ideas person or a completion expert – or both!
  • Really delve into whether they understand your target market and sector

3. What does a successful working relationship look like to you?

  • Investigate what kind of personalities they like working with
  • Ask for clarity on what they need from you to get started, and then what they need from you to achieve the results you have set out
  • Discuss what sort of work/responsibilities you can outsource to them, further than the initial brief
  • Also clarify whether they will be doing all the work themselves or if they outsource/have employees

4. How would we communicate during our project/work/relationship?

  • Ask what their preferred communication channel is
  • Talk about how they manage workflow and deadlines
  • Understand their boundaries – when are they contactable (business hours/working days etc)
  • Discuss whether they work virtually or are they happy to meet in person

5. Tell me about your clients…

  • Who is their favourite client right now and why?
  • Talk about who their ideal client is, and is that you
  • Ask for the back story on a testimonial you have found – talk about tangible value and timescales
  • Discuss how they monitor results and client happiness
  • Ask how many clients they work with at any one time and how this looks in terms of weekly/monthly contact
  • Ask how close they are to capacity and whether there really is space for you
  • Discuss whether it is possible to speak with a current long-standing client

6. Tell me about a business challenge you’ve had, and how you overcame it?

  • Ask them to tell you about a time when they have missed a deadline or underdelivered to a client’s expectations
  • Discuss what their clients like most/least about working with them
  • Ask whether a client has ever ended a relationship with them abruptly – if so, why
  • Ask whether they have a contingency plan for emergencies (power cuts, equipment disasters, illness etc)
  • Delve into their business ethos – who supports them in their business development and growth

7. Tell me about your contractual terms, GDPR compliance, fee structure etc.

  • Understand the hourly/project rate and how this is tracked, plus, other than that are there any additional charges
  • Discuss contract terms, notice periods, service level agreements, invoicing procedure etc
  • Talk about how they will they keep your business information secure and confidential, whether they are registered with the ICO and their understanding of GDPR
  • Are they insured, registered with HMRC and fully aware of IR35 legislation

Seven key questions to really get beyond the fluff and into the value. Freelancers can add so much to your business and/or team but, as you can see, it’s not always easy. The perfect freelancer for you is likely to be someone who will help you create the momentum and results you need to thrive. Finding them can be tricky but it is worth putting in the time so that the relationship gets off to a flying start and your business feels the benefits quickly.

Happy searching!

You can find out more about our team of business support professionals by clicking here!

Further blogs from The Passionate PA: 

Kate’s quoted in the Mail Online

I didn’t quite “declare war” – trust the Daily Mail to exaggerate 🤪 – but I’m pleased to be quoted in this article. This is a really important read for all PAs, VAs and freelancers.

In response to over 500 secretaries at Deloitte being told their jobs were at risk last week, the Daily Mail has picked up on the huge wave of PAs and EAs moving into the freelance world due to the difficulties in finding suitable roles for their skill sets, post covid. The article talks about whether the role of the EA is dead and how successful start-up VAs really are.


Firstly, we (the whole Business Support industry and recruiters) all need to work harder to educate the business community and news reporters on the difference between a Secretary, VA, PA and EA. But I’ll leave that for another blog!

Secondly, making a successful career out of freelancing is not easy – this was my point, which has, to some degree, been lost in the article. Becoming a Virtual Assistant just because you’ve lost your job is not the right thing to do. (Note the word ‘just’.)

I have spent over 10 years honing my skills as a freelance PA and helping others carve out successful businesses for themselves too under The Passionate PA brand.

Here’s the reality; being a successful freelancer or VA takes more time, energy, dedication and stamina than most full-time jobs ever do!

Sadly, the ‘quick-fix’ freelancers and VAs that are popping up daily, only to disappear within a few months, are really making it so difficult for the business world to understand the value a professional outsourced business support solution can offer. I appreciate going freelance is sometimes out of desperation. Of course. But sometimes it’s just pure naivety and rose-tinted glasses.

The whole reason I franchised my business was to help talented, ambitious individuals have an easier route into self-employed success. If you’d like to know more, visit our Join Us page.

I’ve heard so many horror stories of business owners trusting start-up freelancers and VAs, investing valuable time and energy into their on-boarding, only for them to quit when they find suitable employment. This leaves the business in the lurch and feeling very burnt by the whole experience.

➡️ My best advice to business owners – if you are serious about using freelancers to help you structure and grow your business, invest in people that make it their business to ensure you succeed. Check out Karen Murray‘s latest podcast where I talk about how to do this.

➡️ My best advice to employees staring down the barrel of unemployment or experiencing job loss – UPSKILL, invest in your own professional development and commercial awareness and really, really, really delve deep into your own values, passions and strengths.

Freelancing and being self-employed is NOT the easy route that so many gurus try to persuade you it is. Only embark on becoming a freelancer when no plan B will do! By that I mean, when your soul is hungry for choice, fulfilment and awesome clients and you are ready and willing to give your new adventure the focus it needs. You need an awesome support network and it you really want to thrive, an experienced, hands-on mentor that will open doors for you and help you navigate the challenges from day 1.

I’m very happy to talk to anyone thinking of doing so who’d love some unbiased and very honest advice.


Further blogs from The Passionate PA: