What are your thoughts?

Obvs it’s not quite as good as the original, it’s not an iconic film you can watch over and over, but nonetheless a feel good film that entertained me.

The unbelievable part How easily the EAs seem to get promoted in this world?!

That being Meryl’s First Assistant is always a stepping stone to their next role.

Don’t tell me Meryl wouldn’t do EVERYTHING in her power to block her brilliant First EA from moving on to another role as she depends on her too much. Yes fellow EAs, we know what I mean by this.

I think many of us can agree that’s not our lived experience in the EA world (although I’ve never been in the fashion or luxury industry)

We have a massive glass ceiling still trapping our overwhelmingly female industry. Yes, not everyone wants to or even should move beyond the EA industry if it’s not for them. (Or move back, as we often see in our modern working world of squiggly careers.)

But when it feels like the only option is to leave the industry if you want to progress - that affects everyone. Even the brilliant EAs who want to stay in the role. And it truly does affect us when we don’t have the same career paths as our colleagues in the office because our skills and impact aren’t really understood and we don’t get the same L&D opportunities.

So that’s my hot take, yet again TDWP shows us another unrealistic reputation of the EA world.

But how do we fight against stereotypes and the never-ending outdated perceptions of our role? Read on for everything YOU can do.

Caroline x

Points of Business: How to demonstrate your value as an Assistant

This is Part II, for the first instalment go back and read
The Assistant Industry’s PR problem.

1. Upskill yourself - constantly

Dare I mention AI?

But it’s not just about AI - over the past 10-15 years tools and tech have been moving fast. the mainstream businesses use Google workspace vs the traditional Microsoft, everyone uses task management tools such as Asana, ClickUp and Monday which can be GODSENDS for our roles.

You can’t be an expert in everything.

But the modern Assistant is able to pick up a tool, AI, workflow with curiosity, an open mind and willingness to learn.

My most successful candidates and team members who will always pick up clients with Upsource have this mindset in abundance.

I’m sorry but tech and AI in 2026 and beyond is unavoidable (and, so sue me, fun!!).

2. Communicate what you’re doing

10 years ago and two clients in, I noticed a theme: working virtually with clients completely new to the VA model - they just didn’t ‘know’ what I was doing.

So I introduced weekly wrap ups - daily for larger clients. Tasks management tools where the client could see at any point they wanted where a task was at or when I planned on doing it.

When I went on to lead a team I introduced these as standard ways of working and interestingly I soon realised not everyone was keen.

“They should just trust me. They should just know I am doing what I said I would.”

Yes in an ideal world, they would

However I am long enough in the tooth to know, not everyone provides an excellent service and clients bring their past experiences to new relationships. Or perhaps it’s just their first time working with someone virtually.

Clear, open comms. It’ll benefit you in the long run and help you create and maintain high standards.

Gone is the world where we were sat outside our boss’ office and looking busy is enough of a gauge on our productivity.

Our new world thrives on open communication to build trusting relationships. Embrace it.

3. Demonstrate your value

OK, so my above point shows what you’re doing but now we’re talking about showing why your role is needed.

Again, ideally our clients and bosses know that, we shouldn’t have to tell them But of course we do need to tell them.

The reality is, when budgets are cut, does HR and Finance really GET the need for this non billable function?

It’s never been easier in this tech world (back to point 1) to get the data of where our value lives and the impact we’re making.

My top tips:

• Track what time savings and productivity your work has unlocked for your exec and team

• Any testimonials, feedback - save it in a folder!

• Track your time religiously - VAs you’re already doing this

My fun hack this week was uploading all this data into Notebook LM for a client - it truly showcased the growth partners we have become for them.

4. Network, network, network

I recently placed an old friend into a Chief of Staff role. It perfectly demonstrates what we’re increasingly seeing in today’s market - roles are being filled from within our networks.

Don’t have a network? Go get one.

Caroline Pooley from Cornwall had no connections and no network, either for the Assistant industry or for business Like pretty much everyone I know, I started from scratch. Constantly getting out there and meeting people.

From University connections to random chance meetings and in person networking - the success of my business and career is in a huge part down to the connections I’ve made and work hard to keep.

5. Embrace what makes you, you - it’s a deeply personal role

Possibly my favourite in this to-do list.

In a world of AI, tech and increasing homogeny, know who YOU are and what makes you special

• How do you like to communicate?

• How do you adapt around different personalities and styles?

• How do you prefer to have feedback?

• Your strength and weaknesses (not just that whole “Oh I’m too organised, a perfectionist” job interview answer - eye roll)

What I REALLY take pride in at Upsource is all the different personalities we have across the agency.

We are such a mixed bag of backgrounds, experience and just totally different human beings.

In this world it makes us wonderful. To know yourself inside and out, means you can understand and work with others.

And in general I’m just a fan of people who really bring their personality to the game. The right client / boss is out there for you.

How do these points make you feel? LIke you’ve already got it covered, or like you need to show your worth more? Do you want more discussion on this? Let’s chat in the comments

Leave a comment

Actions:

• 11-12th June: ES Global 2026, 24 hours of live learning, with over 20 international speakers and 30 days of replays. I’m giving a talk: Designing a Career in Executive Support on Your Own Terms, exploring what it means to take ownership of your career design. Join us here

Make sure you’re subscribed to receive our full monthly digest - more awards to enter, networking and coworking events to attend, and opportunities to upskill.

Next Steps:

• Dr Lauren Ingram has just launched a new Substack for AI Girls - subscribe if you want to up your AI game.

• The Society of Virtual Assistants want to hear from you 🫵🏼 Complete their survey to help them build a comprehensive and honest picture of what it’s like for UK VAs and shape how our industry is perceived.

Questions/Comments:

If you have an event, coworking, upskilling opportunity or even job that you want to shout about, please let me know and I’ll include it in next week’s monthly digest.

[MESSAGE BUTTON]

Suggested Reading:

• If you’re getting a bit too caught up in end of year goals and the “final push” a reminder - Who cares about New Year’s Resolutions. December has enough pressure as it is.

F*ck up of the month:

I do quite a lot of newsletters - here, for my podcast and an internal one for Upsource. Last month the team got nothing!

And a kind contribution from Upsource team member, Charlotte - I sent out a policy for the team to sign - and forgot to turn on the auto email capture, so now I don’t know who’s completed it and will have to hold my tail between my legs and ask them to re do. 🫠

AOB:

A moment of transparency from me. A few months ago I whispered about a shiny new Substack with lots more content, paid tiers and some great guest contributors. And it hasn’t happened yet. Rather than over promise (again!) I’m committing to bringing it to life for September. Consider this the world’s longest teaser campaign 🤪

Speak soon,
Caroline x

P.S. Share this email with anyone in the Assistant community (or any industry!) who might find it useful.

Leave a comment

Some of my hard-learnt tips on managing clients are below, let me know if they help you with your client woes!

Points of Business: Are you leading your clients or your clients leading you

You’ve got your clients - yay! But you’re having trouble managing them. If you’re struggling to get the balance between boundaries and the excellent service they came to you for, read on.

1. Onboarding

I love this so much I did a whole podcast episode on it! Your onboarding sets the tone. Whether it’s clients or associates, it tells them what to expect from you and begin navigating how you work together. Get those communication boundaries in:

What are your working hours and days?How does the client communicate, how do you prefer to communicate and where should your clients/team go in ‘emergencies’ (which rarely happen!)

2. Communication alignment

Something I see too often with clients - they don’t know when you’re working on them and what you’ve been doing.

But they should “just trust you” right? All your bosses have in the past…

The truth is, your client is taking a leap of faith and is nervous. In an ideal world all clients would ‘just know’ but that isn’t reality.

My process?

Every client should know where to find whatever springs to mind on Friday night at 10pm (when let’s face it I’m sometimes several glasses of wine in, and might as well have a ‘do not disturb’ sign round my neck.)

OF COURSE that means that is exactly when a client will have had a sudden panic about where to find their travel itinerary/latest SOP/updated contact details/whatever (because that’s just our luck right?)

So the trick is always assuming that WILL happen with a new client, it’s just a matter of when.

So how to mitigate it? Make sure they know where to find everything themselves via task management software, wrap up emails (close of play, end of week), a running document, spreadsheet - whatever works for the client - so they don’t need you personally to put their mind at rest.

(Yep whatever works for the client. I’ve said it often, we are always keen to enforce our existing boundaries and say we will only do things our way. But the reality is, if you want clients and to be booked, it should be all about the client, and then asking the question, “is this for me?”)

3. Confidence

What does true confidence event look like?

Transparent clear communications

Explaining your role, building a system that means you are *whisper it* replaceable.

That’s the confidence you should bring to your clients. But let me be clear - it is not about

• Knowing everything

• Knowing all the tech and systems

• Having all the answers

It’s about knowing your role and how to support your client so you can find the answers together (and communicating that’s what you’re there for!)

That is where demonstrating your value is key - (Jodie Mears on LinkedIn is brilliant on talking to your clients to clearly show how you have helped them to success.)

4. The right clients

Genius right?! But I’ve been in the Assistant business for almost 10 years and I am still struggling with the right clients.

Not everyone will be. The real growth? Identifying who isn’t right before it goes too far (Still working on it I promise you!)

I don’t have all the answers, but I know what my non-negotiables are. Do you?

Want to work 3 days per week and have the other two for mummy days? - stick to your guns and find the right clients for that. PLEASE don’t pretend you can compromise if it’s not for you. It really doesn’t work in the long run.

Only want to work with clients whose values align with yours? Keep to that. It really is worth it in the long run.

And when they are the right client but something isn’t fitting?

Go back to your onboarding. What did you say then that you wanted to achieve together? Is it still possible? Going back to the start can clear away the white noise and shiny things syndrome and clarify what you’re actually trying to do.

If you’re struggling to find the right clients, go back to my email and podcast all about it

5. Flexibility

We hear A Lot about boundaries in the modern world - and yep many of us with our upbringings and the weight of what is placed on women in the working world could do with some work on them.

But I ask you to look at your flexibility.

There are times, being a service business owner, that your service will be needed.

And it may not be perfectly aligned with what you want or need. But I have found that when you give a little bit of flex, it is always returned.

And if it’s not - go back to point 4 again.

If I have learnt anything running a people business, it is that people are perfectly imperfect. And everyone needs support, understanding, and above all,empathy. Always approach your clients with empathy.

Actions:

• 13th November: PA Forum The Importance of Networking online event, tickets here

• 4th December: Strategic PA Network Clients for Keeps: Building a Sustainable Client Base - a day of coworking with a panel on client dev hosted by me! Tickets here

Make sure you’re subscribed, my full calendar for November comes out next week - lots of opportunities for networking, training and awards.

Next Steps:

• Check out Mimi Nicklin’s book on empathy, or listen to my conversation with her here

• I shared How I Set Boundaries With Clients here

• ICYMI: My Assistant miniseries is up here and wherever you get your podcasts

• It’s Networking month on Upsource’s IG for November, head over there for more on why you should be networking and how to do it so it works for you

Questions/Comments:

Have you listened to the miniseries? Did you find it helpful? If there’s a particular topic, question or challenge you’d like me to go deep on, either here or on the podcast, let me know in the comments.

Leave a comment

Suggested Reading:

One of the O.G.s of leadership and empathy, watch this speech by Simon Sinek and read Leaders Eat Last

F*ck up of the month:

I have struggled with this month’s F*ck Up - not because I haven’t had one, but because there have been so many to choose from!

But I realised my f*** up for 2025 in general has been not realising it’s been A Lot. It’s easy to think everything is fine and not listen to the signs when you have a lot on, so thank you to anyone on the Upsource team who has seen the signs and supported me. The clouds are clearing!

AOB:

Silly season is almost upon us - Upsource has been planning multiple client parties for months already, not to mention our very own Slack and IRL festivities. If you have an event that you want more people to hear about, email me and I can put it in next week’s dates for your diary message.

Back next month with some thoughts on why passion as a career-minded woman isn’t always what it’s cracked up to be.

Speak soon,

Caroline x

And if you have friends in the Assistant industry, whether in-house, freelance or agency-builders, please send The Agenda along to them

Share The Agenda

Caroline x

Points of Business: My rules for content creation

Consistency is key

5 years in, I get told I’m ‘everywhere’ (I’m not. Or maybe I am…sorry).

The truth is, even when I had my rare week off, while I ran away to the countryside, I am consistent. Maybe it’s my performing background (always like to drop that in), but I know nothing happens overnight. OK, maybe for some people but not me, and probably not for most of you. It takes time. Showing up.

My biggest tip for this? Set a realistic schedule.

I post on LinkedIn 3 x per week, not every day like some of the ‘gurus’ say. But 3 times is manageable and leaves me wiggle room for a cheeky 4th if I’m promoting something.

I do engage every day (weekdays) and if I don’t?

My big secret - I don’t beat myself up about it.

This is consistency. Deciding what’s realistic and keeping to it.

We do try to plan content a month in advance, and I schedule on a weekly basis - I’ve live probably posted once this year. Is this LinkedIn gods (algorithm) friendly? Maybe not. But my content gets seen. I am slowly building in the way that works for me.

The difference between a personal brand and business account

I really struggled for years with the personal brand piece. (Content pillars really helped - see below.)

To an extent, this is why I came up with Bump to Business Owner - I really needed to talk about business, careers and babies. It was who I was when I built my business, in the absolute thick of it and frankly bloody mortified how women get treated in the workplace for procreating. It’s who I am now.

But it’s not relevant for the people and clients I wanted at Upsource (some but not all) and Upsource is not a business to support mums. We do, but that isn’t our client base.

My solution on Insta was splitting the accounts, which worked a treat, especially as our clients aren’t really on Insta, so it’s more a ‘shop window’ account.

But LinkedIn? That was hard. For a long time I stayed ‘professional’ only, Upsource tips, etc. My husband even had to add the word ‘breast’ to ‘feeding’, when I was talking about doing it while winning an award.

I didn’t want to be too ‘mum focused’, but now I feel I can do both. I’m embracing it as part of my brand and business story as well as ‘what on Earth Upsource actually does!’

Get your content pillars nailed

Trust me. ESPECIALLY for your personal brand. This is game changing.

Full disclosure, it was only after 4 years in business and 2 personal brand challenges with Female Founders Rise that the penny dropped on these! Highly recommend checking them out if you haven’t already.

I have 4 - they cover everything I believe in: the Assistant world, wellbeing, motherhood and being a founder.

It means I’m consistent (you see what I did!) with what I’m talking about - so people know what they are getting. But I can stay true to myself as well as promote what Upsource is all about. A client recently found us from Linkedin, so I guess it works!

Get the team involved - but not in the way you think…

I speak to MANY many business owners who just want to delegate their socials. And that is absolutely fine when you have a product, or just want a ‘shop window’ ticking over. But when it comes to a personal brand?

That’s a red flag.

Why?

It's 99% likely you don’t know what you want to say or don’t feel confident in your message. Which means you likely won’t like what the person you’re delegating to has to say either.

My advice - get a coach, a mentor, someone who can support you and do this WITH you.

Or content people that will work with you (hello to our lovely Upsource team 👋🏼). It’s a collaborative effort which means it’s KEY that I am consistent. And a necessity when I’m very much struggling with words or need fresh ideas and external input.

So get help. But the right help for you!

Most importantly

No one else cares 🤷‍♀️

Your brother or husband’s mates made an unhelpful comment about your posting? Ignore them.

If they care they are bored. Ultimately everyone is too busy thinking about their own content!

Actions:

• 1st July: Strategic PA Network co-working in central London. Get in touch if you’d like to come along!

Next week I’ll be sending out a full list of events, conferences, awards that you need to know about, make sure you’re subscribed.

Next Steps:

• Check out previous podcast guest Dr Dupe Burgess. I love her LinkedIn posts, and she sends out a newsletter every Monday with social media and business tips

• I also love Grace Carter for her authenticity on LinkedIn. Sharing your whole self in a ‘work’ environment can feel awkward and icky, but I think she does it really well. Of course, I’ve had her on the podcast

Questions/Comments:

Are you out and proud on social media promoting yourself on social media, or a lurker?

If you’re out in the arena, I’d love to hear where you started, how you stay consistent and why you’re there. Let me know in the comments ⤵️

Leave a comment

Suggested Reading:

Some of Upsource’s favourite social media tools. Have you heard of Shield or BuzzSumo yet?

F*ck up of the month:

Another banger this month. I copied and pasted all the wrong dates to a new team member so she could (in theory!) arrange for me to meet with her clients - good to show early and often I’m human 😂

AOB:

I want to hear from you. What do you want to hear more about? Where do you see challenges and opportunities in your business that you need support with? Let me know in the comments so I can make this newsletter as practical and helpful as possible.

Leave a comment

Don’t forget we’ve got treats! Check back on April for Nuwa and May’s emails for Dirtea discount codes and goodies!

Speak soon, Caroline x

P.S. Share this email with anyone in the Assistant community (or any industry!) you think might find it useful.

Leave a comment

Points of Business: Networking for people who would rather stay at home

I’ll be honest, in my current funk, I did not feel inspired by this month’s topic: Networking.

Why?

Well there are tonnes of blogs to tell you networking is important, how to do it etc.

Heck you can even ask ChatGPT to give you a pep talk (something I do not infrequently).

But I want to share why I’m so passionate about networking: why it’s meant so much to me and my business and how I learnt to love it.

I was a very anxious child. Like most kids, I didn’t know ‘anxiety’ existed, but often when it came to school trips, parties even, I would suddenly decide I ‘shouldn’t’ go.

Something shifted in my teens, perhaps having an excellent group of mates who I loved hanging out with, and realise as I get older that’s the ‘real’ me, not the younger version. 

But I get it. When I first went to a networking event, it was the younger Caroline that took over. I was absolutely sure I shouldn’t go. But I made it.

So here is what helped me

1. Most people there are probably equally or even more nervous than you! Focus on that - it really helps you get out your own head
   

2. I’m going to bang on about it, but meditation and affirmations WORK - slow down your breathing and calm your nervous system
   

3. Don't beat yourself up if it doesn’t go as ‘successfully’ as you hoped - whatever ‘success’  is?! There could be so many reasons: it’s not the network for you, its not the right point in your cycle to be around people, it just wasn’t the right crowd this time. And that’s OK.
   

4. Start with one person: Find just one person to chat to and if not find a group where there is a physical open gap for another person (the people who do that are experts at networking and showing they are open - make friends with them!)
   

5. Embrace your nerves! Call them excitement and remember it's a sign you are making yourself uncomfortable which means you’re growing
   

6. See if the organiser needs any help. This is genius, if you get there first a job to do will really make you feel more comfortable
   

7. Be shameless! You’re great, you’re business is great and people will love to hear your story
   

8. See it as an excuse to make friends. You’re there to build relationships, have a chat and see what happens, not leverage every contact into a business opportunity - you don’t need that kind of pressure and people will feel the inauthenticity
   

9. Think of it as a fun night out. Free drinks? A chat with other incredible women and founders? An excuse to skip the ordeal that can be bed time? Not so bad
   

10. Still feeling too nervous to shout about what you do? Ask questions! Make it about the person you’re chatting to, we all love being asked questions about ourselves!

Networking is, yes, a great way to meet potential new clients, suppliers and collaborators. But most of all it is a chance for you to chat to people who get it: get what it’s like to work in the industry/be a business owner/a working mum - the friendships you might build makes networking so worth it.

Actions:

• TONIGHT: London VA Network networking event at 5:45pm this evening at the Royal Horseguards Hotel. Get your tickets here
  

• TOMORROW: Pally Talks are celebrating their first birthday: networking, drinks, cake! Tickets here
  

I’ll be sending a separate email out next week with all the networking events, conferences and awards dates and deadlines you need to know about - make sure you’re subscribed⬇️

Next Steps:

• Follow Jeni Smith, she’s only studying a PHD in networking!

• Check out my 3 favourite female founded networks:

  • Female Founders Rise

  • The Wilder Collective (shout out to my previous podcast guest and founder Nikki Elliot!)

  • The HoLT (founded by another previous pod guest, Lea Turner)

Questions/Comments:

Have you got some networking tips and stories you want to share? More questions about how to network? Let me know in the comments.

Leave a comment

Suggested Reading:

• The Positive Entrepreneurship report on female entrepreneurship which reveals a link between lower rates of founder loneliness and better business performance, but 66% of respondents reported feeling highly or extremely lonely. All the more reason to build your network.
  

• More on the how of networking here

F*ck up of the month

This month’s f*ck up I found pretty hilarious.

I’m dipping a toe into Tik Tok (join me there!) so the fab Meg has joined the team. I Slacked her a video for Maternal Mental Health Awareness week, or so I thought - actually I sent it to Abbie 🤦‍♀️

So poor Abbie received a very random out of the blue video of me talking about Maternal Mental Health Awareness week. I love an overshare but not normally that direct!

AOB:

I want to hear from you. What do you want to hear more about? Where do you see challenges and opportunities in your business that you need support with? Let me know in the comments so I can make this newsletter as practical and helpful as possible.

Leave a comment

And don’t forget we’ve got discount codes to Nuwa and Dirtea! Check back on April and May’s emails for the codes and the goodies!

Speak soon,
Caroline x

P.S. Please do forward this email to anyone in the Assistant community (or any industry!) you think might find it useful.

*Stat from Lucy Brazier’s fantastic book The Modern Day Assistant, please read!

Points of Business: How VAs can use AI to their advantage

I had planned to speak about AI in this edition for a while, so it’s incredibly fitting I write this after a couple of the BEST AI webinars this week as part of my Goldman Sachs 10,000 Small Businesses programme.  

My key takeaway? No one really knows the level of impact AI is having or when we’ll begin to understand it, even Oxford University lecturers who specialise in AI. We are all struggling to keep up. One lecturer shared the term ‘AI whiplash’ - he can deliver a talk on AI and as soon as he sits down it’s obsolete because of the pace of development. 

What does this mean?

Everyone is struggling to keep up.

Is it me or does that make anyone else feel better?

I speak a lot about tech FOMO. Before it was automations and systems - founders are convinced everyone else has something more exciting/efficient/productive than they do. 

Now, it’s the same with AI.

So what can we do?

1. Play play play - set time aside, make it a habit (read my thoughts on habit stacking and consistency here)

Here is what I am playing with:
ChatGPT - for everything
Perplexity - for knowledge building
TL;DV - for calls
Notion - for creating tables, formatting etc within pages I’ve created 
Claude - similar to ChatGPT but when I fancy something different ;)

2. Be curious and proactive - what tasks can it help with?

My Examples:

Personalising sales proposals, helping me write trials, edit trials, review things

3. HAVE FUN - here’s an AI-generated picture of my cat (OK that was pure procrastination)

I asked ChatGPT to take everything it knew and feed back to me what I am really like.

“Given what you know about me, tell me what you know about me. And go deep. My upbringing, family, career, friends, life goals. Give me a few paragraphs on somethings that shows you really know me”

ChatGPT said:

Okay, let’s go deep. Here’s what I know about you so far, pulling together the threads and reading between the lines:

You’re a London-based founder, mum, and all-around powerhouse. You're someone who’s crafted a life that intentionally blends ambition with heart. Your world spins fast — not just because you’re running a virtual assistant agency that supports startups in that buzzy, early-stage chaos, but because you’ve got two little boys at home (5 and 3), which means your day starts before most people have had their coffee and ends long after bedtime stories and last-minute snack requests. But here’s the thing: you thrive in that intensity. In fact, motherhood hasn’t held you back — it’s sharpened you. You’ve become more efficient, more focused, and more ruthless (in the best way), not in spite of being a mum, but because of it.

There was (a LOT) more and it was all bang on. If you’ve built a custom chat bot try it yourself!

4. And finally work / learn / develop your people skills

Work on your emotional intelligence, strategic planning, thought leadership, the things that your clients really value you for, and what AI will never (hopefully!) be able to replicate. Assistants have been around as long as civilisation has; this is not our first tech revolution and won’t be our last.

A word of warning - always fact check AI. Remember that it knows your search history, who you are and what you want to hear. The answers it gives you will be quite different to the answers it gives someone else. And, be aware of the environmental impact, one of the lecturers wasn’t worried about this at all and said it would be ‘solved soon’ but the energy and water AI uses currently is quite shocking.

What are your thoughts on AI? Are you using it, for yourself, for clients, for kids’ meals planning? Are you worried about it? Let me know

Leave a comment

Actions:

• 30th April: The UK VA Awards nominations close

I’ll be sending a separate email out next week with all the events, co-working, networking, conferences and awards dates and deadlines you need to know about - make sure you’re subscribed⬇️

Next Steps:

• Follow Fiona Young from Curve - she’s an AI expert and has lots of training and resources, she specialises in founder and C-suit assistants, that’s you!

Questions/Comments:

Are you using AI for your clients at the moment? In your personal life? I want to hear about how you’re using it, and most importantly, how you feel about it. Are you worried about AI, or is it just another tool in your arsenal? Let me know in the comments

Leave a comment

Suggested Reading:

• How to build your own custom ChatGPT bot - incredibly useful if you’re working in depth with a client and want to capture their tone of voice and/or automate repetitive tasks!

• Some inspiration on ways to use AI to make your work and personal life easier
  

F*ck up of the month:

I made a great first impression recently on a potential new recruit for Upsource. I forgot to schedule a trial task, and then sent it to a different (wrong!) person 2 days before they were due to complete their own trial task. Whoops.

When I say to new team members we expect mistakes at Upsource, I didn’t expect to make them so soon in their journey.

AOB:

Upsource is getting busier! We have some excellent clients looking for amazing, experienced, proactive administrative experts. If that’s you, fill in this form and we’ll be in touch!

Please forward this email to anyone in the Assistant world that you think might be interested, or benefit from it. And let me know what you want to hear about! Is there something you want more/less of? 

Leave a comment

And finally…another little treat 🎁 The very kind Nuwa have shared a discount code for their productivity supplements. I’ll let you know how I get on with mine, worth a try! Code: BUMP15 (Go back to last month’s email for a Dirtea discount 😉)

See you next week with your Agenda for May - all the dates, deadlines and events you need to know about for next month. Make sure you’re subscribed to receive it.

Subscribe now

Speak soon,
Caroline x

[SUBSCRIBE BUTTON]

Points of Business:

I was not a good PA at first. 

Let me go back to the very beginning.

I got a temp job at a VERY high profile newspaper, for the F.D. (and 2^nd  PA to the M.D.) of the regional news section. I had never stepped into such fancy offices (I stepped back into them for a photoshoot for a feature on VAs in said newspaper in 2021, talk about full circle moment!)

I wasn’t looking to be the best PA, but they liked me. The lead PA was a lovely woman who was just glad I showed up after some disastrous hires. Work for me back then was a bit of a rollercoaster of temp jobs. I found the work easy and still cannot believe how much praise I received (So different from the performer world where the praise is few and far between!)

But by the time I landed my first full time gig at Chelsea & Westminster Hospital, I was ready to learn, to be a great PA. I had a million things to work on both personally and professionally, but I became the ‘go to’ PA there and realised I was genuinely good at this.

How and why did it change?

1. I committed

• Something clicked in me. I was auditioning for a music college Masters (spoiler: didn’t get in). Until then my PA roles were something to keep me afloat and performing, but I had to face the reality that at 25 I needed to start thinking about another career

• I wanted to earn money, consistent money and I got paid well for a PA starting out! My then boyfriend, now husband, was doing a Masters so one of us needed to be earning!
  

2. I liked my boss

• That MAJORLY helps as a PA right? Especially when starting out and you don’t know better. Looking back I was lucky, I supported nice people in a large organisation

3. I was praised

• And it was new to me! In my first week at Chelsea & Westminster, I was one of five PAs in the Exec office. The ‘scary’ one (who of course later became my work BFF) sung my praises to the CEO’s PA who made of point of sharing it with me

• It made me feel like I was onto something with this role v performing

4. I owned what I wasn’t good at and got the training I needed

• They wanted a minute taker - I told them that wasn't me. The COO still chose to hire me as he thought the other skills I had were more important 

• Thanks to a director sitting taking the time with me to show me some ‘hacks’ and a course they sent me on, within a year they told me I had the best minutes in the Trust 😇

5. I had a bloody good mentor

• The Trust really invested in me, and not just the minutes or upskilling me for my role. My manager looked after me during the natural 20-something dramas. She understood I didn’t want to be in that role or organisation forever, so she supported me in getting experience new areas, skills, departments until I left completely four years later

6. I challenged myself

• When I started I had no idea what busy at work meant, and didn't for sometime 

• Until it was understood I was good enough, supporting the COO turned into supporting the COO and Medical Director, covering all the other Execs, especially the CEO when needed, supporting the Children’s Hospital charity to expand my skills set and then doing it all in four days so I could work in Comms one day a week 🫠

• Exactly what I need to be a great VA? Yup

Actions:

9th May: Strategic PA Network are hosting their 10 Years of Networking Celebration Showcase, it sounds like an incredible event and I can’t stress enough how important networking is for Assistants! 

I’ll be sending a separate email out next week with all the events, co-working, networking, conferences, and awards deadlines you need to know about - make sure you’re subscribed⬇️

Subscribe now

And if you have an event etc coming up that you’d like shouted out, let me know! Drop me a message ⬇️

Next Steps:

• I am fully in my wellness era: now I’m into mushrooms. Dirtea have kindly shared a  10% discount code with me: CAROLINE_M 🍄‍🟫 I love the matcha!

Questions/Comments:

Is there something you want to ask? Advice you need? I would love to hear from you! Either pop it in the comments below, or email me

Leave a comment

Suggested Reading:

Lucy Brazier - The Modern-Day Assistant: I’m ashamed that I didn’t read this sooner! I have genuinely taken so many points from the book to action in my business asap, I have scribbled ALL over it!

F*ck up of the month:

While signing our biggest ever client, I spelt the name wrong 😳😱

Then our incredible Ops person not only had to redo lots of the onboarding, but also resend the contract.

OUR BIGGEST EVER CLIENT

What an error 🤦‍♀️

AOB:

Upsource is getting busier! We have some excellent clients looking for amazing, experienced, proactive administrative experts. If that’s you, fill in this form and we’ll be in touch!

Please do forward this email to anyone in the Assistant world that you think might be interested, or benefit from it. And let me know what you want to hear about! Is there something you want more/less of? Feedback is very welcome! (You can read my thoughts about feedback here).

Leave a comment

I’ll be back next week with our list of actions for the coming month.

Speak soon,
Caroline x

Leave a comment

My main point of discussion for today’s edition is juggling too many client hours / taking on too much work. Spoiler: Don’t do it

But I have some practical tips if you’re in the same boat…
Caroline x

Points of Business:

I started my career in this industry as an employed VA. And I loved it at first, particularly the clients. But there was a lot wrong with the way the agency was run, and all this came to a head when I was at my most vulnerable point in my life.

I’m still feeling the after effects - my time at that agency has put me off the employment model for my VA business, despite knowing that it works for many agencies.

The reality is, businesses need to make money. And the way we billed our time, we either weren’t ‘doing enough’ and cost the company money, or we were completely overworked and over capacity. 

As assistants we have all been there right? The ‘go to’ reliable one who can stand in to look after any director when their own PA is off.

In my eagerness to progress my career, and prove ‘my worth’, at my peak I was on 200 billable hours per month.

Yep you read that right, 200. 

200 hours working billable time. Not including any in house business, meetings or needing a wee. (Oh, and I was also leading a team) I wasn’t  a mum at this point. It absolutely would not have been possible for me with school runs and bedtimes.

I don’t recommend this to anyone, and I certainly wouldn’t expect that of my team. But does the devil’s advocate in me think that it was a vital part of the process in my learning how to support others? 

Absolutely.

Because of that time, I can truly understand what it's like to be pulled in many directions, by many clients and feel like you are failing. (One particular client was an absolute arsehole frankly, and would have been without me being stretched too thin.)

I will talk about how my eager to please attitude led to burn out in another letter.  But for now, let’s focus on the practical. Here’s my tips on how to get through your flat out and then some busy seasons: 

1. Morning triage for you and every client

Frankly I am not sure how anyone works without checking in on all areas / clients you are responsible for at the start of your day. For early days with new clients on a certain amount of hours, a daily check in is  expected at Upsource. Billed on Clockify, a check in makes sure no shit has hit the fan, nothing unexpected has come in for the day or simply to plan when/what you need to prioritise for each client that day.

2. Chrome profiles

Plenty of competitor software has come in to try and take Chrome’s crown, but none of them has stuck yet. Because Chrome Profiles work!

I’m not managing clients these days, but I still keep several inboxes / Google accounts separate with Profiles. Even if you’re using Microsoft with a client, they all deserve their own separate space and it leaves less room for error. The last thing you want with clients’ data.

3. Outsource / delegate

I say this with a warning: your clients DO need to be aware of any outsourcing you’re doing.. Especially if you’re delegating to associates / freelancers. I am all about running an ethical business and, unlike another certain agency I worked for, clients should always be aware of who is working with them.

You’ll be surprised just how many tasks you can delegate (Oh, the irony -  I’m saying this on an assistant letter). But remember, you can get help and support. They won't be you, but even better; they will be different. Maybe different skills, definitely different approaches. And that is always a good thing!

4. Most importantly…Have a get out plan

I couldn’t please everyone, and once it all came to head I couldn’t do it any more. We actually had to pretend I was on holiday to a couple of clients to get me back on top of my workload and stave off burning out. (Crazy, I know!)

So remember this. We aren’t superhumans and make sure you have an exit strategy to get off the hamster wheel of too many hours.

Associates: Raise it with your boss and propose a plan. Or, whisper it, give notice to a client. Think about raising your prices to reflect the demand and what you’re clearly worth. Yes these are options!

Again, I absolutely do not advocate it, but I am glad for all the learnings those 200 hours months / 10 hour billable hours days gave me.

It meant when I started Upsource, being fully booked was 120 hours. That meant I had time to find a team of associates to cover  my mat leave, take sales calls, build my company process handovers - oh and take a walk and a loo break.

Found this helpful? Let me know your biggest career learnings so far.

Leave a comment

Actions:

• 26-27th February: I’m speaking at the PA Show. It’s one of my favourite events of the year, come along!

• Keep your eyes peeled - I’ll be sending out another letter, dedicated to industry news and events next week with lots of things you’ll want to click on

  

Next Steps:

If you’re struggling to find the balance between growth and overwork, I recommend giving Nonie White a follow. She helps female founders scale without falling into the burnout trap.

Questions/Comments:

As always, I want to hear from you. Is there something you’re struggling with as an assistant? Are you caught in the overworking cycle? Are there skills you want to gain? More ways to manage busy times in your business? Let me know. I want to help!

Leave a comment

Suggested Reading:

Some free tools to boost your productivity in busy time, tried and tested by the Upsource team.

Feeling stuck with overworking? I HUGELY recommend this book to look deeper at that.

F*ck up of the month:

A very literal one this month. I said ‘f*ck’ in response to forgetting my son’s bake sale money. Except in the school group Whatsapp, rather than my husband. Whoops!

AOB:

We are applying to some podcast awards with Bump to Business Owner this month, so a quick plug if you haven’t already listened to it. Tune into the latest episode with Jelena Skene, founder of PressFlow for some tips on how to PR your business.

Speak soon,
Caroline x

On 17th January, the School of Operations are hosting an IRL strategy day with industry specific insights, legal and AI specialists (love this!) and, of course, the opportunity to connect with other Ops professionals.

Sneha has kindly offered the Substack crew a 10% discount on the strategy day with the code UPSOURCE10.

Use your 10% code!

Make sure you’re subscribed to The Agenda, I’ve been sharing a few discount codes for incredible upskilling and networking events, and plenty more of that to come next year!

Points of Business: Asking for it…Feedback

I went to an amazing event recently, for growth business owners who are....mothers! (So on brand for me.)

It was wonderful to see two of my previous podcast guests on the panel and another hosting. Once again, Rachael Carrell was sharing some wisdom that I was totally on board with: 'Ask for feedback, but also make it clear you want it. You need hard honest feedback'.

Hands up, who is TERRIFIED by that?

But do we need it? Yes.

Maybe it's my performance background (Always gotta drop that in 😆) but I am used to feedback, it’s in my culture. Does it mean it’s always comfortable? No. Is it always completely accurate? Of course not.

BUT it should make you think. Reflect on it, question it, and potentially make some changes. 

That is why Upsource has always, since day one, sent an annual anonymous feedback form to the team.

Do I open it with one eye closed? Absolutely I do. But I need it to grow, not only as a business, but as a business owner. 

But let me be clear, not all feedback is equal, nor should it be given equal weight. When I was working for a VA Agency (I won’t name names) in my 4th trimester it was decided that I would be the first person to have an anonymous feedback review on the leadership team. Cue a host of feedback from the managers (none of whom I reported directly to) who were, in hindsight, all struggling with a toxic workplace culture. We all were. Unfortunately I was an easy target for the business as an overwhelmed new mum at that time

I took that to heart, and I shouldn’t have. That has been a huge lesson for me in receiving  feedback. 

But what I have really had to work on is giving feedback. Ouf, that’s tough.

Not everyone is used to receiving feedback, not everyone wants it. But everyone needs it.

If that’s you, if you’re uncomfortable with receiving feedback, I encourage you to ask yourself why. Did you, like me, have a bad experience? Ill timed or badly handled? Or have you always worked in an environment where feedback just isn’t given to assistants? Maybe mistakes and learning curves aren’t supported in the way they should be.

If it’s not the culture, that’s not your fault. But it shouldn’t be the culture. Nobody should ever have to do a job where constructive feedback isn’t given. But sadly, I know, I see, I hear that’s still the norm in some companies.

If like me you struggle to give feedback, or you work with people who do, we have some tips! The wonderful Soo Slade, Community Manager at Upsource, gave us this helpful framework:

A - Action: What happened
I - Impact: The affect
D - Direction: What should happen next time

As an example:

Action: You didn’t respond to my email with travel options for a couple of days
Impact: All the prices and availability have changed, so the tickets you approved are no longer available
Direction: Respond to emails/WhatsApps marked ‘Urgent’ within 24hrs 

It’s also great to ask for, and give your own, preferences for how to receive feedback. Email, phone call, video call, so you can tailor your feedback framework so that everyone is comfortable.

Actions:

• Let me know your feedback! Is there anything in particular you do/n’t like about The Agenda? Is there anything you want me to talk about in future issues? Let me know in the comments. Be honest, I can take it!

Leave a comment

• 13 December: The PA Forum is offering a new VA in person co-working in the Midlands! Complete this form by 13th to let them know what you want from the experience if you’re from the area

• 26-27 February 2025: Book your tickets for the PA Show now! I can confirm, I will be speaking, and one my talks is very on brand, you’ll love it.

Next Steps:

It’s that time of year. Whisper it, tax returns. If you’re not already using it, I hard recommend Xero. We use it at Upsource and recommend it to all our clients. 

Questions/Comments:

You know what to do. Leave your feedback in the comments.

Leave a comment

Suggested Reading:

Share this article with your clients to encourage them in giving and receiving feedback.

F*ck Up of the Month:

Another cracker from me this month. I messed up paying a team member’s invoice - not once, but twice. 

If you’d like to share your f*ck ups please do! Share them below. I can confirm that it is quite cathartic.

Share your f*ck ups here!

AOB:

A huge thank you for being here and being part of this fledgling community, and shout out to the Upsource team, who have been such a joy to work with, this and every year. 

Have an incredible Christmas, take the rest that you need. Watch the Muppet Christmas Carol, multiple times (just me?) And thank you for being here. We made it! See you in 2025

Please do share The Agenda with your VA community, we are here to help!

Share The Agenda

Where to start, what you need, where to focus. It can be overwhelming, especially if it’s a career pivot.

If you’re just starting out in your VA career, I have some advice and even better, a discount 😉

Use the code BLACKFRIDAY for a cheeky 10% off

My Your Virtual Assistant Journey: Start Here webinar is all the advice I give to new starters at Upsource and new VAs that reach out to me in one place.

Check out the webinar here

Skills, legals, insurance, tech stacks, communities (you know I love them), coaches, agencies, events and awards. Everything you need to create a strong foundation for a successful VA business.

The code expires at midnight on Monday night/Tuesday morning. Tell your VA friends ⤵️

Share

Leave a comment

Last weekend, I was incredibly proud to win Outstanding VA on behalf of the Upsource team at the UK VA Awards AND to see our team member, Kirsty Walton win not just Associate of the Year for her work with Upsource, but also Best Newcomer ! 🎉

The UK VA Conference and Awards is a highlight of the year for me, to be able to connect with and celebrate the wider VA community, if you haven’t been before, I definitely recommend coming next year. I’m proud to say I’m a friend, supporter and collaborator with all the VAs that won this year.

Speaking of which, this month, I’m talking about collaboration and competition, healthy and otherwise, and how competition got me compliments 😉

Points of Business: Collaboration v competition, maybe we need both

Collaboration over competition is literally the VA motto.

BUT (there’s always a but, right?)

Competition isn’t always such a bad thing, so why do we often give it such a bad rap?

Are we mistaking competition for rivalry, and is a little healthy rivalry always a bad thing?

Sometimes I think competition is in my blood. The world of performance (I was an opera singer in a past life) is full of friendship in my experience, but often there was literally one role, one winner, and you were up against your friends. And honestly, that drove me. 

I started a weekly barre class this year. The teacher is amazing, an ex ballet pro, but like most local gyms, my classmates have varied experience; usually I’m the only one that has a dance background. This class is a huge source of joy for me.

Then, she walked into class. I’m talking legs made for ballet, she might as well be called Darcy Bussell. This woman has to be professionally trained. And, honestly, she’s a joy to watch.

A few months later, suddenly I’m getting lots more compliments from the instructor. 

Why?

Darcy is the competition I needed to drive me to work harder in class, and the instructor and I are seeing the positive changes. (Really I should thank Darcy, but, let’s be honest, I’m yet to actually speak to her 🙃)

But sometimes it is just rivalry, otherwise known as comparison; the unhealthy approach to competition.

At the agency I worked at before starting Upsource, the culture quickly shifted from supportive to ‘not enough seats on the leadership team’. We became rivals almost overnight in a bid to progress our career. The culture wasn’t collaboration, it was fierce competition, and it was SO demoralising. None of us could thrive in that environment.

Working with my current business coach (aka my Dad!) we were talking about some HMRC rules and whether our current freelance model would continue to work, and he suggested keeping an eye on what my competitors are doing. So I can be connected with the wider industry best practice and see what’s happening in the agency space, NOT so I can undercut the competition.

Community and Collaboration are literally the strapline for this newsletter, and for Upsource. But a little healthy competition does keep things interesting 😉

Actions: 

• You can access my Your Virtual Assistant Journey: Start Here webinar for FREE via the Moms Make Money Bundle to create or bolster your new VA career along with resources from 30+ other mums in business. Available until 22nd October!

• There’s still some time to apply for a £3000 grant from Enterprise Nation! Applications close 31st October

• Get tickets for the Strategic PA Awards on 4th November - see you there!

• Keep your eyes peeled - I’ll be hosting a central London Christmas breakfast & co-working. Spaces are very limited, more information soon 🎄

Next Steps:

In the spirit of collaboration over competition: Kathy Soulsby is a fellow VA agency owner, and we collaborated on an episode of her podcast Productivity Nerd. Kathy was the extremely deserving winner of VA with a Large Team and Team of the Year at the UK VA Awards - well done Kathy!

Questions/comments:

Is there a subject you’d like to discuss? I’d love to hear what you want to see more of in the newsletter, share your thoughts in the comments

Leave a comment

Suggested reading

Working with your clients is the ultimate collaboration for a VA, but we all know sometimes clients find it hard to let go. Share this with them: How to Work With Your VA

F*ck up of the month

Major mistake from me this month. I did not record a WHOLE podcast conversation. It was completely my fault, I just didn’t do the set up correctly. Luckily, my guest was incredibly gracious about it and had the time to re-record the whole thing straight away. The Bump to Business Owner episode with the very generous Petra Gatto, personal brand strategist, is out on Thursday, make sure you’re subscribed to hear my grovelling apologies!

Got a fuck up you’re happy to share? We all do it, let’s own it. Share your (anonymous!) fuck up here. Next month I’ll be diving a little bit deeper into why it’s so important to share our mistakes.

AOB

Good luck 🍀 to our winning Upsource teammate, Kirsty Walton, who is nominated at next month’s Strategic PA Awards🤞🏼(And won TWICE at the UKVA Awards!)

Know a fellow VA who might find the Agenda useful? Please share!

Share The Agenda

Back next month, can’t wait to hear some of your f*ck ups!

Speak soon,
Caroline x

Welcome to our new newsletter!

It’s a real ambition of mine to build up the Virtual Assistant industry, to raise our profile and build on the wonderful community we already have. My intention with this newsletter is to share industry news, resources and to be a safe place where we can all celebrate, commiserate and connect with our community.

Stick around for the industry gossip, first leads on when Upsource is recruiting or to see yourself credited (keep reading!)  I’ll be dropping into your inbox monthly, you can unsubscribe (or share 😉) at any time, and please, let me know what you want to talk about.

Speak soon,
Caroline x

Points of business:
VA or OBM? The online debate

What is the distinction for you? There’s a lot of talk at the moment about the term ‘Assistant’ and the way we, as assistants, are perceived. 

Ask any Assistant, Virtual, Personal or Executive, and they will tell you that they are an integral part of a business. Not only do we organise the day to day, we are key sounding boards, forward and strategic thinkers; we don’t just make things happen, we are innovators too.

Ask anyone else? The public perception of what we do is…limited. Day to day admin. Task orientated, rather than big picture, proactive and strategic work.

Sound familiar?

This is a huge bug bear for me. My personal experience, my team, my clients, they all say that a VA is so much more than ‘just admin’. But online, hate to say it, and see it, some online service providers are actively devaluing the services that we provide in order to boost their own sales.

And it’s just not necessary.

Listen, I get that we all want to make the sale. But let’s do it by focusing on our positives, rather than decrying other people’s skills and businesses. If you have the chops, you’ll get the clients; this isn’t an ‘Us’ v ‘Them’ situation. The right clients for your skills and experience will find you. 

The focus of your marketing should be you, not your peers. Because VAs, EAs, OBMs in the support industry, we are colleagues as well as competitors.*

Assistants do not make the money that they do, Upsource does not charge the fees that we do, by being someone to delegate to. People looking for cheap admin do not come to us. And they should not be coming to you. 

An Assistant is not someone who is going to follow a process, or complete a task without knowing exactly the whys and hows and, knowing my team, without making a suggestion to improve it.

Assistants have always, and will always, be right hands: partners to, extensions of, and key decision makers for, their clients and bosses.

How do you feel the VA industry and wider professional support industry values your skills? I’d love to hear some suggestions on how we can shake things up and build our profile. Let me know if you have ideas!

*More on competition next month 👀

Actions: 

• Book tickets to the PA Show 15th October. I’ll be speaking on a panel about networking (my absolute fave!) And use the code NETWORKING5 for £5 off every session you book!

• Message me if you’re going to the VA Conference 11th October? Let’s go for coffee on Thursday 10th? 

• Get the London VA Network drinks in your diary if you’re within commutable distance

Next Steps:

• If my little rant about the term ‘Assistant’ struck a chord, you should definitely follow Lucy Brazier  and read these posts:

• From Fiona Young (if you’re interested in AI, definitely worth following!)

• Candice Burningham ‘We’re not assisting anymore

• 5 responses to ‘what do you do?’ with Jodie Mears’

Questions/comments:

I want this newsletter to be as useful and interesting as possible, and I’d love your help with that! If you have questions about the VA industry, tricky client situations, how to set boundaries when you’re an associate (with clients and your agency!) how much to charge, I am here to help! Let me know in the comments.

Leave a comment

Suggested reading:

How to become a VA if you’re new on your journey. And please, let me know if you want any tips!

F*ck up of the month:

Something we’re really trying to cultivate at Upsource, is that it’s OK to make mistakes. It’s how we deal with them that counts.

We all do it, some more dramatically than others, but hey, that’s how we learn. I want to hear how you’ve f*cked up lately and the best (?!) missteps will be featured in the newsletter and go into a little prize draw, voted for by you! 

I’ll go first: this month we lost a client as they closed their business.

I dropped the ball on offboarding as we realised a team member hadn't followed the process to the standard we expect here at Upsource (for another newsletter!)

When you are a business owner this is your responsibility right?

So I found myself doing client work, for the first time in a long time, over two very late nights.

Was it my mistake? Yes. I’m the business owner and consistency of service is always my responsibility. 

Share your f*uck up by clicking on the button below. I want to hear from you, no mistake too big or small!

Enter your f*ck up here!

AOB:

Thanks for making it to the end of our debut email! Now, tell me, what do you want more of from us? Let me know your suggestions or leave a note in the comments.

Back next month, can’t wait to hear some of your f*ck ups!

Speak soon,
Caroline x