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What it’s really like to hire your friends and family

by Holly


There are many gifts to starting a business and being the ultimate boss is one of them; getting to hire whoever you please certainly is sweet. But don’t get me wrong, sometimes in your early years (and my recent guest on my podcast, Conversations of Inspiration, with David Hieatt has me howling in laughter speaking about this. Out in September!) you can find yourself in a cafe speaking to a really brilliant barista and finding yourself offering them a job as the head of ‘something’ because “I’m sure it will work out” and I have to say, please avoid this thought! It’s a romantic thought and we really all do wish scenarios like this worked out, but the reality is the odds are 1000 to 1 it will. Believe me, this isn’t the way to hire! On the flip side, when you know someone ever so well, is this a sure fire way to successfully build your team? It all depends. Not on them, on you, and how you handle the situation. Why do I know? Because I’ve been there and got the embroidered t-shirt and hand carved keyring!

If I take myself back to the start of notonthehighstreet, the first person we hired was my sister, the second – her best friend from uni, the third – my sister’s godmother’s daughter and then her sister! This was closely followed by Sophie’s sister, my dad, my cousin, my best friend, my other best friend and everyone’s best friend I mentioned in the first sentence! I kid you not. So I know a thing or two, the ups and downs, of hiring friends and family. 

Today I’m going to concentrate on friends and if they’re a wise decision when it comes to building a team. 

When it comes to this question and my hindsight (which is hopefully here to help you) a question I didn’t ask myself back then, but one I ask myself now, is “Do you want to merge your two worlds – really?”

I speak often about building a ‘Good Life Business’ and it’s all very well and good to tap the heart on a post, or speak about it to others and have them nod, but actions like hiring friends is a step you can’t reverse easily and it affects everything for the long-term. So looking back, you should definitely determine if you want to bring your personal and professional life together and form one existence. Where you’ll muddy the ability to meet friends in the pub and chat about anything and everything except the old definition of work. Because once you make the choice to hire friends and other decisions like this; once you have merged your past two worlds into one, it’s very hard to unpick them apart again, let alone not have your shared life at work take up the majority of the conversation. 

This question understandably didn’t even occur to me as a young 28 year old mum who was building something which was quickly turning into a runaway stallion. I hired friends and family as there wasn’t any time to recruit, they inadvertently took less money, less time to manage, I knew them well, trusted them, they liked me and we needed soldiers – fast! I’m hazarding a guess you might be reading this, in a similar situation and pondering, what’s the worst that could happen? Surely the odds are stacked in your favour that it will work out? 

If I look back and jump to the conclusion of this article, I’d say you’re right. In my experience it’s worked out, more than it hasn’t. But when it hasn’t worked out, it’s shockingly painful as I have, and you could too, lose these people forever. Is this something you’re willing to risk? Can you see how the first question I asked you is so relevant? Are you ready to connect your two sides of your life where the consequence of friends being unable to become colleagues, has your past ‘personal’ life diminishing? 

‘When it comes to hiring friends and family, and whether it’s a wise decision when building a team… I didn’t ask myself this question back then, but it’s one I ask myself now, is “Do you want to merge your two worlds – really?”’

Let’s get through the more negative thoughts and realities first, before I speak about the magic which can occur and some tips I’ve learnt along the way.

The main issue which faces founders in the early years, is you need people fast who you can trust 150% and so your friends are perfect for this conundrum. But after building two businesses I now know for a fact, that the beautiful humans you need at the start of the mammoth task, rarely are the same people you need as the business matures. Where at the start of the journey a team mate having the role of 5 people, being a Jack or Jill of all trades is a huge accolade, this changes over time. You begin to need experts in their field and unless you hire friends who happen to be that specialist to start with, you’ll find yourself having to have very hard conversations or worse, you’re paralysed into not having the difficult chats and thus risking everything you’ve all built.  

I have unfortunately lost many friends or dear people in my life, to this scenario. Having hard conversations with people, who you know you’ll be seeing at a mutual friend’s birthday the following week, is tough! So it’s with a heavy heart I share the truths of this scenario. But…

When it’s worked out, it’s as if you hired 1.5 x a normal employee and the whole experience is quite something. Because they’ve also decided to live a ‘Good Life’ and they too made that step at the same time you did. You’ve met with a shared understanding of what you’re both walking into and that’s fundamental when it comes to being forearmed. This is not just your responsibility, it’s theirs too and one you should explore, slowly, before jumping into the small business bed.

‘I want to look back in 20 years and have the majority of the team still with me. I believe in the wisdom we’re all gaining, the knowledge each of us accumulate, the growth we’re all experiencing personally can be one of the most successful melting pots to build the future.’

If I take a step into my life now, thanks to understanding the true meaning of the highs and lows of building a ‘Good Life Business’, I don’t have a huge amount of friends outside Holly & Co. I work with my nearest and dearest. The wonderful humans who were friends and now work in the business, or started as colleagues and are now my closest people – there’s an understanding we’ve developed and over the years, we’ve found our way and it’s pretty awesome.

I’d go as far to say, I want to look back in 20 years and have the majority of the team still with me. I believe in the wisdom we’re all gaining, the knowledge each of us accumulate, the growth we’re all experiencing personally can be one of the most successful melting pots to build the future. How can one possibly not be personally and professionally ‘the closest’ on this intimate journey and why wouldn’t you want it to be? So let me share a thought which I hope will help you, when you might travel this path. 

Take it slowly. Even if the deal is sealed over the flowing Sauvignon Blanc, wake up and have another conversation! 

Write down all the questions and don’t leave out the hard ones such as (and I’ll jump to the hardest) ‘what if you no longer are the person the business needs?’ The distinction you’re trying to get across is that ‘you’ and ‘the business’ aren’t the same thing. When the business needs a marketing specialist and let’s say your friend has inherited this part of the company, how should you chat about the fact they’re potentially redundant? 

Ask them to open up to what they think is the best way to have a ‘hard conversation’ with them.  Will they understand your position? How will you navigate the future? Do they take the responsibility for the fact you’ll be having to look after everything in the company and not just their wellbeing? You will both travel to places you can not predict. 

How would you like them to behave in the future? How will you handle the ‘kids are sick’ conversations, even if that child is your godchild? How will you both take care of what is special between the two of you? Write all the questions, only drink tea and ‘go there’ – this is one of my biggest tips, my only tip. 

Talk about money! This is a biggy, as it is notoriously something we all feel uncomfortable talking about, but it has to be done and know this can be one of the biggest ‘danger zones’ for employment generally. I like to rip the plaster off first, as in make sure the salary for this role is within the conversation right upfront, almost one of the first things you say. The next thing to remember is that they will have an expectation (and generally a need) for a certain amount of money, so their pushback is NOT personal, it’s essential for them. You might want to write about money in an email, as it can be easier. But know what you can afford and explain this well to them, that you’re aware it’s not competitive etc but then list the benefits of working in a small, entrepreneurial, exciting business. Often people want the world you are offering, you’ve just got to get to that number that works for you both. Don’t pour too much emotion into these numbers, you are in a negotiation/selling period here. But a last word on this….don’t leave this to the last point in all the conversations and let it be the elephant in the room – you don’t have energy to waste and it’s better to know if this is a non-starter, right from the off or with a tiny tweak you’re both on the same page. 

Generally though,  it will only be when both parties take the responsibility that’s required in this working relationship, do you build the foundations to hopefully something quite extraordinary.

How I found the Good Life

Before making any big decisions about who you're hiring, have a think about how this works as part of your Good Life plan. Read Holly's experience on this now.

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