Is it a good idea to work with friends? Does working with friends work?

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 guest on my Conversations of Inspiration podcast, David Hieatt, has me howling in laughter speaking about this), 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’...

I have to say, please avoid this thought. It’s a romantic idea and we really all do wish scenarios like this worked out, but the reality is the odds are a thousand to one. Believe me, this isn’t the way to hire!

On the flip side, when you know someone ever so well, is this a surefire way to successfully build your team? It all depends — not on them but on you and how you handle the situation. How do I know? Because I’ve been there and got the embroidered t-shirt and hand carved keyring. Let me tell you…

Hiring friends? Are you really ready to merge your worlds?

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 about the ups and downs of hiring friends and family.

Let me concentrate on hiring friends though and if that’s a wise decision when it comes to building a team. A question I didn’t ask myself back then, but one I always ask myself now is, “Do you want to merge your two worlds — really?”

I often speak about (and have written an article on) how to build a Good Life. 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 to form one existence.

Is hiring friends a bad idea?

Hiring friends means you’ll muddy the ability to meet them in the pub and chat about anything and everything except the old definition of work. Because once you make the choice to hire friends, 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 and this saved time
• They inadvertently took less money
• They took less time to manage
• I knew them well and trusted them already
• They liked me so really wanted to help

Plus what’s the worst that could happen? Surely the odds are stacked in your favour that it will work out?

Are you willing to risk your friendship if working together goes wrong?

In my experience, hiring friends has 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? 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.

What happens if you no longer need the friends you’ve hired?

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 five 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. Having hard conversations with people, who you know you’ll be seeing at a mutual friend’s birthday the following week, is tough. But as Mo Gawdat says on his Conversations of Inspiration podcast episode, “What if it all goes right?”

What are the benefits of working with friends?

When it’s worked out, it’s as if you hired one and a half times 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.

By hiring friends, you can build a ‘Good Life’ together

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 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 accumulates and the growth we’re all experiencing personally. It can be one of the most successful melting pots and a great way 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.

When working with friends, take it slowly

Even if the deal is sealed over the flowing Sauvignon Blanc, wake up and have another conversation. It’s important and some of the best business advice I can share.

Write down all the questions (even the hard ones)

Such as, ‘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 the best way to have a ‘hard conversation’ with them

Will they understand your position? How will you navigate the future? Do they get that you have to look after everything in the company and not just their wellbeing? You will both travel to places you cannot 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 greatest tips.