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The control freak's six rules to delegation

Lisa Messenger

Lisa Messenger is the CEO of The Messenger Group and founder and editor-in-chief of The Collective. She has authored and co-authored over a dozen books and become an authority in the start-up scene

Lisa Messenger

Lisa Messenger is the CEO of The Messenger Group and founder and editor-in-chief of The Collective. She has authored and co-authored over a dozen books and become an authority in the start-up scene

Most business owners know what they want, but few can do it all in the digital age. Lisa Messenger explores how you can learn to let it go and control a successful business without being a control freak.

How many items are on your to-do list right now? Or – if you’re anything like me – how many to-do lists do you have on the go? Whether your tasks are jotted down in a notepad, on the back of a napkin or neatly typed onto a Trello board, I think I speak for everyone when I say: “Where does it all end?”

If you run a small business, your tasks are probably always stuck in the double digits, and that’s not counting all the other things you haven’t even had time to write down because you’re too busy. But what if I said you could halve your to-dos in the next fifteen minutes? Interested?

It’s time to stop, delegate and listen, because self-sufficiency is overrated. Here are six rules to get you in the right mindset.

1. Silence your ego

I have a personal trainer who puts me through my paces three times a week. What does this have to do with business? Well, for years I tried to work out on my own but not only would it take me twice as long (10 minutes fiddling with my shoelaces, 10 minutes adjusting my top…), but it was also far less effective, as I had absolutely no idea if I should be squatting, lifting or tucking.

Once I admitted that I needed to pay an expert to help me (cue Rule 2), I instantly realised the benefits. The same applies to business: if you don’t have an accountancy qualification, hire someone who does. If you’re not a digital marketing expert, find a gun employee or contractor who is. If you didn’t go to law school… well, you get the point.

2. Outsource outside your inner circle

Even if you’re a ‘solo-preneur’ with no employees, you don’t have to go it alone. Thanks to virtual assistants and gig-economy sites like Airtasker and TaskRabbit you can now outsource tasks – especially everyday odd jobs.

When I ran The Collective magazine, I had a taskforce of over 70 freelancers around the world who I called on for different projects – and it worked well. However, if you’re delegating outside your contracted employee pool, don’t forget to cover your back against security breaches by marking important documents as private and asking freelancers to sign confidentiality agreements, even if only performing admin tasks.

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3. Stop being stingy

As a small business owner working on a shoestring, it can be tempting to save money with a DIY attitude. But is this really profitable? Most of the time, probably not. I could spend a morning organising travel plans for my upcoming speaking gigs, or I could spend that time meeting with advertising clients and potentially striking deals – making much more money on the latter compared to the cost of hiring someone to perform the former. It’s simple economics.

If you really don’t have budget flexibility, think about other ways to get creative with outsourcing. Maybe you have a lawyer friend who’ll help you draft a contract in exchange for your services somewhere down the track. Think about it this way: the expert you require probably has an extensive to-do list of their own. 

4. Use your words wisely

The secret to successful delegation is clear, precise instructions. If you have a ‘my way or the highway’ attitude – an uncompromising mentality that a project should be completed based on your exact specifications, which isn’t necessarily a bad thing ­– then it’s your responsibility to communicate this eloquently. Email is ideal as it creates a paper trail for later reference.

Don’t confuse this with micro-managing, though. You should be able to brief someone once – and then leave them to do their thing without hovering over their shoulder, so to speak.

5. Don’t aim for zero

Remember at the start of this article when I said you could halve your to-do list? Why didn’t I say you could finish it instead? I don’t adhere to the ‘inbox zero’ school of thought – where the end goal is having every piece of correspondence read and filed, and everything neatly ticked off your list. I don’t believe in it because I don’t think it’s realistic: tasks come and go – if your work is anything like mine – in a consistent flow. If you’re constantly trying to reach a finish line, it’s likely that you’ll constantly be disappointed (until you retire at least), and even more likely that your work will be sloppy.

I love the attitude of former Yahoo! CEO Marissa Mayer, who celebrates her never-ending to-do list. At the start of every day, Melissa writes a to-do list with the important items at the top and unimportant ones down the bottom. She once said: “If I did [get to the bottom of the list] it would be a real bummer. Because think about all those things at the very bottom of your to-do list that really shouldn’t take time out of your day.”

6. Don’t give away your joy

Even when you do become an expert delegator, don’t forget to savour the tasks you do enjoy – even if they are a time zap. There will always be the little everyday tasks I love, even though sometimes they might be less financially viable than other tasks. I love to write, for instance – usually not the greatest cash cow in the world!

I’ll also always take time out to reply to emails. You might have an odd love for filing, transcribing or cleaning the office kitchen. No shame – do it because you want to, not because there’s no other option. Control freaks need an outlet, after all.

Originally published December 18th 2015. Updated December 5th 2019.

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