10 Leadership Lessons I Gained From Hiring a Freelancer

10 Leadership Lessons I Gained From Hiring a Freelancer

After reading The 4-Hour Work Week book, I was determined to hire freelancers to automate my personal life. Tim Ferriss, the author of the book, suggested that I learn about outsourcing jobs in order to improve my management and leadership skills. My ambition was to hire freelancers to help run my future business as well.

I knew instantly which job I wanted to automate – weekly meal planning. Meal planning and grocery shopping are one of the chores that I hate the most, and I was more than keen to pass that job to someone else. Since we already do our grocery shopping online, I was confident that we could easily ask anyone else in the world to get it done for us.

I jumped onto the Upwork, a freelancing site, and in a few a days, hired a promising young lady from Jamaica. But as soon as I hired her, I realized I was not ready to hire someone at all. As I thought through the instructions I wanted to send to my new hire, I realized there were so many parts to my meal planning process that I hadn’t thought to organize and document!

If you’ve got a job that you want to hire someone for, resist the temptation to jump straight onto a job board. Make sure you get yourself organized and be ready for the new hire first. Here are the ten things I learned about leadership and management from hiring a personal meal planner.

Review the whole process

It is important for every leader to understand what their employees do. Before you start hiring anyone, go through their entire work process from start to finish. This ensures that you haven’t missed any specific instructions or requirements. The best way to review the process is by doing the tasks yourself. What is the first step you need to take? Do you need any specific tools for a particular job? Do you need to know anything in particular? Put yourself in the mind of your future freelancer. The goal is to create your own Standard Operating Procedure (SOP) on how to get the work done.

Remove any assumptions

You know the saying – ‘assume’ makes an a** out of you and me. Don’t assume that your freelancer would know what you’d want or don’t want. The importance of removing assumptions became pretty clear to me when my meal planner started ordering the wrong products. She’d order pre-made udon noodles instead of my preferred organic udon noodles. Or a whole chicken when we needed separate chicken breast and thighs for different dishes. Being a business analyst, I understood the importance of documenting precise requirements. So I started documenting specific products that I wanted for certain ingredients. But I hadn’t completed the list due to not having enough time before hiring the meal planner. Removing any assumptions can avoid costly mistakes.

Keep a fast and open communication

It’s important that your freelancer can contact you quickly. Fast communication is especially important for the first few days, weeks, months (depending on how often they work). My meal planner always had a question for me before ordering the groceries, due to the lack of a SOP. And because I hadn’t responded to her questions in time, she couldn’t order the groceries in time. My delayed response consequently delayed the arrival of the grocery order. I advise that you choose a communication channel that will capture your attention and allow you to respond instantly. Then, ask your freelancer to contact you through that channel, especially for urgent questions. Great leadership means being approachable and easy to reach.

Use Google Drive for sharing documents

Efficient document-sharing is something that I actually did right when I hired my meal planner. I put all our shared documents, such as meal planner templates, instructions, and checklists onto a shared Google Drive. Using products like Google Doc meant that I could quickly check what meals she had planned for us, or she could instantly see what extra groceries I needed for the coming week. There was no wasting time with worrying about saving and attaching new versions of documents and sending them via email.

Set reminders for your inputs

Once you have a freelancer to automate a part of your life, it’s easy to forget completely about it. If the work doesn’t need any input or action from you – congratulations. You’ve set your life up for full automation. But if the work does require anything from you, set up reminders to approve, check, or provide input in time. With my meal planner, I asked her to wait for my approval on any meal plans or basic ingredients that I might need. But I’d completely forget to approve anything in time. Since she didn’t receive my response, she’d miss out on getting our groceries delivered on time.

Great leaders ask for feedback

One of my regrets with my meal planner was not asking her for regular feedback. Sure, I told her to let me know if anything came up. But I didn’t make it a priority to ask her on how she was finding the job and its process. To show great leadership, I should have followed up with her actively to discover if I could’ve done anything to improve the process. There could have been enhancements to make her life easier or need less input from me. This way, I would also have an improved process for any new freelancers that come along to do the same job.

Set up all necessary tools and equipment

One of the biggest mistakes I made at the start was not sorting out how she was going to pay for the groceries. I didn’t feel comfortable giving her my personal credit card. But I didn’t know how else she was going to pay for my groceries either. After hiring my meal planner, I looked into a temporary Visa gift card that she could use. But when I went to the shop to buy one, I found out that I couldn’t reuse the same card and could only top it up once. Luckily, I had a genius idea of creating a permanent Visa card at my bank that only connected to our ‘food’ account. However, it was a stressful experience to sort this out last-minute. I wish I had organized this way before I hired the meal planner.

Trial to see if they’re a good fit

I’m going to be honest – I was mainly attracted to my meal planner because of her hourly rate. How can you not say no $4/hour when I had other freelancers offering rates of $25/hour? But the cheapest rate doesn’t mean that they’re the best person for the job. I wish I had asked all potential hires to do a trial exercise before agreeing to hire them. This way, I would’ve known whether they’re truly the right person to hire or not.

Keep other people in the loop

If other people are going to be affected by the freelancer’s work, remember to keep them in the loop. Another mistake that I had made was not sharing the documents on Google Drive with my partner. Considering that my partner does the actual cooking, it wasn’t helpful when I didn’t share the meal planner with him. Effective leadership stems from great communication skills and stakeholder management.

Sort out payments

Make sure that your freelancer is getting paid on time. Late payments can cause lowered morale and motivation for your freelancer. Fortunately for me, the Upwork website automatically took care of the payments for me. But when I offered a bonus to my meal planner at the start, it took me awhile to sort it out. I had finally paid her after 2-3 weeks due to technical difficulties and procrastination. I felt really bad for it, and it kept bothering me on the back of my mind until I paid up!

Have you ever made any mistakes from hiring a freelancer?

Let me know by leaving a comment below!

3 thoughts on “10 Leadership Lessons I Gained From Hiring a Freelancer”

  1. I think your first point about reviewing the whole process is a good one, but not necessarily a hard and fast rule. There are definitely times when I want something done a particular way, in which case I’d work through the process beforehand. But other times I just want it done without expending any more personal time and effort on it, so would leave the freelancer to get on with it (once I had clearly articulated my requirements and budget, obviously).


    1. Hey Kirsty, thanks for dropping by and for your comment! Yep definitely – if you’re not fussed on how a particular piece of work is done, then that’s absolutely OK to not document a detailed process. In that case, you’ll still want to have a clear outcome in mind and make sure you’re not assuming that the freelancer is going to read your mind on exactly what you want. The key is to eliminate any assumptions! It sound like you’re doing that already with your requirements + set budget. 🙂


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