Reliable help is so difficult to find,” someone wrote. Anoth- er chimed in, “Yes, and harder to keep.” Before long, everyone shares their outsourcing nightmare stories. The refraining cry becomes, “Why do I always get the bad apples?”
Here’s the painful truth. It’s probably not them. It’s you. Don’t misunderstand me. I’m not saying everyone you hire is an angel. There are people who ghost you, over-inflate their skills, are dishonest and more.
On the other hand, I’ve been on the other side of the equation as a service provider. I know others doing the same, and many of them are just trying to make an honest living. If you’re look- ing for reliable help, who are eager to work for you, stop doing things that frustrate them.
The following items are super frustrating to out sourcers and could be why you are not getting the most out of your helpers:
1. You Pay Late. Always
It should go without saying. Pay people on time! After all, don’t you like to get paid on time? Sure, you do—so does your team. Paying late happens more often than you might think. Don’t be that client. If you want people to continue working for you, make this a priority.
THE FIX: Calendar it. Things on your calendar get done. This way you never “forget”, and your people have a consistent day/ date to plan around.
2. You Don’t Give Them Enough Time
People understand there is an ebb and flow. Some things have a short lead, and some become urgent from time to time. But every time, for every piece of work you ask for? That’s exhaust- ing. Besides, you won’t get the best work out of your team this way. Quality work takes a reasonable amount of time. Don’t rush your team.
THE FIX: If you are always working too close to your dead- line, perhaps you need to get better organized. Consider handling the urgent things yourself while delegating the ones with longer lead times, at least until you can get the schedules straightened out.
3. You Don’t Take Time To Teach
Ideally, you want to hire someone who has familiarity with the apps you use and maybe even the industry you are in. This cuts down time spent training people. Sometimes this is not possi- ble. Even when you find someone with experience, they still do not know your ways, and they can’t read your mind.
Don’t just start throwing them a to-do list from day one. In- struct them. Explain why you do things a certain way. Tell them the consequences of not doing things that way. Be patient and trust them to learn your process.
THE FIX: Before outsourcing, take time to document your work. There are plenty of tools out there to do that. Some of them are even free. If you choose to video your process, don’t do hour-long or more videos. This is not a workshop or a webinar. I’ve found short, 2-5-minute videos that address a single task works well. This way, you don’t overwhelm your team, and you can update it easily if you change your process.
4. You Don’t Get To Know Them
It’s OK if you want to keep to your work and personal life sepa- rate. Getting to know the people who work for you is not about pulling them into your personal life. Although, that’s totally up to you.
What I’m talking about here is taking some interest in the peo- ple who make up your team. To see them as people with real hopes and dreams, not merely as people who help you achieve your goals.
THE FIX: Notice their birthdays. Ask them what their long- term goals are. Inquire about their family. Know their hobbies. Take the time to learn to care about and for them. When people know they are appreciated, it’s sure to show up in their work!
5. You Never Apologize
Every now and then, everyone falls short. Maybe you said some- thing you didn’t mean, maybe your words came out wrong, you lost your temper, or maybe you were just plain wrong.
Your team will understand and respect you more when you can be vulnerable with them. On the contrary, if you never admit when you are wrong, they think you’re arrogant, and they don’t feel valued.
THE FIX: A good leader apologizes for their behavior. It shows people you’re human and if anything, shows strength, not weakness. If you’re wrong. Apologize and mean it. Don’t let it slide.
6. You Don’t Affirm Them
Outsourcing is a lot like parenting. It’s easy to point out things people do wrong and be silent when they do things well. If all they get from you is negative affirmations, you’re not very nice to work with.
I’m not talking about giving everyone a trophy for doing their job every day. Rather, give credit where credit is due and thanks where thanks is due.
THE FIX: What do your people do well for you? Did they go above and beyond? Did their work impress you? Say so! Tell them how much help they were.
7. You Don’t Allow Autonomy
Outsourcing requires some level of trust. You shouldn’t give people the keys to your kingdom from the beginning. You should, however, allow people a certain degree of autonomy to perform their duties well.
For example, if you have someone setting appointments for you. Give them parameters. What days or time of day is reserved for you? What type of meetings are OK to schedule and what type are best to hand off to someone else?
THE FIX: Give them some leeway to make small decisions on your behalf. This gives them a level of ownership, and it saves you from decision fatigue.
8. You Don’t Have Systems In Place![]()
Disorganized clients are difficult to work for. If your people are always confused where things are placed, they won’t be produc- tive, and you end up paying more.
If they don’t have a predictable workflow, that means they have to ‘re-invent’ each time the same task comes up. They’ll spend more time doing their job and you’ll be paying more for your haphazardness.
THE FIX: Get organized. Store your files in a consistent manner. Have a naming convention. Create repeatable workflows and checklists. This also prevents things from slipping through the cracks and becomes easier to onboard new team members.
9. You Switch Apps All The Time
Online, it is easy to get caught up with shiny object syndrome. New project management systems, shopping carts and website builders pop up all the time. It’s tempting to jump on these new-fangled tools, especially when you’re offered unbeatable early adopter prices.
Each time you make a switch, it’s almost like re-tooling a fac- tory. It takes time, energy and resources. You may even have to rewrite your process. These are things that your team have gotten familiar with and now have to re-learn. If you do this on a regular basis, it gets frustrating.
THE FIX: there are times when you have to make a switch. For example, when you’ve outgrown your system or it’s no longer working. Those are legitimate reasons. But don’t go switching each time you find something new. If it’s working now, stick with it until it doesn’t.
BONUS: You Don’t Reward Them With More Work
Many people think outsourcing is finding someone on Fiverr to do something once. When you want that same job done again, you look for someone else. You’re always shopping for the “best talent” at the “best price.”
Each time you do that, you’re spending valuable time shopping. More than that. You have to re-invest time instructing people.
Do yourself (and them) a favor. If someone does the job well, re-hire them. Do it again and again until it doesn’t work out. When you do this, people learn your preferences. You spend less time explaining, work speeds up and the people you hire come to appreciate you for returning.
Like I mentioned before, none of us are perfect. We all do things wrong when we don’t know better. From time to time, we slip up. These ‘sins’ may not all be deal breakers for your team. Except for not paying on time. There’s no justification for that. If you find outsourcing a painful experience every single time, perhaps there’s something on this list you need to stop doing. Just think about it and be honest with yourself!
