January 5th, 2023 | The Key To Success as a Solopreneur and Bootstrapper: How To Work With Subcontractors?

3. Choose People Who Can Laugh (Especially at Themselves).

Having that said, it doesn’t mean that you cannot have preferences toward other people. I personally have preference to work with people with sense of humor. This is a for at least two important reasons.

Firstly, if you have similar type of humor and laugh at each other’s jokes, you also probably think alike in certain aspects, no matter where you are and what your background is. 

Secondly, goofballs — especially those who can also laugh at themselves — are easy going and tend not to take critics of their work personally.

Last but not the least, life is by design monotonous, especially if you work hard, so why not make it a bit ore colorful by laughing together? Laughter is a medicine for almost anything.

4. Look At the Progress, Not The Starting Point.

And now, the big question comes up: how to choose the right subcontractor? I believe it is a mistake to only look at the quality of the first project. You can skip many gems this way.

Instead, I look at the progress: I make comments after the first mini-project and track how the second mini-project goes. Some people take criticism, grow, and become better, while others start making more mistakes or even cheating.

In my experience, the quality of work never stays on the same level — it either goes up and up and up, or it gets worse. And everyone makes mistakes in their first project; this is the nature of new projects. So, look at the progress, not the starting point.

By the way, also be careful with how people label themselves. My discovery is that lazy people often introduce themselves as hard working, and hard working people often whip themselves call themselves lazy. So, if you encounter someone who pitches as an extremely hard working person, beware.

5. Avoid Yes-Men.

I only work with people who know three magic expressions:

a) “Bullshit!”

They don’t just nod at my academic titles, doing whatever I say, but process information and have their own opinion. Sometimes, I have a stupid idea (even often, I can admit it to public), and it is good to have people around who can say, “You know what, maybe we should do it that way instead?”

b) “I won’t do this.”

I enjoy working with people who are not desperate and wouldn’t take just ANY project, especially if they disagree with the message or the project is against their values. Who wants to work with obedient puppets?

c) “I don’t know.”

Working with someone who can openly admit they don’t know something instead of pretending that they do, is a blessing. It’s a sign of team spirit, actually. So, I always seek for people who don’t have complexes and can openly admit if they don’t know how to do something. 

In some cultures around the world, admitting that you don’t know how to do something is seen as unprofessional. So, I often have to teach people how to say “I don’t know” as they have reservations from saying it at first.

6. Always Share The Motivation and the Purpose.

People are not sheep, who just walk from the left to the right and back without thinking. Everyone enjoys knowing that their work matters, including a subcontractor who is only around for one project. 

So, I aim to always tell people why they are doing what they are doing, what the purpose of the project is, and why it is important for this project and for the world in general — even if it is the tiniest task.

Plus, think together with your subcontractors. What they can learn and gain for the future from doing this project? Everyone builds their own career story. Your project is yet another brick in the construction they are building, so give them ideas for what they can build on top of it.

Also, give people the floor to speak up, contribute their own ideas, and be creative: test new tools and tricks. They will be more emotionally engaged in the project and surprise you with the outcomes. 

7. Laissez-faire Management Style.

Especially as a solopreneur, you need to trust people. You don’t have time to look at their hands every day — and you shouldn’t. Freelancers are self-motivated by nature; you don’t need to put an additional pressure by trying to audit their billed hours (well, unless there is a valid reason to believe that someone doesn’t do things by the book).

Of course, there is a plethora of project management software designed to measure the time subcontractors spend hands on on the project. 

However, I personally believe that these programs do more harm than good as they put time pressure on subcontractors. My belief is that you should be so good that your people would round their hour count down to show how productive they are rather than round the hour count up. 

Also, leave your subcontractors space for research, experimenting, and improvising, and the results will be much better right away. And, unless someone on board is certifiably insane, nothing bad will happen.

Just look at it this way: as a laissez-faire manager, you win twice: you free your time and you empower your subcontractors at the same time.

I also tend to be casual rather than formal — which is important to me for the same reason as sense of humor. Life is hard enough as it is; why to make it even more dry and boring by being formal with people?

8. Classic Principles of Management Do Apply.

Working with subcontractors doesn’t differ much from managing a “regular team” when you think about it. Classic management rules do apply, including the classic rules such as “focus on commenting the work not the person” or, “praise in front of others, criticize in private.”

So, if you have recurring bad experiences with subcontractors, perhaps reading classic books on management would be helpful. Although I still think that reading the classic “How to Win Friends & Influence People” by Dale Carnegie is more effective than all the management books of the world altogether.

I also believe that in order to manage someone’s work well, you need to get to know that person a little bit and find enough time for them. Your motivation for work fizzles out very quickly if your boss or client doesn’t ever have time to go through what you did in detail, right? 

I personally hold “the rule of seven:” I work with no more than seven subcontractors or partners at a time. Taking more people on board might soon lead to a severe burnout. If I need more work to be done, I simple tell my subcontractors to hire their own subcontractors.

Lastly, it is extremely important to stay accountable for your actions. If you are wrong, you need to admit it. Business developers often wrongly assume that if they admit to their mistakes, they will lose authority. Nothing is further from the truth! Using the magic phrase “I’m sorry! You were right!” will only make you more relatable and likeable. So, do not abstain from showing emotions and admitting that you are not perfect.