6 Useful Tips for Managing Outsourcing

Stef Hagistefanou
6 min readJul 11, 2018

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It has become rather popular for today’s companies and organizations to outsource many of their projects, whether that has to do with content writing, localization, customer support, software developing or designing. You name it. Businesses, simply, do not have the hands and time to keep up with the requirements and expectations. As a result, online platforms, such as Upwork, Peopleperhour and Fiverr, are flourishing by providing a wide range of talented freelancers, ready to serve your needs. However, working with a number of outsourced members can be quite challenging and demanding.

So the question is: How can project leaders better manage and make the most out of their outsourced projects, while building a healthy and stable relationship with their contractors? Following are six useful tips.

1. Do the right Pick

Whether you believe it or not, the first step for a successful cooperation with a freelancer depends entirely on the one who’s hiring. I know it can be tedious, but give yourself the time needed to find the best candidate for the job. Don’t just pick the first one available. First, have a very thorough job description in order to let the potential applicants get a better idea of the project. Second, go through every candidate’s profile. Reviews and relevant experience are crucial elements when it comes to hiring. Third, as soon as you come down to the final-four (more or less), prepare a set of initial questions regarding availability, past experience or even rates. Last but not least, set-up mini live audio/video interviews. Live interviews are your ice-breaker and give both to you and the freelancer the opportunity to better understand each other and, most importantly, the project’s requirements. Fortunately, there are many applications, such as Skype, Hangouts and Slack that make the procedure easy and fast. Finally, evaluate all the information collected, such as skills, experience, past reviews, availability, rates, use of language, response time, etc, and rest assured that you won’t be disappointed with your choice.

2. Help the outsourced members fully understand the project and goals

Ready to start working? Wait a moment. Unfortunately, a simple job post and a hiring of the appropriate vendor are not enough. Now I am not saying that you have to go through multiple training sessions and exchange dozens of files, but you must be able to pass to your freelancer the importance, complexity, volume and goals of the project in the most easy way in order to ensure that he has all the expertise required for the job and, at the same time, minimize the risks of failure. Thus, do not jump straight to the job at hand. Instead, use effectively your live discussions by making a short introduction concerning the company’s nature and culture. I guess that’s what you would do in a real “office” interview and an online one is no different at all. Second, make sure you have a descriptive guide of the project for your new stuff and also try to include audio/visual handouts. Keep in mind that no matter how well you explain the job, the private contractor does not have direct access to you and in cases of international outsourcing, he might be even struggling to understand your language or accent. To conclude, in my opinion, nobody can fully understand the project if the leader lacks awareness concerning the job’s objectives and operations. Therefore, before you decide to outsource an assignment make sure that you are fully aware of what needs to be done and be comfortable with solving the problems that may occur in the process.

3. Use project management tools

So you have the team and you have the skills. All that’s left to be done is track the work flow. You can always ask the freelancer about his progress or go through his work manually, but micro-managing is something we are trying to minimize and avoid. Luckily, there are multiple applications that can help in this process. For instance, JIRA, Trello and Asana are only a few project management programs that I can name off the top of my head. Evidently, metrics and surveys have shown that the use of such applications make the remote employees more engaged and increase their performance. At the end of the day, even a well-made Google Excel spreadsheet could do the job if you don’t want to get your hands dirty with the aforementioned apps. The point is that a well-designed and robust work management flow promotes consistency, accuracy and overall effectiveness, while making the monitoring process quick and simple.

4. Be available

Sorry to be mean, but if you thought that you can manage your outsourcing from 09:00 am to 05:00 pm and have a carefree afternoon at home, then, I don’t want to disappoint you, but this job is not for you. Freelancers are freelancers because they don’t work in the same schedule as yours. Moreover, when dealing with outsourcing, mainly international outsourcing, you have to be mindful and respectful of the contractor’s time zone. This implies that you may receive a message regarding a problem, such as a bug, at 12:00 am or even later. Don’t be surprised. It happens. I suggest by no means that you should not do anything else rather than wait for unexpected notifications, but try to be available as much as possible despite the hour of the day. From my experience, I must say that being eager and ready to assist my outsourced party/ies at anytime was a decisive factor of building a trusted and respectful relationship which, at the end, benefited me (occasionally ruined my schedule…) and the company I work for. In addition, I strongly believe that in the next years the demands of the outsourcing will bring a more distinct and permanent role in each and every company — the Outsourcing Manager. You can always have fun with your laptop at hand!

5. Sync-up regularly

Another way to keep moderate track and monitor your outsourced projects, while investing in the relationship you hold with your freelancers is to sync-up regularly. Scheduled weekly, bi-weekly or monthly video calls can do the trick and ensure alignment regarding the objectives and milestones. Maintaining effective communication with your remote team members is the key. However, as I said before, do not jump straight to work. You have to remember that on the other end of the screen there is a human, not a machine. For example, before you start talking business ask them about their day. It sounds very small and minor, but trust me, it’s going to make a difference in the long run. Since I have done the freelancing job as well I can say with certainty that it’s pretty stressing to talk with managers and make sure to satisfy their needs, especially when you’ve been selected out of such competitive environment, with dozens of other freelancers ready to take your spot. To finish, I will take the matter a step forward by suggesting to keep in touch with your outsource members even if you are not working together on a project at the time. You never know when you are going to need them again.

6. Treat your outsourced members as colleagues

Finally, the last and most important tip. If you made it up to this point, well, congratulations and thank you very much, but let’s move on to more concerning matters. The fact that you are working with someone on the other side of the world on a one-time project or more is no different than working with your side-desk colleague at the office. In fact, your outsourced members require additional attention. You have to guide them, motivate them, congratulate them, celebrate their successes and be firm when mistakes occur, as you would with your everyday team. Overall, you have to be not only the leader, but also, act like one. I am pretty sure that Scrum Masters would have to say more about it. People who have extensive experience with managing outsourcing certainly know that it’s not always a walk in the park. Failures and wrong decisions are a part of the job, but it is in your capacity to achieve better results when managing outsourcing by following a set of principles — of course not necessarily mine.

In conclusion, there is much more digging that can be done regarding the subject of the outsourced management and I believe that we will start seeing more and more articles written about it very soon. Who can go against the trends, right? Every individual has his own methods, tips and guidelines. Here are mine and I would love to hear yours. And as for you, remote workers, how can we better assist you when assigning you tasks?

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