How to Successfully Expand Your Team with Outsourcing?


Some of the questions we’ll touch upon:

  • How do I decide which jobs to start with?
  • Can I do this in-house or go through an agency?
  • How to choose the right geographic location?
  • What sort of management structure to put in place?
  • How to train your team remotely?
  • How to effectively communicate with your remote team?
  • How to promote company culture in your remote team?
  • What are the biggest risks and what are the real benefits of outsourcing?

Attendee questions:

  • Best practices for outsourcing?
  • How to manage outsourced/offshore team members effectively?
  • I'm keen to understand about how other people structure their remote team. Also, the question of culture - what can one do to make sure the remote team feels part of the team?
  • How do you know if outsourcing is appropriate for your team?
  • What companies would you recommend to outsource operations to! I’m ideally looking for a company that could help us do everything, hire staff in that country, on boarding processes, legal, have an office for the ops staff to work in etc!
  • If permanently outsourcing a capability, how often is it expected to change vendor balancing needs of the company and eventually out-growing a current vendor?


Companies mentioned:

  • Taskeater
  • HeySophi
  • Mechanical Turk
  • Upwork

Reasons for being here:

  • How do we maintain a certain culture in an outsourcing team when that team grows abroad?
  • Where does outsourcing sit and how it works?
  • Learning more about the process and hearing about people’s tips and tricks

You have to define what your needs are together with your team. You need to know what you’re exactly solving for. You don’t want to overpay for things, so that discussion and understand what you need exactly is crucial. Through Google you can do a comparative analysis, different vendors and then the different criteria you’re scoring against.

How many people you’re looking at, it’s good to cast a wide net so that you really can show why some vendors are much better than the rest. Structure your comparative analysis so you compare all vendors equally (apples-to-apples) and don’t hesitate to apply numbers to non-quantitative characteristics (e.g. do I like them? 1, 2, or 3)

It’s very important to have direct contact with the owner of the project and who’s managing the team, this way you can have a better grasp on what needs to change and what can be done better. When you give people a brief or a task, do the whole process yourself first so that you don’t rely on the outsourcing team to come up with the details. It’s a waste of time, but it also lets you know how you would do things and how to correctly brief the team.

It’s important to discuss things with the teams affected about how outsourcing will influence them. It might not just influence the one team that needs the support, but it will also affect other teams in their way of working and in their strategy. It’s also important to think about the future of the company and the team, you want to take that into account because you don’t want to have to switch your outsourcing company in 12 to 18 months because now the brief is different.

When you’re creating the criteria, think about everything that you will do to train someone in house. Talk to the team, ask the questions, follow-up via email with the questions and answers you’ve understood to see if they agree. This way you have it in writing that they will or won’t do a certain thing. Also also if you could speak to a client who might have had a similar problem to solve.

“What if there’s an outage.” How do they react to this? How well are they prepared for it? → See if they ask more questions and if they have had this situation before.

Creating comparative research is a living document, if you find that along the way you want a vendor to do X,Y or Z. You can add that as a new criteria and go back to previous vendors to see if they offer this. How long does creating such a matrix take? Of course you want to get things going, but you don’t want to be too quick. You will have to work intensely with the team in the beginning to ensure they are doing the job well and are trained correctly. It also depends on the work they will have to do. Ensure the communication is fluid and that you can tweak the brief as you go. Initially they should be able to ask as many questions as necessary. It depends.

Don’t rely just on your own experience because even a year or two later the company may have grown and by the time you use them again everything that was great about them, they may have changed their way of working. Or become less responsive, have a different rapport with their clients.

It’s easy to get upset about something over email, but once you have a call or a video call a problem diffuses so quickly. It’s better to not reply over email, but suggest a call instead because it will improve the relationship, but it will also acknowledge that you’re working with a person on the other end and you want to make sure you keep that human interaction high.

Once you have chosen who you’re going for, you have to over communicate. Ensure that the quality is good and that everything is going well. Ensure that your communication systems internally are also adapted to the outsourcing company. If you use Slack, set them up in the right channel, this way effective communication is set up and their email is not stuck in the backlog, but they can connect with you directly. Be careful with timezones tho, you might wake up to a ton of questions and that can be stressful.

The metrics might be different for the outsourcing company eg quantity vs for your which is quality or conversion rate. It’s important to remember that your metric is not their metric and there can be a misunderstanding and miscommunication around this. They are usually more used to going after high volumes rather than more specific outcomes. The best outsource teams are part of your team, they should be included in your strategy and your success metrics. The more they understand what you’re trying to do, the more they will understand what works well for you. When you explain what is good for you vs what is good for them, you can start teaching them what you’re looking for. They will also start feeling more connected.

It’s not as simple as, I’m going to give them a task and expect them to do it. Big mistake is to treat them as inferiors, not including them into the team as everyone else. The mindset of the company was not good towards the remote team. There was a shift in the company, they were included more, treated as people, involved in meetings, Slack channels, faces were now seen on camera. The relationship between them and the rest of the team made a huge difference in the output of the team and the quality of their work.

Be sure that everything you need to be done is in the contract. Because everything that you agree on might get interpreted differently overseas. You will also want to share milestones with them, this way you can reevaluate over time if what was supposed to happen happened. This should also be in the contract.

Shift in words: “outsourcing companies” vs “remote teams”. Are people more inclined to feel closer / better manage remote teams vs teams that they call “outsourced”? No sense of “them” and “us” because you all have the same goals. So: outsourcing, offshoring, remote teams?

Outsourcing vs hiring your own remote team. Why would you choose one or the other? Working with vendors means that you need to do a lot of work with them and contract work.

  • There are regulatory reasons, but they should be able to be overcome quite quickly
  • How quickly do you need to move? Do you already have the process and structure in place and other people take over?
  • It depends on the situation
  • Flexibility and resources, you’re looking for a stopgap resource while you’re automating things. Usually it’s cost and duration of need, guaranteed quality and scalability. Outsource companies can scale much quicker than you.
  • Hiring and onboarding some takes a lot of time, if you have to do that with 1 person, it takes a lot of time on multiple teams.
  • You can keep tactical control over the processes if you keep it within your own company rather than outsourcing.
  • Having enough backup, consider that people get sick and things go wrong, so if you only rely on your internal team then you might not have that extra support.
  • Do you have the time to create a process, or do you want to rely on the knowledge and experience of the outsourcing team? If you don’t have a strong team for a certain task, you may want to get that know how bought in by using a specialised outsourcing team.
  • With outsourcing companies, some things end up being no longer your problem. For example, if someone is sick and they don’t show up to work, they will have to handle this, not you. Or if the team is growing, you won’t have to oversee the management over the different levels, this is something they will have to organise.
  • Don’t forget that outsourcing is also a risk and you want to assess that risk correctly. Also have an exit strategy on how and when to cancel the contract and how to continue without that outsourcing company.

How much management is needed when the team is outsourced?

  • There should be a process of working on the contract, talking about the different company cultures, but that’s up to the outsourcing company to manage. There shouldn’t be any level of micro-management.
  • When the team is small, it’s preferable to manage them directly. They have a supervisor in the outsourcing company, but they are not as much involved. But if one of the people in the team changes, the expectation would be that there doesn’t need to be a new training of that team. But if the team is bigger, it’s better to have someone else manage them.
  • There’s a cost element to it too, the outsourcing company should be able to prove that they can manage the team, that you don’t have to do it yourself. But it depends on scale.

What can you outsource / usually end up outsourcing in the startup setup / spectrum for outsourced resources:

  • Customer support
  • Content production
  • Logistics
  • Sales (lead gen)
  • Specialist services e.g. finance, legal
  • Engineering