Managing a Freelance Workforce — Benjamin Shapiro & Todd Hines // MarTech Podcast

In this fourth installment of the 2020 year in review, Ben and Todd talk about breaking up roles to make the organization more resilient and less vulnerable, what losing the Swiss Army knife member of our team revealed as being emblematic of a business problem organizations face, and the importance of contingency planning for your workforce.

Show Notes


  • “The first thing we wanted to think about going through this year was the separation of tasks and teams really, between both shows we have, Voices of Search and the MarTech podcast. So we thought about rather than having individuals working across our shows, we thought about splitting a team that focuses on VOS and a separate team that works on MarTech.” -- Todd“In the midst of re-shuffling and organization there we also had a teammate who has been with us, dedicated to the show for years and as her career goes to change, she continues to do new things and we definitely support that, and she decided to go on a different direction so we were forced to start thinking about re-hiring and with that the onboarding and training that goes along with that.” -- Todd “Zori was our Swiss Army Knife for years, somebody that we found on Upwork writing some content and doing some publishing. Originally it was, write a single-line episode, take this file and publish it on Art19, our host. Then it was, can you create our Squarespace pages, then it was emailing the guests from my inbox and then it was can you help us with content syndication scoring. So, Zori, who we love working with and we had a great relationship with, had a huge role across two shows. She had a very big important role.” -- Ben“But Zori is emblematic of a business problem that lots of companies and marketers face where you have someone who is the glue of your entire organization and because Zori had such diverse tasks and was sort of spread across the entire organization, she was taking our content from, ‘Okay, it’s been edited, published and all the way to the guest communication. It was great but what happens if Zori gets sick or if they decide they want to go to another team? Or their career path changes. Whatever it is, when you have a key contributor, there is more risk.” -- Ben “After Zori, we learned thinking about better resiliency and lesser vulnerability if we break them down into very specific pieces and assign individuals to a very narrow set of task, have one team for one podcast, and one team on another that also makes a redundancy in case we have an issue where we need extra help or we need to focus on one of the podcasts, we have essentially, another full team that could step in and helps with one show or the other as we need to adjust things around.” -- Todd “This is an important part of managing a freelance team. We’re not exactly talking about two time zones that are next to each other so when you are working with this distributed workforce what’s incredibly important is building out pads of communication, setting clear expectations, having people understand what their roles and responsibilities are, and making sure that the handoffs are very clean.” -- Ben “As it was different in the past years where I’ve done a lot of screenshots and a lot of written word and training documents, I now switched to video and started leaning very heavily on video, I’m using a tool called Loom. I am creating under five-minute video snippets walking anyone through these individual tasks and we now have this archive of great videos you can click into to figure out how to do any given task.” -- Todd “The takeaway here is that there is a life cycle for working with freelance teams. People come in and you give them small tasks that are incredibly important but you have to give them documentation of what your processes are and an understanding of what they need to do and when it is due and that needs to be crystal clear.” -- Ben “Moral of the story here is we feel like we’ve created an incredibly talented, thoughtful, valuable staff of freelancers but we are also trying to be realistic that when someone is freelancing they might not always want to do the same role. So we need to start thinking about either rotating those roles, adding additional responsibility, moving people into managerial processes as well to keep people motivated” -- Ben “Then there is the notion that people are going to want to change jobs so you gotta be ready for it, you gotta have some contingency plans as well.” -- Ben

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