Pulling and Pooling Talent

When Freelancers Band Together

“I am a bit of an odd bird in this world”, Gideon Simons says of his career. He started out as a consultant, working from anywhere with a laptop. He was managing his own bands of freelancers well before digital nomads and the gig economy broke into the mainstream. 

Gideon is Head of Design at Anafore, where he heads UX Research and leads a Product Design team across the US, Mexico, and the APAC region. He is also the owner of SeeSaw LLP that consults for many startups and top tier corporations out of Singapore. His expertise lies in AI, Innovation, Usability, Prototyping and Product Strategy. He tells us about his journey leading remote teams all over the globe to turn wild ideas into viable products.

Learning to Conduct the Orchestra

Initially, Gideon took on long projects with different startups and corporates as a freelancer. This put him on an unexpected path to leading remote teams. Gideon was based in Israel, where most of his clients were but he was running teams with people in Europe and Asia. At some point, he found himself working with over 20 people - animators, designers, engineers, content creators. He needed to figure out how to get the individual contributors to work together to bring one product to life. Like a conductor of an orchestra, Gideon would keep everyone in sync. 

The world is catching up with this way of doing things. This is how many new organisations, NewCampus included, are being built. They’re decentralised to be more agile and flexible. A step beyond outsourcing, the modern company now has everyone working remotely, communicating and executing from where they are. 

“ The funny thing is my first corporate job was in IBM and it was totally like that [decentralised] as well...like the Wild West, people all over the world collaborating where they could. When there was an opportunity, we just jumped on it like a SWAT team.”

Gideon realised that he had mastered the art of managing decentralised teams at IBM, building something from scratch. Back then, nobody knew how to do mobile development. Equipped with the right instincts, he went on to assemble his team, target markets and deliver projects. From then onwards, he moved to more conventional teams where everyone was working from the same location. Now that COVID has forced many to work remotely, Gideon feels like he’s come full circle and is back in the Wild West. 

Selling Opportunities: Pitching Projects to Freelancers

To thrive in the project-based freelance landscape, Gideon says one needs a different mindset. People who do well here have a high sense of independence, responsibility and accountability. As people acclimate to remote work, they are developing a skillset that he predicts will be an asset in the future with more hybrid work models rolling out. 

As a leader of decentralised teams, one of the primary challenges is getting everyone working as a unit. There is no corporate culture to bind everyone together. In this context, motivation is deeply personal. Freelancers may have several opportunities under consideration. “You cannot expect people just to jump because it's [the project] there and work needs to be done.” Leaders need to make a case for why they should join the team, selling the opportunity. What is their angle in the project? Recognising their agenda and goals enables one to feed their motivation throughout the project life cycle. 

Gideon needs to bring out the best of his team with each project. One technique he’s developed is to focus on the creation of artifacts. He encourages UX designers to approach the work as a project to showcase on their portfolio. They can import the actual project into their portfolio rather than retrofitting something they’d created previously. “My kind of philosophy is that it's almost like Tai chi… where you take the energy and divert it to the same place that you want.” He finds that this tends to align goals across the team and yields better discovery, thought process and output. 

Real Relationships for Repeat Recruitment

Running a squad, relationships continue even when engagements end. Over time, you build a pool of people you trust and issue invitations as needs arise with each new project that comes along. One’s access to specialist skills very well can depend on their desire to work with you again. A lot can happen in the months between projects. “You don't have control over everything, but you do have control of the period of time that you are together working on something.” 

Gideon offers practical advice on creating those positive experiences and nurturing relationships with independent contractors. He makes himself available to discuss things they may want or need. He is a serial referrer, happy to put in a good word when they’re applying for new jobs and leaving shining reviews on LinkedIn. “It not just selfishly keeping them to myself, but making sure that they succeed with my help as much as possible.” His generosity makes freelancers eager for the next engagement knowing they can count on Gideon and the team he’s assembled. 

Deploying SWAT Teams for Hypergrowth

Corporates are beginning to understand the value of these distributed, dynamic and fluid teams. This is especially true for businesses looking to innovate or explore emergent technology.  “You do want to have a lot of people inputting the best of what they can give at the right time.” Instead of paying fees for a subject matter expert for two years, this sort of SWAT team can come in when the business is ready to lean into the new product or offering. 

As companies warm up to the idea of iterating and changing things, it is easier for them to bring on people accustomed to working this way rather than fighting the inertia of structured in-house teams. 

Personal Branding Matters

Pursuing a long term career as a freelancer requires building a personal brand as someone who can deliver results. “It does not entirely make sense for you just to be specialised at like being a change maker…a lot of companies don't really buy that. They need somebody who can build them X or Y.” Gideon recommends constantly updating portfolios to establish expertise and stay relevant, including things that are at the frontier of business like AI capabilities. He concedes that the ability to change culture is good, “but at the end of the day, they also need somebody who knows the domain to come in.”

Reflection questions

Flexibility and agility are likely to be increasingly important in the workplace and new opportunities are becoming available to those keen to take on projects. 

  • How might you keep your squad in sync while working remotely? 
  • In what ways can you redirect the energy of your reports to improve performance?
  • How are you nurturing relationships with previous and current team members to build your own SWAT team?

Contributors

Gideon Simons

Senior Director of Product Design & User Research


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