Empowering the Freelance Economy

Freelancing for a startup? Here’s how to manage your expectations and navigate iffy management experience

Startups can be dynamic places to work, but freelancers must prepare for inexperienced managers running the show
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Working for a startup can conjure up visions of dynamism and self-satisfaction as teams overcome challenges and break new ground. However, a recent Sifted article, “Almost two-thirds of startup employees say managers are unprepared to take on the role,” serves as a timely reminder: temper your expectations when freelancing for a young company.

A common hurdle within the startup landscape can be that many startup managers find themselves in leadership roles without prior management training or experience. This can lead to a cascade of challenges, including miscommunication, unrealistic expectations, and inconsistent feedback.

The Sifted report found almost two-thirds (63%) of respondents said that only a minority of the managers they’ve had at startups were equipped to take on the role, with some reporting that their managers didn’t know how to lead, and were poor at communicating. 

“Juniors are promoted too early and too fast into management positions,” said one respondent. 

“Some treat career advancement like a checklist of tasks to do instead of honing critical soft skills that can’t always be achieved through training but with time and maturity.”

For freelancers, this inexperience can translate into a less-than-ideal working environment. Project briefs may lack clarity, deadlines could shift unexpectedly, and payments might be delayed. While not exclusive to startups, these issues can be amplified in an environment where managers are still navigating the complexities of leadership.

Career development comes naturally for freelancers as they have more opportunities to build new experiences with each client, project or assignment. However, salaried staff do not always have as many growth opportunities. Just 9% said their managers at startups had helped them develop their careers. “Naturally the priority is getting the work done with limited resources, but managers at startups should remember that staff will move on at some point and they should leave equipped with new skills and projects under their belt, not just job title changes,” noted one respondent.

How to safeguard yourself when working for a startup

The key is setting realistic expectations from the outset. Don’t assume startup managers possess the same level of expertise as seasoned professionals. Be prepared for potential hiccups and have a clear strategy for addressing challenges.

However, just because they are a startup does not mean the management gets a free pass to mistreat freelancers when it comes to unrealistic expectations and long hours without pay. Many founders start out as freelancers before setting up shop, so they should be able to relate to any payment concerns. They should also know how quickly the reputation of employee relations will be shared within the freelance community, which could backfire when they need skilled flexible workers.

Practical tips for freelancers collaborating with startups:

Working for a startup can be an exhilarating experience that provides multiple skills and learning opportunities. Some freelancers may even be asked to join a startup team permanently, which could include amazing financial growth if the company takes off and you get some equity or shares in the business. But startups have good and bad days, so it is best to prepare so you don’t get burned financially or burned out physically and mentally. Here are some suggestions:

Prioritise clear communication: Don’t hesitate to ask questions or seek clarification on expectations. Open communication minimises misunderstandings.

Establish boundaries: Clearly define your availability, rates, and scope of work. Don’t shy away from declining projects that aren’t a good fit. You will only regret it and even end up paying for it (literally).

Document everything: Ensure a written contract or agreement outlines project details, payment terms, and other relevant information before you are engaged with the client.

Anticipate delays: The startup environment can be unpredictable. Factor in buffer time to accommodate potential delays.

Do your due diligence on the founders or startup: It never hurts to put the feelers out to any freelancers who may have worked for the startup in the past or one of the founders to get an idea of what the working environment could be like. What might be challenging for one freelancer might be fine for another, but it pays to do your research.

Invoice promptly and follow-up: Don’t let invoices fall through the cracks. Follow up on unpaid invoices in a timely manner.

While freelancing for startups can be rewarding, it’s important to approach it with realistic expectations. By understanding the potential challenges and taking proactive steps to protect yourself, you can enhance your chances of a successful and mutually beneficial working relationship.

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