Guidance! | What to Ask for 1099 Roles - Reader Question

Contract work can be a fantastic way to gain ID experience, build your portfolio, and embrace flexibility. And with companies tightening their budgets, we're likely to see a lot more of them this year.

So before you say yes to the role, consider (and ask about) the following:

Payment Structure

• What’s the rate? Is it hourly or project-based?
• When and how will you get paid? Some contracts pay every week. Some only pay once the project is complete. So knowing their payment structure is a must. It would suck to find out they pay all invoices 60 days after the final deliverable is turned in. That's a long time to wait for the cheddar.

By the way, if you're on a 1099 contract, you're in charge of paying your income taxes. So set some aside!

Long-term Opportunity?

Some companies use contracts to "date" an associate before giving them a full-time contract. Some just need a contractor for a short period of time. You can ask about the possibility of this 1099 contracts turning long-term during the interview. But keep in mind that some people say yes even if the likelihood is slim. If they say yes, it's a maybe. If they say no, it's very likely a no.

Non-competes and NDAs

Signing an NDA is pretty standard. Non-compete clauses are not that common in my experience. And I'd be highly unlikely to sign something with a non-compete clause that precludes me from working as an ID somewhere else. (Some non-competes are simply "You can't work for our competitors for # years, which I suppose makes sense.)

How realistic the scope is

• Ask about milestones: What are the key deliverables, and how do they envision progress? Breaking it into phases can help you gauge whether the timeline is reasonable, especially against your skillset.
• What process they went through to scope the work: A lot of times 1099 work is in response to a needs analysis already being done and the project being greenlit. But if your stakeholders' answer(s) feels vague, you might need to ask follow-ups to clarify.
• Discuss anticipated challenges: Ask what they see as the biggest risks or roadblocks to meeting the goals. It’s a great way to uncover any potential disconnects early and helps you proactively plan for them.
• Scope Creep: How do they anticipate they'll handle scope creep or revisions to the timeline? Are they open to renegotiating contracts if expectations shift?

What Success Looks Like

Knowing their goals helps you deliver work that meets, if not exceeds, expectations and potentially be invited back for future projects. So get really clear about how they're measuring the success of the project and evaluating your performance.

Other considerations

• Provided Resources: Do they have style guides, templates, or branding materials ready for you? Are you starting from scratch or working within existing frameworks? Have they sourced the content already? Will they provide tools & software, or will they provide it? (Psst, often 1099 workers are expected to already have the software and tools, but if the contract is W2, that's often provided for you.)
• Stakeholders: Who's on the team and whom will you be working with? How often will they expect a check-in? What's the preferred method for communicating? What's their process for feedback and revisions? (Some may not have a process, so be ready to suggest one!)

A note on ownership: Often the work you're paid to do no longer belongs to you once you hand it over. Sometimes, the company is okay with you including portions of projects in your portfolio, but I don't recommend asking about this in an interview. If you look like you're already planning your exit strategy while interviewing, you're not likely to get the job. This would be better to ask once your contract is coming to an end.

Final Thoughts

With all of these questions, consider what you want to say if they turned the question back on you. (i.e. "How does your company usually handle scope creep?" "That's something you'd be in charge of. So how do you manage scope creep?") There's nothing worse than asking a question you want them to answer only to realize you don't have your own... 🤦‍♀️

1099 contract work can be a rewarding way to break into instructional design or transition careers, but it’s essential to ask the right questions upfront. By clarifying expectations, payment terms, and ownership, you’ll set yourself up for success—and avoid unnecessary stress down the road.

Disclaimer: This is informational content and not legal or financial advice. Please consult professionals for guidance specific to your situation.

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