Plugging the generalist gap in AI safety with freelancers

Emily, this is really interesting to me, particularly your observation that there seems to be a need for generalist skills that isn't necessarily visible in the job market.

I wonder whether a source of operational freelancers could be a useful resource for EA—and potentially AI safety organizations specifically. A pool of experienced people who could come in for defined projects, fractional work, or short-term operational capacity could lower the barrier on both sides.

But I'm also wondering whether the bottleneck is actually less about a lack of talent and more about talent recognition and organizational design.

A lot of what you're describing sounds very familiar from the startup and growth environments I've worked in. Organizations know they have too much to do, but they don't always know exactly what role they need, how to structure it, or what capabilities should sit together. That's an organizational design problem as much as a recruiting problem.

I'm particularly curious about the emphasis on “context.” Obviously, there is domain-specific context that matters enormously for technical research and policy work. But for operations, I'm less convinced the amount of context required is as high as it sometimes seems to be.

The basic building blocks of building and scaling an organization—clarifying priorities, designing roles and decision rights, establishing processes, creating operating rhythms, improving systems, identifying bottlenecks, managing projects, building capacity—have a remarkable amount of commonality across industries.

So I keep wondering: how much context is actually necessary before an experienced operator can start producing useful work, when that work is neither technical nor research in nature?

I've actually started considering offering myself as a freelancer into the ecosystem for exactly this reason—not necessarily to arrive knowing what the organization needs, but to help an organization figure that out. Come in, understand the work and the bottlenecks, help define what capacity is missing, determine what the roles should look like, and then either help build that capacity or hand off a much clearer hiring plan.

It seems like that could be a useful bridge between “we need more capacity” and “we have a perfectly defined job description for you.”

And your point about the amount of unpaid work required to establish credibility makes me wonder whether we're inadvertently filtering out some of the very experienced people the field needs. Not everyone who has valuable operational expertise is going to be able—or willing—to spend six months proving that they belong before they're allowed to use it.

Anyway, I'm still thinking this through, but I really appreciated you articulating the problem so clearly. It has me looking at the generalist bottleneck less as a talent-supply problem and more as a possible talent-routing + organizational-design problem.

Hi Emily-- I enjoyed and took inspiration from your previous post on your pivot journey. This inquiry on freelancing and atomization of tasks is a smart follow up. 

As an experienced grantmaking generalist currently working for a non-EA foundation, I think there is a useful distinction between generalist tasks that can be projectized vs longer-term functions that are harder to separate from deep-seated organizational context.

Tasks that lend themselves well to freelance work have a clear end state and a well defined standard of quality:

• creative-forward projects like web design (traditionally left to freelancers given lack of continuity)
• clearly scoped writing projects like research memos, due diligence, landscape scans, or grant applications (assuming the org has heavily documented their own priorities and context)
• one-time database hygiene checks, workflow documentation, template creation
• bounded process analysis and automation projects (when the org knows how to define its desired end state-- difficult / not a given!)
• surge capacity for proposal review, event logistics, heavy reporting

All of this scoping and documentation that (I feel) is required to hire a freelancer responsibly requires significant internal capacity to spin up. If those conditions are missing, the freelancer may be set up to fail. 

It is also common for any of the above tasks to overflow their clean deliverable scoping and brush at deeper matters of prioritization judgment, internal inconsistencies, informal or unwritten context, org chart tensions, etc. One piece of the value of a full-time generalist is their ability to notice and take initiative to address these kinds of problems, which may require deep, long-term, and emotionally aware engagement. They can be especially prevalent for orgs with a startup culture or those that scale rapidly. Freelancers may notice these deep issues but tend not to be in a good position to address them out of fear of overstepping or creating relational friction that a full-time employee is far more incentivized to tackle.

I've also observed that EA orgs are extremely discerning about their hires, and rationally so. Freelancers occupy an awkward position where it is not cost-effective to conduct a similar vetting process given short project timelines and expected turnover, but the risk surface for the org is still fairly high if this person turns out to deliver subpar work: the deficiency needs to be identified, the contract reassigned, and the work repeated.

This very cost-benefit tension is the kind of issue that a high-level, embedded operations person could identify and solve. When do we take on the risk of a freelancer to power through something urgent in the short-term, and when is it more sustainable to take time to solve the underlying capacity issue?

I do love the idea of a freelance generalist directory. It may benefit from some scaffolding: tips on turning organizational pain points into scoped projects and perhaps some sort of pre-vetting process. Either way, I'd love to support!

Hi Emily, I'm a fractional CFO (in Australia) and mostly work with high impact organisations - in fact, I scale my hourly rate accordingly, with the theory that at least I donate 10% (via GWWC pledge) of my income so one way or another I'm having an impact. Fortunately, I've been lucky enough to work with really great high impact orgs (paid work with non AI but EA-aligned org, and volunteer Board role with AI safety org) so haven't felt like I've been compromising too much there.

In asnwer to your questions

• Could you do freelance work if you wanted to? I already do - but hadn't been aware of Freelancing for Good, in fact I was looking for a resource like this when I first started out on my self employed journey!
• Does the country you live in make it easy to try out freelancing? Yes (Australia)
• Would you be open to freelance work? Yes, although I prefer ongoing regular monthly support, rather than project based freelance work, as it takes time to get to know the organisation properly, and also that fits with what they were looking for.
• Could your work (e.g. in operations, communications) be projectised? Some work - for example developing a marketing strategy, building a website, providing PR advice, is where the organisation I'm working with is looking for contractors to provide this.
• Does your role need a lot of org-specific context? Not really - certainly nothing insurmountable that can't be learned quickly on the job, but the more I know the organisation and field in general, the easier to add value.
• What worries would you have in taking on freelance work? I'm lucky that I'm deliberately looking for flexible work as I wear a few different hats, so this is the only type of work I could do.

In general regarding using freelance / 'fractional' resources directory, it has been important and relevant for the organisations I work with to know that I am values-aligned, and better understand the EA mindset for want of a better term (i.e. has completed various EA or bluedot courses etc) rather than just finding a contractor via a typical freelance jobs board, where everyone is competing on rate. These roles came through direct relationships (we met in person at an EAGX event, and had been virtually introduced prior to that), but I believe work would be given preferentially to freelances/fractional people that are focussed on high impact work - mainly because I think it would be assumed that those people would 'get' the mission, want to be bloody good/effective at their job, and not waste the company's time (because wasted time/money = foregone impact)!

Not sure if this helps you - but happy to talk more if you wanted to reach out. 

Thanks for sharing Emily. I think it’s totally doable and each potential problem is solvable: boundaries, payment terms, scope and quality etc. Upwork has solved these already–of course it’s never perfect, but neither is having a talent shortage. 

I wonder how much the orgs factor in the opportunity cost of each path. Surely hiring a freelancer with good reviews, a solid portfolio, a clear scope, and strong motivation is preferable to having critical work left undone. 

My concern is that even if you create the freelancer directory, the orgs who are hesitant still won’t participate if there’s a feeling it’s risky (even if it isn’t). Getting to the bottom of their concerns will be key. I’d ask “what would make you change your mind?”

 

Thanks for writing this, Emily!  I have had many similar thoughts and am part of a few groups for those who do contract work for cause-based organizations. I wkk ok next what they have to say about uptake. I started doing consulting, contract, and fractional marketing and communications because I wanted to try my fit in different organizations, and because I felt that the kinds of organizations I wanted to work with didn’t have much money to afford a full-time me (with many years of experience and a wide range of skills sets), but could afford smaller or fractional engagements. I thought I could do more good this way. It has proven to be not as impactful as I’d have liked. I’m trying to improve my targeting so that I can do more good, instead of just “get work”.

If there’s a way I can help, let me know! Perhaps I’m wrong about my assumptions, but they are similar to yours about hiring being expensive and  that full-time commitments can be a risk for organizations. 

To your questions:

• Could you do freelance work if you wanted to? Yes but the barriers are just that the freelance opportunities for someone with my skill set seem few and far between
• Does the country you live in make it easy to try out freelancing? Canada is good for this. Except that we no longer qualify for employment insurance or get other benefits, though healthcare is freely available
• Would you be open to freelance work? I’m already doing it!
• Could your work (e.g. in operations, communications) be projectised?  Yes, even the strategy work I do can be done as a project. I offer a few different models including marketing and communications function set-up, project based work, and fractional engagements
• Does your role need a lot of org-specific context? To some degree, yes. Some organizations have much of it written down in an accessible format, and in some cases, I’d be creating that context. That’s part of my offering. And in some projects (often campaign-based) sufficient context is easily come by and can rely on general best practices for execution
• What worries would you have in taking on freelance work? Not getting paid :) Which does, in fact, happen. With little information about the company’s finances, it’s hard to know ahead of time how secure they are.   It takes a long time to take a delinquent client to court, and may not result in full payment, even if you have a good contract.