Contract ’til Fired or: How to reach out to candidates the exact wrong way

Kyle Cyree
Jun 6, 2019 · 10 min read

tl;dr As an experienced worker in a competitive industry, who has worked for risky startups for 10+ years and survived a mass layoff, contract-to-hire (C2H) fills me with distrust, fear, and loathing. This article combines the author’s opinions, personal reflections, and some investigative ~research further down the page. It’ll be meandering.

Like pretty much anyone working in tech with 5+ years of experience in a specialized field, I see a fair amount of unsolicited emails (via LinkedIn or my personal site) with contract-to-hire opportunities. I’ve often wondered why a business believes this is logical, especially when contacting someone salaried. It seems that there are only a few reasons why an employee would take C2H:

1. “I hate my job and/or my boss”; or

2. “I’m unemployed and just need to pay the bills”; or

3. “I don’t have any experience in Exciting Industry, but I’d like to see what it’s like.”

Thinking/talking like a (former, frequently and so far failed) CEO, I’d have some concerns around these reasons:

1. If they’re miserable, how will the transition affect their productivity, and how do I know that they aren’t the problem or that they’re not in the wrong job? I know that morale is contagious, and it’s risky to bring someone into a situation and create reverberating network effects for which all of my workers may potentially pay. Ultimately: is this a role where success is paramount, and if so, why am I forcing candidates to audition instead of finding the right candidate to help my business produce results, whatever the costs? Is the salary too unattractive? Is my internal recruiting team that terrible at their jobs, and do my employees dislike their jobs so much or are our referral incentives so weak that no one is willing to recommend a friend or someone from their network?

2. If they’re unemployed, do they have an incentive to stretch their actual experience or competency? Will bringing them into a “carrot and stick” situation aggravate their desperation, causing them to put in more hours initially but suffer long-term due to burnout, fear, and/or lack of recognition? Do I actually have plans to hire someone if they’re a long-term fit, or am I not sure if we really need the role and I just want to test the waters? Are the incentives I’ve created for my recruiters not aligning with my business’ long-term goals? Are they understaffed, undertrained, or under too much bureaucracy to do their jobs? Beyond all that, is it ethical to hire someone who is desperate and then dangle an uncertain “future” job offer so that I can make them prove their value? Have we thought about hiring an agency or proven consultant(s) to fill this gap if timing is sensitive and progressive success is key?

3. Is my need to fill a role so great that I would want to find someone with no industry experience, train them, create a freedom-to-fail environment, and then create a “will they hire me, am I secure, am I doing a good job?” anxious situation with a competent employee for whom I spend time and money training? This seems like a recipe for inconsistent results and bad blood — am I willing to risk my product and company’s success by creating an atmosphere where employees labor under uncertainty toward a business objective I value, under rewards that I’m uncertain I’ll be able to offer?


I’m not a recruiter or an industry expert, I’m just a guy who gets a lot of emails for tenuous C2H jobs at companies that aren’t interesting to me. Once upon a time, I dedicated two years of my life to a company called Bingo that employed personality metrics, professional testing, and leveraging emotional synchronicity to achieve business value. I believe that most companies want to achieve business value, and I believe that most employees want to find meaning in their work, their workplace, their company, and their coworkers. This “employees” category includes recruiters, who are undeniably some of the hardest working people I’ve ever met.

I suspect that the reason C2H is becoming normalized results from incentive misalignment, management compartmentalization, geographic limitations, and ultimately corporate bureaucracy, incompetency, and laziness.

To be fair, I’m writing this article from a place of frustration with relatively little (by most standards) investigative research. My goal isn’t to solve this problem, it’s to represent a perspective from the candidate-side, and if I’m lucky, to generate a bit of conversation.

I’d like to examine the reasons I gave above (bolded) and perform some extremely basic research, approximately following how I’d conduct research if I were doing idea validation research as a designer or a founder debating whether an idea was worth more than conversation over beer (users first, SMEs second, forget everyone else at this stage), while taking a restroom break at the bar. I will say that I’m writing this post rather quickly in one sitting, so I’m only providing feedback as a user up to this point. I am, for better or worse, a service/UX designer and rely upon the lures within my tackle box. Hereafter, I may shift opinions but won’t edit anything aside from grammar prior to this point to preserve its usefulness as a first impression.


Incentive misalignment, management compartmentalization…corporate bureaucracy, incompetence, and laziness

If you’re a candidate reading this, know one thing: your recruiters seem random and haphazard because they are, but it’s not (entirely) their fault. If you’re a recruiter reading this, and you’re working for an agency or as an indie, I’d love to hear your feedback and read any resources which you find that may confirm/refute these opinions.

When performing user research, I often say that the best feedback you can get is from seriously impatient people. If I were able to consistently source “people who recently quit smoking” as my user testers for a general audience product, I’d be a very happy and informed designer. The next best thing is pseudonymous message boards or Reddit (I love Reddit, forever and always — support free speech and innovation here).

There’s a decent subreddit on this topic, mostly from the candidate’s position, called r/RecruitingHell. I generally trust Google’s algorithms, and when I performed a basic Google search as a pretended frustrated recruiter user, I found this on the first page. Here’s a comment that struck me as true and real:

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So , there are a couple of issues that our esteemed colleague mikemonk2004 has introduced:

  1. The issue is with the company, not recruiters; and
  2. There are a lot of applications and the recruiters aren’t equipped with the experience/power/bandwidth/all-of-the-above to make informed recommendations; and
  3. Providing feedback to applicants individually is cumbersome; and
  4. Recruiters have an incentive to fill positions; and
  5. Internal politics are a factor; and
  6. Policies to publicly offer positions so that insider hiring doesn’t happen are a joke, but everyone’s telling that joke anyway in the same vein as ubiquitous small talk, e.g. “Mondays are the worst…” or “See you next year!” around Christmas; and
  7. Like everyone else, recruiters are trying to do a good job, and a “good job” isn’t determined by their own internal compass but by someone with more power than them who hasn’t utilized that power to make a good UX for recruiters, applicants, the company, or anyone but themselves. Lest we confer too much disdain on these middle managers, we must realize they are also subjected to the same constraints enumerated in numbers 1 through 7. The burden of power isn’t stress; rather, it is complacency.

Demum: there’s a lot of misaligned incentives. Based on perfunctory research, my hypothesis is confirmed, which is just how I like it when I’m trying to prove myself right. ; D

Pretty much all of the hiring process isn’t something the candidate or recruiter is doing wrong, it’s just “business as usual.” As a recruiter or as a candidate, most of the “process” is outside your control. That’s why we use the word “process” after all: to obviate blame from ourselves, to say that we were just following the corporate chain of command.

C2H is basically a loophole that removes obligation from middle management and the company, while also empowering the recruiter or “hiring manager.” The candidate has near-zero power, it’s like he/she is a 3D printed prototype before the actual injection mold is made; they’re at best a PLA cog. If you happen to be an executive and think this is giving the candidate freedom, your recruiters agency, or your managers success-driven incentives, I offer a suggestion that you may want to reconsider the bigger picture.

At this point in writing, I’m reflecting on Bingo and thinking I got a lot of things right six years ago, even if the execution was wanting and laughably underfunded. Incentives are really unaddressed, unoptimized, and just straight up stupid in between executives and users generally, and those acting as a medium often sacrifice personal goals or good ideas because it’s too difficult to enact change. As a user advocate and more or less full-stack designer, I feel this pain in a real way. What users want and what executives budget for is processed into product the same way that an orange drink is identifiably “orange” while tasting exactly nothing like a real orange. It is recognizable, it is ubiquitous, it is unhealthy, and it is shockingly prevalent.


Geographic limitations

I’ve thought about this recently and discussed it in my private Telegram group and on Twitter (Tweets to follow). I think geolocation bias will soon be a ~thing of the past, but for now I realize it’s a necessity. Before I descend into offering a solution, describing the problem merits some exposition.

Accepting the restraints in the above section, geographic limitations are a natural consequence. One of the constraints I imagine legitimately awesome recruiters face, such as my startup buddy in Raleigh-Durham Ellen Gowdy with Curious who you should contact if you’re looking in the area, is the facetime value which employers place on applicants. For some roles (including design) and some companies (including the agency I work for) and in some folks’ opinions, facetime makes for a better product. Some teams, some formalities, and some products necessitate human-to-human contact more than others. It’s obviously worth mentioning, but there’s a subreddit for this.

I empathize with recruiters: given constrained positions, in specialized industries, in a small area of the world…how can they find the perfect fit? If a recruit lives too far away, he/she will underperform over time due to life constraints balanced against the commute, and if they’re relocated from afar that means often substantial costs. I’ve interviewed with Microsoft, Mozilla, Apple, and Others You’ve Heard Of who offered varying degrees of relocation that paid for moving expenses but who offered conditionally appropriate salary adjustments that mean I’d sacrifice quality of life ($100k in RDU means a very happy family) for quality of opportunity ($190k to $300k in SF means roommates, long commutes, unstable local inflation, and all of the above, forever and always).

I haven’t done the specific research, but I’m fairly certain that women (in the US, at least) face greater pressure from balancing the commute against life obligations than similarly employed men might experience. Unresearched, I again grant, but telecommuting realities effect women and families more than it does single men (want to date? I’ve got a blog post for that). Given low unemployment and the quit threat, balancing the applicant’s realities with the daily grind should be a consideration, and quality of candidate that’s subjected to corporate definition (as espoused above) often results in suboptimal placements. I suspect location sometimes isn’t a driver, but nevertheless it must be considered now, and dependency upon it should be reduced in the future for both worker and company benefit.

In terms of C2H, the premise is often dishonest. C2H applicants often get a “dangled carrot” offer based on performance, whether or not a position exists in a specific place at a specific time. In most cases I’ve seen, it’d be better to RFP out these requests rather than carrot these opportunities, but the colocation and “immediate value” constraints make this an impossibility.

I’d love to see a system wherein VR/AR allowed us to collaborate more effectively. I think that design and presentations are one area where VR actually makes sense. Recently I chatted on Twitter with notable American-Australian futurist/journalist Mark Pesce (some assumption on my part) about this very thing:

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While Mr. Pesce is entitled to his opinion, and without the context of some non-public messages which I think I remember but can no longer locate, I still think figuring out ways to make remote work easier is THE challenge of this century, and perhaps our species.

If your organization is concerned about sourcing top talent for low prices, if our society wants to reduce carbon emissions from vehicles, and if smaller cities want to address traffic without infrastructure overhauls, then eliminating commutes and times/resource consumption for goods delivery is THE problem to solve.

C2H may solve part of this problem, but it introduces many problems which don’t have systematic solutions: plugging one gap with one person has limited effect, and employing this as a policy across the organization means it becomes a crutch rather than a strategic tool. Bullwhip/Chainwhip (give me some creative/metaphorical license with that link) effects exacerbate changes at the end of the product/procurement cycle. At the bullwhip’s popper are third-party recruiters, and when the popper creates a sonic boom, it leaves most C2H applicants deaf, whipped, and ready to charge.


Are you a recruiter, frustrated candidate, friend, or Rando who has a response to this? Please comment on this article and help me Get Famous, or if you’re like me and prefer to talk in the margins, send me an email at kyle@kylecyree.com. It’s my least compromised email (I’m OG with Gmail, basically get all of Tupac’s forwarded mail because I Know How to Party) and it’s less likely I’ll choose to knit, pet my cats, or eat Reese’s instead of ignoring your email. :D

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