Do You Need to Hire?

10 minutes, 10 links


Updated August 24, 2022
Technical Recruiting and Hiring

You’re reading an excerpt of The Holloway Guide to Technical Recruiting and Hiring, a book by Osman (Ozzie) Osman and over 45 other contributors. It is the most authoritative resource on growing software engineering teams effectively, written by and for hiring managers, recruiters, interviewers, and candidates. Purchase the book to support the author and the ad-free Holloway reading experience. You get instant digital access, over 800 links and references, commentary and future updates, and a high-quality PDF download.

The most important thing you can do is to figure out a way to have as few people on your team as possible. The fewer the people, the less you need to recruit. Recruiting is really hard and it takes a really long time. Recruiting one hire can take up to 100 hours of your team’s collective time. That’s time that is not spent making the product better or getting customers.Auren Hoffman, CEO, SafeGraph*

One of the biggest mistakes companies can make is hiring for the wrong reasons or at the wrong time. Whether you’re a founder at a two-person operation or a hiring manager at a larger company, the first question you need to ask yourself when creating a hiring plan is this: do you really need to hire? Recruiting is an immensely time-intensive task. Just because you might have the money or budget to hire and some work you think needs to get done, that doesn’t always mean you necessarily should hire someone new. Given the financial costs and risks to teams and infrastructure, hiring should not be taken on just because you think it’s time to scale up.

So before you define specific roles and start writing job openings, it’s a good idea to work back from what your team or company needs to build or deliver, and then ask:

  1. What is holding (or could hold) your team back from accomplishing those goals?

  2. What do you believe your team should be doing that it isn’t doing already, and why not?

  3. Is it simply execution bandwidth, or is your team lacking certain skills and abilities needed to accomplish your goals? If your team’s technical infrastructure is flakey, is that because the team lacks knowledge in that area, or because the culture or process is pushing them to undervalue work on infrastructure? Depending on the team, either of those issues could be solved with or without hiring more people.

  4. What is the anatomy of your team now, and what elements do you need to add to it?

The elements your team needs can take many different forms. For instance, they might be concrete technical skills, like frontend engineering or building machine learning infrastructure. On the other hand, they might be traits that are harder to define and assess, like the ability to prioritize tasks and iterate quickly in product development without incurring technical debt. They might be skills or proclivities to meet challenges your team expects to face in the future.

My first piece of advice about hiring is don’t do it. The most successful companies we’ve worked with at YC have waited a relatively long time to start hiring employees. Employees are expensive. Employees add organizational complexity and communication overhead. There are things you can say to your co-founders that you cannot say with employees in the room. Employees also add inertia—it gets exponentially harder to change direction with more people on the team. Resist the urge to derive your self-worth from your number of employees.Sam Altman, chairman, Y Combinator*

dangerSome common patterns we’ve seen that lead companies to hire prematurely:

  • Vanity hiring. Founders may fall victim to vanity hiring, bringing on new employees just to signal success—we have enough money to hire, and growth is good. Hiring managers at larger companies can also be susceptible to trying to grow their team when they don’t need to because it’ll get them a promotion or more influence within the company.

  • Because you can. Large companies might be inclined to hire because there’s “room in the budget.” Startups can also find themselves in similar situations immediately after a fundraising event, when there’s suddenly money in the bank.

  • Mythical man-month hiring. A team that is behind schedule on delivery may believe that hiring will accelerate their progress. In reality, there are short-term costs of hiring (the time spent on hiring and onboarding new engineers) and long-term costs of growing your team (increased complexity and overhead). The underlying idea of the “mythical man-month,” which many managers hold dear, is that they can speed up their team by hiring more people. But, as award-winning computer scientist Fred Brooks put it (in what is commonly known as Brooks’ law): “adding human resources to a late software project makes it later.”

  • Project-based hiring. When teams are contemplating a new project they want to pursue, they might think that hiring someone new is the best option. But how long will this project last, and what will the new hire be expected to do once the project is complete? Instead of hiring someone new, consider hiring a contractor for a short, scoped project, or purchasing a product or service that does some of the work. Team leaders must also be certain that a new project is worth pursuing. Or perhaps there’s a project already in play that can be aborted, freeing up team members to work on something more worthwhile.

  • Not looking inward. Whether there’s a specific project that needs to be completed or a new role that needs to be filled, there may be a team member ready for a promotion, or someone in a different department looking to transition. Perhaps they are capable of doing the work required, but they just need a bit more training. Current employees may already have the necessary skills, or be interested in a new role as a growth opportunity—does your company have the ability to help someone already on the team develop new skills, through mentorship or external training (hiring a consultant to deliver expertise to an existing team member might be possible)? Since they are already a known quantity at your company, understand its mission and values, and likely have some context on the project or new initiative you’re hiring for, evaluating a current employee’s fit for a new role should be easier than doing so for a completely new candidate.

Hiring to Overcome Risks

You want to identify the key risks in what you’re trying to do, then you hire for those risks.Vinod Khosla, founder, Khosla Ventures*

In standard approaches to hiring, teams focus on what it will take to accomplish their goals and be successful. However, in situations that require high innovation, these goals might need to change very quickly over time. In his essay “Gene Pool Engineering,” Vinod Khosla writes “It is easy to hire to boost a team’s strengths without addressing a team’s weaknesses. Fundamentally we believe that a team can be ‘precisely engineered’… to manage the risks and to take advantage of opportunities to create disruption without running afoul of key requirements of the industry.” Khosla argues that in these situations, a team should hire based on both opportunities and risks. The steps he recommends (which we reproduce here) are:

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  1. Identifying the five biggest risks a team is facing.

  2. Defining the skill-sets necessary to address those risks.

  3. Locating the “centers of excellence” where those skill-sets might exist.

  4. Finding and hiring the top experts in those “centers of excellence.”

Hiring Opportunistically

I always have a role for talented people.Mark Suster, Managing Partner, Upfront Ventures*

Say you come across a fantastic candidate, but they just don’t fit into any of the open roles you have right now. Should you try to hire them? Exceptional talent is rare; exceptional talent that is attracted to your company is even scarcer; exceptional talent that is attracted to your company and at a serendipitous moment where they would make a move requires the stars to all align. Can you miss that opportunity?

Stripe CTO Greg Brockman had a philosophy of hiring for people, not roles. He suggests that “If you can think of one thing this person can do, then there’s probably ten more you’re not thinking of that he/she can do two months from now.”*

I encourage entrepreneurs and CEOs to create positions for strong candidates—even if that position doesn’t exist.Vinod Khosla, founder, Khosla Ventures*

On the other hand, adding people to a team has immediate cost and overhead. Hiring someone talented and driven without a clear role can result in a frustrating experience for you and for them if things don’t work out. For instance, they might feel underutilized and underchallenged. In an interview with forEntrepreneurs, Jordan Burton notes that turnover increases when companies try too hard to fit a role to a candidate, especially if that means they end up joining without a specific mandate.


Principles16 minutes, 7 links

The overall goal of your recruiting activities is to hire the right candidates for your company’s objectives now, in a way that’s as efficient, timely, and fair as possible.

In this section, we’ve distilled the most effective and practical hiring advice from dozens of highly experienced managers to create a list of principles that will guide your hiring process toward candidate-company fit, regardless of your company’s stage or specific needs.

The Candidate Focus Principle

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