Try working with people before you hire them…and pay them for it!

January 18, 2024

August 25, 2022

TLDR: Working with candidates during the interview process helps you hire with conviction

  • Most companies hire based on candidate interviews; try hiring based on a candidate’s work
  • Add working projects or working sessions to your talent acquisition process to hire people who you actually know will do the work, not just tell a good story
  • Assign paid async work projects during the hiring process to hire junior, high-slope people to your team
  • Schedule paid working sessions during the hiring process to hire senior autonomous leaders
  • Pay candidates fairly for all work projects

Most startups copy other companies’ ineffective hiring processes, which look something like this: 

  • Publish a job description, recruit candidates
  • Do first-round interviews with a bunch of candidates
  • Interview your favorite candidates a couple of times
  • Hire who you think will be best
  • Cross your fingers and hope they’ll work out 

Hiring like this is guesswork at best and a risky disaster waiting to happen at worst. There are better ways but most companies continue to use the old methods either because they don’t know about alternative methods, or think a more detailed process is not worth the time and effort. We suggest working with candidates before you hire them full-time, every time. 

You shouldn’t have the same pre-hiring requirements for a potential C-level hire as a junior hire, but figuring out how to add even small paid projects before hiring someone full time is time and money well spent.

Recruitiment process guide: Precruiting, interviewing, working with candidates, candidate references


Even if you’ve followed our how-to interview guide, making hiring decisions based exclusively on how someone interviews is far from foolproof. As a16z’s Marc Andreessen says, “If you are super-scrupulous about your hiring process, you’ll still have maybe a 70% success rate of a new person really working out—if you’re lucky.” Most companies are not super-scrupulous, so even a 70% success rate is likely high for most startups.

Interviews are a conversation about the work, but importantly, they aren’t the work, which is why they can often be a false proxy. A false proxy is when you use the wrong indicator to make a judgment about something. Some examples of false proxies are:

  • Judging a worker’s productivity exclusively by how many hours they work 
  • Judging a student’s intelligence exclusively by their grades
  • Judging a company’s success exclusively by how many team members they have
  • Judging someone’s health exclusively by their weight 

Being good at interviewing is a false proxy. As Seth Godin says, “unless you’re hiring someone to be an interviewer, being good at interviewing is a false proxy.” Some people who are great interviewers will be great team members, others won’t. As Frank Slootman says, interviews are a sniff test. And your nose can mislead you.

In Latin America, hiring the wrong people is extremely costly. Each country has slightly different laws, but in Mexico, for example, if you decide to fire a full-time hire after one month, you have to pay them a minimum of 3 months of salary as severance. Investing a bit more time upfront with work projects or work sessions can help you avoid this turnover and is a worthwhile investment.

Use different work projects to hire different people

Startups want to hire two types of people:

You hire these two groups for different skill sets, so test them with different work projects before you hire them full-time.

Use async work projects to hire high-slope people

High-slope people are curious, proactive, driven, and have follow-through. They usually aren’t experts in one area. You hire them for their attributes and potential for growth, not their expertise. Typically, they are early on in their career, but usually already in their second or third job.

Add async work projects to the interview process when you are hiring for junior roles where you want to hire high-slope people. Async projects have set deadlines but allow candidates to work flexibly within that period. 

Ensure your work projects directly relate to the job so you can see first-hand if the candidate would do well in the role, an extension of a16z’s Marc Andreesen’s basic skills tests.

If you are hiring for a:

  • Writer, have candidates write something for you.
  • Designer, have candidates help on specific parts of an internal design project you are working on. 
  • Developers, have candidates work on real and relevant code for you or something that would be nice to have but won’t be a blocker if it doesn’t get done.
  • M&A analyst, have candidates write a 1 pager describing what M&A opportunities they would prioritize, and why.
  • Recruiter, have candidates build you a recruitment roadmap.

Use your best judgment for how many candidates you want to do work projects for you. If you’ve interviewed candidates, and don’t think they’ll be a good fit for the role after filling out a post-interview checklist, then don’t assign them a work project.

Try to make these projects small enough that a smart person who has a job and other responsibilities can get it done, but deep enough that you get enough information about the person to justify the work. Generally, work projects for junior people shouldn’t take more than a full day of work, so that the candidate can do it in their free time. Be sure to pay them fairly for their time.

Use work sessions to hire senior autonomous leaders    

Senior autonomous leaders are your direct reports to whom you can delegate important work and know it will get done well. You need to trust that senior autonomous leaders will deliver high-quality work, have good judgment, and that you work well together. 

If you answer the 14 key questions before hiring executives, you should know exactly what you need from the executive you are hiring. After deep-dive interviews, schedule working sessions with finalist candidates to assess their judgment, work quality, and how you work together first-hand. 

To plan effective working sessions with executive candidates:

  1. Choose the work you want to do with the candidate during the working session 
  2. Plan how long you’ll need for the working session, anywhere from 90 minutes to 2 half-days 
  3. Have the candidate sign a simple NDA for security 
  4. Send the candidate the necessary information before the session so they can hit the ground running
  5. Involve other leaders in the working session who will work closely with the candidate 
  6. Block 30 minutes post-session for note-taking: 10 minutes to write your notes down individually, then 20 minutes for a team review. At a minimum, fill out the post-interview checklist

What you work on during the working sessions will vary drastically depending on what you are hiring for. Here are some examples of working sessions:

  • Hiring a Head of Finance: half-day working session with CEO and COO reviewing financial statements, cohort data for their clients, and building a budget for next year
  • Hiring a Head of People: 2-hour working session with founder reviewing current team, HR policies, and prioritizing a People strategy for the next 6 months
  • Hiring a Head of Growth: 90-minute deep dive with the CEO and Sales lead analyzing the acquisition funnel and building a growth strategy

Pay for all work projects, every time 

Pay candidates for work projects that they do with you during the hiring process, even if you don’t hire them. Never ask for free work. I’ve seen cases where companies use their position of leverage to get free work out of candidates or assign candidates unpaid case studies that take 10+ hours of work to finish. I strongly disagree with making candidates do unpaid work. It’s exploitative and reflects poorly on company culture. It’s also likely counterproductive, as good candidates who can work anywhere probably don’t want to spend their free time doing unpaid work.

Before you start assigning projects: 

  1. Define a set fee for how much you’ll pay the candidate for the work
  2. Tell the candidate what the project is, and why it’s part of the hiring process
  3. Tell the candidate they’ll get paid regardless of whether you hire them or not and how much they’ll get paid
  4. Define what you are looking for in the work project, and what the criteria is

The outcomes of paid work 

There are three outcomes from work projects and work sessions:

  1. You think the candidate and their work is great, and the candidate loves working with you. Great! You’re as sure as you’re going to get that you are hiring the right person for the role.
  2. You think the candidate and their work is great, but the candidate doesn’t like working with you, and they pull their application. Although counterintuitive, this is a great outcome. Odds are that if you hired the candidate, they would have left a couple of months after joining your team or been unhappy and unmotivated in the role. Either outcome would be costly to your company and is better to avoid altogether.
  3. You don’t think the candidate is right for the role. You realize hiring the candidate would have been a mistake. If you hired them, you would have had to fire them. You’ve saved yourself both time and money, another great outcome!

In each of these three scenarios, you leave the work project with conviction on whether you want to hire the candidate or not.

How many candidates should I work with before hiring?

For senior autonomous hires, you should have working sessions with 1-3 finalist candidates as a final step in the recruiting process. Working sessions are time-intensive, which is why they work, but also makes them expensive investments of your time. You need to interview well enough to narrow down your choices to 1-3 top candidates for the final working sessions.  

For junior, high-slope hires, you can more freely assign work projects. Because work projects are async, they are much less time-intensive for you than working sessions. Work projects for junior roles should be integrated as part of the interview process, usually between your first, short interview, and longer interview. Never do deep-dive interviews with candidates whose work isn’t at the level you need. 

Downsides of working with candidates

Many hiring managers are resistant to adding candidate work to their interview process. Some argue that it can force the best candidates to self-select out of the process because they don’t want to go through the hassle of working with you before signing a full-time contract. 

Others say that doing work and then not getting the job makes candidates resentful towards your company and is more likely to make unhired candidates badmouth you and your company. Work projects and sessions can hurt your interview process if you’re not clear with candidates about the purpose of the work the candidates are doing, give them too much work, or don’t pay them fairly. Each work project or session should be unique, based on the role you are hiring for. If you assign unclear or irrelevant work to candidates, they will get frustrated.

As your company grows, work projects become harder to scale. You need to train your team how to assign and judge work projects for more junior hires, or you will create a diluted interview process. If you realize that the work projects have become a hurdle that adds bureaucracy and pushes the best junior candidates out, rethink or completely get rid of work projects for junior hires.

Most startups I’ve seen stop doing working sessions for senior hires as time goes on. They are either “too busy,” or think that they can hire well enough through interviews and don’t need working sessions. Eliminating working sessions for senior hires almost always results in turnover, which at the leadership level, hurts team morale. The best companies with the best leadership teams always have some sort of working project as a final step in their interview process for senior hires.

Work with candidates and hire better

Hiring people based on what they tell you in interviews isn’t a sustainable talent acquisition strategy, especially in early-stage companies where each hire is critical. Improving how you hire means getting more data points about candidates to help you make better decisions. As legendary poker player Annie Duke says in Thinking in Bets, “Improving decision quality is about increasing our chances of good outcomes, not guaranteeing them.” You can never guarantee that the person you hire will be an A player, but working with the person before you hire them will help you make a more informed decision. Work with people before you hire them, it’s better for you and better for the person you hire.