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Our Work Trial Process at Pesto

Daniel Liem
Daniel Liem
Sep 2, 2021 - 8 min read
Our Work Trial Process at Pesto

We get a lot of questions around how we hire and run interviews at Pesto. One of the unique things we do is run "work trials" - a borrowed concept from Linear and the early days of Coinbase. A work trial is the final stage of the interview process where a candidate gets assigned a couple of projects to work on and works alongside the rest of the team. It allows the company to assess the candidate's abilities as well as culture fit. It goes both ways too - the candidate gets a better sense of what it's like to work at Pesto and if there's a long-term future with the team. The individual also gets paid for his/her work, so it's not free labor.

A work trial has its pros and cons - on one hand, you really get to know the candidate at a deeper level (as opposed to a 5 hour interview). On the other hand, it is time and resource intensive. Each and every one of us on the Pesto team went through the same work trial process, and we've found it has helped build a more connected and performant team.

In this post, I'll walk you through our overall high level interview process, the specifics of how we run work trials, and the learnings we've made to-date.

❓ Our Interview Process

At the high level, our interview process is simple:

  1. Quick initial 15-30 min call to establish mutual interest
  2. Technical 1 hour interview, for certain roles and levels
  3. 2-3 hour interview consisting of two cultural interviews with the two co-founders and a technical screen typically conducted by the hiring manager
  4. Lastly, we conduct a work trial

Our process for 2 and 3 is standard. Like any other company, we have cultural and technical questions prepared to rigorously screen for quality before moving forward. We'd send a note like this beforehand:

Example of interview invite email to candidate

We try to keep this stage to a minimum (max 2 hours) to be considerate of both parties' time. We also make sure the candidate gets to engage with our founders and get a better understanding of the company's vision.

If the conversations go well, we move them forward to the final round - the work trial.

πŸ—οΈ Our Work Trial Process

When it comes to the specifics of the work trial, we have a long checklist of things we want to get done to ensure a smooth experience on both sides.

The Setup

Before bringing them into the Pesto team, we set up a 15 minute call with the candidate to go over basic details such as:

  1. A sense of salary / equity to ensure the candidate is roughly on the same page with respect to compensation.
  2. Finalizing the dates of the 3-5 day work trial which we're flexible with, as we know it's not always possible to take a week off from work. We're also happy to bleed over to the weekend if need be. We do 1 work trial at a time for a specific role, but may have overlapping work trials for different roles to be efficient
  3. Scheduling a one hour "work trial kickoff" meeting the morning of the first day in one of our Pesto rooms.

We'd generally send a note like this beforehand:

Example of work trial email invite to candidate

Note: Don't assume the candidate will always agree to the work trial interview. You never know if there are constraints that may prevent the candidate from participating.

It's also worth mentioning the potential challenges around managing multiple work trials. How do you communicate to other applicants if you've moved forward with one candidate? Or, what do you do if you have multiple candidates who performed well for a single role? We haven't had an issue with this so far because we screen rigorously in our prior stage (onsite) before bringing someone to work trial. But in general, we assess each candidate independently, regardless of how far along another candidate is (up until someone accepts an offer, during which you stop sourcing new candidates).

This ensures all active candidates have equal shots on goal. If multiple do move on to work trial at the same time, we do our best to stack them week-to-week. That way you keep the recruiting pipeline healthy while not leaving candidates in the dark.

The cost here is risk of multiple offers to great candidates for a single open role - if that happens, you'll have to take both candidates or make the tough decision to give an exploding offer to (ideally the first) candidate and telling the second candidate to wait for your decision.

The Kickoff

On day one of the work trial, we generally run through the following list of items:

  1. Add the candidate to the Pesto team.
  2. Add to relevant systems and tools: Linear, Notion, Figma, Github etc.
  3. Schedule the following meetings: ~8 hrs
    1. Team lunch (mid-way through) - candidate decides on theme
    2. Company and culture 1:1
    3. Product and engineering 1:1
    4. Remote / Hybrid market 101
    5. 1:1's with relevant members of the team
    6. Check-in meetings in between (optional)
    7. All regularly scheduled team meetings
    8. Final Presentation (end of last day)
  4. Decide on a project

It's an action-packed week full of heads-down work, onboarding sessions, 1:1s and more. It's equally important to be cognizant about how much time you're spending with the candidate vs. how much time you're leaving them alone to focus on their project. For example, if we are approximating 8 hrs worth of meetings:

  • Working 5 days, 9 - 5 PM β†’ 40 working hrs β†’ 32 heads down hrs
  • Working 4 days, 9 - 5 PM β†’ 32 working hrs β†’ 24 heads down hrs
  • Working 3 days, 9 - 5 PM β†’ 24 working hrs β†’ 16 heads down hrs

32 vs. 16 heads down hours is a huge difference. One way to solve this is by trimming down the number of meetings (ie. by making some meetings optional) to optimize on more heads down time, or assign a smaller project.

The candidate's calendar might look something like this:

Example of candidate's work trial schedule

The Project

This is arguably the most important part of the work trial. It gives candidates a chance to show off their chops and what they can do. We take this seriously and want to ensure candidates are fairly assessed - giving them a challenging but realistic project that can be completed in a week's time.

We often have a couple project ideas and invite the candidate to voice his/her opinions to ensure both sides feel comfortable and excited about the project. It generally culminates to one major project combined with one small project.

The general rule of thumb is to start the project scope small and gradually expand it over time as the candidate progresses. That way, you achieve a base understanding of what the candidate is capable of as well as his/her potential. Additionally, we highly encourage candidates to ask questions to any member of the team at anytime, to foster a collaborative working environment.

To get a better sense of different work trial projects, here's a list of the ones the Pesto team did in our work trials:

  • Ryan - Software Engineer
    * Large project: Voice memos in chat
    * Small project: Discussion channel descriptions
  • Katherine - Growth Marketer
    * Large project: Marketing channels strategy and timeline
    * Small project: Pesto memes content
  • Daniel - Founding Head of Product
    * Large project: Remote/hybrid work market sprint
    * Small project: Seed fundraising VC pipeline
    * Small project: GTM strategy
  • Anna - Founding Engineer
    * Large project: Birthday customizations
  • Sean - -Founding Engineer
    * Large project: Reaction popovers
    * Small project: Adjustable user volumes in meetings
    * Small project: Room color picker in room settings

πŸŽ‰The debrief and, hopefully, offer!

The final step of the process is typically a 1-1.5 hr long debrief with the entire team after the final presentation. We start with an anonymous voting poll from each person of either:

  • strong yes
  • weak yes
  • weak no
  • strong no

It's important to be objective here - you don't want other people's votes to bias your own decision (avoid groupthink). After putting in our initial vote, we then go around explaining why we voted the way we did. From our experience so far, an hour long debate ensues. This is a good thing though, because we're able to address any concerns anyone may have. At this point, it's okay to be influenced by others' opinions now that you're getting a full picture of the candidate - that's the point of a debate!

As with any interview process, we hope there's an unanimous decision on the candidate. If the team is still split or on the fence, it's best to give everyone some time to think it over. Ultimately, you want an authoritative "yes" or "no".

Of course, the hope is to always cross the finish line and provide an offer! Should that be the case, it's critical to make the offer experience as exciting, memorable and fun as possible.

Celebrating the addition of new team members!

We move quickly with our offers, and it's possible because we're upfront with our compensation and there's mutual agreement. Generally on the last day of the work trial, we pull in our entire team to verbally congratulate the candidate. We want to make sure they are feeling wanted - because we DO want them!

🧠 Learnings From Work Trial

Work trials are a relatively new concept for the working industry. We're biased, but we think it has worked very well for us and don't plan on stopping it for the foreseeable future. That said, there are some disadvantages as well. Here's a couple pros and cons we've noticed:


  • True demonstration of candidate's core competencies. We firmly believe the conventional 5-hour long onsite interview is a dated concept that large companies use to be more efficient. In such a short amount of time you can barely scratch the surface of the candidate's potential, which is why we opt for the more in depth work trial.
  • Mutual assessment of cultural fit. We get a better sense of long-term cultural fit with the team through interactions over team lunches, team bonding events, 1:1s and more. Likewise, the candidate can get a better sense of what it's like to work (and hangout) with us as a team!
  • Helps you get "off the fence". If you've interviewed hundreds of candidates before, you've probably run into the issue of being on the fence about someone at least once. That's because traditional 1-hr interview screens do a poor job of assessing the quality of candidates - it's simply not enough time! With 1-week work trials, you're able to air out any concerns to better decide if s/he is a good fit or not.


  • Time intensive. As you noticed in the calendar screenshot above, it's a week's worth of meetings, onboarding and setup. If you want to ensure the candidate has a great and successful experience, you need to put the hours into setting it up and guiding the candidate throughout the week. Additionally, we mentioned above the potential challenges around juggling multiple work trails at once, especially for a single role - this can add more complexity and time from the Pesto team as well.
  • Resource intensive. Work trials aren't free nor are they cheap. We pay candidates fairly for their week's worth of work time, and generally adds up to $1,500 - $3,000 per candidate.
  • Time consuming for candidates. It's not always easy to ask candidates to take a week out of their busy schedule to work with us, which is why we have to be flexible with a 3 - 5 day option, or pushing some days over to the weekend to accommodate.
  • Stressful for candidates. It can be a hectic week for someone trying to juggle between building a quick relationship with a large team while multi-tasking a project and ensuring it's done at the highest quality. We hope that paying the individual compensates for the stress, but it can still come at the expense of facilitating a good interview experience for the candidate.

Have you considered running work trials in your organization? Drop a note to us at [email protected] if you'd like to trade notes!

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