How to Hire at a Startup
Hiring is always hard. Even with 10 years of experience leading teams at startups, I make mistakes, and I’ve never met another founder who hasn’t.
For a long time, my approach was to hire based on “gut instinct.” I’d interview people and based on a 30-45 minute call, try to decide if I liked the person enough to hire them. As you might imagine, this led to me hiring a lot of very average performers who happened to be good at interviews.
In 2018, I read a book called Recruit Rockstars which changed everything for me. Author Jeff Hyman points out that if you don’t have a process for hiring, you’re always going to fall prey to biases and you’ll miss really good candidates who don’t do well on a phone call.
Picking the wrong hires hurts morale, leads to higher turnover, and slows down your startup’s capacity to grow. Once you’re past the product-market fit stage, hiring is one of the most important things a CEO does, so whether you steal my process or come up with your own, you’ll need to get good at it.
How We Hire at Draft.dev
Draft.dev is a very people-focused business. We’re a productized service, so having a great pool of writers, editors, and management staff is a critical part of our business.
Whenever we need to hire, our goals are to:
- Define the role and expectations clearly
- Build a significant funnel of candidates
- Evaluate candidates quickly and objectively
- Make an offer and transition seemlessly into onboarding
In this post, I’ll outline our process, but every role and company is a bit different. Still, I hope this functions as a workable starting point for other founders who want to get better at hiring in their startup.
1. Create a List of 3-4 Essential Job Skills
Before creating job collateral or promoting a job listing, we create a list of the 3-4 most important skills candidates should have for this role. Each skill should include a description of how an ideal candidate would demonstrate those skills.
For example, here are the skills required for our most recent Account Management hire:
- Communication - Candidates should have excellent written, verbal, and interpersonal communication. They should be able to listen and comprehend complicated requests and creatively solve interpersonal issues. Their email communication should be clear and concise.
- Organization - AMs juggle a lot of priorities. Candidates should demonstrate the ability to track many different metrics and prioritize appropriately.
- Sales - Candidates should be able to quickly understand our offerings and upsell existing clients appropriately. They should be able to problem-solve and build trust/rapport with their clients.
- Work Style - We are an all-remote company, so candidates should be very comfortable working independently, proactive in communication, and professional in video and email communication. They should also care about their job and what we do.
The job description, resume review, trial assignments, and screening questions should all be based on assessing candidates based on this list of skills.
2. Create the Listing and Application Form
The ideal job description should excite candidates while being honest about the requirements. Typically, we include the following sections:
- Intro/Compensation - Hook candidates. Make them excited to read more.
- About the Company - Prove that we’re legit while being honest about how small and young the business is.
- We’d Like Someone Who Can - What does this job entail? What are the day-to-day responsibilities?
- Expectations - What skills, experience, or capacity must candidates have to be considered?
- Perks - What do candidates get from us in return? It’s not all about money, so be sure to highlight the team, learning/growth opportunities, benefits, and any other intangibles.
Finally, we customize the job application form for each role, but we always include one question to help weed out people who are clearly just “spraying and praying.” Typically, we ask them why they want to work with us or what appeals to them about this role.
At least 30% of candidates don’t fill out that field and we eliminate them immediately.
3. Set Compensation
We currently use a fixed, transparent pay rate for each role. We show compensation as a range or fixed number in the job description so that candidates can opt in or out accordingly.
I would rather not waste a candidate’s time if their salary expectations are outside our limits. This also helps limit pay bias because we don’t let candidates who are more confident negotiating set the compensation rate.
4. Build a Candidate Pipeline
It’s hard to evaluate candidates without a basis for comparison. We try to gather at least 20-30 applications before evaluating anyone so we can easily see what top tier and bottom tier candidates look like.
Here are some ways we typically build a candidate pipeline:
- Post to job boards - Dynamite Jobs, WeWorkRemotely, Remotive.io, Linkedin, Indeed, Angel List, and niche job boards are our best sources.
- Share with the team - Let everyone know we’re looking and ask them to share on social media.
- Direct outreach - For more competitive positions (eg: management, engineering), you will need to reach out directly to candidates. Start with your network and branch out from there.
If you still don’t get enough candidates, you need to go back to the drawing board. Typically, your options are to spend more money promoting the listing so you get a larger “top of funnel” or add more money to the job’s compensation to attract better candidates.
5. Resume/Application Screening
As we build up a pipeline, we start to screen candidates based on their application form questions and their Resume or Linkedin job history.
Typically, one of our application questions will require them to write a fairly detailed story. This helps us evaluate their written communication skills and other required skills, and it often weighs more heavily than their resume.
But, work history is still a valuable method of screening out bad fits. For example, if someone is applying to our Account Management role, but they’ve never been an Account Manager, Salesperson, or similar role before, we’re likely going to reject them right away.
6. Mini Assignment Evaluation
Next, we ask our top 10%-25% of candidates to complete a “mini assignment” that can be done in 15-30 minutes via email.
This mini assignment ensures the candidate is actually interested in the role and it allows us to quickly assess one or two of the required skills via email. In an ideal case, it also gives the candidate some insight into what the job requires.
For example, Account Management candidates are given a list of client scenarios and asked to draft responses to each. This lets us see how well they communicate via email, their ability to empathize, and how well they can upsell a happy client.
This usally helps us screen out 50% of candidates before inviting the remaining ones to a call.
7. Conduct a Screening Call
Next, we invite candidates to have a 30-45 minute screening call. We use a pre-selected list of questions during the call and take notes on their answers.
Each question is designed to assess one or more of the essential job skills outlined in step 1. We avoid “What would you do if…” questions in favor of “Tell me about a time when you…” questions.
Finally, we close each screening call with a bit of a sales pitch for the role and we give the candidates 5-10 minutes for their own questions.
8. Give a Paid Trial Assignment
After we finish the screening calls, we typically have 2-5 top tier candidates left. These candidates are then given a 3-6 hour paid trial assignment.
We design these trial assignments to be as close to the real job as possible, and we try to assess all of the essential skills.
For example, Account Managers are given a client dossier and asked to plan and conduct a renewal presentation. Our existing Account Managers will play the role of the client while the canddiate gets to see what it’s like doing the job.
For engineers, I used to do a half-day paired programming session. This showed them the kinds of technical problems they’d see and let me understand how they solve problems and communicate.
Before making an offer to the top candidate, we contact two to three professional references. We have phone conversations (as this allows them not to leave a papertrail) and we often try to find a “backdoor reference” too (someone who worked with the candidate in a past role but who was not on their official reference list).
Only once have I gotten a negative reference about a candidate. I hired them anyway and regretted it for the next 5 months until I ultimately had to let the employee go. That painful experience taught me to be more serious about reference checks.
When reference checks are done, we extend an offer email to the top candidate. The offer letter should include:
- Potential start date
- Salary/other comp
- Job description
- Hours/week expectation
- Acceptance deadline
You want them to decide quickly so you don’t loose your next few candidates during the wait. Typically, we give candidates 3-5 business days to make a decision, but if the candidate needs more time, we will grant it.
Once you have a strong process for hiring that’s based on objective assessments instead of “gut feelings,” it’s a lot easier to be confident about making hires.