How to hire employees for startups: Interviewing and evaluating early hires

There’s one thing your startup can’t ship and improve over time—it’s your recruitment strategy.

Having a poor hiring process can negatively impact business growth. For an early-stage startup, that can mean missed revenue, higher churn, or even missed opportunities to fundraise.

Not to mention the huge cost of employee turnover and having to re-do the onboarding process.

It takes time to rehire and educate future hires about your customers or industry.

To avoid a poor startup hiring process you need to:

1. Have an actual interview process—that means having the steps outlined, aligning it to the job’s objectives, knowing who’s involved, making sure it’s competitive vs other startups, plus other steps we’ll include in this guide
2. Avoid using a overly templated hiring process—those just don’t work because you need to screen for the objective and competencies you need for your business, early hires aren’t just another role to fill (which is how most templates treat hiring)

So if you’re ready to build an effective early-stage hiring process for your startup, here’s what you need to do to get the best potential hires.

What to do before you start hiring your earliest employees

Look at the role and where your company is first aka work on “Job Design”

Before you even write your job description or center on a job title, you need to decide:

• What objectives do I want my potential employees to achieve
• What core competencies and practical skills do I need prospective employees to have (should be complementary to other current employees you have or founders)
• What time period am I looking to achieve those objectives in
• What are the things that can sell our startup as an attractive company to work for

You need to answer all of these questions before you create any job listings.

Decide on the core team for the interview process

To decide who should be involved from your team, you need to look more at the hiring roles that need to be distributed.

We recommend having the following roles covered in early hire interviews:

• Someone that can screen for culture and core values
• Someone that can screen for a prospective candidate's current skills and experience
• The person that is going to be the direct manager for this role
• Any other internal stakeholders that can screen for cross functional compatibility

Each startup is going to have a different number of people it takes to fill these roles. Some might be able to fill these roles with just a couple people while others might need additional team members.

It's critical that every single person involved in the hiring process understand and agrees on what the ideal candidate profile looks like.  Without this, you will waste time and create a ton of friction in your process resulting in a poor candidate experience.

- Kevin Mulrane, 4x Sales Consultant and Former CRO

If you’re using a recruiting agency like Captivate Talent and have internal recruiters, you shouldn’t double up on recruiter interviews.

However you decide to distribute these roles, we recommend that you keep the interview process no longer than 6 steps for leadership hires and 3 steps for individual contributors.

So if you have more than 6 people that need to be involved in the hiring process, you should consider having a group interview with multiple stakeholders or even better, reducing the number of people involved.

Should my investors, advisors, or consultants be involved in the interview process?

You should only add people to the interview process that can either

• Help screen for company culture fit
• Have the knowledge of the space or have hired for the role
• Help sell the company

Investors can help push qualified candidates over the line, but only when they have a knowledge of the industry or customers or can help sell your company—they should not be involved because you are unsure about interviewing a candidate.

For advisors, the same is true. It can be helpful to have advisors in your recruiting process that have a board seat, have knowledge of the space, or have hired for a similar role.

All other advisors should not be involved.

For consultants, you need to be careful about how you involve them in your recruitment strategy.

Is it going to be advantageous for a consultant to slow down a hiring process because they can collect a paycheck for a few more months? Is the consultant going to be phased out as a result of any future hires?

If you answered yes to either of those questions, you might want to reconsider including them.

Mistakes to avoid when assigning interview roles

The biggest mistake you can make is assigning someone a role that looks at interviewing as something to get off of their checklist.

Everyone involved should be committed to hiring the right person vs willing to push someone along just to get it off of their plate.

Design a competitive interview process

Follow an interview timeline that’s competitive

Your interview process should take no longer than 3-4 weeks from first interview to offer.

This doesn’t mean that you should hire startup employees in 3-4 weeks. It means that each candidate should not spend more than 3-4 weeks in the hiring process.

You want to avoid having a candidate interview for multiple months before making a hire.

Most candidates will be interviewing at other startups too and a lengthy hiring process can result in missed talent because someone got their offer out well before you could.

Map out the steps for the interview process

The number of steps in the hiring process should differ between leadership hires and individual contributor hires.

For leadership and executive hires, we recommend having 4-6 hiring steps.

For individual contributors you should do about 3 steps.

It’s ok to have multiple steps in a week too. If you speak to a candidate on a Monday and want to advance them, you can try to schedule time for the next step in the same week.

Don’t feel like you can only schedule one step per week.

In terms of the actual steps here’s what we recommend

Step 1—Assess for culture fit and alignment to company values

You want to evaluate for culture fit early because if you don’t, you risk getting deep in the interview process before realizing that someone is the wrong person for the role.

Keep an eye out for those soft skills that will align with your team.

When you don’t screen for culture fit immediately, you risk:

• Hiring someone that doesn’t align with your culture or company values because you fall in love with their skills (and sacrificing your company values)
• Wasting your time and the candidate’s time because even if they have the skills for the role, they won’t fit culturally within the team

Step 2—Assess for current skills from potential candidates

After evaluating for culture fit, you want to make sure the candidate can do the job.

You’ll need to assess for:

• How closely each candidate matches the skills on your job description
• How well the candidate knows the personas and industry you sell to
• How well the candidate understands where your company is in terms of revenue and where you’re trying to go

For leadership hires, this might be more of a conversation vs for an individual contributor where you might ask them to complete a short exercise.

You should avoid lengthy assignments for leadership hires.

There’s a fine line between consulting work and showing you’re capable of doing a job. Make sure you’re on the right side of that line.

Ask for previous work samples if you need more content to evaluate on.

Steps 3-5—Additional leadership meetings and internal stakeholder meetings

Once you find that a candidate fits culturally and has the skills to do the job, you want to have them meet with any other full-time employees, business owners, etc. that they might be working closely with.

You want to make sure that candidates can work well with everyone else and everyone else feels like this candidate can help your startup reach its objectives.

Final steps—Walk through execution for the first six months

Every leadership or executive hire should be able to walk through what they are planning to do in their first six months.

This should be a conversation that includes any key stakeholders.

You want to make sure that you get tactical here. Look for strategy AND execution. When you do this exercise right, you should be able to avoid any surprise asks in the first six months.

Make sure there are backup interviewees

One of the worst things that can happen during the hiring process is that you find a candidate you like but you’re unable to have that next interview because a key stakeholder is out.

To avoid situations where someone may be on vacation or out for personal reasons, you want to have backup interviewees that can step in.

If you have to wait for a key stakeholder to return before a certain step in the interview process, you risk having another startup scoop up a great candidate.

How to manage the interview process for early-stage startups

Most of the hard work you do to hire your earliest employees should be around designing the job and the hiring process.

It doesn’t get easier when it’s time to actually conduct the interview, but if you set up the right process, you should feel confident heading into interviews.

The goals during the interview process are:1

• Find candidates that are a culture fit and have the right intangible skills
• Find candidates that have the tangible skills to do that job
• Reject poor fit candidates early
• Find what potential candidates are looking for so you can use that to pitch them the job

For any early hire, you should identify 5-7 skills you are looking for and score candidates on those accordingly.

Evaluate for intangible skills and company culture fit

You don’t need us to tell you that building a successful startup is hard.

But do job applicants know that?

The first few skill sets you will want to evaluate all candidates for are:

• Scrappiness
• Grit
• Creativity
• Ability to execute with minimal resources

In my experience, somebody's passion, ambition, and hunger to accomplish something usually gets them through the how. On top of that, I would say the second most important thing for me is curiosity.

Somebody who is deeply curious about the world, somebody who during the interview, you leave them 10 to 15 minutes about questions, four questions, and you're running out of time and you need to end the meeting because you're five minutes late and they still have more questions.

- Sebastian Stryker, Head of Sales at RepeatMD

Make sure to evaluate how candidates match your company values and ability to work with others on your team to establish culture fit.

These skills are especially important to evaluate on if you're hiring remote employees.

Some other things you may want to consider evaluating on are:

• Industry
• Company size
• Company stage

This can help identify ideal candidates that understand the amount of resources they’ll have and ones that know the space well enough to decrease ramp time.

Without evaluating for this, you risk hiring someone who’s expecting vastly different resources than the ones you have to offer.

Evaluate for tangible skills

Here, you’re not looking for a candidate that can do everything on the job description.

You’re more looking for the candidate that most closely matches the job description.

It will be almost impossible to find candidates that have every single skill that you’re looking for.

For the candidates that you find that don’t match all the skills, if you decide to move them forward, you need to have strong reasoning on why you’re willing to sacrifice that skill.

What questions should I be asking potential employees?

If you’re having trouble coming up with questions, here are two of our favorites to screen for:

What’s the driver for you to move into a new role?

Here, you’re looking for why they are considering leaving their current role.

The strongest answers should align with what your company has to offer. For most startups, you’ll want to avoid candidates that are just looking to make more money.

What do you find attractive about our startup?

Here, you’re looking for signs that they’ve done their research about your company and they have sound reasoning on why they are interested.

Are they interested in the product? The industry? The founders?

Look for answers with substance and be comfortable asking “what do you mean?” to avoid generic responses.

Keep candidates around the same stage for a more seamless hiring process

As you set up interviews, try to focus on having candidates around the same stage in the process.

You want to avoid situations where one candidate might be in their first interview and another is in their final. It will make it hard to compare those candidates.

Find out motivations to win best-fit candidates more often

As we mentioned earlier, you should be finding out what a candidate is looking for in their next role and why they are looking to leave.

Since most candidates will be interviewing at other places in the same time period, knowing the motivators can also help you win in the offer stage.

"One of the early things that you should talk about with the candidate is their drivers.

This is usually part of the culture interview, like what's the driver for them to move into a new role and what do they find attractive about your company.

This will help you continually manage them and close them down at the end of the interview process."

- Chris Gannon, Founder of Captivate Talent

If a candidate lets you know they received another offer with a bigger compensation package and asks you to match, you can actually use this as an opportunity to remind the candidate why your offer might actually be a better match.

It’s not always about the cash. Figuring out motivators and using that during the interview process can keep candidates around without you having to come up with extra cash for an offer.

What to do after the interview

Once you interview candidates, you want to make sure you debrief and provide feedback as quickly as possible to the candidate.

Don’t keep them waiting too long, it can signal you’re not interested or worse, you don’t have an effective system in place.

For candidates that you decide to offer, work fast on any reference checks after you agree on a verbal offer.

How to communicate with candidates post-interview

To provide the best candidate experience, make sure you give feedback to all candidates within 24 hours after any interview. The earlier is better.

You want to avoid situations where a candidate goes into the weekend without receiving feedback.

Communication should be open and transparent. Avoid being cold but provide helpful feedback to a candidate on why they’re not moving forward if that’s what you decide.

If you’re rejecting a candidate after the first interview, a canned email is fine (although a thought-out response is better).

If you’re rejecting a candidate after multiple interviews, you need to call them.

Remember, candidates are investing their own time in the interview process. Think about what your expectations would be with similar time investment.

Once you agree on a verbal offer, work on reference checks

You want to avoid doing reference checks early for three potential reasons:

1. You might not be able to agree to terms, so you're wasting a lot of time and energy doing reference checks on something that might never materialize
2. You could alert a candidate’s current employers and they might fire them from the job before you've decided that you want to make a final offer
3. You might let other people in that candidate's network know that they're on the job market or potentially looking to change their job before you have them locked in with your offer—we’ve seen cases where someone’s mentor offers them a job because they find out they are available

"Candidates, good candidates should be able to give references pretty quickly though. If somebody is working and currently employed, you should not expect to do reference checks until you at least have a verbal offer agreed upon."

- Chris Gannon, Founder of Captivate Talent

For prospective hires, you should stick to two to three reference checks max.

If it’s a leadership or executive hire, we recommend the 360 approach for reference checks:

• Get a reference from someone they reported to
• Get a reference from someone they managed
• Get a reference from a peer

Good candidates should be able to provide references quickly, but make sure it’s only done once a verbal offer has been agreed on.

Closing thoughts on interviewing and evaluating early hires

The effectiveness of your early employees is largely dependent on the effectiveness of your hiring process.

If you come unprepared, you’ll end up picking candidates who might be:

• Highly-skilled candidates but aren’t a good culture fit
• Poor-skilled candidates that can’t help you reach revenue goals

Your interview process should have a plan that includes clear questions to ask (behavioral and situational) and clear ways to evaluate (assignments, work samples, six month plans, hiring scorecards, etc.).

An effective interview process has the following traits:

• It’s competitive and the time from first interview to offer is 3-4 weeks
• Candidates stay around the same stage so that you can evaluate them equally
• The interviewees in the process have been picked and everyone knows their role
• Culture fit is established first, then skill fit, then ability to work with the rest of the team
• Communication happens fast and candidates aren’t waiting too long for feedback
• References are used to double check what’s said in interviews match reality

Startup hiring is hard—candidates don’t know your brand, you typically are pressed for time, you don’t have as many resources available to offer, and things are quickly changing.

But by creating an effective interview process, you can hire with more efficiency and more confidence.

If you’re struggling to create an effective recruiting process, consider going with a recruiting agency like Captivate Talent. We can help design your interview process, run it, and give you time back that might be spent on some of the early stages of the hiring process.

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