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The Ultimate Startup Hiring Guide: How to Build A Winning Team

By Emily Smith on Mon, Mar 30, 2020

As your startup begins to grow beyond its founding team, every new hire fundamentally changes the company DNA, and it becomes increasingly important to take a strategic, systematic approach to hiring:

Startup hiring - Yevgeniy Brikman - Gruntwork.jpg

Choose the first 10 employees very carefully, as they determine the next 100.

Yevgeniy Brikman, Gruntwork

After funding, the biggest barrier to startup growth is hiring – not having the right people, in the right roles, at the right time. To help you make smart, strategic hiring choices, and build a killer startup team, in this post I'm covering the ins and outs of startup hiring, from the challenges you’ll face through to creating a simple but effective hiring process.

The Challenges of Growing a Startup Team

Startup hiring - Gil Belford - Hole19.jpg

Being able to find, hire and maintain the right kind of talent for your company will make or break it.

Gil Belford, Hole19

Hiring your first employees is an exciting, significant milestone for any startup founder. However, it’s also a challenging time: if you hire the right people, you’ll bring on board the skills and experience needed to grow your company and develop your product; but if you hire the wrong people, the success of your company is at risk.

Growing your startup beyond the founding team is daunting – particularly for first-time founders, or anyone who has never been involved in the hiring process before. While hiring for any role at every stage of company growth is always difficult, for early-stage startups, growing your team is a particular challenge, for three main reasons.

1) Every Hire can Make or Break Your Team

A poor culture fit can bring down the entire venture, while a strong fit can strengthen morale, boost productivity and encourage innovation.


As your startup grows beyond the founding team, every new addition to your team will fundamentally change your company's DNA. New hires impact everything: product development; company culture; team morale; work quantity and quality; team capabilities... The list goes on and on.

In a small team, and in the fast-paced, high-stakes startup environment, the impact of any mismatch in values, processes or culture will be magnified. Hiring a good-fit team member can increase your capacity and skill set, as well as improving team morale. However, if your new employee is a bad fit for your team's culture, they will have a negative impact on the work environment, and can actually lead to a decrease in productivity levels, despite an increase in team numbers.

2) You’re Perceived as a High-Risk Opportunity

Zoe Barry - ZappRx.jpg

Working at a startup isn’t for the faint-hearted.

Zoe Barry, ZappRx

It's important to realise that joining a startup won't be the right choice for everyone: for some, the opportunity will be exciting and energising, but for other people it will be overly stressful and risky.

Working at a startup is very different to working at an established company, and many skilled prospects will be reluctant to leave the perceived security of a job at an established company to join a startup with no funding, and no track record of success.

As a personal example, when I was joining Cobloom as the first non-founder on the team, I received advice from many trusted sources, advising me not to take this job and stick with my 'safer' former employer. When you're getting that advice from people whose personal and professional opinion you trust and respect, it can be very difficult to trust your instincts and go against that.

3) You’re Unknown

When nobody knows who you are, attracting top talent is extremely difficult. Unless you or one of your co-founders has a noteworthy background, you and your company are unknown - particularly if you're bootstrapping or you're yet to raise your first round of funding.

This means you'll need to work especially hard to attract good-fit prospects, and you'll have to sell your company, your vision and your existing team to them. Too many companies forget that hiring is a two-sided process - not only does the job applicant need to impress you, but you also need to impress them.

Overcoming the Biggest Startup Hiring Challenges

Startup hiring - Will Steward.jpg

Hiring is the most important responsibility a manager has: so invest the time to do it right.

Will Steward, Cobloom

Hiring should be one of the top priorities for startup founders, and you should be prepared to dedicate a lot of your time to everything associated with the hiring process.

To move beyond your first handful of employees will require careful planning. So, how can you attract top talent to your as-yet-unknown startup?

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How to Hire Employees for Your Startup

Startup hiring - Ryan Allis - Hive.jpg

Your first few hires will absolutely be critical in the long term success of your business

Ryan Allis, Hive

The success of your startup depends on your ability to build a team of great people. But when you're a small team working on a product that only a handful of people have heard of, convincing top talent to join you is no easy feat.

The first step in hiring the first employees for your startup is attracting talent: creating a company that appeals to top-quality applicants, getting your job advert in front of the right people, and getting them excited about the work your startup is doing. Fortunately, there are several things you can do to ensure you're attracting top talent for your next job vacancy.

1) Build an Attractive Company

Your first few employees are likely to come from your founders' extended network, and in this case the hiring process is likely to be much more flexible than with subsequent hires. In these early days, before you worry about getting job descriptions spot-on, or sharing your job adverts in the right place, you need to focus on building a company that people want to work for.

That doesn't mean you need to invest in expensive employee perks or slick offices (though by the time you're hiring your first employees, it will look better if you're not working out of your garage or spare bedroom). Instead, it means sorting out your identity as an employer: nailing down your company's cultural values and making the most of your social presence.

Company Values

Your company values are one of the most important facets of your identity as a company and an employer. It's essential to define these early, and to share them publicly on your website and blog to help prospective employees get to know you.

One stand-out example of a startup who's done this is Buffer, whose Open blog is an ongoing embodiment of their key values of transparency and openness. Similarly, here at Cobloom we have our Insider blog, where we share real-life examples of how our company values of continued learning, data-driven decision-making and self-improvement affect the work we do, the way we hire and how we make decisions.

Defining and sharing your company values is a great starting point from which you can start to evaluate prospective employees based on culture fit – something which is essential for building a close-knit startup team.

Online Presence

One of the biggest challenges of building a startup team from scratch is that in the beginning you're a complete unknown, so it's essential that you make a conscious effort to build an online presence and identity.

The first company I ever worked for had no website, no blog, no social media presence - nothing. In hindsight, that was a major red flag: I started work there with no idea at all about the company, its values or company culture, and it didn't take me long to realise I was a poor-fit.

While it's unlikely your startup will be in the same situation, it's worth taking a strategic approach to your website content and social media activity to create a consistent identity and presence across different platforms.

Compensation Packages

Startup hiring - Jose Ancer.jpg

Make sure you’re hiring talent with realistic expectations for your company’s stage. Salary v. equity expectations are often a valuable signal here, and can select for the right or wrong people

Jose Ancer

Competitive pay is essential for attracting talented employees, and it's even more important for employee retention.

In the early stages of your startup, it's likely your employees will be underpaid, relative to the market rate for their skills and the work they're doing, as you won’t have the cash available. It's crucial that you bear this in mind, and work to bring employee salaries up to market rate as soon as it's feasible to do so. However, in many cases this doesn't happen until you've secured your first round of funding.

Additionally, it's common for early employees to be granted equity in the startup, as part of their compensation package:

Conner Forrest - TechRepublic.jpg

Equity compensation—getting a piece of the company—is one of the defining aspects of working at a startup. It is attractive not only for its perceived monetary value, but for the sense of ownership it gives employees.

Conner Forrest, TechRepublic

Offering equity is a good way to attract right-fit potential employees: many will be happy to sacrifice a portion of their salary and tolerate being "underpaid" for a while, in exchange for the ownership and long-term reward that equity provides.

A Note on Salary Negotiation

When you're thinking about compensation packages, you may want to consider implementing a no-salary-negotiation policy - for all candidates, across all roles.

Salary negotiation is a big contributor to the gender pay gap: men are more likely than women to negotiate their starting salaries, but even when women do negotiate their salaries, they're viewed less favourably than their male colleagues and are deemed "aggressive" and "not team players".

With the lack of diversity in tech being such a widespread, ongoing issue, getting rid of salary negotiations across the board can be a good starting point for creating a startup with equality as one of its core values.

2) Reaching Candidates

As a startup founder, you should always be recruiting. Even if you don't have the workload or resources to actually grow your team right now, it's essential that you are nurturing relationships and building connections for when a specific hiring need arises.

Building an attractive company will help convince potential employees that they want to join your startup, and will attract inbound leads who are interested in your product, team and company culture. However, when it comes to hiring the best people, you can't wait for them to find you: you need to look for them, too.

Startup hiring - Dharmesh Shah.jpg

In order to get the best people, you have to help them find you. This is particularly challenging, because many of the best people are not looking.

Dharmesh Shah


Tom DeVoto - NextView Ventures.jpg

Personal relationships are far and away the biggest source of talent.

Tom DeVoto, Nextview Ventures

If anonymity is one of your biggest hiring challenges, there's a relatively easy fix. As well as sorting out your online presence, it's just as important to dedicate time to networking in the real world.

Attending conferences, talks or tech meetups are great ways to grow your network. You might even meet your next hire there.


Think of networking as a passive way to reach potential candidates; in contrast, sourcing is the active way.

If you have a good idea of the role you're going to be hiring for next, you may want to invest some time in identifying good-fit applicants within your extended network, and reaching out to them directly.

Startup hiring - Will Steward.jpg

We found active sourcing to be highly effective – I reached out to potential candidates personally, and received responses to the majority of my messages.

In our experience, the key to success has been taking a hyper-personalised approach: you don’t want to come across as ‘just another annoying recruiter’. Engage the person on an emotional level: do your research and tailor your message accordingly.

Some ideas you can use to start a conversation include: connections in common, similar interests, similar skills/experiences, social media posts, or even content they've written. Remember – your goal is just to start a conversation in the first instance.

Once they're engaged, try to line-up a casual conversation, explaining that you have an exciting opportunity you think they'd be interested in.

Will Steward, Cobloom

Active outreach isn't just something for you and your co-founders to do, either. Your early employees are likely to all have strong networks of their own - talented people know other talented people. Share next-hire requirements with your team, and encourage them to reach out to any of their contacts who they think would be a good fit for the role.

Attracting the Best-Fit Employees

When it comes to startup hiring, quality beats quantity, every single time. You don't want to attract anyone and everyone, and spend hours sifting through countless resumes and applications. Therefore, it's essential that you have a clear idea of what a good-fit employee will look like, before you begin networking in earnest.

In the next section of this post, we're covering what you should look for in prospective hires, and how to evaluate skills and culture fit.

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What to Look for in Prospective Employees

Finding great employees can feel like searching for a needle in a haystack. Before you begin the hiring process it's essential that you identify the top priorities for your new hire:

  • What level of experience does the applicant need? Do you need a developer with 10 years' experience, or will you consider new graduates?
  • What skills are essential for the role?
  • Do you need someone with in-depth knowledge in one specific area, or will someone with a broader range of knowledge and experience be a more valuable hire?

Fortunately, with careful consideration you can identify key traits to look for in prospective applicants, before you begin the hiring process. To help you establish your top priorities, we've identified five key areas to consider.

1) Attitude vs Skills

On paper, it's easy to assume that the most qualified candidate is your best option - the one with the most experience or a particular skill that you're looking for. However, it's important to realise that, in a small startup team, attitude can be just as important:

Bryan Lee - Tutum.jpg

It doesn’t matter if you’re the best developer out there; if you can’t work with the rest of the team and if you actively cause disruptions with everyone you work with, we can’t hire you.

Bryan Lee

This is something that you won't be able to directly identify from a resume alone, but is important to bear in mind when it comes to interviewing candidates.

2) Potential vs Experience

Is it better to hire an experienced candidate, or one with less experience but more potential to learn and grow with your startup?

This is an important question to ask, and there's no easy answer.

The 'right' mix of potential vs experience will depend on many things: your company culture; the role you're recruiting for; your long-term growth plans for your startup; and the capabilities of your existing team. This will change each time you hire someone, too, as your startup team grows and develops.

3) Culture Fit

Tom DeVoto - NextView Ventures.jpg

Finding applicants who can do a job on paper is not overly difficult. The true challenge is to find candidates who will mesh into a small, budding team and culture.

Tom DeVoto, Nextview Ventures

Like attitude, this isn't something you can assess from looking at a resume. Culture fit, particularly for your earliest employees, is just as important as finding someone with the right skills. This is because your earliest employees are integral to building your company culture. The type of person you hire now, in terms of their attitude and values, will have a significant impact on the type of people you hire in years to come.

A Note on ‘Culture Fit’ and Diversity

It's important that you don't confuse 'hiring for culture fit' for 'hiring someone just like you'; this can contribute to a lack of diversity within your startup team and mean you're missing out on the creativity, experience and knowledge of more diverse applicants.

Tom DeVoto - NextView Ventures.jpg

At the seed stage, each and every new hire must be a fit, and that word “fit” implies different pieces to a puzzle — not pieces that all resemble each other.

Tom DeVoto, Nextview Ventures

4) Soft Skills

Things like communication skills (both written and verbal), interpersonal skills, teamwork, creativity, adaptability and empathy are easy to overlook when you're sifting through job applications and interviewing multiple people, but are just as important as the practical skills which are easier to demonstrate.

5) Generalists vs Specialists

What will be the best option: hiring someone with a wealth of experience in one specific area, or someone else with a wider range of experience in a number of areas, but less in-depth knowledge?

The generalist vs specialist question is a difficult one. You may find that for your earliest employees, you are better off selecting employees who are generalists, with a wide skillset. However, as your startup grows and roles become more clearly defined you'll need employees with specific skills, as it will become less important for all your employees to be able to 'do it all'.

Startup hiring - Alexander Taub.jpg

Companies in their infancy need people to do many things... At a certain point, generalists need to develop a speciality or they will not make it to later stages of a company.

Alexander Taub

To this end, it's becoming increasingly common for startups to look for 'T-shaped' employees as their earliest employees - that is, people with a broad range of experience in various areas, but a depth of experience in one.

T-shaped employees.jpg

Startup hiring - Andrew Chen.jpg

I’ve come to believe that the first batch of people you want on your team are going to be T-shaped, meaning they are broad in a bunch of different areas and deep in a particular one.

Andrew Chen

Your 'Perfect Candidate' Will Change Over Time

Your first employee is likely to be a very different type of hire to your 10th, 20th or 50th. What you identify now as your priorities for your next hire won't always be what's best for your startup. Therefore it's important to reassess your priorities regularly, to avoid falling into a trap of making cookie-cutter hires that are perfectly suited to what your startup needed six months ago, but don't fill the skills/experience gap that you've got now.

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When and Who should your Startup Hire?

Building a fantastic startup team is an ongoing act of prioritisation. You need to constantly make decisions about who your next hire should be, based on the ever-changing needs of your startup's workload and your team's skill set, and when you should be looking to hire, based on the fluctuations in your workload and the types of work required.

Who to Hire

Startup hiring - Ryan Allis - Hive.jpg

You must begin the process of scaling yourself by hiring others who can free up your time to focus on growing the business instead of working in the business

Ryan Allis, Hive

As your startup grows, your main priorities will expand: from product development, to reaching prospective customers, to acquiring paying customers, to retaining them. As a result, the type of roles you are most commonly hiring for will change over time.

When your focus is on product development, you'll need more developers than customer support personnel. In contrast, by the time you've got a sizeable customer base, you'll need to invest more in customer success in order to improve customer retention. Therefore, making decisions about who to hire will be closely linked to the stage your startup is at.

Additionally, your decisions about who to hire will be dependent on your startup’s existing skill set: have you identified particular skills or experience gaps within your team? To keep track, you may want to inventory your team’s skills, compared to the types of work your startup is doing. Then, as your team’s workload changes, you can identify where gaps are appearing, and bring on additional team members to fill the gaps before they become a major problem.

When to Hire

Hiring too early can leave you stretched for cash, and hiring too late can leave your team struggling under an ever-mounting workload. Deciding when to hire is a delicate balancing act:

  • Can you afford to bring on a new hire?
  • Do you have the workload to support a new hire?
  • Do you have time to recruit and onboard a new hire, before your team’s workload becomes overwhelming?

You’re juggling time, money and workload, and in an early stage startup these three factors are constantly changing at a rapid pace.

When it comes to hiring your first few employees, your decision about when to hire will probably be mostly gut instinct: you’ll have a sense that your existing team is becoming stretched and that it’s necessary to expand your team.

However, with later hires it’s important to take a strategic approach: you might want to map out planned hires several months in advance, and identify key financial and workload indicators that will mean you’re on-track for needing to bring that additional team member on board.

A Brief Note on Investment

Startup hiring - Nick Marsh - Lost My Name.jpg

Rapid hiring happens after investment rounds... investors expect a sudden uptick in headcount

Nick Marsh, Lost My Name

Raising investment will have a significant impact on your hiring strategy and roadmap. On the one hand, it will provide you with the capital needed to hire top talent, but on the other you may find yourself under pressure from investors to grow your team more quickly than planned - and possibly more quickly than you need.

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How to Write a Job Description

Now it’s time to get a bit more practical, and take a closer look at the nitty gritty involved in hiring someone. First, I want to cover how to write a job description, before we move on to building-out a seamless hiring process for your startup.

Startup hiring - Gil Belford - Hole19.jpg

A good job description should reflect the culture of your company, down to what you include in it and the type of language used in it.

Gil Belford, Hole19

In many instances, a job description is a candidate's first impression of your startup. To help you nail that first impression, we're digging into the dos and don'ts of writing a great job description.

Standing Out From the Crowd

One of the biggest hiring challenges facing your startup is standing out from the ever-growing crowd of other early-stage startups. Your job description needs to engage and excite potential candidates, while also listing skills and experience required to be suited to a role.

Startup hiring - Joel Grossman.jpg

Pen job descriptions with personality that’s unique to your company alone.

Joel Grossman

To overcome this challenge, it's essential that you avoid copycat job descriptions that sound just like the twenty other open vacancies for that type of role on popular job sites. Work out what makes your startup unique, what makes your company culture unique, and find a way to inject that personality into your job description.

Startups who do a great job at this: Buffer, Drift, HubSpot.

Job Description Language: A Word of Warning

Startups (and established companies) work hard to inject personality into their job description. However, it's worth considering your choice of language from an inclusivity and diversity standpoint. Many of the phrases used to bring energy and personality into your job descriptions can be perceived as indicators of an ingrained 'bro culture', and can put-off female and minority candidates from applying.

Which words to I mean? Well, here's a short selection (Huffington Post covers this in more detail):

  • Ninja
  • Hacker
  • Kill / crush the competition
  • Work hard and play hard
  • Ambitious*

Laura Mather - Unitive.jpg

I don’t ever recommend using the word [ninja]... It is a very strongly ‘bro-grammer’ type term.

Laura Mather, Unitive

*Of the five words and phrases above, the top four are fairly similar: they indicate an ingrained 'bro culture'. However, the fifth is slightly different: 'ambitious' is one of those words that has different connotations when associated with different genders; an ambitious man is viewed much more favourably by society than an ambitious woman.

Particularly when listing desirable traits for candidates that go beyond practical skills and focus more on attitude and culture fit, it's important to assess the terms you're using for inclusivity and gender neutrality, to avoid building yet another all-male, all-white startup:

Startup hiring - Adam Pisoni - Abl Schools.jpg

It is more difficult to find, hire and retain people whose backgrounds are not presently represented at your company... If you have 10 employees who are all men, you will find it far more difficult to find, hire and retain women. Women who interview with you will be skeptical about how inclusive your company is when there is little evidence to support it.

Adam Pisoni, Abl Schools

What to Include in Your Job Description

Startup hiring - Gil Belford - Hole19.jpg

When writing about the job and the company, you should strike a balance between letting candidates know what skills and characteristics they need to have, and what benefits and challenges they’ll find once they join your company.

Gil Belford, Hole19

There are three main parts of a written job description: a section about your company; one about the role and specific requirements; and finally, one about the benefits, perks and compensation.

1) About the Company

Startup hiring - Andy Jagoe - VentureGrit.jpg

Getting your startup to stand out from the crowd takes some work. Especially since the best talent is fully employed and not spending their time actively scanning job boards.

Andy Jagoe, VentureGrit

This is where you need to sell your startup to prospective candidates. What is your startup's mission and key values? What do you do, and why does it matter?

The 'about the company' section of your job description is where you aim to make your startup stand-out: it's likely you'll be listing your job advert on popular startup hiring sites where it will be viewed alongside dozens of other roles, so it's essential to make it unique and memorable.

2) About the Job

For your earliest employees, writing about the on-the-job requirements can be difficult, because there's so much to cover. An extensive list of requirements is likely to negatively impact diversity in your startup: men apply for a job when they meet only 60% of the qualifications, but women apply only if they meet 100% of them.

To counter this, a better approach could be to focus on expected results, rather than specific requirements. What will the ideal candidate need to achieve in the role, in order to be successful? Alternatively, if you do want to include a list of required skills and experience, you may want to consider splitting the list into 'essential' and 'desirable', rather than having a long list of requirements that appear set-in-stone.

3) Perks and Compensation

Startup compensation for early employees comes in two parts: salary and equity. If you're offering equity to employees, it's essential that you mention this, as it forms a crucial part of their overall compensation package.

Listing salary can be difficult, particularly for cash-poor early-stage startups. However, it's important that you provide a salary range where possible: equity won't pay the bills, and it will be a waste of your time to interview candidates who have over-estimated your startup's salary offering.

Perks are another important consideration. True story: one big thing that appealed to me when applying for my job at Cobloom was that we provide employees with free books.

You might look at later-stage startups, who offer a wealth of employee perks, and see nothing but dollar signs. But there are plenty of perks you can offer relatively inexpensively: snacks in the office, a monthly book order service, a fitness tracker, dedicated personal development time every month... None of these are prohibitively expensive, but these perks are a great way to translate your startup's values into something tangible.

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Creating a Hiring Process for your Startup

Having a clearly defined hiring process is essential to help you avoid expensive hiring mistakes that can destabilise your entire startup team. Hiring isn't something that early-stage startups do regularly, so you want to put a process in place as soon as possible - something to guide you through step-by-step so that nothing gets overlooked or forgotten.

Once you’ve written a job description and started advertising your vacancy, you should start to get applications coming in. To manage the hiring process in a simple and easy way, there are five stages you need to follow, from application to making a hire.

1) Screening Written Applications

The very first step of your hiring process will be to screen written applications. In the first instance this will involve comparing applications against the required skillset listed in your job description. Candidates who don't meet your 'must-have' requirements will automatically be counted as a poor-fit for the role. Additionally, you may have identified other red flags that indicate someone will be a poor fit for working with you, that are linked to your startup's culture and values.

Once you have identified good-fit candidates, you can progress them on to the next step in the process. To get an idea of how they work, it's a good idea to integrate some sort of practical skills test into your hiring process.

2) Practical Skills Test

This will vary depending on the type of role you're recruiting for, and can be done either as part of the interview, or can be a way for you to further qualify candidates before inviting them to interview with you.

For example, when I applied for my role with Cobloom, I was tasked with writing a blog post to demonstrate my practical skills, so that the team could assess whether or not I had the right skill set to be a good fit for the role, before inviting my in to interview.

As well as confirming that candidates' practical skills are in-line with your expectations, a skills test is a great way to get insight into less tangible traits such as attention to detail, their ability to work to a brief, and how they respond to feedback.

3) In-Person Interview

By the time a candidate reaches the in-person interview stage, you should be confident that, on paper, they're a great fit for the role. They will have demonstrated that they've got the necessary skills to succeed in the role and meet the requirements you laid-out in the job description.

Therefore, your interviews should be less about quizzing the candidate on their skills and knowledge of the job, and more about making sure they'll be a good culture fit for your startup's values.

Your interviews for a specific role should all follow the same format, so that you ask the same questions to each candidate. This will enable you to objectively compare candidates, and ensure you're not favouring one over another due to a perceived gap in one area, simply because it wasn't covered at interview.

I’ll cover interviewing in more detail in the next section of this post.

4) Making a Decision

At Cobloom, we have a spreadsheet that scores applicants on culture fit (are their values aligned with the company), practical fit (travel time, salary expectations etc) and skills fit (how well they completed the practical skills test). This enables us to be objective in our comparisons.

Cobloom Interview scoresheet-1.jpg
Additionally, where possible, you want to involve other people in the interview process, so you should individually take some time to evaluate each candidate before collating feedback. This can help negate unconscious bias and group-think, and also prevent you making decisions based on your gut reaction.

When you've identified the best candidate for the job, it's time to make an offer, and to inform unsuccessful applicants that you won't be moving forward with their application.

5) Communicating with Unsuccessful Applicants

One often-overlooked part of your hiring process is responding to unsuccessful applicants. It's essential that you remember to do this in a timely fashion: there's no point in making applicants wait for weeks to hear back from you, only to find out they've been unsuccessful at interview.

Responding to unsuccessful applicants promptly, with helpful feedback from their interview, can make a lasting impression, and mean that even if you don't hire them, they might recommend your startup to someone in their network, further down the line. Alternatively, they might be suitable for a different role, or the same role if you re-recruit in the future, when they have additional skills and experience.

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Developing an Interview Process for your Startup

As I've already mentioned, by the time a candidate comes in for an interview with you, you should already feel confident that they have the required skills to do the job well. Therefore, your interview should focus on learning more about them as a person, and working out how well they would fit in with the rest of your startup team.

So how should you structure your interviews, to get the best insight about what each candidate would be like to work with?

1) Introductions

Sure, it's tempting to dive right in to the interview, but remember to take a few minutes to introduce yourself and the other members of the team who will be running the interview with you. Explain how the interview will be structured (will different team members be leading different parts of the interview? Will the candidate be completing a practical task as part of the interview?), and then give them a chance to introduce themselves.

2) Assess Culture Fit

Ian Sutherland - Lost My Name.jpg

Work hard to build an interview process that applies as much weighting to culture fit as to suitability for specifics of the role.

Ian Sutherland, Lost My Name

In order to ask questions that will enable you to assess a candidate for culture fit, you first need to define your startup's key values. You can then come up with some questions that align with that value. As an example, here are some of the questions I was asked during my interview when joining Cobloom, and the values they align with:

  • Transparency -> What's more important: transparency or confidentiality? Why?
  • Self-improvement -> What habits have you developed to improve yourself or your skills, personally or professionally?
  • Work smarter, not harder -> What's better, a perfect solution that takes 6 months, or an 80%-perfect solution that takes 3 months? Why?

These will help you understand candidates' personal and professional values, as well as how they think, how they prioritise and what they're passionate about.

Recommended weighting: 50%

3) Discuss the Practical Task

If you've asked your candidates to complete a practical task before the interview, it's important to spend some time discussing this. Not only will it help them understand how the task relates to the type of work they would be doing day-to-day, it also helps you get a better insight as to how they think, how they approached the task, and how much time and effort went into completing it.

Recommended weighting: 25%

4) Ask About On-the-Job Practicalities

It's a good idea to assess the practicalities of hiring this particular candidate as part of the interview process. If they're going to be working in-house, ask about whether the commute will be a problem for them.

Alternatively, if your startup has a completely remote team, consider timezones and ask about their work set-up: do they have a dedicated space to work at home, or will they be using a nearby coworking space, for example.

You'll also want to ask about salary expectations. Hopefully you included compensation information in your job advert, so by the time they reach interview your candidate's salary expectations should be aligned with yours.

Recommended weighting: 25%

5) Provide an Opportunity for the Candidate to Ask Questions

While candidates might have asked questions throughout the interview, it's a good idea to close out the interview by specifically asking if they have any further questions. Additionally, always give them the opportunity to contact you with follow-up questions by email after the interview - in case they forget anything, or later think of something that they'd like further clarification on.

Selecting the Best-Fit Candidate

The end-goal of your interviews is to enable you to select the candidate who is the best-fit for the role, and for your startup team.

The simplest, and most objective way to do this is to score your candidates based on culture fit, practical fit and their work capabilities, based on your assessment of their practical task. I've recommended a weighting split above: 50% culture fit; 25% practical task; 25% practical fit. In a small startup team, hiring the wrong person can irreparably damage your company, so finding someone who is a good fit for your existing team is essential.

Example interview scorecard.jpg

Scoring candidates in this way makes it possible for you to objectively compare them, so you can select the candidate who will be the best-fit for your startup team.

New Employee Onboarding Process

Hiring a new employee will have a significant impact on the rest of your startup team. In their first days and weeks, it's likely that your team's collective output will decrease, even though you've got an additional team member, as your new team member gets to grips with their new role.

Your new employee's onboarding experience is directly linked to how long it takes for them to get up to speed with their workload, so it's essential that you give this some thought, prior to them joining. Here are the six most important things to cover during onboarding:

1) Meet the Team

It's hopefully obvious that you'll need to introduce your new employee to the rest of your startup team - as early as possible on their first day. As well as names, you should ensure your new hire knows who works on what, so they know who to go to for specific queries.

One of the most effective resources we've seen startups use for new hires is a who's who Trello board (or similar tool), which includes everyone's photo, name, job title and areas of expertise. While you can add as much or as little detail as you like, something as simple as this is an invaluable reference point for new starters surrounded by unfamiliar faces.

2) Key Tools and Technologies

Your new employee will want to get up-to-speed as quickly as possible. To facilitate this, it'll be helpful if you have all the key tools and technologies set-up and ready to go.

For example, when I joined Cobloom, as well as having my computer set-up, I also had an email account and accounts for key technology such as HubSpot, project management tools and time-tracking tools already set-up.

This saved valuable time on my first day, and meant that I started off with access to all the most important tools I would need to use, day-to-day.

3) Socialise Outside of the Office

When I joined the Cobloom team, one of the most valuable parts of my onboarding experience was having time scheduled in to spend with the team outside of the office.

Arranging a team lunch or after-work drinks will make it easier for your new employee to get to know your startup team, away from their desks and the constant distraction of work. It's a relatively easy way to help your new starter feel like 'part of the team'.

Key to this is going out of the office: many startups we speak to are trying to build a relaxed, welcoming office culture and so have might often get takeaway in the office, or have a couple of drinks in the office at the end of the week, but going out of the office means that your team focuses on socialising with each other, rather than eating/drinking as quickly as possible and then getting straight back to work.

4) Check-in Regularly

Don't just sit them down, assume they've got everything they need, and leave them to it - that's the easiest way to make your new hire feel like an outsider on your team.

Providing sufficient support is essential for helping someone settle in - especially if they're joining a small, very tight-knit startup team. You might want to have a dedicated team member for them to go to with small, day-to-day queries - someone more accessible than you or your co-founders.

Additionally, you should make it a priority to catch-up with them regularly - perhaps after their first week, two weeks, one month. This will provide them with the opportunity to ask any bigger questions, and get feedback on their initial performance.

5) Ramp-up

The goal of your onboarding process is to provide your new employee with the skills and information they need to transition from knowing nothing on their first day, to being a fully-contributing member of your team.

As a result, your onboarding needs to gradually ramp-up over their first days and weeks. Their first day will most likely be very light, with lots of time dedicated to meeting your team and general orientation and administration. Then their first week will be mainly information-sharing and time for learning about their role. From there, over the next few weeks you should plan their workload to gradually shift their focus from learning about the work to actually doing it.

For developers, this may mean pair programming with a more experienced member of your team; for marketers they could create content working from an outline provided for them; for your sales team they could sit in on sales calls and gradually shift from listening to leading the call themselves.

6) Don't Skip the Small Stuff

It's easy to get so focused on the big picture - helping your new employee settle in and get up-to-speed with the rest of your team - that a lot of the small stuff gets missed.

Employees will have a ton of questions about the minutiae of your startup: how to use the printer, how to claim expenses, office hours, lunch, when they get paid... If your startup is growing rapidly and hiring a lot of people in a short amount of time, it's a good idea to put together some sort of welcome pack that addresses these small, frequently asked questions; it will save you time answering them every time, and will give employees something to refer to rather than feeling like they're constantly interrupting to ask another question.

Recommended Reading

Closing Thoughts

Tal Oron - Lost My Name.jpg

We think of recruitment as hiring of partners, not employees. The people working with us have as much say and opportunity to impact the business as the founding partners.

Tal Oron, Lost My Name

Building a successful startup is hard. You need to develop the right product at the right time, and have sufficient resources available, to enable you to out-grow your competitors.

This means that you’re constantly juggling three competing priorities:

  • Money – are you running out of cash? When do you need to raise your next round of funding?
  • Product – have you built a product people actually want? Would a product pivot more closely align you with the needs of your customers?
  • Team – where will you find your next hire? Who should your next hire be, and how will that fit in with your existing team structure?

It’s clear that hiring is one of the most pressing, ongoing considerations for startup founders – and one of the biggest challenges you’ll face. Many startup founders aim to build a startup that improves people's lives - but forget that the people whose lives they can have the biggest impact on are their team, not their customers. Building a great team is a prerequisite to developing a great company culture - one that gets employees excited about their work and passionate about the problems they're solving for customers.

In the early days, one wrong hire can literally make-or-break your company. But a great team working in a company with a positive, inclusive and dynamic culture can be the competitive advantage your startup needs to outgrow your competitors. That's why it's essential to get a comprehensive hiring process in place early, to help you avoid the critical hiring mistakes that can cripple an otherwise-promising startup.

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