UncorkHiringPlaybook

By Adriana Roche

Here are the typical steps towards hiring a fantastic team and tips to make you successful.

We will cover

• Why is this important

BEFORE YOU RECRUIT

• How to define a role

• How to write a great Job Description

THE RECRUITING FUNNEL

• Top of the funnel

• How to conduct a structured interview

• How to make an offer

Why is this important

Hiring is a critical component in the journey of building a successful business. It serves as the foundation for assembling a competent team that performs exceptionally, which is a crucial determinant of your success, especially in the early stages and as you expand your operations. Prioritizing the recruitment of the right individuals is essential, as it establishes the fundamental elements of your company's growth and provides you, the entrepreneur, with the necessary leverage to achieve your objectives.

However, hiring is far from straightforward. For startups, the challenges are more pronounced due to their relative obscurity in the market. Such companies often lack a recognized talent brand, significant validation, or the ability to offer competitive salaries, making them a high-risk choice for potential employees. Furthermore, the candidates you aim to recruit are likely to have numerous attractive employment options elsewhere.

Understanding where to begin can be daunting, especially if you have limited experience in hiring. This is the reason behind the creation of this guide. The hiring process demands considerable effort and a willingness to experiment and refine your approach to discover what is most effective for your unique situation. Your goal should be to transform your hiring process into a strategic advantage, which, in turn, will generate a self-sustaining cycle of attracting top talent in the future.

Before you recruit

Tools

You don’t want to get too complicated or spend too much $ on tools, but some might be worthwhile.

• LinkedIn (free) or LinkedIn lite for prospecting

• Clearbit can help you find e-mail addresses

• Juicebox, Wrangle, or Noom can help with sourcing and data enrichment

• Spreadsheets to keep track of your candidates (or Ashby if you have a lot of folks to keep track of)

What is your pitch?

Recruiting is very similar to sales; in this case, what you’re selling is your company and the opportunity it presents, as well as you as a founder. You want to spend some time understanding how your company will change the world, what kinds of problems this person will solve (for that initial team, generally, its hard technical problems), and how their career will be accelerated by joining this team.

Spend some good time rehearsing this with other people so they can give you feedback. Generally, you will do this pitch in person or over Zoom, so you must pepper the conversation with your nuggets at the right time. You can achieve this by asking many questions to see what matters to the candidate.

Here’s a sample of how your initial conversation can go:

• Small talk - you want to make sure the candidate feels welcomed. Either about non-polarizing current events, travels, etc.

• Asking them questions about themselves. What are they looking for in the next role (if they say they are happy where they are, what would make it 10% better), what have they enjoyed the most in their career, and what have they not? How do they think about deciding the future?

• Tell them the origin story of your company and why you’re excited

• See if they have any questions

• If you think they are worth exploring further, set up the next steps

How to define a role?

You know that a million things need to be done, and you need people to help you do them. Below is a little exercise that can help you hone in on the job description. This clarity will make it easier to identify and sell the right talent for the role and even onboarding.

So what are the questions you should be asking yourself:

• What is the problem that you need to solve? Timeboxing it to the next 12-18 months gives you enough immediacy so that you’re hiring for the skills you need now but also looks far enough into the future so that your hire doesn’t tap out too quickly.

• How can you solve this problem? Think about possible solutions to the issues and alignment on the initiative. This is not 100% necessary since things change quickly in start-up life, but having an opinion can help you hone in on the right questions to ask.

• What are the skills that are needed? Based on the initiatives you think are essential, what skills do you think this person needs? Say you need to hire a marketing person: do they need to spike on branding, or do you need someone more into demand generation? You will likely need to hire someone who can wear many hats, but understanding where you want them to spike is critical.

• Talk to people in the seat. It’s good to talk to a few people doing this role or have done it recently. You can also go to LinkedIn and look at people’s profiles to see what things might look like.

Once you have clarity - what the person will do and some of the skills needed, you can move to the next step, the Job Description (JD).

How to write a great Job Description?

Writing a job description can feel daunting, but it's an essential step in the hiring process. Not only does writing down what you need to add clarity to your search, but a well-written job description can attract the right candidates, while a poorly written one can repel them.

Let’s review the key elements of a job description and tips on writing one that accurately reflects the position and company culture.

• Job title: The job title should be clear, concise, and accurately reflect the position. There’s a fine line between being creative with the title and having something that quickly tells people what the role is all about. If you want to hire your first marketing person, a “Founding Marketer” title might be a more appropriate creative approach than “Evangelizing Guru.”

• Summary: Right after the title, you want to add a quick 2-3 sentence paragraph expressing what this role will do and where it will impact. You want to ensure you hook someone into reading the rest - and applying if they are a good fit.

• Responsibilities and duties: Outline the main tasks and duties the employee will be responsible for. Be specific and avoid using general terms like "assist" or "support." This section should give candidates a clear understanding of what the day-to-day responsibilities of the position will be. If you have particular areas where you think this person will add value (help us reduce software costs), you should add those there.

• Qualifications and skills: This section should give candidates an idea of the qualifications they need to have to be considered for the position. Be sure to use your exercise above to define what you need in terms of experience and be thoughtful about the things that are nice to have vs. need to have. Remember that some groups tend to not apply to roles if they don’t have 100% of the items listed - so you want to be sure to account for that. List the education, experience, and skills required for the position. Be specific about the necessary level of experience, for example, "3 years of experience in digital marketing."

• Benefits and perks: Include any benefits or perks the company offers, such as health insurance, paid time off, or retirement plans. People won’t select your role based on the benefits, but some are draws.

• Company culture and values: Provide information about the company's mission, values, and work environment. This section should give candidates an idea of the company culture and the type of work environment they can expect. This is also reflected in your tone in the job description and what you highlight in the duties.

Datapeople is a fantastic tool for helping companies analyze the language of their job descriptions. Create an inclusive process by avoiding biases such as Racism, Tokenism, Ableism, Ageism, Nationalism, Elitism, and Religion bias. (read more here)

https://datapeople.io/article/inclusion-is-more-than-gendered-language/

A trick I like to use is to look on LinkedIn for similar roles and see what they add under the duties and responsibilities. It gives you an idea of what your “competition” is doing and what might be attractive to folks in that role.

The interview process

Recruiting and sales have a lot of things in common - and thinking about it in this way might help you figure out which tactics to employ along the way.

You want to inform the candidate and add legitimacy to your company.

Sourcing

The best way to hire those first few team members is through founder-led recruiting, not necessarily via recruiters or agencies. Just like you must talk to customers to understand what works and what doesn't, you want to spend time talking to prospective candidates to understand what sort of feedback you’re getting. You might want to consider agencies if you need to hire a lot of people all at once and need leverage or are looking to hire someone in a role you don't have an extensive network in, say, your first seller.

Here are your best bets:

• Level 1 connections: These are the people that you know personally. You want to start here because it is easier to get these folks engaged. It is also easier to get signal on them through your network and backchannels. You might have even worked with them, which makes it more meaningful.

• Referrals: This is your second-best bet. You can ask your close L1 connections to refer someone. It can feel like work sometimes for folks to go through their network or even send messages, so you could make it somewhat fun and do a referral party. Get together for breakfast or pizza, open up your LinkedIn, and start creating lists. Then, give them sample emails/texts that your friends can send to their contacts to make it easier.

• Level 2 connections: These are the people that your strong network knows. You can reach out to them directly, but make sure your connections are someone they know well or highly reputable.

Some tricks of the trade:

• Make sure the notes you’re sending are personalized. There is nothing worse than getting a Dear {{Insdert name here}} note.

• It might take 2-3 tries for people to get back to you

• Have a call to action - suggest the next steps, such as a date or time to catch up

• If they say yes, schedule something as soon as possible

• If they say later, make a note to stay in touch

• If they say no, ask for referrals

The Interview Process

Ok. So you have the proper job description and found some really cool resumes. Now, the most nuanced part of the hiring process begins: The interview process.

You want a structured interview process to ensure you get the most out of these conversations. And by structure, we mean something well thought out and designed from the beginning. This will help you cut through the noise and help you see the signal

Below are some tips that will help you:

• Questions to ask in the discovery call ( and NOT ask ):

• Use the work you have done in the past around what the person needs to do and what skills they need to create a list of questions. Consider using a mix of behavioral and situational questions that will provide insight into the candidate's past experiences and how they might handle similar situations in the future. You also want to ask questions that get to the “soft skills” required in a role and a start-up, such as grit, comfort with ambiguity, and proactivity.

• Try to have a consistent interview panel. More is not better in this case; having about 3-5 people max interview the candidate is a good number. An excellent way to pick who should be in the panel is to triangulate folks who will work closely with the candidate and those uniquely equipped to assess the responses. Sometimes, you need to find someone external (such as advisors or operating partners) to help you do the interviews.

• Once you have the questions and the panel, ensure each person knows which questions they are asking. Always ask the same questions for each candidate to compare responses. But also make sure you don’t have different interviewers ask each candidate the same questions. It makes the candidate feel like you were unprepared and takes time away from other questions you can ask.

• Establish an interview schedule: Create a program that allows for sufficient interview time for each candidate. This will ensure that all candidates are equally able to showcase their qualifications. It's also essential to schedule interviews promptly so that candidates don't have to wait too long for an interview or decision. Generally, you can do a resume screen in 30 minutes, and each interviewer should spend about 45-60 minutes talking to the candidate.

• Conduct the interview: Create a comfortable and professional environment during the interview. Remember, it’s a two-way process; they are interviewing you as much as you are interviewing them. In the first 5 minutes, take the time to introduce yourself and explain the interview process. Make sure to take notes you can refer to on the answers and leave room at the end for the candidate to ask questions.

• Evaluate the candidate: After the interview, evaluate them based on their qualifications, skills, and fit for the position. Consider their responses to your questions, communication skills, and enthusiasm for the job. It's also helpful to consider how their qualifications and experience align with the position's requirements that you set at the beginning and the company culture. Also, use the questions they asked you to evaluate how much they understand what they will need to do and their interest.

• Follow-up: After the interview, follow up with the candidate promptly, generally, after 48 business hrs. If you still need time to decide, let them know when to expect a response. You should also ask them if they are in the middle of other interviews with other organizations so you can align your timing. Note that Engineering processes move A LOT faster than business ones, so try to be ready to make an offer within two weeks of talking to someone (provided you feel comfortable with your assessment - never rush to make an offer if you’re not ready!).

• Debrief: It’s generally good practice to debrief, especially at the beginning of a search. Get together with the interview panel to review the answer and the assessment. This is the time to review any red flags or areas of concern. If needed, have another interview with the candidate to go over things that were not clear.

• And remember to ABC - always be closing! You don’t to wait until the last minute to close your candidates, this is something you do throughout by asking the right questions, being prompt with scheduling, showing interest, and answering

How to make an offer?

You’ve picked your candidate and got stellar references. Now, it’s time to close the deal. Let’s talk about a few tips on acing the offer stage.

Before opening up the role, try understanding what this role pays in the market and how it aligns with your comp philosophy. This will help you stay consistent with what you’ve determined is the right approach and not be swayed by what your candidate asks you. Remember that every company approaches compensation differently, so someone from FAANG will think differently about compensation than someone from a start-up.

Ideally, you will have gotten an understanding of the candidate's compensation expectations early in the interview process. If you have someone from a large organization, they must understand from the beginning that their comp structure will likely look very different. Generally speaking, it is lower on cash and high on upside potential. It’s essential to have this conversation early so people either self-select out or stick with the process but are not caught off guard (Note: with the new pay transparency laws, you might have to have this conversation at the outset of the process anyway)

Make sure the timing is right. Sometimes, candidates are still interviewing with other companies or have questions about your opportunity. Make sure they are ready to hear your offer. One way to do this is by asking: “Other than knowing the compensation information, is there anything keeping you from accepting this offer?”.

Give the offer in person, via video or phone, not email. You want to get cues on how the candidate responds to numbers and answers any initial questions. Generally, the call will go as such:

• How excited are you to make an offer

• Where will they have an impact

• Ask if they have any questions or hesitations that are outside of compensation (you want to make sure you address these before you talk numbers)

• Explain your compensation philosophy

• Talk about base

• Talk about equity - don’t assume people understand options, so you will likely need to do some education, which builds trust. Also, most candidates will need to understand what the upside would look like. In the early stages, it’s normal to talk about % (and number of shares), and later on, you can move to value (and # of shares)

• Also, go over any perks and benefits.

Before you hang up, it’s always good to say something like: “This is a big decision, so take your time reviewing the offer. When do you think would be a good time to check back in?”. And schedule a follow-up call a few days later. After your conversation, you should follow up in writing with the terms via email or sending an offer letter.

This is also an excellent time to ask the candidate if they are exploring other offers and the timeline to decide. If they have anyone weighing heavily on the decision (spouse, etc.), you also want to ask what they think about the opportunity.

It is normal for people to have many questions about the offer details and some asks. Seasoned candidates will know to make all their asks simultaneously vs. piecemeal - so ideally, you don't have to do more than one of two revisions. We recommend being as transparent as possible. Not only does it build trust but you also don’t want to have someone accept and then find out information that would lead them to leave or question whether they should have joined.

Once the person accepts verbally, ensure you get a signed offer letter. If the start date is more than a few weeks away, stay in touch with the candidate so you don’t lose them (sometimes this happens). Send them a cool article, some swag, or anything that keeps the exciting momentum going. Get the interview team and investors involved by having them send e-mails or sign a card.