How To Hire
Proven strategies to find, attract, interview, and on-board world class people
TL; DR: making a good hire starts with knowing what you want. Be clear in defining both the type of experience and the type of person you’re looking for, but keep the scope broad to attract a wider candidate pool. Recruiting is an action verb and should be treated as such: go out and find candidates and convince them to apply (tip: leverage hackathons and conferences). Use panel interviews to position yourself to make a fast and reasoned decision. Ask tough questions and leave time for the candidate to speak! (it’s amazing how often the interviewer speaks more than the interviewee). Complete the debrief promptly with clear evaluation criteria. Don’t skimp on the reference checks. Be proactive in making the offer…this is where you should be the one selling the candidate on why they should join your team or company. And don’t overlook on-boarding!
Hiring is one of the most, if not the most, consequential activities faced by startups and established companies alike. Yet for all its importance, I find hiring is something most companies and people do quite poorly. This post is meant to serve as a composite of some of the tactics I’ve found most helpful around how to hire exceptional people. Most of what follows is structured around how to interview and assess candidates, but brief notes are included for finding and attracting candidates, as well as how to successfully on-board a new hire.
Finding & Attracting Candidates: This should be pretty intuitive, but here’s how I think about this crucial first step.
Making a good hire begins with having an idea of what you’re looking for, which starts with a clearly written job req. A good job req should outline what is meant to be accomplished in sufficiently broad terms, the required objectives, as well as the assessment metrics for the role.
To borrow from Peter Drucker, “Jobs need to be well-designed (and) should be demanding and big so that there’s scope for any strength that is relevant to be highlighted…”
Writing the job req in a sufficiently big and demanding way will tend to attract smart and ambitious people, and this is what you want!
For instance, the famed explorer Ernest Shackleton allegedly attracted over 5,000 applicants to join him on an early expedition to Antarctica by tapping into man’s inherent desire to solve big, hard problems:
The job req should be written by the hiring manager and/or whomever that role reports to. From there, be proactive in recruiting — hiring is an action verb, and relying on LinkedIn ads alone will not generate the strongest candidate pool. Conferences and hackathons are a great way to efficiently reach large pools of qualified candidates.
At Booz Allen we started using hackathons as a way to help clients efficiently outsource innovation, and after one of these events I ended up hiring the data scientist who led the winning team (check out the You Can Hack That playbook we developed to learn more).
Interviewing & Assessing Candidates: OK, you’ve got a strong pool of candidates and you’ve convinced them to become applicants, so now the fun starts with interviews. Interviews should be done in phases, typically starting with a brief phone screen, then some sort of panel interview with a competency test, and finally a “closing” round once you’re ready to make an offer.
Phone screen (15mins): use this opportunity to thank the candidate for applying and to ask a few guided questions to make sure you’re on the same page. Start by introducing yourself and your role, and then share what attracted you to that potential candidate and why you think they could be an interesting fit. Some flattery is good — you want the candidate to feel excited about the opportunity to join your company and work with you!
From there, ask an open-ended question such as “what interests you about this role?” to help confirm alignment. Finally, close with a few tactical questions such as salary expectations and availability or ideal start date.
If you’re still on the same page, end by discussing the next step(s) in the interview process and immediately scheduling the follow-up. Depending on the role, I typically also ask the candidate to send me a few sample work products that we’ll assess as part of the next round of interviews.
Scheduling the panel: there are lots of different ways to organize this part, but for both efficiency and effectiveness, I’ve found it works best to wait until you have a good sample size of candidates who have made it out of the phone screen (at least 3), and then work to schedule the panel interviews all on the same day with the same 3–4 interviewers participating. This way you can quickly evaluate the candidates and debrief with the other interviewers.
The interviewers should always include the hiring manager, and then the rest of the panel could include a VP or Director from a related function, perhaps the person who was previously in the role, a direct report, someone from a supporting team/function, or someone from HR.
For timing, I’ve found that 2–3hrs is the sweet spot, and I prefer having each interviewer meet with the candidate separately for 30–45mins each as opposed to doing group panels. The people conducting the interview should all be familiar with the candidate beforehand (reviewing the CV, sample work products, etc.), and it should also be clear what each interviewer is focusing on (e.g., technical ability, cultural fit, relevancy of experience, market knowledge, etc.).
See below for a sample schedule I’ve used (4 people interviewing 4 candidates), and note the dedicated time to debrief after completing the interviews. It’s best to debrief when everything is still fresh. Pro tip: treat the interviewing team to lunch to thank them for their time and also to ensure you have adequate time to debrief.
How to interview: this might be obvious, but it’s worth repeating: the reason we ask questions in an interview is to assess competency, capability, and cultural fit.
You’re trying to determine “does this person have the skills and the demeanor to complete the job and succeed in the role?”
Important note: for a 30min interview, the candidate should speak for about 25mins of the time. Way too often interviewers spend too much time pontificating about their own role or providing more context than is necessary. Try to just ask simple direct questions, and allow for “awkward silence” when it happens.
While the exact questions need to be contextual based on the role (you should always know what you’re trying to assess before each interview), here are a few of my favorites that are also quite generic:
- Please summarize your resume in 2mins and highlight the experience(s) you believe make you a good fit for the role.
- What do you know about our company or team? What do you imagine some of our priorities and challenges might be?
- When was the last time you convinced someone to change their mind about something? What was the context?
- What is the biggest misperception other people have about you?
- How do you think about organizing your time or structuring your day? How do you prioritize?
- Should you get the job, what would you hope to accomplish in the first 100 days? What are some of the metrics you’d use to assess your performance?
- So, (if) you already interviewed with _____ and/or _____. On a scale of 1 to 10 how well would rate your performance and why?
Note: I’ll often ask follow-ups as I go thru this list (for instance, asking someone to give more detail around one of their answers). These questions are meant to assess a mix of skills that are likely important on the job regardless of function, ranging from doing their homework and preparing, having self-awareness and empathy, and being strategic and results-oriented in their thinking.
I’ll then follow-up with a mini-case study or two. If I was interviewing someone to join my current team, this question might be something like:
Imagine you just met the CEO of an enterprise software startup that is building a new cybersecurity encryption product. They recently completed a $10MM Series A raise and are interested in raising additional venture debt to accelerate growth. How would you go about assessing this opportunity? What are some of the key metrics or other data points you’d want to know? Describe your thought process…
The point of a question like this is to learn how the candidate thinks through a problem, and this question is still relevant (albeit less so) even if the candidate had no experience with enterprise software companies or venture debt because a large part of the analysis is basic logic.
Suitable answers include things like: “I’d want to know more about the founding team and their past experiences. What’s the company’s business model and go-to-market strategy? Is the company generating income yet? If so, who are the customers and what do contracts and churn look like? What is the company’s growth rate? How much money do they have left in the bank and what’s their burn (i.e., how many month’s runway do they have left)? What is the overall market opportunity and who are the key competitors? Who are the investors, what’s the investment thesis, and how supportive are they with this business? What are the company’s differentiators or “right to win”? What’s Plan B look like and/or the path to profitability look like? Etc. etc.”
Evaluating the interviews: Just as you entered the interview with an idea of what to assess, you should also have an idea and/or framework of how you’re going to measure. Confirmation bias is real and if you’re truly interested in hiring the best people (as opposed to those who most resemble you) then you need to quantify the assessments. That said, there’s also not a reason to over-engineer the assessment. I’ve found that a simple 4 question test can be very effective, such as: On a scale of 1 to 10, rate:
- What did you expect out of this candidate and where did they ultimately land (and why)?
- To what extent has the candidate’s existing skills, experience, and demeanor prepared them for this role?
- To what extent does the candidate possess inherent ability that would make them effective regardless of experience?
- How confident are you that we should make a competitive job offer to this candidate? Would you want this person on your team?
The first question is meant to tease out some of the inherent biases that likely exist, and the rest of the questions are meant to assess the strength of the candidate. In general, any score of 7 or less should lead to a discussion around why the candidate was scored as such, and if the ranking holds after debate, the candidate should be discarded. It should also be an immediate disqualification if someone says “I think we should hire, but I wouldn’t want them on my team.”
Amazon is famous for their rigorous interview process, and to make sure they keep leveling up they ask “is this person better than 51% of the company?” They only hire if this answer is a definitive yes.
Making the offer: Ideally after the debrief there’s consensus and you’re ready to make the offer. This is where the tables shift and now you need to start selling the candidate on why they should accept the offer and join your team. If possible, the offer should be made directly by the hiring manager. Invite the candidate to lunch, drinks, and/or dinner. Explain why they stuck out and why you feel they’d be a great fit for the team. Outline the aspects of the offer and be honest in answering questions that might arise. The objective here is to make it clear what the person is signing up for, and make them very excited about signing up for it (assuming they accept, but this same approach also helps weed out people who might accept but then flair out a few months later).
On-boarding: This is often the most overlooked aspect of recruiting which is a real pity. Oftentimes the most excited anyone will ever be about their job is when they show up on Day 1. Make this a momentous occasion. It shows you value that person and their future contributions, and it sets a precedent for other teams. Have a structured on-boarding session (even if it’s just a 1hr meeting where you explain what needs to be done immediately and who that person will be working with), send around a company-wide email welcoming the person to the team, arrange a lunch or happy hour, and in general try to build up camaraderie.
Given all the work and diligence you put into finding, recruiting, interviewing, and hiring this person, presumably you made a good choice. But that said, you need to set them up for success by bringing that person up-to-speed and inculcating a sense of ownership in the business that will help them perform at their best level.
The person you hired will inevitably bring certain strengths and weaknesses, so your job now is to help tweak the role to emphasize their strengths and make the weaknesses irrelevant. This harkens back to the earlier Drucker quote around designing a job to be sufficiently broad to enable people to get creative in how they use their skills to accomplish a set of objectives.
Often times startups are moving fast and structure is sacrificed for speed. This is fine and oftentimes even desirable, but clearly outlining the objectives and goals the new hire should complete over the first 100 days is absolutely critical. For a VP Sales, this could be something like:
- Week 1: meet with all relevant internal people for 1:1s, shadow whomever was leading sales previously on customer calls, get smart on the product
- Month 1: build sales pipeline and present initial forecasts and assumptions to exec team
- Month 3: recruit and on-board 3 sales associates, refactor sales pipeline based on market feedback
This is also the time to start building in regular performance assessments. This goes back to having an idea of what success looks like for a given role and then measuring to determine how well the person is meeting the objective.
Closing thoughts: to re-iterate one of the points above, recruiting and hiring seems like a time-consuming process and in many ways it is. However, the ROI for making a good hire versus the pain and suffering from getting the wrong person will pay dividends in the future. In almost all cases it’s more time consuming and costly to get rid of a bad employee than to wait and hire the right one (not to mention the signals this sends to the rest of the team).
Of course, retention is also key and making the best hires in the world won’t help if they decide to quit after a couple months. Fortunately I’ve found this sort of hiring process is also a good filter for attracting and retaining the right people.
To summarize: Hire slow, Fire fast.
Note: views are my own and do not necessarily reflect those of my employer.
