The Definitive Guide to Interviewing for a Startup: What I Learned After Screening 42 Candidates for One Position
by Claire McTaggart
Hiring is full of guesswork. Every employer is faced with the same dilemma: a large number of total applicants, a limited amount of review time, and minimal information to determine the most promising few. As employers, some of our most important talent decisions are reduced to heuristics, inferences, and filtering mechanisms. We are looking for signals that will help us identify who we can cut, so that we can spend more time with a handful of candidates. We scan resumes in under a minute, conduct rapid phone screens, and look for any short cuts available.
As someone who has screened and interviewed hundreds of candidates over many years, I can assure you, we are always more confident in the noes than the yeses. The whole process is much more art than science, and most data out there shows that our success rate is pretty low.
With this in mind, I founded a tech startup that is trying to modernize hiring by using more meaningful data to match job seekers and employers. SquarePeg uses science-backed assessments instead of resumes, and connects candidates to companies based on fit, not just keywords. We are positioning ourselves as experts at the crossroads of hiring and technology.
When it came time to start building out our own team at SquarePeg, we wanted to cast as wide a net as possible. We would use SquarePeg’s platform and analytics to source candidates and conduct phone screens to determine who to bring in for a full interview. Not only did we have the challenge of finding an all-star foundational team member to help us grow the company, but we were also conducting a trial-by-fire to determine the efficacy of the product.
Title-wise, we were searching for a Head of Product and Operations. But, in an early stage startup, the first few hires wear a lot of hats. Their tasks may range from sales to marketing to admin to data science to designer to copywriter. We needed someone willing to do all this and more.
As such, we looked for specific qualities in this person. S/he would need to be adaptable, collaborative, strategic, and proactive. Adaptable, because the job changes with whatever fire we are putting out or hurdle we are trying to climb. Collaborative, because we are a small team and need to work together closely to make a sum bigger than its parts. Strategic, because an early-stage startup can get buried in tactical maneuvers and lose sight of its mission. Proactive, because we are all swamped with work, and all the members of our team need to take initiative without waiting for direction.
In exchange, we were offering lower-than-standard market pay, long hours, a tiny office in a co-working space, no admin support, no job security, and a long, uphill climb.
But, we were also offering the opportunity to build something new from the ground up, to innovate, take risks and experiment, and to own a piece of a company that could impact the way people hire and find jobs. We have a powerful mission and we needed our next hire to value that over any perks and benefits.
We had over 150 applicants, and invited 42 to a phone screen. The candidates were diverse in age, background, experience, and personality type. They also differed in their perspectives and interview styles. What struck me most about interviewing these candidates is that no two were alike. In my management consulting days, candidates were so well prepared with canned answers that they blurred together after a while. In this interview process, we quickly found ourselves comparing apples to oranges. So, a candidate’s SquarePeg profile and the data we collected from the phone screen was invaluable.
I started the screening process with a set of standard questions. In the great interviews, I was often too engaged to take detailed notes, but short bullet points were common. I wrote thoughts like “articulate about roadmap,” “knows customer/mission,” “good ideas/solutions for dashboard,” “very structured,” and “tough questions”. These people I invited to speak with us in person.
But for the obvious noes, I found myself jotting down what looked like a laundry list of frustrations. Certain tendencies or answer styles sent up red flags, and sometimes were bad enough to cut the interview short. By the 10th phone screen, I was using shorthand for these mistakes — scribbling them in my notebook and adding the points to Trello.
It surprised me how often so many different people could make the same interview mistakes. Had no one told them what they were doing wrong? I was rooting for these candidates; I wanted to give them a shot. But, given the stakes and number of people vying for the position, I also had to be ruthless about moving on once I had enough information to do so.
Ultimately, authenticity is one of the most important things to convey in an interview, and in that sense, there is no formula for the perfect answers. In startup interviews, we are not just looking at if you would be right for the job, but also if you’d be right as a partner in the business as we grow. So while there are no foolproof responses, here are some common mistakes anyone looking to join a startup should avoid:
1. “I’m here to learn and get experience.” This sounds like a fine response at the outset — who doesn’t want to work with someone who is curious and open-minded? Startups are all about learning on the job, and the ability to learn quickly is an essential skill. In fact, this was the most common answer to “Why do you want to work here? / What are your career goals for joining SquarePeg?” But dig a little deeper and this answer gives me pause. As harsh as it may be, here’s the truth: No one is going to pay you to learn for learning’s sake. As a startup founder, I don’t have a 6-week on-boarding program and quarterly training and development sessions. I’m barely able to accomplish the hundreds of things on my to-do list. If I have to think about someone not knowing what to do and needing us to teach it, none of us will succeed. You need to want more than experience, and to know what that is from the outset.
Corporations have large hierarchies and seasoned managers whose job it is to train new joiners. Startups do not. If specific learning is required for you to contribute, to produce, and to take action, then we’d love to facilitate that. But first, we want to know what you will do with the learning. We are here to grow a business. Learning should therefore be purposeful, specific, intentional, and involve a large degree of self-instruction.
I don’t want to hear that you want to join a startup to get experience in startups, or this role, industry, or skillset. I want to feel that you have a mission and purpose, and can do whatever it takes to achieve it.
What I don’t want to hear: “I’d like to learn more about marketing.”
What I do want to hear: “I’ve run large analytics programs and can help you set that up on day one, but I’m less familiar with some of the social tools. I’d like to experiment with a few and teach myself how to incorporate more social marketing analytics into your user analyses.”
Now you are telling me you have a perspective, a viable skill set, and also that you want to teach yourself something specific to be better at your job.
2. “After college, my first job was…” A surprising number of candidates felt the need to reread their resume to me. I don’t mean walk through their career history and why certain experiences or roles might be of interest to me or to SquarePeg . I mean literally reread their resume. I’d assume at least 80% of interviewers will have skimmed a candidate’s resume before the interview and have a grasp on the main points. When they ask you to take them through your resume, they mean: “Tell me what is relevant that is not on your resume.” Over and over, I heard something like: “I was in X role at Y company for a year before realizing that industry wasn’t a good fit for me, so then I moved to Z company where I had this role.” This is the easiest way to a) make your interviewer zone out and start checking email, and b) show that you are unable to discern relevant from irrelevant information. I want to know what you did in the past that makes you the perfect hire for SquarePeg. And it doesn’t need to be full of all your accomplishments.
I had great interviewers tell me they left the corporate world because they kept getting in trouble for pitching clients before they had approval or because they kept losing arguments with their boss when they wanted to do something faster or riskier or differently. If we are going to discuss your career history, I’d like to know what was it about you that made you excel in previous situations and how you did it, or why you didn’t excel in past roles and would therefore be a great fit for our startup.
Try to go through your career history and think of the three things that are most relevant to the role you are interviewing for. If you are switching careers, why will your past experience be informative for your next? Maybe you were a lawyer who wants to try product management. Tell me about your crazy work ethic and attention to detail. Tell me that you managed five people and can communicate really well , with examples. The “Tell me about your background” question is your opportunity to show an interviewer who you are and that what you’ve done that is relevant beyond what’s on your resume.
3. The 10 minute presentation: I appreciate when someone prepares for an interview. You can tell when they have thought a lot about the company and why they might be the right fit for the role. But the goal is not to have one side talk ad nauseum while the other listens. When you are applying to work at an early-stage startup, you will be working closely — often side-by-side, on a daily basis — with the founders. The initial phone screen is one way for the interviewer to ask themselves: “Could I tolerate being next to this person for 10 hours a day? Could I collaborate with this person? Can this person listen?” So many candidates talked for over five minutes without a break. They didn’t stop to ask a question or try to tailor their answer to my interests. If we are on question one (the resume walkthrough) and you go on a 10 minute rant, we probably won’t get past question five. Keep it succinct and on topic, and give the interviewer a chance to dive deeper where s/he wants to know more.
Or, even better, try to ask some questions to guide how you answer. I had one candidate say: “I’m happy to talk to you about my PM experience at my previous startup, but I actually did a bunch of research on psychometric assessments in grad school if that is of interest.” He gave me three relevant bullet points to answer my initial question, and then we spent 10 minutes talking about a topic of mutual interest.
The point is that the interview is a conversation, not a presentation. Try to find what might be relevant to the other person. Allow your interviewer to ask for more details when needed. Make the process enjoyable. If there are key points you want to get across, summarize them and say you’d love to elaborate if your interviewer shows interest.
4. Answering before thinking: Many people have a fear of the awkward pause. I am one of them. 100% of the time, if there is silence, I will say something to keep the conversation flowing. But interviews are different, and it is acceptable — even preferable — to take your time. Thoughtful and deliberate answers often don’t come immediately, and those are the answers your interviewer is looking for. One of the most common tendencies when faced with a straightforward question was for candidates to blurt out the first thing to come to mind. It often felt sloppy and disorganized, and it usually ended up in a rant (see #3). In an interview, it is absolutely OK to say: “Interesting question, let me think about that for a minute.” I’d rather wait for an informed and purposeful answer than have to go through a bunch of filler before you get back on track. Take a moment, reflect on how you can best answer the question in a meaningful way, and provide a succinct answer. It will be much more powerful.
5. The jack-of-all trades: Contrary to what you might think, the worst candidates say that they can do everything. “Would you be able to lead a social media marketing campaign?” “Sure, yeah, I’d love to do that.” “Would you be able to plan all our development sprints?” “Yeah, definitely, I could plan sprints.” “Do you have experience in QA testing?” “I can do that, sure.” “Would you be able to double our user base?” “I think I could if you gave me the opportunity.” “How would you do this?” “I’d look online and then figure it out.” Doesn’t sound too promising, does it?
The round two candidates I interviewed were highly self-aware and not afraid to admit what they didn’t know. Moreover, some would question my thinking when I’d ask if they could do so many disparate things. They’d say something like: “Yes, I’d be able to build out a product roadmap, but I don’t think blogging would have a great ROI on my time. We could probably have an intern do that so I could focus on the platform updates we’d need to plan.” A great candidate will have a viewpoint on how to best utilize his or her time and should be able to disagree. A founder wants someone with an opinion and a perspective who knows where s/he can best add value.
6. Unsubstantiated generic statements: It is never, ever, good enough to use an adjective to describe yourself and end it there. Anyone in the world can make the claim that they are “hardworking,” “passionate,” or “persevering”. If you are going to use a generic buzzword to describe yourself, you’d better be able to back it up with evidence. If you are passionate, I want to hear your excitement and enthusiasm over the phone along with anecdotes of when you did something so above-and-beyond that it shocked others. If you say you are hardworking, it should come through that you spent hours preparing for our interview and read everything on the web about SquarePeg. Tell me about the time you put together a 200-page pitch book in a week. Persevering? You should have examples of when someone told you “No” multiple times on something and you found a way to make it happen regardless. Your answer to “Why should we hire you?” should never be a blanket statement about who you are; it should be about what you can do, and why — specifically — you are the best person to do it.
7. Not having a Day One Plan: As mentioned, early stage startups do not have on-boarding programs or structured training and development. (Many larger firms don’t do this well even when they have them in place.) What every hiring manager wants to know is what will you do day one, week one, and month one. Everyone will expect that you will take some time to learn the ropes. But you should also be able to start adding value from the moment you walk in the door. Tell your interviewer what it is that you can do that requires no help, input or supervision.
I had a marketing candidate tell me: “In all honesty, your Facebook page is really weak. While I’m learning more about your users, during week one, at minimum, I’ll write five blog posts, optimize your page, and get you more followers. I’ll also reach out to a handful of journalists to get you some mentions.” She was offering me something valuable before we even talked about the role. She was in essence telling me: “If you are busy, don’t worry about me. I have a set of skills I can use to help this company grow and I don’t need to be told how to do it.” Think of the wide array of tasks you have done before, or could do with ease. Then, look at the business you are interviewing for. Could you reach out to your contacts and make intros? Could you pull together a kick-ass presentation for them? Could you optimize their social accounts or get them publicity? Maybe you can review their forecasts and projections, or reach out to 100 customers and put together some insights from the feedback you get. One candidate told me: “Your value proposition isn’t clear. I’d run a survey with your existing and target users to fix the language and copy on your marketing site.” These people were identifying gaps and showing me how they’d fill them and why they would do a better job than what we currently had.
Unfortunately, the majority of candidates I interviewed didn’t do that. They responded with something to the effect of: “I can do whatever you want,” or “I’d ask you guys what you need help on,” or “I’d like to get to know more about the company, team, and product, and then we can figure out the best place for me to start.” Nice to know, but that won’t cut it. Show your interviewer at least three actions you can do well before the end of week one.
8. “I don’t have any questions.” This is a cardinal sin in interviewing. Never, ever, go into an interview without having questions. Even if it’s your 7th round. Never waste this opportunity. When I said: “OK, I want to give you a chance to ask me any questions you may have,” at least 25 people responded with, “I think I’m good, I’m pretty sure we covered everything I’d like to know.” None of them made it to an in-person interview.
Not having questions about the company feels impersonal. It calls your curiosity and motivation into question. A thoughtful question is one of your most powerful tools. It shows how you think about the business and the challenges ahead. It demonstrates that you did your homework. It allows you to engage with and listen to the person on the other line — and force them to invest more in the conversation. (See #3.)
Bear in mind that your questions should never be administrative or logistics related, i.e. about the hours, the office, the vacation policy, etc. They should always force the interviewer to reflect on their business or industry and look towards the future.
In my view, the best questions are those that address the biggest hurdles or challenges the company will face . This shows that you acknowledge some of the difficulties that lie ahead. For us, questions about building a dual-sided marketplace, differentiating ourselves in a crowded and competitive landscape for HR tech tools, and traction strategies were all relevant and meaningful. You want to try to find out what’s on the mind of business leadership. What are the most pressing issues they need to tackle? Find a way to share your thoughts and perspectives through the Q&A.
9. Weak product feedback: The vast majority of startups operate on the Lean methodology, which is essentially about releasing the earliest version of a product or feature to get user feedback, learn and iterate. This means that no product is ever complete, and oftentimes the teams behind them are experimenting and tinkering based on a product roadmap and customer priorities. The product you see is probably quite far from where the founders and developers want it to be by the time it’s released. So when your interviewer asks you about what you think of the product thus far, the answer should never be “It’s great” with a full stop.
Think of this from your interviewer’s perspective. A startup is willing to give up some amount of money and/or equity (both are usually guarded and in short supply) so you can help build a better product, team, and company. Your feedback should show additional insights you can bring and your ability to evaluate areas of improvement with a fresh perspective. Every candidate we interviewed had gone through SquarePeg’s site and assessments, had received a personalized report, and was set up with company matches. At the time, this was an MVP (minimum viable product) that was very far from where we’d have liked it to be. On every phone screen, my first question was: “So what did you think about the product and experience?” and often, the answer was: “It was great! I loved it!” I knew the candidates who answered this way wouldn’t be effective heads of product because we were emailing every single user at the time and getting paragraphs of feedback with what they loved, what was broken, what did and didn’t make sense, and what needed to be improved.
A great answer to that question would follow this pattern: 1) Here is what works well and what was a good user experience. 2) Here is what did not work well and should be improved upon. 3) If I could change it, here are the three top ideas I’d want to try and how I might test and implement them.
This is also a great place to ask questions. Most startups have long lists of features they wanted to add but couldn’t; ask if they thought about XYZ feature and about their prioritization process. You might also ask about the longer-term roadmap, and how Version 2 or Version 7 will look. Healthy critique makes a product better and moves everybody forward.
In the end, Dan and I met four or five viable candidates out of the 42, and we met one which we both agreed upon in full. Raj, our new head of product/ops/candidate acquisition/marketing analytics/pretty much everything else, was the top job fit match from SquarePeg’s results, but what landed him the job was his interview.
His answers were thoughtful, and his questions were challenging and plentiful. We both felt that he was testing us more than we were testing him. That signaled to us that he was invested in a long-term partnership and wanted to feel confident that we (and SquarePeg) would be able to defy the odds. We both knew there were certain areas where he did not have much experience — he was the first to admit this — but in other and more important ways, we would learn a lot from him.
Most of all, the discussions we had with him were always somewhat challenging and very forward-focused. He was not interested in saying what we wanted to hear; he was interested in provoking a thoughtful conversation about how we could be the right product, with the right team, at the right time.
Now Raj does our initial phone screens when we hire.
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