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Hiring, in general, can be a daunting task. Knowing whom you like to fill the role can seem pretty ethereal until you put pen to paper. The struggle is even bigger for smaller companies, such as startups, as they’re not only looking to fill a role based on skills, but they’re also looking to find someone who will jive with their existing employees and culture. And while culture-driven corporations like Apple do this to a degree, too, it’s nowhere near as delicate as hiring can be for a startup.

Startups often struggle in bringing on new hires from beginning to end. A lot more is at stake when you’re hiring for a small company. Any missteps can be detrimental to profitability, productivity, efficiency, and even business projections. But if you’re a startup looking to hire, look no further.

Writer and former Google Vice President, Jessica Powell, has some great questions to ask your potential future hires to limit any possible setbacks.

It’s important to realize that Jessica’s experience is pretty limited to corporations and that she’s spent much of her time at one of the biggest of them all – Google. Therefore, as a seasoned businesswoman with vast experience in startup life, I’ll be adding some colorful insights that should help both employers and employees even further.

1. In her article, Jessica alludes that an employee’s resilience is a big part of being able to handle a startup, and I completely agree. Startups are typically very touch and go. Even if the startup appears successful, policies, processes, and even something as critical as re-allocation of budget are all subject to scrutiny – often until a time when the company sells or goes public. This is exactly why Jessica recommends employers ask resilience-related questions, probing for “weaknesses and missteps”.

Our favorite question related to resilience that she suggests employers ask in interviews is: “Some people tend more easily to put responsibility or blame on others, and some people tend to put it on themselves. Where would you see yourself? Can you give me an example of when this happened?”

We like this question because it’s incredibly important to know if a new potential employee has perfectionist tendencies and is incredibly hard on themselves, or if they are incredibly hard on their co-workers. If you’re speaking with someone who already puts the blame on themselves half the time, you may be looking at a self-starter who has the potential to lead – very important when considering future scaling, especially because many startups like to promote from within. If they’re more on the perfectionist side of things, you may also be speaking with someone who is incredibly resilient. Why? Because they’re already hard on themselves, which often times leads to allowing others to be hard on them. That means they’ve probably experienced a lot of defeat, but they keep on going, which, in my opinion, is exactly the type of employee startups need.

2. Jessica also goes over how ambiguity in the workplace (again, something very common for startups) can affect new hires, which is why she makes it a point to ask pointed questions that not only gauge the potential hire’s comfort with ambiguity, but also what they value their work environment and career and “to see how they approach complex problems”.

We actually have 2 questions we think startup employers should ask in the ways of ambiguity. The first is pretty basic: “Do you love your routines or do you like to do things on the fly? How much structure do you like in your work day?”

We love this question because startups are often moving so quickly that any employee needs to be accustom to changes be made on the fly. It’s a question that basically assesses whether or not something is a go-getter and can work with unknowns. Let’s say you’re an employer hiring for a sales role. What someone who has never worked at a startup might think is that they’re 100% supported with consistent documentation, training, and pay.

What they don’t realize is that startups often shift gears pretty quickly, so any collateral they may have provided you (I’ve worked for startups where this wasn’t even offered), for example, can quickly become out of date – and with the limited resources some startups have, it could be a month or longer before someone actually gets you what you feel you need to do well in your job. If that’s too ambiguous for you as an employee, you may consider working in a more corporate environment.

The second question is one that I see fit for anyone above entry-level, but mostly for those potential hires who are looking for an upper management or leadership role. Reason being, this question brings experience into question and obviously, if you are entry-level, you don’t have much yet. The question is: “Where was your favorite place to work and why?”

There’s a lot that an interviewer can learn about an interviewee with this question. Not only does the topic of past employment come up, but it also asks the potential hire to dig deep and explain why they liked their past role. This can often lead to other probing questions, such as “why are you looking to leave your current role” and “was there anything about this role you didn’t like?” Depending on their answer, an employer can quickly see if the interviewee’s past experiences, and their preferences, line up with what the employer is looking for.

There are many more great questions you can ask in interviews, but when it comes down to figuring out if someone is fit to work at your startup, starting with these questions can push you past the average, cliché questions at warp speed, making room in the often time-crunched interviews for solid and valuable data on the potential hire.



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