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How to Mould the Way You Hire to Your Context

14 November 2022, by Jomiro Eming

When it comes to hiring, there is no “one size fits all” approach, and trying to use the same approach across different contexts will risk turning a great candidate into a bad hire. Benny Ou has hired for different contexts, and has developed a set of useful questions to ask himself before he hires, in order to mould his hiring process to the specific context he’s in.


Benny has worked in two very different contexts, each with their own set of unique hiring needs: a larger corporate that needed mainly devs and technical roles, and a startup that needed everything from project managers to a barista. Over the course of his career, he has seen many companies copy hiring processes verbatim, of big brands like Google, without any regard for their specific business environment and situation.

A huge lesson he’s learned through his own roles is that, although you can have a list of considerations and hiring processes, none of them actually matter unless you know what questions to ask, and how to apply them to your context: “You might see these well-known companies hiring great people, and automatically think it’s something you should adopt too. But the only way to see what’s going to work in your organisation is to think about where you are, and what you need,” he says.

Mapping your hiring process to your context

When mapping his process to the context for which he’s hiring, Benny starts with three overarching considerations:

Know the difference between company “needs” and “wants”

Benny has found that companies will often hire from a top-down approach. In his own words, he says “they simply go ‘I need these folks to do these things.’ But they probably haven’t even spoken to the relevant teams.”

In his experience, this is especially true the bigger the company gets, because CEOs and CTOs tend to stop spending as much time in the daily operations: “They are often so devolved from the day-to-day stuff to really and truly know what the teams need most urgently.” This is when company members hire what they “want”, and not what they need.

Ask how susceptible the company is to change right now

The type of person Benny hired always depended on how likely it is that the company would go through any “changes” regularly: “The person you’d be finding for a startup, for example, would maybe need to be very adaptable, not mind the craziness, and be able to possibly switch roles pretty quickly,” Benny explains.

Similarly, if your company won’t go through rapid growth, someone who’s keen to be a “chameleon” will get bored and leave. By knowing your company’s rhythm, you can hire someone who will match it perfectly.

Get a realistic understanding of the company’s hiring budget

If you can’t afford to hire someone with 15+ years of experience, you won’t. Although this seems obvious, Benny has found that companies - and often startups - might want the best developers in the world, but their current status doesn’t allow them to do so. “Being realistic with your budget,” he says, “will help you better align your expectations with what you can afford.”

What to ask when thinking about context

Although a general hiring process is useful, Benny has found that knowing exactly what you need and why you’re hiring before you start, can help you merge your hiring process with your context. This can avoid turning a great candidate into a bad hire.

These are some of the questions he asks before deciding to hire - no matter the context:

“Do I understand the role am I trying to hire for?”

Some companies might say they need a performance marketer, for example, but what that means on a day-to-day basis is not commonly understood by other people, and other companies. And Benny says it’s a risky misalignment: “I think it’s largely because we’re in an ever-changing market, but at the end of the day I think a job title should first be boiled down to what tasks you need, and then extrapolating from that.”

Doing that, he says, informs how you look for the role, how you engage a candidate, and how you judge what skills apply. “As soon as you go to the market saying you need a senior developer,” he says, “it makes it very difficult for people to hire. The skill set and the job can be understood so differently across companies.”

A neat trick that Benny uses, to assess if a new hire is filling the role well, is a method he calls 30-60-90: By setting criteria a new hire needs to hit after 30 days, 60 days, and 90 days, it’s easier to pick up “red flags” early on, and proactively handling problem areas.

“Do I really need this role filled?”

From Benny’s experience, few companies actually ask this question before hiring: “I think people just say ‘Let’s get more people in.’ But in fact,” he says, “there might be a range of other blockers there. It could be that your team is not communicating properly, for example, and all you need are more effective meetings.”

By critically assessing your budget, what the state of team dynamics are, and your company’s current capacity, Benny finds it becomes far easier to discern if you actually need a new hire, or simply a new system.

“How would this person affect the current team dynamics?”

When hiring someone new, Benny considers what that person would bring to the team dynamics. If they’re someone who works better in isolation, a small and collaborative startup team would probably not enable them to work at their best.

At this stage, Benny thinks companies needs to explicate the qualities they’re hoping to hire: “You really need to understand what that person’s dynamic will add to the team, and say ‘Yes, we know how to integrate them properly’ or ‘Actually, even though they have all the skills they need, we don’t know how they’ll fit into team dynamics.’”

“How adaptable does this person need to be?”

Knowing how susceptible to change your company is, is also incredibly important to figure out what context you need to hire for. Startups change frequently, for example, and not everyone works well in a career trajectory that is constantly changing course.

Benny asks this question to assess whether he needs a part-time or full-time role, and whether the person he hires will need to move to a different role soon after being hired. Does that role require different qualities? And does this new hire have those qualities as well, should they need to move?

Before deciding to hire, Benny says that critically assessing your situation, and understanding in detail the role for which you are trying to hire, are incredibly important.

Only after having answered these questions, does he turn to his hiring process. Now, he needs to figure out how to mould the way he hires to his context:

“What part of the hiring process should I focus on?”

In Benny’s experience, a large corporate often has the luxury of a brand that people already have some idea of, and want to work for. Startups, though, don’t always have that, and simply copying a lengthy hiring process wouldn’t work: “There, you’re doing more fishing. You’re trying to sell, more than they are trying to apply to you, in general. It’s a different playing field.”

In other words, you have to tailor your process to your business’ current situation. For a well-known brand, for example, he’s found that you can often give candidates a technical test right up front, and people do them to get their foot in the door. “But it’s very difficult to do that in a startup,” he says. “You have to tailor it for a smaller filter, and rather pick three questions you want people to answer. Then, once you’ve sold them and ‘matched’ on your vision and mission, only then provide them with a technical assignment.”

No matter what: Iterate, iterate, and reiterate!

At the end of the day, Benny says it’s all a balancing act: “You still need a process, but you need to be smart enough to be flexible with it.” And this, he’s found comes from not hammering-off at the same process over and over again. If you focus on the context you’re in at that moment, you’ll organically come to understand what process works for what hire, and be able to adapt to whatever situation you’re in. “There are obviously fundamental principles to hiring, but it’s important to try different things, get feedback on them, and see if they work for you. Just don’t fall into lanes. Find what works for you, in your context.”

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