One Major Hiring Mistake You’re Making

Julien Emery
5 min readMay 31, 2016

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A lot is being written about how to hire and onboard millennials — and keep them engaged in their jobs. But there’s a whole other labor force out there, and it’s on the rise: the over 45 crowd. It might even be you. These folks have spent years in the workforce and, like millennials, have gained a reputation. Theirs being that they’re not tech-savvy, are slow to learn the ropes of a fast-paced, modern workplace, and expensive to a company from a benefits perspective.

Rather than pinning millennials and non-millennials against each other (as some might argue Dan Lyons does in his new book), let’s consider what character traits we should look for in employees, and how we can set them up for success, regardless of their demographics.

Here are the most important factors to consider when hiring and onboarding a new employee:

The tech factor

Today, few companies function without services, apps, and tools that for some, are second nature. When you’re hiring a new employee, consider how familiar they are with the tools that you use, and how quickly they can get up to speed. Think about which tools are core to their job function, and which aren’t.

  • Your product. Will they be responsible for educating customers about your product? Will they be using your product in their day-to-day role? Or, does their role not require them to be a product expert?
  • Chat apps. Is Slack (or another chat app) core to your operations, or used by handful of people (the design team, for example). If it’s the former, make sure they’re familiar with either whatever app you use, or have used similar apps in the past.
  • Industry-specific tech. Whether it’s Salesforce, Photoshop, or Freshbooks, make sure they’re an expert in whatever tools are core to their job. Ask a lot of questions to dig deep into their knowledge to weed out the resume stuffers and fluffers.
  • Operating systems and hardware. Unless your employees are solely responsible for setting up their own machines and downloading appropriate system updates, don’t worry too much about finding someone with deep tech expertise. If, however, you run a Mac-only or Windows-only business, be sure to ask the candidate about how comfortable they are using one or the other.

Onboarding your employees will be that much easier with Allay. Learn more

How they interview you

The sorts of questions a candidate asks during an interview should give you a good sense of the type of thinker they are.

  • Are they already considering challenges and working backwards to figure out solutions?
  • How have they learned from their past mistakes?
  • Would they even own up to past mistakes?

A great candidate walks into an interview armed with questions that make the the interviewer feel that he/she is already working with her. She wants to know how her role will make your job easier, and what will be expected of her one, three, and twelve months into her job.

One major red flag? A candidate who declines the opportunity to ask questions during the interview.

The importance of mentorship (hint: it goes both ways)

Millennials and — let’s say — more ‘mature’ employees have a lot to learn from each other. Being open to mentorship is crucial to helping both sides learn and grow. Think through the ways that millennials can benefit from a someone who’s spent 10 years at the same job; and vice versa, consider what a millennial employee has to offer this same person: how to navigate certain social media channels, new trends, etc.

According to HBR, reverse mentoring is increasingly making its way into companies and the arrangement gives both millennials and their older colleagues opportunities to acquire new skills. Millennials, who now outnumber baby boomers in the workforce, can offer older employers invaluable insights into new ways to connect with customers, for example, while simultaneously benefitting from their colleagues’ years of leadership experience.

All employees, regardless of their age, value these opportunities to learn and expand their skill set so if your company offers a mentorship program, consider highlighting the ways that your (older) candidate can benefit from it, and also serve an important role in shaping your company culture and industry — if they’re open-minded and excited about the chance to both mentor and be mentored, you’re on the right track.

Resourcefulness (hey, MacGyver)

How an employee approaches the resources they have at hand, or lack thereof, is quite illuminating. Showing you that their work will help you succeed is a clear sign of a resourceful employee, but how else can you predict whether or not a candidate will offer a return on your investment? A few hints include:

  • They’ve hustled in their career. Whether they once worked at a bar while taking night classes, or accepted a late-in-life internship, they’ve prioritized time to step outside their comfort zone.
  • They’ve got their hands in a few pots. They’re plan B and plan C people who have proven time and time again that they can pivot quickly.
  • They’ve failed. They’re the everyday version of Elizabeth Gilbert: they’ve pursued opportunities they’ve been passionate about and continued trucking along, despite occasional roadblocks and perhaps even incredible failures.

Redefining ‘culture fit’

For years, young companies would hire employees based on the dreamy idea of whether or not they’d want to have a beer with the candidate. Not only did this approach breed gender bias and ageism, but it actually prevented employers from discovering and employing some really great people. Instead, focus on other characteristics in a candidate: trustworthiness, loyalty, communication skills, etc. Think about culture fit in the framework of what is and isn’t acceptable in your company culture.

Work ethic: Is the candidate naturally curious? Does he want to continually learn?
Humbleness and honesty: Do they show respect for others, regardless of seniority or job title?
Communication skills: Are they able to communicate clearly, honestly, and respectfully?
Responsibility: Will they take responsibility if something goes wrong at work?
Flexibility: Are they willing to figure out and think through a problem before presenting a solution?
Feedback and criticism: Are they able to give and receive feedback without taking it personally?

Dogs, ping pong, and beer is not culture, but whether or not a person’s character aligns with your company’s mission and goals is.

So go ahead, don’t be too alarmed by Dan Lyons’ experience at Hubspot; mature workers’ value to your company is underestimated and overshadowed by millennials. But evaluating candidates on the basis of age is the wrong way to go about hiring. Instead, strive to hire the best people for the job and diversify your workforce and you may just find that a multi-generational company can help you rise above the rest.

(This post originally appeared on the Allay blog)

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Julien Emery

Hyper curious about everything. Big fan of chocolate chip cookies and Axis & Allies. Co-Founder @HeyAllay https://allay.io/