Looking for a new job? Don’t be boring

The best advice for someone who’s on the job hunt this new year

“Don’t be boring.”

When I asked Amanda Lannert, CEO of Jellyvision, what advice she had for people who are looking to get a job, that’s the answer she gave.

As a CEO of a rapidly growing 400-person company, soon to be 500 people, Lannert has done her fair share of hiring.

“It feels like companies hire people, but in fact people hire people,” she explained. “By and large, recruiters are bored. People play it safe. They commodify themselves into just a bullet-point list of skills and experience.”

By not being boring, Lannert pointed out how you’ll catch a recruiter’s eye, and make yourself much more likely to land that initial phone call or interview.

At the same time, it’s also a great way to assess the fit of the role for you, as a prospective employee. When you show who you are as a candidate — what you value, what environment you work best in — and don’t get a call back, that company may be saving you some time and energy.

How do you not be boring? Here are five things to try:

Focus on the cover letter, not the resume.

At Jellyvision, Lannert shared how they place supreme emphasis on the cover letter. “There’s nothing more refreshing than seeing someone who takes a chance to be incredibly human in a cover letter or an outreach, to put themselves forward,” she says.

This means language that’s real, down to earth — not stiff, business jargon-y, and cut from some googled job site template. As someone who’s reviewed thousands of applicants for jobs for Know Your Team, I’d often set aside an application when the person would start their cover letter with, “I’m interested in X role. Please see my resume attached.” Everybody writes that in their cover letter — focus on saying something different.

Show, don’t tell.

A few years ago, a friend of mine wanted to land a job at Trunk Club, a company he’d been dreaming to work for some time. The only problem was that they weren’t hiring at the time. I suggested that he show them what he had to offer the company — not just tell them. So my friend whipped up a 50-slide PowerPoint presentation detailing ideas, suggestions, and projects for exactly how he could improve their online presence and user experience. He did the work of showing how he’d be an asset to the team — not just telling. Lo and behold, they created a role for him and offered him a job.

Get creative.

As a CEO myself, when I was hiring Know Your Team’s first full-time programmer several years ago, I’ll never forget how one applicant wrote me a poem — yes, a poem — perhaps 20 lines long that described who he was and why he desired the role. While we didn’t end up selecting him (he lived outside the United States and we required that the person live stateside), I remember that application so vividly even years later. He took a chance, got creative, and stood out from the 400+ applications we received in the first 72 hours alone. He was far from boring, and it worked.

Demonstrate you want this job, not just any job.

Another way to not be boring is to make it clear: “I want to work here, nowhere else.” This past year, when we were hiring for our Chief Technology Officer role, someone took the time to build a custom software application, just for Know Your Team. He’d replicated the Know Your Team software to the best of their ability, using what he’d gathered from screenshots he’d seen online. His intention was to demonstrate that he was technically up to snuff for the role.

My greatest takeaway was that it showed he wanted to work here, and nowhere else. I was impressed by him wanting this job, not just any job, and that caught my attention.

Sound like yourself.

Perhaps most importantly, you should make sure you sound like yourself. Don’t try to write a poem if you’re not good at writing poems. Don’t try to be funny in your application if you’re not funny. Be thoughtful in portraying the truest version of yourself — not what you think the employer wants to read.

If you’re concerned about how to do this, the key is simply to take put a little time and care into your application. Don’t rush your writing your cover letter. Think about how you can thoughtfully show who you are and what you can bring to the company. When you pour considered thought and energy into something, your true self will come through. Being not boring is about being yourself, more than anything else.

Keep this credo of “Don’t be boring” in mind, as you apply for a job. Dare to be different, and stand out from the sea of bullet-pointed list resumes and bland cover letters. The less boring you are, the more memorable you are. And the more memorable you are, the more likely you’ll land the job you want.


Claire is the CEO of Know Your Team – software that helps you become a better manager. Her company was spun-out of Basecamp back in 2014. If you were interested, you can read more of Claire’s writing on leadership on the Know Your Team blog.

This article was originally published for Inc.com.

How to tell if a CEO is worth working for

If you’re looking to leave your company to work for another, you’ll want to consider this.

A few months ago, someone asked me for advice about potentially leaving one company to go work for another. He was curious what factors he should consider before making the decision.

He’d already vetted the role, the company, and the offer itself — all important aspects to consider. But I told him, in my opinion, the most crucial thing to vet is the CEO.

If you’re about to join a new company, you must figure out:

“Do I believe in the CEO?”

No company is successful with a CEO who can’t communicate, who can’t get everyone on the same page, who can’t hire well, and who can’t chart out a vision.

Personally, I remember interviewing at one of my first job out of college, and I remember it being really hard to tell if a CEO is “good” or not.

Plenty of CEOs sound like they’d be a good CEO. They’re charismatic, they’re articulate — but does sounding like a good CEO really make it true?

After almost four years of researching and observing hundreds of CEOs, I’ve learned to ask these four questions to discern whether or not a CEO is a good CEO:

#1: “When have you had to sugar-coat the truth — or avoid telling the truth — to your team?”

How a CEO answers this question reveals her barometer for integrity. Your CEO might laugh and say, “Oh, all the time,” a little too flippantly — signaling that she intentionally misguides employees habitually. On the other hand, if a CEO is too hesitant to admit anything substantial, that’s a red flag as well. It’s likely she’s holding something back. Ideally you’re looking for a CEO to level with you and admit in a nuanced, considerate way when she’s chosen to not be transparent with the team, and why.

#2: “What do you think is your own greatest leadership blindspot?”

This is a take on the classic, “What do you think your greatest weakness is” question — but with a twist. The word “blindspot” implies that the CEO has a weakness she might often overlook. So her answer to this will reveal her self-awareness. Does she have a hard time giving you a straight answer? Or is it clear that this is something that she’s thought a lot about, self-reflected upon, and perhaps even talked about with peers or an executive coach. If it’s the latter, it signifies that this leader has the humility and self-perceptiveness you’re looking for.

#3: “What does ‘success’ for the company look like to you?”

This may seem like an unassuming question to ask — perhaps it’s one you’ve asked the CEO already. However, we often don’t listen closely enough to the answer. If all the CEO is focused on is “winning” and “making money” and “dominating the competition” in her answer, I can guarantee that’s 100% what the work environment is going to revolve around. On the contrary, if she also talks about creating a sustainable, healthy culture, and making sure people feel fulfilled, challenged and supported in their jobs — you can bet that the work environment is going to reflect that. The answer to this question makes is crystal clear what a CEO’s priorities are.

#4: “What would an employee who’s left the company say it’s like to work for you?”

This may feel like a tough question to ask you prospective CEO — especially if they haven’t hired you yet. But it potentially is the most important question. The answer to it demonstrates how cognizant the CEO is of how they’ve treated employees in the past, and how willing they are to admit if they’d haven’t been the ideal leader. Be wary of CEOs who say only positive things, as it shows their refusal to recognize their shortcomings, or failure to understand how their own leadership behavior may have driven the other person away.

If you’re worried that asking these questions — particularly the last one — might offend your prospective CEO, that in itself is a sign that the CEO might not be who you’d hope for. The best leaders welcome tough questions, and will be impressed by your desire to better understand how they lead.

If anything, asking these questions will make you look better in their eyes. And, it gives you all the information you need to decide if they’re a CEO worth working for.

Claire is the CEO of Know Your Team – software that helps you become a better manager. Her company was spun-out of Basecamp back in 2014. If you were interested, you can read more of Claire’s writing on leadership on the Know Your Team blog.

This article was originally published for Inc.com where I write a column on leadership.