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.

The power of positive intent

My greatest weakness, and how I’m learning to overcome it…

My parents were in town last week. During one conversation we had, my mom shared an opinion that I strongly disagreed with. And as I responded to her, she said this to me:

“You’re getting defensive.”

Throughout my life, I’ve heard this quite often. Getting defensive is my greatest personal weakness. It’s a terrible habit of mine that I’ve been aggressively working to counteract, especially in the last few years.

When I hear something I don’t want to hear, I jump to conclusions about why that person is saying that thing. Instead of trying to genuinely hear out the other person, I’ve already decided in my head that they’re misinformed, or have an ulterior motive, or don’t have my best interest in mind.

This tendency of becoming defensive doesn’t just show up in my personal life…

As the CEO of Know Your Team, I’ve felt moments of my own defensiveness creep up when our programmer Matt has made a suggestion about how to respond to a customer support request, or when he’s critiqued a layout of a design I’ve mocked up.

This defensiveness is dangerous. Because when you’re defensive, you stop listening. And when you stop listening, you shut out critical information that could benefit you. Whether it’s from your mom or from your co-worker, you have an opportunity to learn something meaningful… such as, how you need to be more generous with your time to others, or an idea that leads to increased sales in your business.

But when you become defensive, none of that information reaches you. Defensiveness cuts you off from learning.

Over the years, I’ve noticed the root cause of my defensiveness: I misread the intention behind what someone is saying.

For example, when I react defensively to my mom’s critique, it’s because I think she’s just being negative. Or when I react defensively to a suggestion Matt has about a design, it’s because I assume he’s trying to advocate for something else that he created.

When you accuse another person of bad intentions, you create defensiveness. Instead, assume good intentions, and your defensiveness goes away. That is the best way to combat defensiveness.

In fact, Indra Nooyi, the CEO of PepsiCo, describes learning to assume positive intent as the best advice she’s ever received:

My father was an absolutely wonderful human being. From him I learned to always assume positive intent. Whatever anybody says or does, assume positive intent. You will be amazed at how your whole approach to a person or problem becomes very different. When you assume negative intent, you’re angry. If you take away that anger and assume positive intent, you will be amazed. Your emotional quotient goes up because you are no longer almost random in your response. You don’t get defensive. You don’t scream. You are trying to understand and listen because at your basic core you are saying, “Maybe they are saying something to me that I’m not hearing.” So “assume positive intent” has been a huge piece of advice for me.

Now when I feel myself starting to get defensive, I remind myself to take a step back and assume that the other person has good intentions.

With Matt, if you know him, you know one thing is clear: he’s vocalizing a suggestion because he truly cares about Know Your Team.

And if you know my mom… Well, I don’t think there’s another person on the planet who has more of my best interest at heart!

Recognizing this doesn’t mean I’ll submit to whatever Matt’s suggestion is when he offers it. And it doesn’t mean I’ll always end up agreeing with my mom when she shares her opinion.

But it does mean I’ll widen my mind. I gain a greater understanding and perspective of a situation. By truly listening to the other person’s viewpoint, I can make a more informed decision.

So when your employees raise a concern, don’t assume that it’s because they’re just miffed about their current job titles or how long the last client meeting was. That might very well be their underlying motivation — but you shouldn’t rush to that conclusion right off the bat before even hearing them out.

Assume positive intent. Thank them for their feedback. And then listen. Don’t interrupt. Ask questions. Clarify where they’re coming from. And then form your own opinion about the content of what they’re saying and what their true intentions might be.

Is it a bit more work to navigate the friction that comes from assuming positive intent, and not merely brush off someone’s idea?

Absolutely. But that friction is productive energy — it pokes holes in my own thinking and strengthens the actions I do take.

When I choose to assume the best intentions in others, I become a better leader, co-worker, family member and person. I don’t practice it as often as I should, but I’m vigilantly committed to working on it until I do.


Enjoy this piece? Read more of Claire‘s writing on leadership on the Know Your Team blog. And, check out Know Your Team – software that helps you become a better manager.

The most helpful thing you can say to a teammate: “It’s your call”

Great people blossom when you nurture them with trust and respect

When a teammate asks me a question, one of my favorite responses is “It’s your call.” It’s such a simple yet powerful phrase. In just a few words it conveys…

Trust | Confidence | Respect | Autonomy | Ownership | Empowerment | Responsibility | Decisiveness

How can such a simple phrase mean so much? Take this common scenario — a team discussing what to work on next. Here’s one version of that conversation:

Julie: What should I work on next?
Shelley: How about a native homescreen?
Melissa: I’ve always wanted breadcrumb navigation!
Sara: Another option would be to squash some 🐛
Erica: File upload feature would be cool

Now there’s absolutely nothing wrong with a back and forth like this. Julie has opened the door for feedback, and the feedback provided makes total sense.

But imagine the same opening line with a single response:

Julie: What should I work on next?
Shelley: It’s your call 😀

Immediately the whole tone of the conversation has changed for the better.

Instead of asking for permission and being given specific directions, Julie has been empowered to make the decision herself.

She now has complete ownership. She’s free to explore and make her own choices. She’ll assess all the open tasks. She’ll drum up her own new ideas. She’ll decide what’s next based on her own criteria of importance.

More importantly the team has expressed sincere trust, confidence, and respect in her and her abilities to do everything. They’ve said “whatever you decide is cool with us.”

Full autonomy like this has significant long-term benefits to teams —no managers, increased motivation, time saved, sharper assessments, faster decisions, happier people, improved independent learning, better teamwork and so much more.

All of that accomplished by just saying a simple phrase.

When it comes to software development, conversational opportunities like this come up pretty frequently. Keep an eye out for questions about:

  • What to work on next
  • How to implement a feature
  • What tools, APIs, or libraries to use
  • How to manage/keep track of work

Of course when you’re asked for your opinion, you can certainly give it — you don’t want to leave people completely hanging.

But before you do that, consider challenging the person asking the question by simply saying “It’s your call.” You’ll be pleasantly surprised by the outcome, and the long-term benefits are well worth it. 🤘


Great things can happen when you emphasize these values — Basecamp 3 and its Android app are the result of a handful of autonomous teams working in an independent, yet highly coordinated environment.

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