The Right Questions Get You The Best Job Opportunities

The Right Questions Get You The Best Job Opportunities

If you don’t ask, you’ll never know.

Heard it a million times.

The part that is missing for me is:  Why ask questions when you might look dumb for it? Especially in front of a boss you want to work for. How do you form a question about something you don’t understand?!

As a child, I wanted to sell bracelets, but they didn’t just magically appear – I had to make them.

I was too young to use YouTube so going around the neighborhood and asking friends for tips was the only option. When you’re a kid, asking for help always seemed so easy. Everyone was so willing to help – right?

Now that I think about it, every other person said they had no clue how to help me, but my ambitious mind completely ignored the naysayers! What I do recall was the advice and pointers my helpful neighbors gave me.

So why was I feeling ashamed of not knowing something when I was only a question away?

As Miley Cyrus would say it: it’s the climb! And asking questions can help you reach the top.

Here are the three most important tips to asking great questions, and getting better answers:

  1. Preparation. Yes – even for questions. Everytime I observed my dad in a meeting during ‘daddy-daughter’ days at work, he always knew what to say and ask to figure out how to proceed. Knowing what you don’t know before going into a meeting will  set the groundwork for you to grow and succeed!
  2. Honesty. Don’t act like you understand the topic of conversation if you’re unsure. People will respect you more for asking questions, wanting to understand, and doing a good job.
  3. Dig deeper. Follow up your questions with a more pointed question if the answer is still too foreign of a concept. During speech competitions as a teenager, my debate teacher said: “The only way to get the true answer is 7 questions deep”.

Using this method/technique, I found my voice and confidence in taking calculated risks. I learned that making a fool out of myself is nothing to be ashamed of.

I come from a small town in the midwest. So opportunities are sparse.

Life took over and soon enough I was living halfway across the world in Europe, a college dropout and former co-founder of a dissolved startup.

I stumbled upon an intriguing purple company called ClickUp on the Angel List job opportunities. I started using the product to prepare for the interview and fell in love with the clean interface and ease of use.

I submitted an application…and never heard back. Bummer.

The weekly new feature updates showed how consistent they were listening to customers, so I decided to put my own two cents into an email to

Wes, the VP of Operations, responded to my email blazingly fast!

After hitting send on that impromptu email, I was incredibly nervous. “What if they think my application is a joke because it’s coming through their customer support inbox?” I thought.

My wife reassured me that the only two results of the situation were either good: I put myself out there, or better – I got an interview.

I believe this motto is applicable to many aspects of life and business: you will only stumble upon innovative ideas by testing the waters.

The only thing the market can say is “No, try again.”

  • Want to know why people love ClickUp? Just ask.
  • Want a Career at ClickUp? Just ask.

We’d love your help in making ClickUp the best Project Management tool in the world!

Landing Silicon Valley Employment is up to you. Not Luck.

  • What are the best questions that you have asked?
  • Have you had the same experience as I have?

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