Career Advice

Lack of doubt and overconfidence are toxic to your career. A curious mind, on the other hand, is invaluable in business and a healthy sense of doubt is one of the most important characteristics of effective people. People in power know that learning and growth start with questions. We pay attention to the questions you ask in job interviews and meetings.

Questions like these really matter and change people’s lives (from big to small):

• What should I do with my life?
• Is this job a good fit for me?
• Where am I going in my job this year?
• How valuable is my work to the company?
• What will I accomplish this quarter?
• Am I getting enough feedback and guidance from my boss?
• Am I on track this month?
• How does this work? Why?
• How could I improve this?
• What can I learn from this?
• Am I prepared for my conference call this afternoon?

How do I know when a new member of the team is unlikely to work out? It’s usually someone who asks few questions during training, then sits down to work and charges ahead with full confidence (usually doing the wrong thing) without checking in for feedback until I request an update.

Some people are naturally more curious than others — but forget about that because you can create your own healthy sense of doubt with practice. Our minds generally do what we ask them to – ask and ye shall receive.

So use this checklist:

1. Hang a list of daily questions for yourself in your bedroom and/or your office.
2. Put questions in locations that will remind you at the right time in the right place. I keep a card on my monitor that says “Prepared? Specific enough? Documented?” No, it doesn’t always work, but I’m still a little better with the reminder than without.
3. Ask yourself “What am I missing? What other possibilities are there? What consequences might flow from this?“ Consider a longer list of options and try to include some wacky ones. Get outside your comfort zone for a moment.
4. Spill your guts. When you’re tempted to ask something but feel inhibited or fearful about asking, pay close attention – it’s usually a question that needs asking. Just ask. You’ll find the cost of not asking is almost always higher.

Get the ebook! If you liked what you read here, and think you may want to refer back to this guide later, grab the Kindle version – we’re hoping you’ll thank us with a five-star review on Amazon if you found this material helpful. The ebook also includes our job search guide.

For comprehensive advice on the entire job search process, read our complete guide to landing a job at a great company or visit our career advice hub.