The best career advice I’ve received, a decade later.

December 11, 2020


“Its all about asking questions.” Ron’s advice landed and stuck in my eager early-career brain. Ron is a business coach and through luck and circumstance I wound up in a 1:1 with him before I knew I needed it. But this idea stuc k. It knocked me out of a mostly selfish career trajectory and got me thinking about the group win.

“Ask questions.” From that day forward this idea has guided my approach to business relationships, and process. Ask questions. Be curious.

I have a tendency to talk fast. I like an active conversation, participants riffing off one-another, full of interruption and rabbit holes. With the right person or group, it's fun and effective. But too often (I have come to understand) it can be all wrong. Fast, interruption-laden chatter can be intimidating to reports, overbearing to peers and off-putting to managers. For me, asking questions has been a way to slow down, listen better, and work well with a wider variety of colleagues.

OK, so how does one ask good questions? There are many resources on the anatomy of a good question, and the basics include timing, context and open-ended-ness. My favorite resource on the topic is a book by Warren Berger called A More Beautiful Question. Check it out.

And in the meantime, here are some of my favorite tips on the art of asking questions:

1. Be genuine.

Be sure your questions come from an authentic and curious place. For some, this comes naturally.

If for some reason you find yourself less than interested - perhaps you are tired, burnt out or maybe even making the best of a bad professional situation, find a way to really want to know the answers. Otherwise you risk the appearance of pandering and damaging your relationship.

Practice the gratitude mindset to get to a place of genuine curiosity. What are you grateful for? Think on this, and write some things down. Now, next, what do you want to know about your colleague, their business and their world?

2. Try it with friends.

Perform little tests with friends and family. Ask about something that matters to them, but that you don’t usually bring up or already know about. See what happens. Look for their reaction, and the amount of information they offer. Your goal is twofold: learn about what matters to them and develop rapport.

As with any learned skill, practice, practice, practice.

3. Leave space.

This is always a tough one for me. Get comfortable with silence. Allow time, WAY more than feels comfortable, for a response. You’ll get a better and more complete response. And space also has the benefit of keeping the conversation balanced- so it does not become a one-sided inquisition.

Learning to leave space and becoming comfortable with silence is a critical skill all its own, useful in negotiation and especially helpful for know-it-alls like myself. Asking questions is actually a GREAT way to practice allowing for silence and finding the right cadence for any conversation.


Ten years later and the practice of asking questions has actually INCREASED my curiosity about the world. The more I ask, and learn, the more I want to know more. I am thankful to Ron for this wonderful insight.

And I am curious, how will YOU use the idea of asking questions in your work?

Photo by Jac Alexandru