The Art of Asking Questions

Curiosity is the hallmark of a great teammate. When I am recruiting people, I will often look for signs of an inquisitive mind. Do they ask questions? More importantly, How do they ask questions? A person who is truly interested in a topic will ask questions in good faith.

One of the worst things about the internet is the freely available anonymity. You can be anyone in the digital realm. On Twitter, you can say anything to anyone. You can be rude or hurtful and no one will ever know its you.

South Park had a great episode about shitposting

Where do these two ideas (curiosity and anonymity) intersect? I have been holding team Q&A monthly sessions and originally the questions were anonymous. I noticed the tone of the anonymous questions was almost always harsh and assuming negative intent.

I made the decision to ask everyone to put their names on their questions. I followed that up with a message that I would never ever give someone a hard time for a question they asked. Curiosity must be encouraged at all costs.

Immediately I noticed the questions were posted in a much nicer format. The topics were the same, but the edge of negativity disappeared. I knew that some people may not have asked their questions, but the volume seemed to remain about the same.

It got me thinking about whether people are ever coached in the art of asking good questions? I’m my own education, I can’t remember any teacher helping with this. I think it may be one of the most overlooked skills we are taught as children and adults.

How do you cut to the heart of the issue and ask the question that illuminates the topic for yourself and others? How do you frame a topic in a way that doesn’t put the speaker on the defensive? How do you stay concise but also give enough context?

Journalists may be the only profession that gets training in this. I certainly don’t have the answers, but here are some tips.

  1. Don’t assume the answers. The whole point of asking is that you didn’t already know.
  2. Assume positive intent. Putting someone on the defensive is not going to get you a clear answer.
  3. Assume nuance. Every question has an area of gray. Almost nothing is black and white.
  4. Mirror what you hear to make sure that’s what they meant. This is a good follow-up technique to make sure you are aligned.

Have you thought about the way you ask questions? What is a tip you would suggest?

UPDATE: My son educated me on how SDRs and Salespeople are trained on asking questions of prospects to make sure they don’t put them on the defensive. I wonder if they apply that valuable skill internally when asking their managers questions.


Comments

One response to “The Art of Asking Questions”

  1. In the programming world, I feel like there are 2 parallels sentiments. First, people are often terrible at asking why code doesn’t work. They will say things like, “I installed the library and it’s broken – how do I fix it?” Ok, what is broken? Are you seeing any error messages? Does any of it work? What have you tried so far? People seem to think that everyone can just read their mind.

    Similarly, people are often terrible at making suggestions. If, for example, you bring up something interesting about MySQL, people will comment, “You should check out PostgreSQL”. Or if you bring up something interesting about Photoshop, people will comment, “Try using Affinity Photo”. But why? Backup your suggestions with something – is it solving a different problem? Is there some radical new take that I have to know about? Is it incrementally better or 10x better?

    I feel like people just want to be heard – but they don’t want to truly engage.

Whatya think?