Never stop asking “stupid” questions

When I joined Microsoft, the team running my NEO[1] session shared a piece of advice with my “class” of fresh-faced new hires:

“Think of your first year as a grace period where you can ask any question you want, without anyone thinking it’s a stupid question for which you should already know the answer.”

This sounded like empowering wisdom at the time, but the unspoken side of it was damaging. Between the lines, I heard this message as well, and it was this part that stuck with me:

“You’ve got one year to figure things out, and after that you’d better have your act together and know everything – because if you keep asking stupid questions we’ll know that we made a mistake hiring you.”

I hope it’s obvious that this wasn’t the intent of the advice, but I’ve spoken to enough people over the years to know that I’m far from the only one to take it this way.

bored-3126445_640
How Matthew pictures everyone reacting when he asks questions.

In retrospect, I believe that I should have known better, but I let this unspoken message find a home in my brain, and I listened to it. I remained quiet – and remained ignorant – when I should have been asking questions.

Over the past few years[2], I have finally broken this self-limiting habit. Day after day, and meeting after meeting, I’m the guy asking the questions that others are thinking, and wishing they could ask, but don’t feel comfortable or confident enough to speak up. I’m the guy asking “why” again and again until I actually understand. And people are noticing.

How do I know that others want to ask the same questions?

I know because they tell me. Sometimes they say thank you in the meetings, and sometimes ask their own follow-up questions. Sometimes they stop me in the hall after the meeting to say thank you. And on a few occasions people have set up 1:1 meetings with me to ask about what I do, and how they can learn to do the same.

How do I know that people are noticing?

A few of the people I’ve interrupted to ask “why” have also set up time with me to discuss how they can better communicate and prepare to have more useful and productive meetings.[3] These are generally more experienced team members who appreciate that my questions are highlighting unstated assumptions, or helped them identify areas where they needed a clearer story to communicate complex topics.

I’ve been with Microsoft since October 2008 – a little over 11 years. I’ve been working in the industry since the mid 90s. At this point in my career it’s easy for me to ask “stupid” questions because the people I work with know that I’m not stupid.[4][5]

This isn’t true for everyone. If you’re younger, new to role or new to career, or from an underrepresented group[6], you may not have the position of relative safety that I have today. My simple strategy of “asking lots of questions in large groups” may not work for you, and I don’t have tested advice for what will.

My suggestion is to ask those questions in small groups or 1:1 situations where the risk is likely to be lower, and use this experience to better understand your team culture… but I would love to hear your experience and advice no matter what you do. Just as your questions will be different from mine while still being useful, your experience and advice will be different, and will be useful and helpful in different ways.

Whatever approach you take, don’t be quiet. Don’t stop asking questions.

Especially the stupid questions.

Those are the best ones.

 

P.S. While this post has been scheduled and waiting to go live, there have been two new articles that showed up on my radar that feel very relevant to this topic:

  1. The Harvard Business Review posted on Cracking the Code of Sustained Collaboration and how leaders can build and encourage cultures where these behaviors are rewarded.
  2. Ex-Microsoftie James Whittaker posted on Speaking Truth to Power, which presents critical observations of three eras of Microsoft, with examples of how different generations of leaders have affected the corporate culture.

These are very different articles, but they’re both fascinating, and well worth the time to read.


[1] New Employee Orientation. Sadly not anything to do with Keanu Reeves.

[2] I wish I could say that this was a deliberate strategic move on my part, but it was more reactive. Credit goes to the rapid pace of change and my inability to even pretend I could keep up.

[3] Yes, that means meetings where fewer people interrupt to ask “why.”

[4] I’m waiting for the flood of snarky comments from my teammates on this one…

[5] Or in any event, my asking questions is unlikely to change any minds on this particular point.

[6] If you’re not a middle-aged, white, cisgender man…

2 thoughts on “Never stop asking “stupid” questions

  1. Jeff Weir(d)

    This is powerful, Matthew. Many of the places I’ve worked haven’t encouraged one question in particular: “Why?” Maybe that’s because I work in a Government town. I’ve recently left a cushy, overpaid perm job in Government because I knew asking “Why?” almost never got a reasoned response. I’d got so disheartened with this that after 1 year I stopped asking. And then I started to slide toward depression. So after nearly three years I quit, and went to work for myself. Should have done that 2 years earlier.

    It’s tricky to ask “Why?” as a contractor, mind. I can’t afford to overly critique the thing they are hiring me to work on. But I do critique…just very carefully 🙂 And it’s often fairly easy to find a silver lining, when you’re getting well paid to sharpen your technical skills.

    One day I’d love to work in an organization that embraces something akin to “Radical Candor” because I imagine “Why?” is a big part of that.

    Liked by 1 person

    1. I found that asking “why” was easier as a consultant, but in retrospect I would ask it differently than I ask it today. As a contractor I would ask “why” when I believed that the client was doing something with negative impacts – often because “that’s how they’ve always done it” – and I wanted to guide them to that realization on their own. Saying “this is dumb” often results in an antagonistic response, because someone made the “dumb” decision in the first place, and their ego is invested in its success. But by carefully asking questions and letting the customer answer them, it’s often possible to help the same people make decisions that are better aligned with their current requirements and goals…

      Like

Leave a Reply

Fill in your details below or click an icon to log in:

WordPress.com Logo

You are commenting using your WordPress.com account. Log Out /  Change )

Google photo

You are commenting using your Google account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s