That Was A Yes Or No Question

I think I’ll avoid all the “are super angels colluding“, “no they aren’t“, “go fuck yourself and stop talking horseshit“, and “guys, quit being narcissistic and do something productive” blog chatter today and focus on something that came up yesterday.

I was on a call when someone asked a straightforward question that had a binary answer (yes or no).  The person responded with a five minute explanation with a lot of details, all factually correct and contextually relevant, but at the end still didn’t answer the question.

My partner in my first company (Dave Jilk – now the CEO of Standing Cloud) used to have an endearing way of dealing with this.  Here’s how it would play out.

Dave: “Is the release going to be on time?”

Software Engineer Dave was Talking To: “Blah blah blah, five minute explanation of all the things that he was struggling with, why everything was difficult, what the risks were on timing, blah blah blah, why the client was giving mixed signals and changing things, and can’t I have a faster computer please?”

Dave: “That was a yes or no question.”

We spend a lot of time getting derailed in our work.  I’m as guilty of it as anyone as I often answer a question with a story from my experience. Sometimes that’s a helpful thing to do; other times I should just answer “yes” or “no.”

The corollary to this is to ask why.  I’m a huge fan of the 5 Whys approach and went through it with a long time friend and CEO of a company I have an angel investment in at dinner last night.  He’s been struggling with some stuff and I explained how (and why) he should be using 5 Whys to try to get to the root cause of the issue, rather than staying on the surface and not actually learning anything. In his case he was experiencing the opposite of the yes/no problem – he was trying to ask an open ended question and getting a yes/no answer.  For example:

CEO Friend: “Are the trials converting into customers?”

CTO: “No”

The appropriate response from my CEO Friend in this case would have been “Why?”  And I’d predict he’d need to ask “why?” several (four?) more times before he got enough information to actually know what was going on.

I encourage all CEO’s in the world to use these two approaches judiciously.  Don’t ask me why – just do it.

  • Great post.

    Reading it I immediately flashed to how my 3 year old son has entered the "5 Why?" phase (Although sometimes it feels like 20 of them). More importantly, it is clear that by the 4th or 5th why I have answered his question with far more clarity and reason than my quick/initial answer.

    Amazing how we jump to give a quick answer instead of a considered one. And equally amazing how curiosity that is so natural at age 3 would serve us well for the rest of our lives if we could stay connected to it.

  • smurchie

    Nice one, Brad. The 5 Whys is new to me, but is a great tool.

  • Om Malik

    Of course, some (ahem!) believe that nuances have a place in discourse as well, especially when used judiciously.

    That aside I think you offer some great advice! All of us should pay heed.

    • DaveJ

      Brad loves to quote things I said when Reagan was still President.

      The key is to separate the 'what' from the 'why,' not to focus on only one. The yes or no answer allows one to deal in facts and the reality of the current situation. The nuance (why?) allows one to begin analyzing how to adjust for the future.

      Also there is a difference between nuance and bullshit. See On Bullshit (

  • Ian Peters-Campbell

    You don’t want to focus on the angel scandal? Why? I keed, I keed. I think sometimes people actively avoid looking for root causes. Digging into problems can be a scary thing, like looking st your credit card bills or going to the doctor to see about that lump. Of course in the end it is usually not as bad as you feared and looking at it head on helps, but I suspect that a lot of the time when people don’t look for root causes they are afraid of finding out that a company’s issue might turn out to be terminal or, worse,are afraid that the failings are entirely theirs. Forcing oneself to shine light in those corners is a hard thing.

  • zack

    I like this approach

    I'm OK; The Bull Is Dead

  • jack

    Excellent advice for Mr McClure

  • I do not get the point here, Brad. What are you trying to say??

    Keep in mind, there are mortals reading your posts….

  • aviah

    For releasing on time the safest answer is "no".
    No need to mess with the "yes" option.

  • Nice one, great adivce!

  • Dr. RTFM


    Have you stopped beating you wife? it's a yes/no question, please don't give me a 5-minute blather.

    • WHY are you asking that question?

    • Brad, feel free to take this down. It doesn't contribute to the conversation and no one likes seeing this. Commenters that hide behind this sort of anonymity don't deserve a response or their comments to be seen publicly…

      • I agree, but I thought it was a good chance at asking an anonymous coward "Why" as an object lesson.

  • Dr. RTFM

    Wow. I'm impressed. You censor comments in real time if they show how stupid your article is.

    • I have no idea what you are referring to here. I only delete spam – I rarely delete any legit comments, no matter how offensive they are. I assume you are responding to your question above about "have you stopped beating your wife"? As you can tell, I responded to you with "Why are you asking that question?"