The Negative One

I am having problems at the moment; I am being labelled the negative one. Why? Well I am asking a lot of questions. Probably not asking them in the right way I guess. So why am I asking so many questions.

I want to go deep. People use to tell me their plans, their ideas, they sounded great, and I had even seen a lot of them work in other companies, other contexts. But instead of playing along, now I ask questions.

  • What problem is this solving?
  • Why do you think this is a good idea?
  • Have you considered this?
  • I am not sure that is a great idea because of X & Y, what do you think about X & Y?
  • I disagree because of X & Y, no? I added this as I recently said this. Writing it and re-reading it, it isn’t asked how it could be. E.g. Ok, but what about X & Y, could you see them impacting this idea?
  • How did you get to this idea?
  • Many more…

Why go deep, not sure I am yet to reflect a lot, just had the urge to write something. I feel it may have something to do with experience, I have a lot of experience now, I feel like I can add to most people’s ideas, I guess. Ask the questions now before its implemented, see if they really understand why they think something is a good idea or force them to go deep to ensure they have really questioned themselves. Questioned their own ideas and understandings, are they biased by their own experiences? I am not questioning them to tell them they are wrong, I guess I am trying to see how much thought they have put into it, how deep have they gone. I am not setting out to be negative, more inquisitive.

Learning. Sometimes I have questioned ideas that I think are great, ideas that fit my understanding, and ideas I believe would work. But I still question. I want to learn from them, I want to understand why they think it will work. Have they picked up on something I haven’t, have they considered the same things as me, the things I think make it a good fit. How did they answer the questions that immediately came to my mind, did they answer them the same as me, did any questions even arise for them? If they did, what caused them to ask those questions, what experiences or insights made them make these queries?

Why do they feel I am coming across negative? I guess in most recent cases it’s because they feel like I am “raining on their parade”. They feel like their idea is really going to solve something. They feel like this is the best idea ever. They feel like their idea is perfect, they have done their analysis and are content. Many others I’m sure. But then I come a long and ask similar questions to the bullet points above. Perhaps they are thinking; What is this guys problem? Who is he to question me? Don’t question me, I have done all the analysis this is full proof, no chance I am listening to him. Because labelling someone else negative is an easy way out of going deep? I don’t really know, and something I am going to ask the individuals over the coming days. Something I intend to study and get more insight in with your assistance.

If you have got this far, it’s probably clear to you that I don’t know much about this. I stated on twitter that I was going to write this blog post. People have responded with various things such as: -

So, if this makes sense to anyone, hopefully it does.
Can you please comment suggestions below on things to read, watch and study? I would really appreciate it, because I am not purposely being negative, my aim is to understand their thinking, compare it mine, learn from them, teach them, find a mutual foundation to build on.


  1. The way you describe how other people see their own ideas, makes me wonder if you're being too rational about this. Being asked to-the-point critical questions can make your feel as if someone is telling you your baby is ugly. It's not a pleasant feeling even if you know your baby is in fact ugly.

    1. Thanks Joep, what advice do you have for asking questions differently? Less rationally?

    2. Hi Richard,

      It's both difficult and easy for me to comment from the sidelines, but here are some things you could consider:
      - What would happen if you don't ask questions? Will something go horribly wrong? Or is the only bad consequence you lost an opportunity for learning. If the latter, you might want to forgo on the questions or take a softer approach (some suggestions below).
      - In what frame of mind are people when you ask questions? It has happened to me that I just threw out an idea brainstorming-mode and someone started to question the idea. That's not a pleasant experience. And even when you say to the other person and to yourself: "I just came up with it right now, haven't thought it through, am not invested in it, etc." some of the negative feelings of being questioned will remain.
      - How is your tone and demeanour? For lack of better words, are you asking from a higher (criticizing, prodding, challenging) or a lower ground (exploring, investigating, trying to understand)? And bear in mind that the other person will feel you're asking from the higher ground sooner than you would, especially if you're enthusiastic about questioning the idea and the plan.
      - You need to feel a certain connection with a person before you can engage in a full-out discussion about a subject in which you never feel that you as a person are on the line because of something you say. For some people it's easier to get to that place than for others. I have the impression that for some people it's flat-out impossible to ever get there.
      - Try to get your answers in a more roundabout way. Go into brainstorming mode in which you feed the other person items to think about. Or say "This is getting complicated, let's sketch it out on a whiteboard." This will get the other person in a constructive mood, telling the story about his/her idea. So when you ask "And what if A/B/C happened?" it will be perceived less as criticism and more as you trying to help to make the idea better.

      I didn't read Simon's comment before writing the above, but yeah what he said. :-) I would add one need to the ones Simon mentions: feeling understood. I want to feel that you understand how invested I am in my idea, plan, whatever. Don't take it more (or less) seriously than I do.

  2. Dammit - just lost my comment! Writing it again...

    It's reasonable to assume that it's not the questions themselves that are the issue. More likely it's the way they're being asked or your relationship with the person on the receiving end.

    I try to think about "universal human needs" when I'm in a potentially sensitive questioning situation. A couple of examples:

    [1] I might be dealing with somebody who needs to feel *safe* - in which case I would be wise to build a relationship/rapport with this person ahead of in-depth questioning.

    [2] I might be dealing with somebody who needs to feel *competent* in which case I would avoid asking questions in a way that risks making them feel the opposite.

    A list of human needs can be found here, if you're interested: - figuring out what the need is, is of course a topic in it's own right. :-)

  3. In writing about my experience with the Software Test World Cup (2014) I tried to write some of the good and bad I experienced. I thought what I captured would be helpful for future revisions or even other competition pieces. I later posted the grading and looked over it saying what was and wasn’t helpful in the feedback given. I wanted to make it a form of mutual learning. In case you want to read about what I saw, here it is:

    It turned out there was at least a few people who worked hard on the project that took what I had to say as a major downer. They saw it as a criticism. I struggled to come up with a response but I wrote about it in my blog:

    I have not heard back in regards to the topic, perhaps because time had healed some of the hurt. My very rough conclusion is that people can read into your questions what they will. Tone and relationship matter, sometimes sandwiching a question between compliments helps. Ultimately, I don’t think you can capture the answer, as it feels like those who do it well have a very tacit relationship to the skill. I think critique, like all soft skills, is difficult to analyze and understand. Largely because social situations are very dynamic and having hard coded rules don’t work well in those scenarios. I think it is 100x worse when you can’t see or hear the person nor know how they reacted to the last thing you said, such as this interaction.

    Which leads me to the last thing. I assume you meant ‘in person’ but online seems to have a different set of rules. Dealing with online interactions has a different set of rules compared to offline. As you can see from my example, I am not sure, how to give useful critiques in this arena. In part because I never got any feedback for several months, making it impossible to know someone took offense. I certainly couldn’t talk about it, and I don’t know how most people took it, even though it has been read hundreds of times.

    Since it appears you posted this many months ago, I wonder, have you learned anything since writing this?

    - JCD