I don’t know.

2014-03-02 by Jason Freedman
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I wanted to share an interesting conversation I had with Kiran Divvela back when he was still interviewing.

Kiran runs all of our data supply chain activities. He’s one of those rare types that communicates well, has solid management skills, is fluent technically, and was a perfect startup culture fit.  We knew we had to have him.

But Kiran was one of our toughest hires.  We knew he had options.  We thought that we were in the lead for him culture-fit wise.  The big question left for Kiran was learning enough about our industry since commercial real estate was new to him. He needed to truly believe he was going to be part of building a big company.

After we made him the offer, I made myself available to talk through any questions he had.  It was like fundraising due diligence all over again. We went through the deck, and I showed him our short, medium and long terms plans. We went on long walks where we talked about each piece of our strategic plan.

One moment has stuck in my mind.  He was asking me how we were going to keep our data updated once we were at scale.  It was an important question. If you fail at it, users have the worst experience possible, calling on listings that actually aren’t available.  If you’re great at it, you become known as the best source of information anywhere and everyone flocks to you.

Kiran would be leading our data efforts and that would include not only acquiring the data but keeping it updated.  At this point, in the young life of our startup, simply getting commercial real estate listings was the most important activity.  Keeping them updated was a challenge I knew was on the horizon but we hadn’t had to deal with it too much yet.  With our small scale at the time, we had been able to solve this problem manually. That wouldn’t really work at scale.  As we walked down the street, doing yet another lap around South Park, I shared a few of my ideas with him.

But they weren’t great ideas.  More like trying to write with a crayon when the rest of our conversation had been written in pen.

Finally I cut myself off and told him flatly, “Look, I don’t really know.”

It was the truth.

Every commercial real estate listings company – actually every real estate tech company, commercial or residential – has struggled to figure out how to keep listings updated. While there are lots of tactics, there is no one true silver bullet. I had lots of ideas I wanted to try. One of the reasons I was so excited to have Kiran on board was that he would be the one who would actually get to try them, as well as come up with tons of new ideas.  But at this moment, the most truthful answer I could give him was, I don’t know.

And he smiled and responded back, “I was waiting for that. I like it when people say I don’t know.”

I burst out laughing.

Kiran explained that he likes it when people say I don’t know because it lends credibility to everything else that they’ve said.  He was already pretty close to making up his mind that he was coming to 42Floors, he just wanted an honest accounting of what we had answers to and what remained as questions.




Ever since that encounter, I’ve tried to pay attention a lot more when people say I don’t know.  We did a whole bunch of Y Combinator mock interviews during the last session. The YC alumni in our company try to offer some time before each batch to work with the people that are preparing.

I found that very few of the startups were willing to use the words I don’t know.  A couple of times a founder was in such a salesy mode that we both knew he was bullshitting his answers, but he refused to show anything other than total confidence.  I just saw it as foolishly naïve.

One startup that got in actually used the words ‘I don’t know’ several times.  The founder was super confident in her product, super confident in her team but had some uncertainties about how she was going to acquire users and didn’t really know how big her market was, both of which were problems she said she would address.  But it was so refreshing to hear her honesty.

I don’t have enough data points to generalize yet, but it seems promising.  If you have the confidence and honesty to say I don’t know, you’re probably going to win over a lot of people.




One place I’ve always struggled to say I don’t know is when talking with engineers about technical stuff beyond my knowledge.  No one wants to look stupid so it’s easier to nod your head when you don’t know what someone is talking about. I realize now it creates the opposite effect.  Every time I appear to understand something I don’t, it just makes me look foolish.

I try now to just simply say that I don’t know and ask people to explain things to me.  Fairly regularly, one of our engineers, Aaron O’Connell, will take time to explain what it is he’s working on. He’s got a Ph.D. in physics and he’s a gifted coder, but he never seems to mind taking the time to explain it to me in a way that I can understand.

See, no big deal.

I also say I don’t know a ton to my board.  We have super smart guys on our board and nothing gets past them.  Saying I don’t know with them turns a question into a homework assignment.  As long as I follow up with the answer later, they never mind.  And it’s 1000x better than bullshitting a half answer.




Thank you Kiran for inspiring this post.



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About Jason Freedman

Entrepreneur, Co-Founder at 42Floors, Co-Founder at FlightCaster, YC-alum, and a Tuck MBA

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  • http://www.ModelInsider.com/ Christopher Ambler

    There’s a flip side to this that I’ve dealt with – I once had a manager who had, as one of his go-to lines, “You must know!” In any meeting, even one-on-one, he would delight in asking questions, looking for the gaps in your knowledge and then berate you for not knowing.

    “You must know this!” he would say.

    No matter how on top of things you might be, the ONE gap would then become the focus. Saying, “I don’t know, but I’ll find out” was never an acceptable answer.

    As you might expect, I got out of that situation as quickly as I could.

  • scottradcliff

    Maybe I was burned early on by talking my way through something I didn’t have the answer for and ended up stuck in the bullshit I was flingin’, but I mostly recall saying I don’t know a lot.

    It’s usually something along the lines of ‘I don’t know, but I will find out’. That says a lot when you’re talking to someone. Few things are worse than having to go back with your tail between your legs because you said you knew something that you didn’t.

    Now I remember why I say I don’t know.

    Because saying I don’t know is better than answering the question ‘I thought you knew what you were doing?’

  • http://lyosninbeta.com David

    Second paragraph, superfluous space at the beginner of the paragraph.

    Third paragraph has a double space between “question” and “left”. :-)

    As for the content; I completely agree. I worked in technical support for the early part of my career and we always made a point when someone asked a question we didn’t have the answer to say “I don’t know, _but I’ll find out and get back to you in [x amount of time.]_”

  • doddler

    I completely agree to this. I’m also trying really hard to ask as much as possible.. even if I look dumb :)

    One down side is, if you have to deal with people who suffer from dunning-kruger effect. In this case it’s probably the wrong approach to say “I don’t know”. I was discussing this with a few people, and the feedback was more or less to ask questions back, instead of admitting not to know.


  • denver_dave

    Saying “I don’t know” to a developer is akin, in my experience, to saying “please tell me about something you find interesting and important.” I’ve never had it turn out to be a bad approach. Management, sure. Engineers, never.

  • Tim S

    This post made me want to work with you.

  • http://www.bucketlistly.com/ Pete R.

    Sometime, people just don’t say “I don’t know” enough, myself included. I always forgot that saying I don’t know can also yield the best outcome. Thanks for the reminder, Jason. :)

  • HN stray

    If you ask me about software engineering and I say “I don’t know”, can you hire me as a software engineer? :P

    – HN stray

  • http://scottymeuk.co.uk/ Scott Robertson

    Especially in software development, there has always been a stigma with admitting that you do not know something. I think that is slowly changing, which is very good.

    I have been terrible at it in the past, with not admitting when I do not know something, but I feel I am getting better at that as time goes on.

  • http://shaishavkr.info Shaishav Kumar

    I totally agree with what you say here.
    I would add one more thing. Saying “I don’t know” is perfectly acceptable and lends you credibility.
    Going the extra mile, doing your homework and getting to “know” what you didn’t know before the next encounter with the other person/group of people is going the extra mile.
    I have seen people who are prompt at accepting “they don’t know” something. They are even more prompt in saying “this is something person X would know. its his area or expertise/his job” and this sort of reply doesn’t sit well with me. Even putting the slightest effort to get the summary of something would make me happier and our interaction more productive. It should you are willing to put effort in learning something and doing that extra bit of legwork

    PS: What approach did you guys take for the data freshness problem. just curious.
    – Shaishav

  • http://www.parkji.co.uk Ben Parker

    I’ve seen this used by interviewers as well, asking question after question on a subject because they’re looking to see if the interviewee will admit that they don’t know, or just start waffling.

    • indian

      I did that in my first interview, Q after Q – all theory Qs on the subject I admitted to be my favourite. The interviewer sounded like a hired professor. He kept on prodding me on – no, you know – no, you know. But alas, I knew I would not land the job and I didn’t. I would have been very dissapointed if they hired me.

  • http://flowerpot.io Frederic Branczyk

    I see this happen every day talking with my co-workers in the coffee corner. It’s great to hear somebody say “I don’t know”, because either somebody knows or everyone starts to think about it, create theories and start a discussion.

    Come to think about it, I’m pretty sure saying “I don’t know” has gotten me a job before..

  • http://www.99.co Darius

    big fan of 42floors — so.. how DO you keep your listings updated?? Darius @ 99.co

  • Haloperidol

    As i get older, i find myself say ‘i dont know’ more and more. In all areas of life, not just in my field of work. I am seriously afraid, that before i die, i will pretty much think i know nothing at all.

  • L.Mohan Arun

    There are also other ways to say “I don’t know”. Macmillan had a life skills post about this sometime ago:
    You could say ‘Beats me’ or ‘Not as far as I know’

  • http://philstrazzulla.com philstrazzulla

    I like the philosophy. But, you just have to make sure the person across the table isn’t going to mistake “I don’t know” for weakness or unpreparedness. I think a lot of lesser VCs/potential employees/etc would roll their eyes at this answer. The majority of people respond to confidence and BS, and don’t appreciate this type of honesty in my experience, unfortunately. Of course, the best ones always do.

  • aledalgrande

    Really loved this article, there are so many bullshitters in the Valley and it’s refreshing to see someone being honest (and smart).

  • 4thaugust1932

    If you meet anybody from India ask him “What Is Your Caste?” If he answers it, then you’re doomed. Because he has already injected Cancer into your society. Caste is like Cancer. It cannot be Cured. It has to be Cut-Off.