[HN Gopher] A Short 100-Question Diligence Checklist
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       A Short 100-Question Diligence Checklist
        
       Author : jger15
       Score  : 227 points
       Date   : 2023-03-27 13:00 UTC (10 hours ago)
        
 (HTM) web link (www.thediff.co)
 (TXT) w3m dump (www.thediff.co)
        
       | WhatsName wrote:
       | Great, another checklist for folks to cargo-cult their own man-
       | made bureaucracy. Maybe that's a speciality of german-speaking
       | government's, but I find questionnaires without clear intend
       | dehumanizing and time-wasting.
       | 
       | > How hard is it for employees to get promoted? > How hard is it
       | for them to get fired?
       | 
       | What do you plan to take away from these questions? Would be more
       | useful to atleast provide your good intentions on what you are
       | looking for when asking.
        
         | pdpi wrote:
         | If I were to invest in a company, I'd want to know if you're
         | going to have a problem retaining talent (either due to firing
         | people for no good reason or for failing to give them career
         | progression), and I'd also want to know if you're going to
         | waste money on payroll (either carrying dead weight that
         | should've been fired, or splurging on inflated titles).
        
         | 0xbadcafebee wrote:
         | With respect, if you don't understand the questions, they're
         | probably not for you.
         | 
         | In this case, those two questions tell someone a bunch of
         | things: whether bad employees might stick around for a long
         | time, whether good employees might want to leave for somewhere
         | with better career prospects, whether there is good process in
         | place to manage and accelerate employee career growth, whether
         | management is doing their jobs right, whether there are wrong
         | incentives or motivators (for example promotions tied to
         | performance alone which incentivizes accomplishing empty goals
         | that promote politically-savvy employees and leave the company
         | hollow).
         | 
         | Famously toxic companies have processes designed to use fear
         | and politics to keep employees so worried about their jobs that
         | they can barely do them, much less contribute to the
         | improvement of the company. Those companies can still survive
         | and give good returns, but they have to trade on market power,
         | and on a personal note they're often unethical.
        
         | [deleted]
        
       | scrapcode wrote:
       | In this employment market, the last thing I'm doing is marching
       | into an interview with a 100-question questionnaire.
        
         | [deleted]
        
         | crazygringo wrote:
         | This is for investors not employees.
        
       | eschneider wrote:
       | This is a great set of questions when job hunting. Not
       | necessarily to ask in the interview (though some certainly are),
       | but to understand the business and more importantly to understand
       | if the folks running the company understand the business.
        
       | mark242 wrote:
       | A fair warning-- there are precisely zero companies in the world
       | to which the answer to all of these questions is positive. Many
       | of the questions are contradictory when applied across the entire
       | scale of an org and will only serve to frustrate all but the most
       | persistent investors.
       | 
       | The true title for this article should be, "A Turing test to see
       | how risk-averse you are."
        
         | whatshisface wrote:
         | Wouldn't that simply be a "test" rather than a "Turing test."
        
         | [deleted]
        
         | blowski wrote:
         | Calling this a checklist is probably confusing. It's better
         | described as a list of answers you should obtain.
         | 
         | For example "Has a co-founder stepped down?". A single yes or
         | no answer doesn't tell you much. But an answer like "Yes, we
         | had two technical co-founders who fundamentally disagreed on
         | technical strategy" should be explored. Why did the disagree?
         | What was the ongoing impact?
        
           | mbesto wrote:
           | Based on a scan of the questions they aren't actually meant
           | to be answered as a Q&A (despite the author's description) on
           | a spreadsheet / document.
           | 
           | They are more about probing questions to start a discussion.
        
         | hammock wrote:
         | >A fair warning-- there are precisely zero companies in the
         | world to which the answer to all of these questions is
         | positive.
         | 
         | Then consider it a score out of 100
        
       | narag wrote:
       | If I had to answer a hundred questions before, I wouldn't have
       | done anything in my fscking life. Actually most of the valuable
       | things I've done, I did because I didn't think twice.
       | 
       | Jokes aside... or maybe no jokes, but alas, this seems an
       | interesting way of assessing any company, even from the inside.
       | Is this for real? Is it too much? Any blind spots?
       | 
       | And the better question: what do you think the list would be for
       | the ten questions?
        
         | eitally wrote:
         | Yes, it's real, and yes, these are the kinds of things many
         | investors, and most acquirers, will be thinking about.
         | 
         | The ten question subset would consist of things like: are
         | business fundamentals sound, and is there a growth plan? is the
         | existing leadership of quality to effect a step change over the
         | next few years leading to exit, or will we need to bring in
         | professional management? is the tech sound, secure and scalable
         | (this is often least important)? is there regulatory exposure,
         | and if so, how has that been addressed?
        
         | cjohnson318 wrote:
         | I think the big thing is: what do you do with the answers? If
         | you assume that all the answers are accurate (lol) then you
         | still have make decisions that will affect yourself and others.
        
           | silvestrov wrote:
           | It is not the answers that are the output. It is making sure
           | you have thought about all the aspects.
           | 
           | Like homework in school: nobody publishes your essays, they
           | only want you to be able to write essays.
        
         | pdpi wrote:
         | > And the better question: what do you think the list would be
         | for the ten questions?
         | 
         | That list would be the section headings. The individual
         | questions in each section are just drilling down on the
         | details.
        
         | buro9 wrote:
         | > Is this for real? Is it too much? Any blind spots?
         | 
         | It's real enough, I've been involved in a few M&A and I'd say
         | that there is always a reason why we've done it and that reason
         | varies but focuses on a section of questions at a time.
         | 
         | Not all of these are always important. Sometimes you're
         | acquiring the IP, or the customers, or the skilled people, or
         | the exec team. Know what you're trying to acquire and why, as
         | which questions matter to you will vary.
        
         | pas wrote:
         | The one question list is "what's the biggest risk of your
         | business". This sounds innocent (and definitely under-
         | specified), but it requires known all the big risks and picking
         | the most important one, thinking about timelines, micro- and
         | macro trends, etc.
         | 
         | And then of course the answer itself is kind of irrelevant as
         | long as you get the feeling that it gives you information, it's
         | honest, it's not trying to cover up something, etc.
         | 
         | The most important part(s) of doing due diligence is that it
         | has to be _done and diligently_ by someone you trust.
         | Outsourcing it to the subject of the whole process, and
         | reducing it to checklists makes it 10 /10 easy to game. It has
         | to be done to the depth, detail, understanding necessary to
         | have confidence.
         | 
         | That said checklists are very important to establish the
         | possible areas for drilling down. But since time is always a
         | premium it doesn't make sense to do everything just because
         | it's on the list. (Hence your question of getting a shorter
         | list.) But that list has to be tailored to the situation - as
         | other comments noted.
         | 
         | And, obviously, this is why many people try to invest in things
         | they know, and/or focus on areas they know. (And then fail if
         | they ignore the tough questions that stresses them out, or
         | forgot to diversify, or forgot to do reference class estimation
         | and then class appropriate risk weighting. In other words the
         | planning fallacy.)
        
       | BLO716 wrote:
       | Sounds like someone had some money in FTX! After seeing all the
       | social media influencers pushing the product and services,
       | absolutely love this list.
       | 
       | The cooperative group think can be ... absolutely terrible, and
       | having someone who is delivery to this level of scrutiny in a
       | check-list style is probably the best I've seen in a long time.
        
       | brianbreslin wrote:
       | Despite all the people in the comments here dragging this. I
       | think its useful for both early career employees or investors to
       | read lists like this. This gives people frameworks and lenses
       | through which to better assess the companies they are presented
       | with. Lots of founders need to ask themselves these types of
       | questions too. Are some of them overly simplistic, sure. Are some
       | of the questions hard or impossible to answer from outside?
       | Absolutely. But do the majority of them give you better critical
       | thinking abilities about companies? yes.
        
       | red-iron-pine wrote:
       | > 100 question
       | 
       | > short
       | 
       | wut
       | 
       | listen, this is a good checklist and I respect the DD that would
       | happen if you followed, but it ain't short...
        
       | bearjaws wrote:
       | Is completely missing the 100+ technical questions you get,
       | essentially a mini ISO27001 assessment.
       | 
       | If you aren't familiar with IS27001 or HiTrust you would be wise
       | to get your IT leadership trained up as these are massive
       | liabilities that PE does not want to take on when purchasing your
       | company.
        
         | yamazakiwi wrote:
         | You might be right about the liability but I would point out
         | that not every investor cares deeply about security and many
         | don't consider it at all.
        
       | uptownfunk wrote:
       | This is the type of list that makes you feel like you're doing it
       | smartly. Most people will miss the point if they just end the DD
       | process at data collection.
       | 
       | The real magic happens in the synthesis phase, where the
       | information is synthesized to yield insight that informs the
       | investment decision. Doing this part correctly is what separates
       | those who really make it from those who don't (or just do
       | okay/mediocre). Would love an article on this part (though no one
       | would probably give this away for free). Most seem to place
       | enough bets where they just get lucky.
        
       | danielmarkbruce wrote:
       | Interesting that there is so little on the details of the product
       | or service itself. This is a trap finance folks fall into -
       | understand _everything_ except the product or service.
        
         | [deleted]
        
         | Zetice wrote:
         | I'm not sure it's a trap so much as arguably irrelevant, if all
         | of the other elements exist.
        
           | danielmarkbruce wrote:
           | Invert that
        
             | Zetice wrote:
             | Then we'd both be wrong.
        
               | danielmarkbruce wrote:
               | ?
               | 
               | I think I might have misunderstood your original point.
        
               | Zetice wrote:
               | You called it a trap. I said it wasn't a trap, but indeed
               | a valid way to evaluate companies. Knowing the product
               | _isn 't_ as important as it seems to be, when you have
               | evidence to demonstrate a number of other key factors
               | such as market size, growth, founder knowledge, etc.
        
               | danielmarkbruce wrote:
               | Ah, then I understood it. Yeah, it's a trap. As an
               | example - you can't know market size without knowing the
               | product/service in a lot of detail - for example, pulling
               | the IDC report for some segment won't help much because
               | you can't understand if the product can even address all
               | that market, or if it might be able to address more than
               | that market as defined. You can't understand founder
               | knowledge if you don't understand the product/service in
               | detail - anyone who knows more than you will appear
               | highly knowledgable.
        
               | Zetice wrote:
               | You can absolutely know and understand all of those
               | things without understanding the product, mostly by
               | asking the people who _do_ understand the product.
               | 
               | Otherwise you're arguing against the concept of
               | delegation, and there are several mountains of
               | counterexamples were you to try.
        
               | danielmarkbruce wrote:
               | >> You can absolutely know and understand all of those
               | things without understanding the product, mostly by
               | asking the people who do understand the product.
               | 
               | You can't figure who to trust (even if you don't realize
               | it, it's analogous to Gell-Mann Amnesia), you can't put
               | the pieces together in your head.
               | 
               | >> Otherwise you're arguing against the concept of
               | delegation, and there are several mountains of
               | counterexamples were you to try.
               | 
               | Delegating works to get work done, not to understand
               | things. There is almost zero history of
               | institutionalizing good investment decision making
               | (Sequoia might be a one generation counter). Guys like
               | Buffett sit in a room all by themselves. Almost every
               | example of investment outperformance through time is a
               | singular brain or very small team. If delegating worked,
               | this wouldn't (and couldn't) be the case.
        
               | Zetice wrote:
               | You can _absolutely_ delegate understanding. If you don
               | 't, you are _screwed_ as a leader. In fact, one of the
               | things you have to give up as a leader is being the
               | smartest person in the room.
               | 
               | I'll even go so far as to say if you can't understand
               | something through someone else's expertise, you will not
               | get very far in life.
        
               | danielmarkbruce wrote:
               | Nope, history shows the opposite when it comes to
               | investment decision making.
        
               | Zetice wrote:
               | Er, no it doesn't. How much about each of Goldman's
               | investments do you think David M. Solomon knows in depth?
               | They make thousands of deals each year, it would be
               | insane and unsustainable for him to have deep knowledge
               | about each, so he delegates.
               | 
               | If you're talking about fundamental analysis, you'd also
               | be wrong, as my copy of A Random Walk Down Wall Street
               | makes pretty clear. "Know a bunch of stuff about a
               | company" is not a good investment strategy, or at least
               | does not keep pace with well diversified index funds.
        
               | danielmarkbruce wrote:
               | History of investing. Goldman is almost all services with
               | a touch of principal investing. Random walk is a book
               | written by an academic.
        
               | Zetice wrote:
               | These aren't sentences, care you try again?
        
         | wintogreen74 wrote:
         | When you look at some of the questions don't they implicitly
         | require understanding of the product or service though? Things
         | like incentives, market impact and unit economics can be
         | presented in a product vacuum, but not understood.
        
           | danielmarkbruce wrote:
           | Oh sure - you don't have to understand the product/service to
           | understand many things about a company. But if you don't
           | understand the product/service, you are hosed - it's the most
           | important thing. A company can have all the other things
           | right and they are in all sorts of trouble if their
           | product/service is no good. In fact, it can actively mislead
           | because the rest looks so good. On the flip side, ask anyone
           | who works at a really successful company - you'll hear horror
           | stories of mismanagement and bad incentives and all kinds of
           | stuff. Companies succeed in spite of it when the
           | product/service is the right product in the right market.
           | Google & Facebook are the textbook examples, but there are
           | dozens.
        
       | richnwan wrote:
       | Seems like I'm in the minority but this is freaking awesome
       | especially for newer investors who want to go beyond passive
       | index funds (spare me any lectures)
       | 
       | Will going through the checklist for each investment mean you'll
       | always be right? No.
       | 
       | But I think going through these questions as an exercise will
       | help you understand what makes a good/attractive business which
       | is a fundamental skill in investing.
        
         | DontchaKnowit wrote:
         | I absolutely agree, I was a bit surprised to see the reaction.
         | This would have been enormously helpful to me early in my
         | investing journey, just after learning basic definitions and
         | reading some buffett-adjacent books.
        
         | sandworm101 wrote:
         | Checklists are only ever as good as the data behind them. This
         | is a goodish checklisk for the uninitiated. Cool. But do you
         | trust the answers you are getting? Do you trust the date as
         | delivered by the company in response to these very internal
         | questions.
         | 
         | This list is also full of useless questions that tell more
         | about the potential investor than the actual company. For
         | instance:
         | 
         | >>If the company succeeds, does everyone--employees, managers,
         | founders, investors, suppliers, customers--get about what they
         | deserve?
         | 
         | "What they deserve"??? Really? That says nothing about the
         | company. That only tells you whether or not the company's
         | reward scheme comports with your personal notion of fairness.
         | It is more about politics than investment potential. But maybe
         | that's what people want these days.
        
           | renewiltord wrote:
           | Perhaps it is useful, but misstated? "At what exit valuation
           | will each of the following categories obtain a significant
           | outcome and a life-changing outcome? Founders, Series X
           | investors, early employees, marginal employee."
           | 
           | The reason to care about Founders is to see if they have skin
           | in the game. Investors to see if you're going to make
           | anything. Employees to see retention and hiring.
           | 
           | Still a bit sideways but perhaps worth thinking about anyway.
           | 
           | But it would still have warned about something like Bolt -
           | the marginal hire will have received an insane strike price.
        
       | ttul wrote:
       | For founders, if you try to generate an answer for every question
       | in this list, you will uncover important blind spots along the
       | way. You can then schedule time to resolve the unknowns,
       | strengthening your strategy while simultaneously making diligence
       | easier.
        
       | AndrewKemendo wrote:
       | Missed a few:
       | 
       | - Are we a net benefit to the poorest of our customers?
       | 
       | - Do we create pro-social interactions by default?
       | 
       | - At maximum scale do the incentives of our shareholders,
       | employees and customers align?
       | 
       | - Are we thinking holistically about possible externalities?
       | 
       | - What are the second and third order effects of our success on
       | the broader society
       | 
       | - Are we intentionally skirting or exploiting gaps or absences in
       | democratically run communities in order to gain market share?
       | 
       | etc...
        
         | nazgulnarsil wrote:
         | >Is there some non-economic outcome you're trying to support by
         | investing in this company? Is the investment really the best
         | way to achieve this?
        
       | jsjshs wrote:
       | this guy is the real thing. byrne hobart. exceptional writer,
       | analyst, expositor; exceptionally precise understanding, at many
       | levels of technical and historical abstraction.
        
       | ChildOfChaos wrote:
       | 'A short' and '100 questions' should not be in the same sentance.
        
         | drummojg wrote:
         | I read it as ironic.
        
         | haswell wrote:
         | Length will always be relative. 100 miles is both short and
         | long depending on the context.
         | 
         | In the context of M&A or strategic investment, and considering
         | the range of topics, 100 seems like a good starting point.
        
           | ChildOfChaos wrote:
           | Maybe, but I don't believe this context changes that, short
           | should be a handful of questions, yes it's a complex subject,
           | so 'concise' maybe a better word, but short? Absolutely not.
        
       | nabla9 wrote:
       | Good list.
       | 
       | but I hope "What do people on Glassdoor say?" is a metaphor, not
       | actual recommendation.
       | 
       | Glassdoor's business concept is at odds with it's integrity.
       | Glassdoor takes negative reviews down if companies request it.
       | Bad companies always do.
        
         | wcunning wrote:
         | I think that was actually the point of that question -- if they
         | have only positive Glassdoor reviews, that means they're
         | working really hard on their image and it's a redflag to
         | investors that every other piece of data needs to be looked at
         | even more skeptically, which I find to be generally true in
         | concept. Or maybe I'm over-reading it to tie into the next
         | question about suspicious reviews, but I knew about the
         | Glassdoor thing you mentioned and assumed that's why those
         | questions came together.
        
         | 0xbadcafebee wrote:
         | I recently interviewed with a company with an _abysmal_
         | Glassdoor rating, hundreds and hundreds of bad reviews. I asked
         | multiple people in the company about it and what they were
         | doing to address it, and the best they could say was something
         | approximating  "there'll always be a few bad apples". I
         | declined to join.
        
       | marban wrote:
       | One example why it's important to double down on human writers.
        
         | jsjshs wrote:
         | the guy who wrote this is truly exceptional.
        
       | 1970-01-01 wrote:
       | Wow, exactly none questions for cybersecurity. This is a
       | skyrocketing problem, and we've all seen the headlines.
        
         | bostik wrote:
         | Those will be a huge part of the _actual_ due diligence
         | process.
         | 
         | I've been on the receiving end of a very intrusive one, and it
         | was essentially an arduous multi-week long audit. (IIRC four
         | weeks of evidence collection, followed by ~8 days of intensive
         | interviews.) With the main difference to audits being that on
         | the requesting side, there was someone who _actually_
         | understood how security, human processes and business all
         | intersect.
         | 
         | 7 audits in one year was a bit much.
        
         | [deleted]
        
         | frakt0x90 wrote:
         | Except when companies have a breach, they mostly just get a
         | slap on the wrist and everyone moves on. It doesn't tend to
         | materially affect the success of the company except in very
         | rare cases.
        
           | [deleted]
        
           | mox1 wrote:
           | Yea, this is the quiet part said out loud.
        
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