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I am the CIO of a mostly remote, cybersecurity startup (50 FTEs). I balance between not single-threading all choices through me and not letting things get too o

I am the CIO of a mostly remote, cybersecurity startup (50 FTEs). I balance between not single-threading all choices through me and not letting things get too out of hand. That means no one is every really happy. E.g., we use Uberconference for videoconferencing. We thoroughly looked at a bunch of others and chose UC for its functionality, price, and simplicity (every conference gets a simple phone number, no stupid 9-digit code plus pin plus participant id). Six months after signing a 3-year agreement (my bad. rookie mistake) I had to resist my CEO’s insistence that we switch to a different provider when we were courting them as a client. A few month later, sales went out and bought 10 mf’ing Zoom licenses without consulting anyone because some client hadn’t heard of UC and asked if it was the budget solution. Thank god our new CFO confiscated all the corporate credit cards and moved us to reimbursement with Concur. Of course, he later unilaterally selected NetSuite (for something like $40k a year!) and insisted on coordinating the roll out himself. It has been a months long dumpster fire, but he still won’t give my team admin privileges lest we try to see other’s salaries. We use a lot of AWS. One of our red-teamers mostly used but occasionally built some of our infrastructure. He left the company last month. Yesterday, salesman from Digital Ocean reached to ask if we are still interested in going forward with the departed colleague’s plan to move all our infrastructure to DO. So for all you folks stuck in big companies, when you wonder why your IT department is so behind the times and won’t let you use Postgres instead of MariaDB or Gitlab instead of Bitbucket, remember my experience. It’s because no matter how smart you folks are as individuals, in the aggregate you are like toddlers. You dump all your toys on the floor and then chase after some other kid’s shinier toy. Your poor CIO is left cleaning up your mess in the middle of the night after stepping on a Lego brick. (All that said, my job isn’t bad and my company is way less dysfunctional than most start ups. I get that start ups are chaotic, and the basic nature of my job is to wrangle it.)

gibolt 7y ago
Seems like there should be some basic review processes in place. Any external dependency/purchase should require sign-off of at least one of only a few decision makers. This should be very similar to a code review, but seen by CTO, CIO, and CEO (whichever combination is most relevant) so that big unexpected, costly structural changes don't cost long term disfunction and pain.
- dzhiurgis 7y ago
  Wonder if there's software for organisational management? Any ticket tracker could probably do.
  - lonelappde 7y ago
    Trackers are for management to control the plebs. Rules don't apply to execs.
    - deleted 7y ago
      [deleted]
projectileboy 7y ago
I wish I could upvote this more than once.
leeoniya 7y ago
> (every conference gets a simple phone number, no stupid 9-digit code plus pin plus participant id) in our case, UC constantly failed hard to properly encode an essentially static excel sheet over screen share - jpeg artifacts the size of basketballs that never went away, even when given infinite time to "catch up". zoom has zero issues with screen share, but randomly drops calls, and yeah the phone + 9 digit id + participant id feels intentionally user-hostile (especially having to repeat that bs again after a dropped call).
- moron4hire 7y ago
  That's weird about Zoom. We have whomever is scheduling the meeting paste their personal meeting ID into the meeting invite. It's one click for anyone joining, including the host.
  - Aeolun 7y ago
    Maybe if you literally call in to the conference? Not sure why you’d ever want to do that, but...
- ipython 7y ago
  You can have zoom call you, making the whole “too many numbers” thing irrelevant.
  - techdevangelist 7y ago
    I think your plan has to support the outbound calling, our Corp issued plans do but the random 3rd zoom bridge I join doesn’t always have the call me option. It may be free tier vs paid; but has bit me right before trying to jump on and having to dial in manually.
Tainnor 7y ago
Eh, the problem with the "IT department dictates all the choices because the devs are stupid" approach is that it takes ownership away from the devs, therefore leading to a self-fulfilling prophecy. If I can't be trusted to make technology decisions for the system I know about (and the IT department knows nothing about), then why should I care about delivering the best possible product? Sorry, I've seen exactly that pattern happen in my (still) current company and it just leads to teams that are completely unable to think for themselves and work like machines in a cog. I'm not saying company guidelines shouldn't exist or that you should allow a proliferation of 200 different programming languages, but I have never seen the "devs are stupid" approach work; if this is indeed a problem in your org, hire better people! (Which doesn't mean: smarter hackers. It means: responsible, professional individuals that work well together in a highly effective team and can be trusted to make decisions in the best interest of the product.)
- ownagefool 7y ago
  I think both view points are true. - In orgs that don't trust dev typically have significantly less understanding of dev, and in my experience have really poor security postures. Everything is a slow manual process decided by people who don't understand apps or automation. - In orgs that trust dev too much, you usually get a federated architecture that doesn't make any sense from a strategy point of you. Some teams are great; others don't have basic controls. You typically have a bunch of different consultancies playing land and expand and selling expensive solutions that don't actually work. As usual, the sweet spot is probably somewhere in the middle.
  - grosswait 7y ago
    Regarding your first point about security, I see the opposite on a weekly basis. Devs, especially in startups, make secure technology decisions, but in a very narrow and entirely technical scope that essentially encompasses "their world". Once induced to see the larger picture either due to a compromised system, or table top exercises that include the rest of the business, they and leadership start to realize they've had a false sense of security.
noir_lord 7y ago
I hear you, I work for a large manufacturing company as a lead engineer (household name in the UK) and this complete lack of agreement between teams on how to do things results in a colossal amount of churn/wastage between "new shiny" and "already working". Lots of "Lets move X to Y" which never gets completed then someone addes "Z" and now you have 3 ways of doing basically everything. Worse is our documentation (which is generally good) frequently documents X but not Y or Z because the person who decided on Y or Z didn't look. It's mentally fatiguing, I feel like every choice on what to use comes with more trade-offs than I should have to consider for something so simple. Video conferencing is a good example, We variously have Hangouts, Skype and others, teleconferencing equipment in one room is one thing, in another something else. The only reliable way to throw video to a screen is a USB-C to HDMI cable I keep in my rucksack. Feels like half my decisions are saying "No" to an engineer who wants to replace Foo with a very shiny but 99% identical and unknown Bar.
- ansgri 7y ago
  > The only reliable way to throw video to a screen is a USB-C to HDMI cable I keep in my rucksack. That's quite progressive! Last I checked, many of our monitors only supported DVI and DP, and only some recently bought laptops have USB-C.
  - noir_lord 7y ago
    Developers who are issued laptops (not all are, juniors get desktops) get either 16” MacBook Pro’s or equivalent priced thinkpad. Can’t complain about that though moving from Linux after two decades to OS X was a bit of a change.
- Frost1x 7y ago
  I've worked with both sides of this argument and I find that "new shiny" is a perpetual problem. Anyone that proposes new shiny should be responsible of showing trade offs, integration feasibility, impact, etc. I'm not against new technology but so many people want to adopt new technology X just for the sake of it being new technology X. I see this on developer teams I work with every day and it makes me want to gouge my eyes out sometimes, especially when I end up being forced to use their nonsensical choice of new technology X which makes my life harder. Part of the problem I believe is that everyone is focusing on their own self-interest. Many developers for the most part don't care much about the business interests/growth. They're already looking for their next higher paying gig and want paid training in technology X at their current gig. Since many businesses provide little concern for long term talent retition, loyalty or investing in professional development that falls outside their business adopted technology preview, I completely understand the developers choosing themselves over the business. At the same time, going overboard shoots yourself in the foot because it strangles the business in the process. There certainly needs to be a balance and a lot could be gained by giving developers freetime and resources for continued professional development.
baxtr 7y ago
> It’s because no matter how smart you folks are as individuals, in the aggregate you are like toddlers. Love the quote
GordonS 7y ago
It sounds like a few simple rules would help - you don't need complex procedures and forms, it can be as simple as "if you want to buy new software, ask the CIO or CTO, and in most cases they'll say yes/no on the spot". I can't help but think this is a symptom of being awash with VC cash - I can't imagine this happening in a bootstrapped business.
- hef19898 7y ago
  I tend to agree. Bootstrapping, and small budgets, force discipline. Even without procedures. Practically infinite budgets tend to have the opposite effect. If senior management isn't forcing discipline things can get out of hand pretty quick.
  - afarrell 7y ago
    > Bootstrapping, and small budgets, force discipline. This is only true in the evolutionary sense -- Example: "parachuting forces people to be good at checking their gear." Telling someone that they are going to jump out of a plane won't magically give them a skill like meticulousness.
    - ryandrake 7y ago
      It’s a skill like any other, and requires study and practice. There is a reason why half of pilot training is checklists and drilling procedures until they are permanently encoded into your muscle memory.
      - afarrell 7y ago
        Right. But I often see people ask "how can I learn to X" and get advice like "Go do Y. It will force you to X". But jumping into to the situation unprepared is not how pilots learn skill X. They learn it through particular methods of study and practice.
        hef19898 7y ago
lifeisstillgood 7y ago
I hear you, but the only times I have seen the balance work is via a "committee" of DevLeads. Senior devs work with the trees everyday but are also able to see the woods. They are at the perfect position to make intelligent future proof decisions, and the second job of senior management is to ensure the DevLeads (or non tech equivalents) across the company are meeting talking discussing and deciding regularly and frequently (no a slack channel is not enough)
- GordonS 7y ago
  Where this totally falls down is where that committee becomes a full-time position, and the members stop doing actual dev work, becoming more and more out of touch with reality as time passes. This was the case at an engineering company I worked with for several years. The committee, or "enterprise architects" as they called themselves, became too far removed from the trenches, and the devs viewed them as sitting in an ivory tower and passing down ridiculous decrees. They brought this view upon themselves, as they made it more or less impossible to even speak to them - almost all communication was through requests and forms uploaded to a sharepoint site! They kept taking it further and further, until you even needed their permission to take a dependency on a 3rd party library for a LoB app. Such requests would sometimes take weeks to get a response. We could never hold on to devs for long, in large part because they hated working under this bureaucratic nightmare. The committee made all sorts of terrible decisions, always without consulting the devs and always with little justification, and these had a lasting impact for years to come. Gods, it was horrible!
  - lifeisstillgood 7y ago
    It's this "committee" job to make sure the organisation has the right tools without descending into anarchy it's senior managements job to make sure the dev leads are working well Basically this is senior / middle management in every company you had senior management that have not realised the importance of software to their business - so they let a situation develop they would never allow in sales or accounts
    - 7y ago
GordonS 7y ago
We got the same catty comments from prospective customers about Uberconference. Eventually we moved to webex, not because it's the best (it's not), not because it's the cheapest (it's not), but because many corporate customers seems to use it internally, and because it's what just about all corporate customers seem to expect.
ThePowerOfFuet 7y ago
This is fucking gold. Thank you.
fivre 7y ago
The individuals in aggregate may be toddlers, but unfortunately the C-suite as individuals are often also toddlers, at least vis a vis their responsibilities. Tasked with providing IT infrastructure that works for the company, they seem to largely shirk their responsibility and choose IT infrastructure that best serves them, the needs of others be damned. CIOs will seemingly gladly choose something that provides a good UX for one central administrator even if the UX for hundreds or thousands of others is "the software literally shoots knives out of the monitor and gouges out your eyes". Reports that the software gouges out everyone's eyes are roundly ignored. I'm not sure to what degree this corporate disdain for quality of work environment is intentional or simply inability to grasp how other people may have different experiences using something, but I'm even more unsure how to solve it. What do we do when attempts to explain how shit sucks fall on deaf ears? Bring back pistol dueling?
- officialchicken 7y ago
  Please recognize the fact that the argument you are making here is based on whataboutism and is dishonest trying to setup a us-versus-them situation and confuse the actual issue. Then you proceed to follow up with illlogical conclusions with absurdist claims ... pistol dueling has nothing to do with the ROI/TCO of an adopted SaaS. The actual issue the parent argument is about managing diversity - and that you can never please everyone - and that isn't a pistols at dawn kind of situation.
- afarrell 7y ago
  Part of the problem here is that there is a balance to be struck with these sorts of things: Cost, User experience, Mange-ability, and time spent shopping around rather than just going with the industry-default or one with the best sales-team. Responsible decision-makers have to make trade-offs. When you say > Reports...are roundly ignored That lack of weight given to your experience as a signal of real business cost is a real problem. So what is the solution? 1. Understand the problem they're trying to solve. What are their real motives and pressures? 2. Understand where your needs align with theirs and where they diverge in reality. 3. Tell a compelling story of where your needs are in fact aligned. 3.1) Prepare Evidence If your case is "This tool is causes literal permanent eye injuries to our staff", then there should be written reports of those injuries. If your case is "This software package has multiple missing-affordances which present operational risks to the business", then you should be able to take screen recordings of that. 3.2) Start with why When turning evidence into a presentation, remember that people listen better when they know why they are listening. So start with: What is at stake? 3.3) Credible language If your words say "the UX for hundreds or thousands of others is 'the software literally shoots knives out of the monitor and gouges out your eyes'" but you can't actually back that up with the factual reality, you seem like you're exaggerating. If I think you are exaggerating, then I can't trust your words when I'm trying to understand magnitudes. If I can't trust your words about magnitudes, then how do I give you a voice in making a well-balanced trade-off? ------- Literally: (adverb) 1. In in a way of speaking that is completely accurate and unexaggerated. 2. In in a way of speaking that is exaggerated for emotional effect.
tonyedgecombe 7y ago
I wonder how much of this is a lack of communication from your CEO. I've worked for companies that operated on very lean budgets. Everybody in the organisation knew what it was, it wasn't much fun but it was a clear policy. There is no reason you can't do the same here, the objectives might be different but unless people up and down the organisation know what they are you can't expect anything other than anarchy.
cl0rkster 7y ago
This post starts by telling it's lauded idea of not single threading large purchasing decisions. It's simply irresponsible not to. Even the poster knows that, and that's why he thanks God that another C-level actually showed leadership. Honestly, reading the post, everything points to this guy being buddy boss. Bosses should create a positive work environment both at and away from the job. They should not be friends outside of work with their subordinates (yes, I know this is speculation about this guy, but the principal is true). I wish all these c-level folks with their making sure any shit they create always rolls right past them and onto someone else would just give their money to the person actually shoveling the shit... Because they recognize value.
LoSboccacc 7y ago
> won’t let you use Postgres instead of MariaDB or Gitlab instead of Bitbucket, remember my experience. It’s because no matter how smart you folks are as individuals, in the aggregate you are like toddlers I actively resist the notion that 'everyone but me is stupid' and propose a more realipolitik explanation: it's because power and budget. in manager heads, if you pick solution A I pick solution B, so that higher ups don't see the same line twice in services costs and get the idea they can obtain savings by merging the two functions, making one of us redundant. yep yep didn't expect anything different from a techie community.
AdrianB1 7y ago
Sorry, but you are not a CIO, you just have a fancy meaningless title with no real correspondence to what it means. If the CFO decided to buy NetSuite without asking anyone, you care not CIO and he is acting as CEO because he can override you with no consequences. Just saying.
- jessaustin 7y ago
  CFOs can't integrate new software themselves, but they can buy anything they want. Some of them let this go to their heads. When I hear NetSuite ads, it's only while listening to the absolute dumbest sports talk shows. Apparently this marketing works...
- notyourday 7y ago
  That's not entirely accurate, if not to say that's completely inaccurate. Contrary to what people might think, companies are not ran as military with the CEO being a commander-in-chief. In most of the companies, members of the C-suite have a certain or total autonomy to make any decisions that they want as long as it is somewhat within their domain. The conflicts between them are resolved via negotiation and horse trading. Just because the CIO does not like what the CFO is doing, does not mean that the CFO is wrong in making that decision, same as just because the CFO does not like what the CIO is doing does not mean that the CIO is wrong. When one CxO steps on feet of another CxO it is either resolved by reaching a new agreement going forward or resolution is punted into the future or one of the CxOs leaves.
  - AdrianB1 7y ago
    I cannot tell how is each company organized, but I am working in a $250 billion company and I had the occasion a few years ago to find out in detail how this works when our CIO had to approve some IT purchase and there were some technical problems with the authorization system: our CFO does not have the authority to sign or approve any IT contract and nobody in the company will ever execute the payment. We are not organized as military, but each of us have spending limits (from $10,000 the lowest to a few hundred millions $ for CxO) and we cannot override that. Yes, we had people that bought stuff in their spending authority but not in their domain authority (that is much harder to limit in a system) and they were fired every time it happened.
xwdv 7y ago
Do you mind sharing the name of your startup?
- chirau 7y ago
  Lol. I doubt they'd be careless enough to do that. As soon as they do, you can then put names to all the people mentioned. Which is obviously not their intention otherwise they'd have done so.
  - xwdv 7y ago
    If it were that easy you could probably just find several cyber security startups and work backwards to find out which one he’s talking about.
calmworm 7y ago
Your CFO got sold ... twice. Concur and NetSuite are both enterprise level software that a company with 50 FTEs does not need. NetSuite is a never ending money pit with varying results. I dealt with a very similar situation, in which a project manager("VP") talked our owner into using NS, but it was over $100k/year and commitments were 2 years per seat at something like $5k. He ALSO wanted to do the roll out himself. 6 months later, it was still not functional. I got pulled onto the team to help. We made _some_ progress and I hired and managed 4 remote programmers to write all the plugins and customizations we would need to make it work with our model (multi-channel e-commerce, multiple warehouses/locations). It was a nightmare all-around and completely unnecessary. PM/VP left the company because he couldn't do the job and we were stuck with a half-assed implementation at that point. It's been around 4 years since the first day, I am no longer with that company, and I am sure they are still struggling with NS and employing multiple developers to keep things going. Good for the devs, bad for biz. I am willing to bet it's never returned a single dollar on the investment and cost them far more than they wanted to spend. If you can't see the light at the end of the tunnel at this point, cut your loses, and don't get another "solution-in-a-box".
- brianwawok 7y ago
  Hah this story sounded familiar. Makes sense.
- wpietri 7y ago
  Weirdly, almost exactly 20 years ago, I sat next to somebody at a wedding who had an almost-identical story about cleaning up after an SAP rollout, but all of the numbers had an extra zero or two. It amazes me that what the SaaS shift appears to have achieved is that now much smaller companies can get stuck in the same "solve everything" money pit. But I guess the fundamental problem hasn't changed: executives want to believe in magic solutions that give them all the feelings of control with none of the actual work. With no regard for actual operational efficiency, and no need to hold themselves to the ROI standards they'd demand of others.
  - zbentley 7y ago
    > executives want to believe in magic solutions that give them all the feelings of control with none of the actual work Corollary: R&D wants to believe they can build magical solutions that solve all the problems--solutions that will scale better and cost less to keep up than off-the-shelf ones made by people with extensive domain expertise--in a week or two, promise. As with most things, the problem is complicated, deeply human, and answers lie somewhere in the middle.
chrisweekly 7y ago
Thank you v much for sharing this first-hand perspective. V helpful.
paulie_a 7y ago
As many people as possible should post their salary on slack.
marcinzm 7y ago
>A few month later, sales went out and bought 10 mf’ing Zoom licenses without consulting anyone because some client hadn’t heard of UC and asked if it was the budget solution. They have a point, the more things you need a client to do out of the ordinary the more friction you will get selling them. New UI for them to figure out, new permissions, etc. Depending on your business model as a startup that can be a bad thing. It seems like you try to enforce a rigid structure but don't provide a quick process to changing or appending to that structure. So intelligent people work around your structure and you have no idea. Seen it at many companies. Generally tied to an inability or in-desire to delegate decision making. Which is different than letting people make decisions, rather it involves creating a structure under which they can make decisions. Employees have the most view into what would make their job more efficient or engaging. You want them to think of optimizations and you want them to feel engaged enough to try and improve the business. If you don't listen then they will work around you rather than with you. Or just find another job. Employees want something? Delegate to them the responsibility of building a business case and give them a structure on what that needs to look like. Then they can present it and the team can discuss. Make sure to say yes sometimes even if you think it's sub-optimal since otherwise they'll feel it's a pointless process.
- zbentley 7y ago
  > Employees have the most view into what would make their job more efficient or engaging. Employees in aggregate know the true answers to those things. Employees individually sometimes do, but often do not. For example, if you have a stone-aged development process on an ancient revision of an unsupported language, and you poll your employees, they'll all want change. They'll all want ... different changes/processes/pet programming languages, too.
  - pm90 7y ago
    Sure but when the decision is left to employees, they will organically choose solutions that makes the most sense for them rather than what makes sense only to an individual. Treat the employees as autonomous responsible individuals; give them the freedom on how to best solve their problem and they will solve it. Seen another way, as a manager who is not involved in the day to day you don’t deal with the same problems that they do. Quite presumptive of you to think that you know what will solve their problems.
TACIXAT 7y ago
Damn I hope I never work under someone who considers their employees to be toddlers.
- karmakaze 7y ago
  Given a large enough sandbox this could be a great working environment. I once worked in an R&D department to produce physically shipped (diskette/cd-rom) software. It was the best of times. Go to conferences, learn shiny tech, make up new toys, sell them as products. We even had annual toy budgets for anything no-questions-asked as well as constant upgrades to the latest hardware running obscure operating systems. Unfortunately the company run too well, eventually shrinking to collecting license and maintenance support fees. One funny story was how whenever we'd be burning the midnight oil to produce the final release, we'd declare it the golden master and hand it over to our shipping department to distribute to our customers. One time I had to make a recall due to a fatal bug. The masters were handed back to me with a smile and when I asked, she said that after the last few recalls of golden masters, she always let them sit on a shelf for a week before actually shipping anything.
GordonS 7y ago
OT, but as the founder of a microISV selling B2B, I'd love to hear something about how you do sales and marketing? It's unquestionably our biggest pain point.
techslave 7y ago
get out ASAP. you are mismanaged and doomed
wutbrodo 7y ago
> It’s because no matter how smart you folks are as individuals, in the aggregate you are like toddlers. You dump all your toys on the floor and then chase after some other kid’s shinier toy. Your poor CIO is left cleaning up your mess in the middle of the night after stepping on a Lego brick. Oh man, respect for putting up with and handling all of that. Those choices don't sound "individually smart" either though... There seems to be a lot of pretty straightforward Dunning-Kruger going on.
ineedasername 7y ago
Yeah, some of this stuff is going to happen and it's a hassle dealing with it. However, and this may not have been the case with you but has happened where I work: If no one is satisfied with the tools they use then maybe the selection process isn't properly taking user needs into account. You, for example, may find Zoom's meeting ID/participant ID system onerous, but if the bulk of your users need or want something else, there's a problem: Smooth comunication with potential clients through a tool they're comfortable with is rather important. Personally, I can't stand the parade of different conference tools that require their own browser plugins or installed clients or single-use download client etc.
tptacek 7y ago
It would be beyond weird for an IT department to have any say whatsoever in whether a development team used Postgres or Mariadb.
- kasey_junk 7y ago
  Not if the IT department is responsible for all vendor relationships and a support vendor exists. This is not a operating mode I’d encourage but I’ve encountered it in companies in the past.
- hnick 7y ago
  Exactly, it's always MS SQL Server no questions asked :) After all it's the "approved" solution around here.
chapium 7y ago
Sounds like your CFO (also CTO?) is performing two huge roles. If he keeps focusing on managing the tech your finances are probably not in good hands (since he/she is probably doing neither job optimally). It sounds like a toxic mess. > It’s because no matter how smart you folks are as individuals, in the aggregate you are like toddlers. You dump all your toys on the floor and then chase after some other kid’s shinier toy. Your poor CIO is left cleaning up your mess in the middle of the night after stepping on a Lego brick. Viewing your underlings as toddlers probably isn't helping matters much. Everyone has very specific needs. They are interested in meeting their needs and need to make local decisions that look dumb from high level. Aka greedy choices. Its a bit academic, but "Cognitive Structure of Emotions", Ortony might help you break down some of the people issues in your org. There is a balance. How do you give lower parts of your organization autonomy to make local decisions and at the same time make choices that are sane from a higher level. 40-50 people is typically a tipping point for human social structure. This is where tribal systems break down and require a strong leader and more well defined roles.
pier25 7y ago
> It’s because no matter how smart you folks are as individuals, in the aggregate you are like toddlers. Or maybe you are biased to go against change because it just annoys you.
cosmodisk 7y ago
Without going into too much detail I can say that I've got very similar situation at work.It looks like THAT next piece of software will solve it all for everybody. The number of various apps we've got is absurd. In your case,the most interesting part is how CFO manages to get to the point where he's responsible for getting NetSuite...
m0zg 7y ago
Never heard of Uberconference. Everyone has Zoom though, so that's sort of the default choice for that sort of thing - to the point where it's becoming a verb. And the product is pretty good.
cmroanirgo 7y ago
> no matter how smart you folks are as individuals, in the aggregate you are like toddlers. You dump all your toys on the floor and then chase after some other kid’s shinier toy You made my day. Quote of the year so far!
PopeDotNinja 7y ago
> It’s because no matter how smart you folks are as individuals, in the aggregate you are like toddlers. That's a great line, and it's only funny because it's true.
pbreit 7y ago
That’s a lot of dysfunction for such a small company and you don’t seem too solution-oriented. Why would a 50 person company even have a CIO?
sytelus 7y ago
Gosh... no one in their right mind should ever select Concur for reimbursement. I could understand a big company talking heads getting lured in because their secretaries would be suffering through Concur crapware, not them. For startups, I would have expected the decision-makers to give a through hands-on treatment before enforcing it on everyone. Seriously, you shouldn't be making technical choices for professional developers as CIO unless you are writing code as one of them. If you think they are like toddlers, your hiring is already busted. More seriously, CIO is a pointless title no one really knows why it exists. Even more seriously, startup shouldn't be having "IT department". If you do, you are already Walmart at that point, not Amazon.
anonsivalley652 7y ago
I was a sysadmin, consultant before going EE/CS and AWS consultant after that for Fortune 200. AWS is extremely overpriced for running a stable amount of resources. For a lab, it's trivial to buy some used, power-efficient enterprise servers to run in a second-tier co-lo, install Xen or KVM on bare metal managed by an IaaS solution similar to CloudStack. On top of that, a PaaS like CloudFoundry or CFCR.
hugesmash 7y ago
I cringe whenever I heard a CIO say, "It’s because no matter how smart you folks are as individuals, in the aggregate you are like toddlers." While I do agree that there are tradeoffs between centralization vs decentralization, not sure that's the best way to frame the tension. Maybe rather than thinking inside the constraints, there are ways to find infrastructure/architecture to relieve them? Going to leave these to consider: (guess from which book) 1 - Processes are supposed to protect people from Distractions and help them deliver their core objectives. 2 - IT is not merely a department, it is pervasive like electricity. 3 - In order to survive, the business and IT can’t make decisions exclusive of each other. (IT = centralized function; "business" = functions being supported, including devs)
tixocloud 7y ago
I applaud you for sharing your story. With the rise of shadow IT, not enough of respect is given to CIOs and IT teams for making sure the entire company’s infrastructure doesn’t implode on its own. The main reason why we have so many data silos is because everyone is going out and buying software on their own specific to their needs without batting an eyelid to the enterprise. Vendors love the fact that they can circumvent IT just to get their solutions going and get your started without ever mentioning that a new data island is being created and work will be needed to bring it all back in-house. Aside: can I ask for some advice on software requirements? We’re designing our solution to meet IT requirements and want to get under the skin of CIO concerns.
overgard 7y ago
I wonder how that attitude comes across to the people you work with. They may be avoiding your processes exactly because you view them as toddlers.
YZF 7y ago
I love that toddler bit. Throw a lot of smart people together and you generally just get some sort of chaos. This isn't just tools, it's the software architecture, libraries etc. The problem is if you go ahead and tell the smart people what to do, they get annoyed, if you don't tell them what to do, they go and play with the shiny toys. If anyone has solved this problem I'd like to know! ;)
yellowapple 7y ago
> Of course, he later unilaterally selected NetSuite (for something like $40k a year!) My condolences.

gibolt 7y ago

Seems like there should be some basic review processes in place. Any external dependency/purchase should require sign-off of at least one of only a few decision makers. This should be very similar to a code review, but seen by CTO, CIO, and CEO (whichever combination is most relevant) so that big unexpected, costly structural changes don't cost long term disfunction and pain.

dzhiurgis 7y ago
Wonder if there's software for organisational management? Any ticket tracker could probably do.
- lonelappde 7y ago
  Trackers are for management to control the plebs. Rules don't apply to execs.
  - deleted 7y ago
    [deleted]

projectileboy 7y ago

I wish I could upvote this more than once.

leeoniya 7y ago

> (every conference gets a simple phone number, no stupid 9-digit code plus pin plus participant id) in our case, UC constantly failed hard to properly encode an essentially static excel sheet over screen share - jpeg artifacts the size of basketballs that never went away, even when given infinite time to "catch up". zoom has zero issues with screen share, but randomly drops calls, and yeah the phone + 9 digit id + participant id feels intentionally user-hostile (especially having to repeat that bs again after a dropped call).

moron4hire 7y ago
That's weird about Zoom. We have whomever is scheduling the meeting paste their personal meeting ID into the meeting invite. It's one click for anyone joining, including the host.
- Aeolun 7y ago
  Maybe if you literally call in to the conference? Not sure why you’d ever want to do that, but...
ipython 7y ago
You can have zoom call you, making the whole “too many numbers” thing irrelevant.
- techdevangelist 7y ago
  I think your plan has to support the outbound calling, our Corp issued plans do but the random 3rd zoom bridge I join doesn’t always have the call me option. It may be free tier vs paid; but has bit me right before trying to jump on and having to dial in manually.

Tainnor 7y ago

Eh, the problem with the "IT department dictates all the choices because the devs are stupid" approach is that it takes ownership away from the devs, therefore leading to a self-fulfilling prophecy. If I can't be trusted to make technology decisions for the system I know about (and the IT department knows nothing about), then why should I care about delivering the best possible product? Sorry, I've seen exactly that pattern happen in my (still) current company and it just leads to teams that are completely unable to think for themselves and work like machines in a cog. I'm not saying company guidelines shouldn't exist or that you should allow a proliferation of 200 different programming languages, but I have never seen the "devs are stupid" approach work; if this is indeed a problem in your org, hire better people! (Which doesn't mean: smarter hackers. It means: responsible, professional individuals that work well together in a highly effective team and can be trusted to make decisions in the best interest of the product.)

ownagefool 7y ago
I think both view points are true. - In orgs that don't trust dev typically have significantly less understanding of dev, and in my experience have really poor security postures. Everything is a slow manual process decided by people who don't understand apps or automation. - In orgs that trust dev too much, you usually get a federated architecture that doesn't make any sense from a strategy point of you. Some teams are great; others don't have basic controls. You typically have a bunch of different consultancies playing land and expand and selling expensive solutions that don't actually work. As usual, the sweet spot is probably somewhere in the middle.
- grosswait 7y ago
  Regarding your first point about security, I see the opposite on a weekly basis. Devs, especially in startups, make secure technology decisions, but in a very narrow and entirely technical scope that essentially encompasses "their world". Once induced to see the larger picture either due to a compromised system, or table top exercises that include the rest of the business, they and leadership start to realize they've had a false sense of security.

noir_lord 7y ago

I hear you, I work for a large manufacturing company as a lead engineer (household name in the UK) and this complete lack of agreement between teams on how to do things results in a colossal amount of churn/wastage between "new shiny" and "already working". Lots of "Lets move X to Y" which never gets completed then someone addes "Z" and now you have 3 ways of doing basically everything. Worse is our documentation (which is generally good) frequently documents X but not Y or Z because the person who decided on Y or Z didn't look. It's mentally fatiguing, I feel like every choice on what to use comes with more trade-offs than I should have to consider for something so simple. Video conferencing is a good example, We variously have Hangouts, Skype and others, teleconferencing equipment in one room is one thing, in another something else. The only reliable way to throw video to a screen is a USB-C to HDMI cable I keep in my rucksack. Feels like half my decisions are saying "No" to an engineer who wants to replace Foo with a very shiny but 99% identical and unknown Bar.

ansgri 7y ago
> The only reliable way to throw video to a screen is a USB-C to HDMI cable I keep in my rucksack. That's quite progressive! Last I checked, many of our monitors only supported DVI and DP, and only some recently bought laptops have USB-C.
- noir_lord 7y ago
  Developers who are issued laptops (not all are, juniors get desktops) get either 16” MacBook Pro’s or equivalent priced thinkpad. Can’t complain about that though moving from Linux after two decades to OS X was a bit of a change.
Frost1x 7y ago
I've worked with both sides of this argument and I find that "new shiny" is a perpetual problem. Anyone that proposes new shiny should be responsible of showing trade offs, integration feasibility, impact, etc. I'm not against new technology but so many people want to adopt new technology X just for the sake of it being new technology X. I see this on developer teams I work with every day and it makes me want to gouge my eyes out sometimes, especially when I end up being forced to use their nonsensical choice of new technology X which makes my life harder. Part of the problem I believe is that everyone is focusing on their own self-interest. Many developers for the most part don't care much about the business interests/growth. They're already looking for their next higher paying gig and want paid training in technology X at their current gig. Since many businesses provide little concern for long term talent retition, loyalty or investing in professional development that falls outside their business adopted technology preview, I completely understand the developers choosing themselves over the business. At the same time, going overboard shoots yourself in the foot because it strangles the business in the process. There certainly needs to be a balance and a lot could be gained by giving developers freetime and resources for continued professional development.

baxtr 7y ago

> It’s because no matter how smart you folks are as individuals, in the aggregate you are like toddlers. Love the quote

GordonS 7y ago

It sounds like a few simple rules would help - you don't need complex procedures and forms, it can be as simple as "if you want to buy new software, ask the CIO or CTO, and in most cases they'll say yes/no on the spot". I can't help but think this is a symptom of being awash with VC cash - I can't imagine this happening in a bootstrapped business.

hef19898 7y ago
I tend to agree. Bootstrapping, and small budgets, force discipline. Even without procedures. Practically infinite budgets tend to have the opposite effect. If senior management isn't forcing discipline things can get out of hand pretty quick.
- afarrell 7y ago
  > Bootstrapping, and small budgets, force discipline. This is only true in the evolutionary sense -- Example: "parachuting forces people to be good at checking their gear." Telling someone that they are going to jump out of a plane won't magically give them a skill like meticulousness.
  - ryandrake 7y ago
    It’s a skill like any other, and requires study and practice. There is a reason why half of pilot training is checklists and drilling procedures until they are permanently encoded into your muscle memory.
    - afarrell 7y ago
      Right. But I often see people ask "how can I learn to X" and get advice like "Go do Y. It will force you to X". But jumping into to the situation unprepared is not how pilots learn skill X. They learn it through particular methods of study and practice.
      - hef19898 7y ago

lifeisstillgood 7y ago

I hear you, but the only times I have seen the balance work is via a "committee" of DevLeads. Senior devs work with the trees everyday but are also able to see the woods. They are at the perfect position to make intelligent future proof decisions, and the second job of senior management is to ensure the DevLeads (or non tech equivalents) across the company are meeting talking discussing and deciding regularly and frequently (no a slack channel is not enough)

GordonS 7y ago
Where this totally falls down is where that committee becomes a full-time position, and the members stop doing actual dev work, becoming more and more out of touch with reality as time passes. This was the case at an engineering company I worked with for several years. The committee, or "enterprise architects" as they called themselves, became too far removed from the trenches, and the devs viewed them as sitting in an ivory tower and passing down ridiculous decrees. They brought this view upon themselves, as they made it more or less impossible to even speak to them - almost all communication was through requests and forms uploaded to a sharepoint site! They kept taking it further and further, until you even needed their permission to take a dependency on a 3rd party library for a LoB app. Such requests would sometimes take weeks to get a response. We could never hold on to devs for long, in large part because they hated working under this bureaucratic nightmare. The committee made all sorts of terrible decisions, always without consulting the devs and always with little justification, and these had a lasting impact for years to come. Gods, it was horrible!
- lifeisstillgood 7y ago
  It's this "committee" job to make sure the organisation has the right tools without descending into anarchy it's senior managements job to make sure the dev leads are working well Basically this is senior / middle management in every company you had senior management that have not realised the importance of software to their business - so they let a situation develop they would never allow in sales or accounts
  - 7y ago

GordonS 7y ago

We got the same catty comments from prospective customers about Uberconference. Eventually we moved to webex, not because it's the best (it's not), not because it's the cheapest (it's not), but because many corporate customers seems to use it internally, and because it's what just about all corporate customers seem to expect.

ThePowerOfFuet 7y ago

This is fucking gold. Thank you.

fivre 7y ago

The individuals in aggregate may be toddlers, but unfortunately the C-suite as individuals are often also toddlers, at least vis a vis their responsibilities. Tasked with providing IT infrastructure that works for the company, they seem to largely shirk their responsibility and choose IT infrastructure that best serves them, the needs of others be damned. CIOs will seemingly gladly choose something that provides a good UX for one central administrator even if the UX for hundreds or thousands of others is "the software literally shoots knives out of the monitor and gouges out your eyes". Reports that the software gouges out everyone's eyes are roundly ignored. I'm not sure to what degree this corporate disdain for quality of work environment is intentional or simply inability to grasp how other people may have different experiences using something, but I'm even more unsure how to solve it. What do we do when attempts to explain how shit sucks fall on deaf ears? Bring back pistol dueling?

officialchicken 7y ago
Please recognize the fact that the argument you are making here is based on whataboutism and is dishonest trying to setup a us-versus-them situation and confuse the actual issue. Then you proceed to follow up with illlogical conclusions with absurdist claims ... pistol dueling has nothing to do with the ROI/TCO of an adopted SaaS. The actual issue the parent argument is about managing diversity - and that you can never please everyone - and that isn't a pistols at dawn kind of situation.
afarrell 7y ago
Part of the problem here is that there is a balance to be struck with these sorts of things: Cost, User experience, Mange-ability, and time spent shopping around rather than just going with the industry-default or one with the best sales-team. Responsible decision-makers have to make trade-offs. When you say > Reports...are roundly ignored That lack of weight given to your experience as a signal of real business cost is a real problem. So what is the solution? 1. Understand the problem they're trying to solve. What are their real motives and pressures? 2. Understand where your needs align with theirs and where they diverge in reality. 3. Tell a compelling story of where your needs are in fact aligned. 3.1) Prepare Evidence If your case is "This tool is causes literal permanent eye injuries to our staff", then there should be written reports of those injuries. If your case is "This software package has multiple missing-affordances which present operational risks to the business", then you should be able to take screen recordings of that. 3.2) Start with why When turning evidence into a presentation, remember that people listen better when they know why they are listening. So start with: What is at stake? 3.3) Credible language If your words say "the UX for hundreds or thousands of others is 'the software literally shoots knives out of the monitor and gouges out your eyes'" but you can't actually back that up with the factual reality, you seem like you're exaggerating. If I think you are exaggerating, then I can't trust your words when I'm trying to understand magnitudes. If I can't trust your words about magnitudes, then how do I give you a voice in making a well-balanced trade-off? ------- Literally: (adverb) 1. In in a way of speaking that is completely accurate and unexaggerated. 2. In in a way of speaking that is exaggerated for emotional effect.

tonyedgecombe 7y ago

I wonder how much of this is a lack of communication from your CEO. I've worked for companies that operated on very lean budgets. Everybody in the organisation knew what it was, it wasn't much fun but it was a clear policy. There is no reason you can't do the same here, the objectives might be different but unless people up and down the organisation know what they are you can't expect anything other than anarchy.

cl0rkster 7y ago

This post starts by telling it's lauded idea of not single threading large purchasing decisions. It's simply irresponsible not to. Even the poster knows that, and that's why he thanks God that another C-level actually showed leadership. Honestly, reading the post, everything points to this guy being buddy boss. Bosses should create a positive work environment both at and away from the job. They should not be friends outside of work with their subordinates (yes, I know this is speculation about this guy, but the principal is true). I wish all these c-level folks with their making sure any shit they create always rolls right past them and onto someone else would just give their money to the person actually shoveling the shit... Because they recognize value.

LoSboccacc 7y ago

> won’t let you use Postgres instead of MariaDB or Gitlab instead of Bitbucket, remember my experience. It’s because no matter how smart you folks are as individuals, in the aggregate you are like toddlers I actively resist the notion that 'everyone but me is stupid' and propose a more realipolitik explanation: it's because power and budget. in manager heads, if you pick solution A I pick solution B, so that higher ups don't see the same line twice in services costs and get the idea they can obtain savings by merging the two functions, making one of us redundant. yep yep didn't expect anything different from a techie community.

AdrianB1 7y ago

Sorry, but you are not a CIO, you just have a fancy meaningless title with no real correspondence to what it means. If the CFO decided to buy NetSuite without asking anyone, you care not CIO and he is acting as CEO because he can override you with no consequences. Just saying.

jessaustin 7y ago
CFOs can't integrate new software themselves, but they can buy anything they want. Some of them let this go to their heads. When I hear NetSuite ads, it's only while listening to the absolute dumbest sports talk shows. Apparently this marketing works...
notyourday 7y ago
That's not entirely accurate, if not to say that's completely inaccurate. Contrary to what people might think, companies are not ran as military with the CEO being a commander-in-chief. In most of the companies, members of the C-suite have a certain or total autonomy to make any decisions that they want as long as it is somewhat within their domain. The conflicts between them are resolved via negotiation and horse trading. Just because the CIO does not like what the CFO is doing, does not mean that the CFO is wrong in making that decision, same as just because the CFO does not like what the CIO is doing does not mean that the CIO is wrong. When one CxO steps on feet of another CxO it is either resolved by reaching a new agreement going forward or resolution is punted into the future or one of the CxOs leaves.
- AdrianB1 7y ago
  I cannot tell how is each company organized, but I am working in a $250 billion company and I had the occasion a few years ago to find out in detail how this works when our CIO had to approve some IT purchase and there were some technical problems with the authorization system: our CFO does not have the authority to sign or approve any IT contract and nobody in the company will ever execute the payment. We are not organized as military, but each of us have spending limits (from $10,000 the lowest to a few hundred millions $ for CxO) and we cannot override that. Yes, we had people that bought stuff in their spending authority but not in their domain authority (that is much harder to limit in a system) and they were fired every time it happened.

xwdv 7y ago

Do you mind sharing the name of your startup?

chirau 7y ago
Lol. I doubt they'd be careless enough to do that. As soon as they do, you can then put names to all the people mentioned. Which is obviously not their intention otherwise they'd have done so.
- xwdv 7y ago
  If it were that easy you could probably just find several cyber security startups and work backwards to find out which one he’s talking about.

calmworm 7y ago

Your CFO got sold ... twice. Concur and NetSuite are both enterprise level software that a company with 50 FTEs does not need. NetSuite is a never ending money pit with varying results. I dealt with a very similar situation, in which a project manager("VP") talked our owner into using NS, but it was over $100k/year and commitments were 2 years per seat at something like $5k. He ALSO wanted to do the roll out himself. 6 months later, it was still not functional. I got pulled onto the team to help. We made _some_ progress and I hired and managed 4 remote programmers to write all the plugins and customizations we would need to make it work with our model (multi-channel e-commerce, multiple warehouses/locations). It was a nightmare all-around and completely unnecessary. PM/VP left the company because he couldn't do the job and we were stuck with a half-assed implementation at that point. It's been around 4 years since the first day, I am no longer with that company, and I am sure they are still struggling with NS and employing multiple developers to keep things going. Good for the devs, bad for biz. I am willing to bet it's never returned a single dollar on the investment and cost them far more than they wanted to spend. If you can't see the light at the end of the tunnel at this point, cut your loses, and don't get another "solution-in-a-box".

brianwawok 7y ago
Hah this story sounded familiar. Makes sense.
wpietri 7y ago
Weirdly, almost exactly 20 years ago, I sat next to somebody at a wedding who had an almost-identical story about cleaning up after an SAP rollout, but all of the numbers had an extra zero or two. It amazes me that what the SaaS shift appears to have achieved is that now much smaller companies can get stuck in the same "solve everything" money pit. But I guess the fundamental problem hasn't changed: executives want to believe in magic solutions that give them all the feelings of control with none of the actual work. With no regard for actual operational efficiency, and no need to hold themselves to the ROI standards they'd demand of others.
- zbentley 7y ago
  > executives want to believe in magic solutions that give them all the feelings of control with none of the actual work Corollary: R&D wants to believe they can build magical solutions that solve all the problems--solutions that will scale better and cost less to keep up than off-the-shelf ones made by people with extensive domain expertise--in a week or two, promise. As with most things, the problem is complicated, deeply human, and answers lie somewhere in the middle.

chrisweekly 7y ago

Thank you v much for sharing this first-hand perspective. V helpful.

paulie_a 7y ago

As many people as possible should post their salary on slack.

marcinzm 7y ago

>A few month later, sales went out and bought 10 mf’ing Zoom licenses without consulting anyone because some client hadn’t heard of UC and asked if it was the budget solution. They have a point, the more things you need a client to do out of the ordinary the more friction you will get selling them. New UI for them to figure out, new permissions, etc. Depending on your business model as a startup that can be a bad thing. It seems like you try to enforce a rigid structure but don't provide a quick process to changing or appending to that structure. So intelligent people work around your structure and you have no idea. Seen it at many companies. Generally tied to an inability or in-desire to delegate decision making. Which is different than letting people make decisions, rather it involves creating a structure under which they can make decisions. Employees have the most view into what would make their job more efficient or engaging. You want them to think of optimizations and you want them to feel engaged enough to try and improve the business. If you don't listen then they will work around you rather than with you. Or just find another job. Employees want something? Delegate to them the responsibility of building a business case and give them a structure on what that needs to look like. Then they can present it and the team can discuss. Make sure to say yes sometimes even if you think it's sub-optimal since otherwise they'll feel it's a pointless process.

zbentley 7y ago
> Employees have the most view into what would make their job more efficient or engaging. Employees in aggregate know the true answers to those things. Employees individually sometimes do, but often do not. For example, if you have a stone-aged development process on an ancient revision of an unsupported language, and you poll your employees, they'll all want change. They'll all want ... different changes/processes/pet programming languages, too.
- pm90 7y ago
  Sure but when the decision is left to employees, they will organically choose solutions that makes the most sense for them rather than what makes sense only to an individual. Treat the employees as autonomous responsible individuals; give them the freedom on how to best solve their problem and they will solve it. Seen another way, as a manager who is not involved in the day to day you don’t deal with the same problems that they do. Quite presumptive of you to think that you know what will solve their problems.

TACIXAT 7y ago

Damn I hope I never work under someone who considers their employees to be toddlers.

karmakaze 7y ago
Given a large enough sandbox this could be a great working environment. I once worked in an R&D department to produce physically shipped (diskette/cd-rom) software. It was the best of times. Go to conferences, learn shiny tech, make up new toys, sell them as products. We even had annual toy budgets for anything no-questions-asked as well as constant upgrades to the latest hardware running obscure operating systems. Unfortunately the company run too well, eventually shrinking to collecting license and maintenance support fees. One funny story was how whenever we'd be burning the midnight oil to produce the final release, we'd declare it the golden master and hand it over to our shipping department to distribute to our customers. One time I had to make a recall due to a fatal bug. The masters were handed back to me with a smile and when I asked, she said that after the last few recalls of golden masters, she always let them sit on a shelf for a week before actually shipping anything.

GordonS 7y ago

OT, but as the founder of a microISV selling B2B, I'd love to hear something about how you do sales and marketing? It's unquestionably our biggest pain point.

techslave 7y ago

get out ASAP. you are mismanaged and doomed

wutbrodo 7y ago

> It’s because no matter how smart you folks are as individuals, in the aggregate you are like toddlers. You dump all your toys on the floor and then chase after some other kid’s shinier toy. Your poor CIO is left cleaning up your mess in the middle of the night after stepping on a Lego brick. Oh man, respect for putting up with and handling all of that. Those choices don't sound "individually smart" either though... There seems to be a lot of pretty straightforward Dunning-Kruger going on.

ineedasername 7y ago

Yeah, some of this stuff is going to happen and it's a hassle dealing with it. However, and this may not have been the case with you but has happened where I work: If no one is satisfied with the tools they use then maybe the selection process isn't properly taking user needs into account. You, for example, may find Zoom's meeting ID/participant ID system onerous, but if the bulk of your users need or want something else, there's a problem: Smooth comunication with potential clients through a tool they're comfortable with is rather important. Personally, I can't stand the parade of different conference tools that require their own browser plugins or installed clients or single-use download client etc.

tptacek 7y ago

It would be beyond weird for an IT department to have any say whatsoever in whether a development team used Postgres or Mariadb.

kasey_junk 7y ago
Not if the IT department is responsible for all vendor relationships and a support vendor exists. This is not a operating mode I’d encourage but I’ve encountered it in companies in the past.
hnick 7y ago
Exactly, it's always MS SQL Server no questions asked :) After all it's the "approved" solution around here.

chapium 7y ago

Sounds like your CFO (also CTO?) is performing two huge roles. If he keeps focusing on managing the tech your finances are probably not in good hands (since he/she is probably doing neither job optimally). It sounds like a toxic mess. > It’s because no matter how smart you folks are as individuals, in the aggregate you are like toddlers. You dump all your toys on the floor and then chase after some other kid’s shinier toy. Your poor CIO is left cleaning up your mess in the middle of the night after stepping on a Lego brick. Viewing your underlings as toddlers probably isn't helping matters much. Everyone has very specific needs. They are interested in meeting their needs and need to make local decisions that look dumb from high level. Aka greedy choices. Its a bit academic, but "Cognitive Structure of Emotions", Ortony might help you break down some of the people issues in your org. There is a balance. How do you give lower parts of your organization autonomy to make local decisions and at the same time make choices that are sane from a higher level. 40-50 people is typically a tipping point for human social structure. This is where tribal systems break down and require a strong leader and more well defined roles.

pier25 7y ago

> It’s because no matter how smart you folks are as individuals, in the aggregate you are like toddlers. Or maybe you are biased to go against change because it just annoys you.

cosmodisk 7y ago

Without going into too much detail I can say that I've got very similar situation at work.It looks like THAT next piece of software will solve it all for everybody. The number of various apps we've got is absurd. In your case,the most interesting part is how CFO manages to get to the point where he's responsible for getting NetSuite...

m0zg 7y ago

Never heard of Uberconference. Everyone has Zoom though, so that's sort of the default choice for that sort of thing - to the point where it's becoming a verb. And the product is pretty good.

cmroanirgo 7y ago

> no matter how smart you folks are as individuals, in the aggregate you are like toddlers. You dump all your toys on the floor and then chase after some other kid’s shinier toy You made my day. Quote of the year so far!

PopeDotNinja 7y ago

> It’s because no matter how smart you folks are as individuals, in the aggregate you are like toddlers. That's a great line, and it's only funny because it's true.

pbreit 7y ago

That’s a lot of dysfunction for such a small company and you don’t seem too solution-oriented. Why would a 50 person company even have a CIO?

sytelus 7y ago

Gosh... no one in their right mind should ever select Concur for reimbursement. I could understand a big company talking heads getting lured in because their secretaries would be suffering through Concur crapware, not them. For startups, I would have expected the decision-makers to give a through hands-on treatment before enforcing it on everyone. Seriously, you shouldn't be making technical choices for professional developers as CIO unless you are writing code as one of them. If you think they are like toddlers, your hiring is already busted. More seriously, CIO is a pointless title no one really knows why it exists. Even more seriously, startup shouldn't be having "IT department". If you do, you are already Walmart at that point, not Amazon.

anonsivalley652 7y ago

I was a sysadmin, consultant before going EE/CS and AWS consultant after that for Fortune 200. AWS is extremely overpriced for running a stable amount of resources. For a lab, it's trivial to buy some used, power-efficient enterprise servers to run in a second-tier co-lo, install Xen or KVM on bare metal managed by an IaaS solution similar to CloudStack. On top of that, a PaaS like CloudFoundry or CFCR.

hugesmash 7y ago

I cringe whenever I heard a CIO say, "It’s because no matter how smart you folks are as individuals, in the aggregate you are like toddlers." While I do agree that there are tradeoffs between centralization vs decentralization, not sure that's the best way to frame the tension. Maybe rather than thinking inside the constraints, there are ways to find infrastructure/architecture to relieve them? Going to leave these to consider: (guess from which book) 1 - Processes are supposed to protect people from Distractions and help them deliver their core objectives. 2 - IT is not merely a department, it is pervasive like electricity. 3 - In order to survive, the business and IT can’t make decisions exclusive of each other. (IT = centralized function; "business" = functions being supported, including devs)

tixocloud 7y ago

I applaud you for sharing your story. With the rise of shadow IT, not enough of respect is given to CIOs and IT teams for making sure the entire company’s infrastructure doesn’t implode on its own. The main reason why we have so many data silos is because everyone is going out and buying software on their own specific to their needs without batting an eyelid to the enterprise. Vendors love the fact that they can circumvent IT just to get their solutions going and get your started without ever mentioning that a new data island is being created and work will be needed to bring it all back in-house. Aside: can I ask for some advice on software requirements? We’re designing our solution to meet IT requirements and want to get under the skin of CIO concerns.

overgard 7y ago

I wonder how that attitude comes across to the people you work with. They may be avoiding your processes exactly because you view them as toddlers.

YZF 7y ago

I love that toddler bit. Throw a lot of smart people together and you generally just get some sort of chaos. This isn't just tools, it's the software architecture, libraries etc. The problem is if you go ahead and tell the smart people what to do, they get annoyed, if you don't tell them what to do, they go and play with the shiny toys. If anyone has solved this problem I'd like to know! ;)

yellowapple 7y ago

> Of course, he later unilaterally selected NetSuite (for something like $40k a year!) My condolences.