After 10 years of business travel, this is how I cope at the airport:

• You’ll get there, even if you’re late.
• Don’t worry about lines, just wait in them.
• Few people know what they’re doing here, don’t let their stress stress you out.
• There are no special snowflakes, unless you have a doctor’s note.
• The word of airline staff is law, you can’t argue against the agent of the FAA.
• Relax and walk slow.
• If you want a better experience, pay more or pay your dues.

When in doubt, and even if it contradicts the above, you can always:

• Move fast and get out of the way.

The premise of this book, for most anyone, is painfully boring: planning out and project managing the installation of COTS software. This is mostly lumbering, on-premises ERP applications: those huge, multi-year installs of software that run the back office and systems of record for organizations. While this market is huge, touches almost every company, and has software that is directly or indirectly touched by almost everyone each day (anytime you buy something or interact with a company)…it’s no iPhone.

If you’re in the business of selling enterprise software and services, however, Beaubouef’s book is a rare look inside the buyer’s mind and their resulting work-streams when they’re dealing with big ol' enterprise IT. As a software marketer, I read it for exactly that. I was hoping to find some ROI models (a scourge of my research). It doesn’t really cover that at all, which is fine.

There’s a core cycle of ideas and advice flitting in and bout of the book that I like:

1. COTS software will do, you know, 80% of what you like. The rest is customizing it through configuration, your own code layered on-top, or getting the vendor to add in new features.
2. The more you customize the software, the harder it will be to change. But, the less you customize it, the less it creates differentiation for your business processes.
3. Most of the problems and challenges you’ll encounter, though, will be human-based.
4. Much of these human problems are about managing the requirements process to make sure the software is matching the needs of the business.
5. Process-wise, to do this we like to take on a waterfall approach (try to specify everything up front, implement it all, then verify if it works). This results in a lot or risk of waiting for that final verification to see if it works and you were right about matching the COTS implementation to business needs.
6. Instead, an iterative approach that focuses on learning and honing the COTS/business match-up seems like a good idea.
7. Role-wise, getting someone(s) who has a tops-down view of the business process and enough technical understanding to map that to the COTS project is a really good idea, though hard to put in place.

While the book focuses on on-premises software, the overall thinking could easily apply to any implementation of a large IT-driven, vendor provided system: SaaS would work, and to an extent the kind of infrastructure software we sell at Pivotal. As the points above go over, the core thrust of the book is about managing how you make sure your IT is actually helping the business, not bogging down in its self.

If you’re pretty vague on what you should do in these large IT initiatives, you could do a lot worse than read this book.

Check out the book: Maximize Your Investment: 10 Key Strategies for Effective Packaged Software Implementations

I get all ants-in-pants about this whole bi-modal discussion because I feel like it’s a lot of energy spent talking about the wrong things.

This came up recently when I was asked about “MVP”, in a way that basically was saying “our stuff is dangerous [oil drilling], so ‘minimal’ sounds like it’d be less safe.” I tried to focus them on the “V” and figure out what “viable” was for their situation. The goal was to re-enforce that the point of all this mode 2/small batch/DevOps/PDCA/cloud native/OODA nonsense is to keep iterating to get to the right code.

Part of the continual consternation around bi-modal IT - sad/awesome mode - is misalignment around that “viability” and scoping on “enterprise” projects. This is just one seam-line around the splits of the discussion being unhelpful

Bi-strawperson

The awesome mode people are like:

You should divide the work into small chunks that you release to production as soon as possible - DevOps, Agile, MVP, CI/CD - POW! You have no idea what or how you should implement these features so you need to iteratively do it cf. projectcartoon.com

And the sad mode folks are like:

Yes, but we have to implement all this stuff all at once and can’t do it in small slices. Plus, mainframes and ITIL.

Despite often coming off as a sad mode apologist, I don’t even know what the sad mode people are thinking. There’s this process hugger syndrome that, well on both sides really, creates strawpeople. The goal of both methods is putting out software that makes users more productive, including having it actually work, and not overpaying for the whole thing.

The Enemy is finding any activity that doesn’t support those goals and eliminated it as much as possible. In this, there was some good scrabbling from the happy mode people laughing at ITSM think early on, but at this point, the sad people have gotten the message, have been reminded of their original goal, and are now trying to adapt. In fact, I think there’s a lot the “sad mode” people could bring to the table.

To play some lexical hopscotch, I don’t think there is a “mode 1.” I think there’s just people doing a less than awesome job and hiding behind a process-curtain. Sure, it may to be their choice and, thus, not their fault. “Shitty jobs are being done,” if you prefer the veil of passive voice.

Fix your shit

When I hear objections to fixing this situation, I try to b nice and helpful. After all, I’m usually there as part of an elaborate process to get money from these folks in exchange for helping them. When they go all Eeyore on me, I have to reframe the room’s thinking a little bit without getting too tough love-y.

“When I put these lithium batteries in this gas car, it doesn’t seem to work. So electric cars are stupid, right?

You want to walk people to asking “how do we plan out the transition from The Old Way That Worked At Some Point to The New Way That Sucks Less?” They might object with a sort of “we don’t need to change” or the even more snaggly “change is too hard” counter-point.

I’m not sure there are systems that can just be frozen in place and resist the need to change. One day, in the future, any system (even the IRS’!) will likely need to change and if you don’t already have it setup to change easily (awesome mode), you’re going to be in a world of hurt.

The fact that we discuss how hard it is to apply awesome mode to legacy IT is evidence that that moment will come sooner than you think.

(Insert, you know, “where’s my mobile app, Nowakowski?” anecdote of flat-footedness here.)

ITIL end in tears(tm)

The royal books of process, ITIL, are another frequent strawperson that frothy mouthed agents of change like to light up. Few things are more frustrating than a library of books that cost £100 each. There’s a whole lot in there, and the argument that the vendors screw it all up is certainly appetizing. Something like ITIL, though, even poorly implemented falls under the “at least it’s an ethos” category.

I’m no IT Skeptic or Charles T. Betz, but I did work at BMC once: as with “bi-modal,” and I really don’t want to go re-read my ITIL books (I only have the v2 version, can someone spare a few £100’s to read v3/4?), but I’m pretty sure you could “do DevOps” in a ITIL context. You’d just have to take out the time consuming implementation of it (service desks, silo’d orgs, etc.).

Most of ITIL could probably be done with the metaphoric (or literal!) post-it notes, retrospectives, and automated audit-log stuff that you’d see in DevOps. For certain, it might be a bunch of process gold-plating, but I’m pretty sure there’s no unmovable peas under all those layers of books that would upset any slumbering DevOps princes and princesses too bad.

Indeed, my recollection of ITIL is that it merely specifies that people should talk with each other and avoid doing dumb shit, while trying to improve and make sure they know the purpose/goals of and “service” that’s deployed. They just made a lot of flow charts and check lists to go with it. (And, yeah: vendors! #AmIrightohwaitglasshouse.)

Instead of increasing the volume, help spray away the shit

That gets us back to the people. The meatware is what’s rotting. Most people know they’re sad, and in their objections to happiness, you can find the handholds to start helping:

Yes, awesome mode people, that sounds wonderful, just wonderful. But, I have 5,000 applications here at REALLYSADMODECOGLOBAL, Inc. - I have resources to fix 50 of them this year. YOUR MOVE, CREEP!

Which is to say, awesome mode is awesome: now how do we get started in applying it at large orginizations that are several fathoms under the seas of sad?

The answer can’t be “all the applications,” because then we’ll just end up with 5,000 different awesome modes (OK, maybe more like 503?) - like, do we all use Jenkins, or CircleCI, or Travis? PCF, Docker, BlueMix, OpenShift, AWS, Heroku, that thing Bob in IT wrote in his spare time, etc.

Thus far, I haven’t seen a lot of commentary on planning out and staging the application of mode 2. Gartner, of course, has advice here. But it’d be great to see more from the awesome mode folks. There’s got to be something more helpful than just “AWESOME ALL THE THINGS!”

Thanks to Bridget for helping draw all this blood out while I was talking with her about the bi-modal pice she contributed to.

I have a larger piece on common objections to “cloud native” that I’ve encountered over the last year. Put more positive, “how to get your digital transformation started with a agile, DevOps, and cloud native” or some such platitudinal title like that. Here’s a draft of the dread-ROI section.

The most annoying buzzkill for changing how IT operates (doing agile, DevOps, taking “the cloud native journey,” or whatever you think is the opposite of “waterfall”) is the ROI counter-measure. ROI is a tricky hurdle to jump because it’s:

1. Highly situational and near impossible to properly prove at the right level — do you want to prove ROI just within the scope of the IT department, or at the entire business-level? What’s the ROI of missing out on transitioning Blockbuster to Netflix? What’s the ROI of a mobile app for a taxi company when Uber comes along? What’s the ROI for investing in a new product that may or may not work within three years, but will save the company’s bacon in five years?
2. Compounded by the fact that the “value” of good software practices is impossible to predict. Drawing the causal lines between “pair programming” and “we increased market-share by 3% in Canada” can be a hard line to draw. You can back-think a bunch of things like “we reduced defects and sped up code review time by pairing,” but does that mean you made more money, or did you make more money because the price of oil got halved?

In my experience, when people are asking you about ROI, what they’re asking is “how will I know the time and money I’m going to spend on this will pay off and, thus, I won’t lose time and money? (I don’t want to look like a fool, you see, at annual review time)”

What they’re asking is “how do I know this will work better than what I’m currently doing or alternatives.” It also usually means, “hey vendor, prove to me that I should pay you.”

As I rambled through last year, I am no ROI expert. However, I’ve found two approaches that seem to be more something than nothing: (1.) creating a business case and trusting that agile methods will let you succeed, and, (2.) pure cost savings from the efficiencies of agile and “cloud native.”

A Business Case

A business case can tell you if your approach is too expensive, but not if it will pay for itself because that depends on the business being successful.

Here, you come up with a new business idea, a product, service, or tweak to an existing one of those. “We should set up little kiosks around town where people can rent DVDs for a $1 a day. People like renting DVDs. We should have a mobile app where you can reserve them because, you know, people like using mobile. We should use agile to do this mobile app and we’re going to need to run it somewhere, like ‘the cloud.’ So, hey, IT-nerds, what’s the ROI on doing agile and paying for a cloud platform on this?”

In this case, you (said “IT-nerds”) have some externally imposed revenue and profit objectives that you need to fit into. You also have some time constraints (that you’ll use to push back on bloated requirements and scope creep when they occur, hopefully). Once you have these numbers, you can start seeing if “agile” fits into it and if the cost of technology will fit your budget.

One common mis-step here is to think of “cost” as only the licensing or service fees for “going agile.” The time it takes to get the technology up and running and the chance that it will work in time are other “costs” to account for (and this is where ROI for tech stuff gets nasty: how do you put those concerns into Excel?).

To cut to the chase, you have to trust that “agile” works and that it will result in the DVD rental mobile app you need under the time constraints. There’s no spreadsheet friendly thing here that isn’t artfully dressed up qualitative thinking in quantitate costumes. At best you can point to things like the DevOps reports to show that it’s worked for other people. And for the vendor expenses, in addition to trusting that they work, you have to make sure the expenses fit within your budgets. If you’re building a $10m business, and the software and licensing fees amount to $11m, well, that dog won’t hunt. There are some simple, yet helpful numbers to run here like the TCO for on-premises vs. public cloud fees.

Of course, a major problem with ROI thinking is that it’s equally impossible to get a handle on competing ways to solve the problem, esp. the “change nothing” alternative. What’s the ROI of how IT currently operates? It’d be good to know that so you can compare it to the proposed new way.

If you’re lucky enough to know a realistic, helpful budget like this, your ROI task will be pretty easy. Then it’s just down to horse-trading with your various enterprise sales reps. Y’all have fun with that.

Efficiency

Focus on removing costs, not making money.

If you’re not up for the quagmire of business case-driven ROI, you can also discuss ROI in terms of “savings” the new approach affords. For things like virtualizing, this style of ROI is simple: we can run 10 servers on one server now, cutting our costs down by 70–80% after the VMware licensing fees.

Doing “agile,” however, isn’t like dropping in a new, faster and cheaper component into your engine. Many people I encounter in conference rooms think about software development like those scenes from 80s submarine movies. Inevitably, in a submarine movie, something breaks and the officer team has to swipe all the tea cups off the officer’s mess table and unfurl a giant schematic. Looking over the dark blue curls of a thick Eastern European cigarette, the head engineer gestures with his hand, then slams a grimy finger onto the schematics and says “vee must replace the manifold reducer in the reactor.”

Solving your digital transformation problems is not like swapping “agile” into the reactor. It’s not a component-based improvement like virtualization was. Instead, you’re looking at process change (or “culture,” as the DevOps people like to say), a “thought technology.” I think at best what you can do is try to calculate the before and after savings that the new process will bring. Usually, this is trackable in things like time spent, tickets opened, number of staff needed, etc. You’re focusing on removing costs, not making money. As my friend Ed put it when we discussed how to talk about DevOps with the finance department:

In other words, if I’m going to build a continuous integration platform, I would imagine you could build out a good scaffolding for that and call it three or four months. In the process of doing that, I should be requiring less help desk tickets get created so my overtime for my support staff should be going down. If I’m virtualizing the servers, I’ll be using less server space and hard drive space, and therefore that should compress down. I should be able to point to cost being stripped out on the back end and say this is maybe not 100% directly related to this process, but it’s at least correlated with it.

In this instance, it’s difficult to prove that you’ll achieve good ROI ahead of time, but you can at least try to predict changes informed by the savings other people have had. And, once again, you’re left to making a leap of faith that qualitative anecdotes from other people will apply to you.

For example, part of Pivotal’s marketing focuses on showing people the worth of buying a cloud platform to support an agile approach to software deliver (we call that “cloud native”). In that conversation, I cite figures like this:

• Developers at Allstateused to spend only 20% of their time coding and now it’s closer to 90%
• A federal government agency wanted to save money on call-centers by converting the workflow to a web app. They’d scheduled to complete the project in 9 months, but after converting to agile, delivered it in 6 weeks.
• When doing agile because testing is pushed down to the team level and automated, you can expect to reduce your traditional QA spend. In fact, many shops on the cloud native journey have massively eliminated their QA department as a stand-alone entity.
• ING’s savings from transforming to a more cloud-y IT setup: “Investment of €200m to further simplify, standardize and automate IT; Decommissioning 40% of application landscape; Moving 80% of applications to zero-touch private cloud.” Resulting in savings of €270m starting in 2018.
• From Orange: “Who isn’t happy to continue working when projects are delivered on average six times faster than with a waterfall approach?”
• “[R]espondents from a recent government study who have already used PaaS say they save 47% of their time, or 1 year and 8 months off a 3.5 year development cycle. For those who have not deployed PaaS, respondents believe it can shave 31% off development time frames and save 25% of their annual IT budget, a federal savings of $20.5 billion.”
• 14 months down to 6 months, 16 staff down to 8 staff: “[w]hen planning the first product developed on Pivotal Cloud Foundry, CoreLogic allocated a team of 12 engineers with four quality assurance software engineers and a management team. The goal was to deliver the product in 14 months. Instead, the project ultimately required only a product manager, one user experience designer and six engineers who delivered the desired product in just six months.”
• “We did an analysis of hundreds of projects over a multiyear period. The ones that delivered in less than a quarter succeeded about 80% of the time, while the ones that lasted more than a year failed at about the same rate. We’re simply not very good at large efforts.”
• From a 1999 study: “software projects that use iterative development deliver working software 38% sooner, complete their projects twice as fast, and satisfy over twice as many software requirements.”
• After switching over to “the new way,” one large retailer has already seen 80% Reduction in cycle time and scope and reduced cycle time from 123 days to 23 days.
• One large insurance company can now manage 1,500 apps with just two operators. There were many, many more before that. Another large bank could manage 145 apps with just 2 operators, and so on.

In most of these cases, once you switch over to the new way, you end up with extra capacity because you can now “do IT” more efficiently. Savings, then, come from what you decide to do with that excess capacity: (a.) doing more with the new capacity like adding more functionality to your existing businesses, creating new businesses, or entering new markets, or, (b.) if you don’t want to “grow,” you get rid of the expense of that excess capacity (i.e., lay-off the excess staff or otherwise get them off out of the Excel sheet for your business case).

But, to be clear, you’re back into the realm of imagining and predicting what the pay-off will be (the “business case” driven ROI from above) or simply stripping out costs. It’s a top-line vs. bottom-line discussion. And, in each case, you have to take on faith the claims about efficiencies, plus trust that you can achieve those same savings at your organizations.

With these kinds of numbers and ratios, the hope is, you can whip out a spreadsheet and make some sort of chart that justifies doing things the new way. Bonus points if you use Monte Carlo inspired ranges to illustrate the breadth of possibilities instead of stone-code line-graph certainty.

Everything is up when there’s no bottom

As an added note of snark: all of these situations assume you know the current finances for the status quo way of operating. Surely, with all that ITIL/ITSM driven, mode 1 thinking you have a strong handle on your existing ROI, right? (Pause for laughs.)

More seriously, the question of ROI for thought technologies is extremely tricky. In that conversation on this topic that I had with Ed last year, the most important piece of advice was simple: talk with the finance people more and explain to them what’s going on.

That’s the most effective (and least satisfying!) advice you get about any of this “doing things the new way” change management prattle: whether it’s auditors, DBAs, finance, PMO people, or whoever is throwing chaff in your direction: just go and talk with them. Understand what it is they need, why they’re doing their job, and bring them onto the team instead of relegating them to the role of The Annoying Others.

Check out another take on this over in my September 2016 column at The Register.

Most of what we do as white-collar workers is help our organization come to a decision. What new geographies to sell our enterprise software and toothpaste in, what pricing to make our electric razors and cranes, which people to fire and which to promote, or how much budget is needed according to the new corporate strategy. Even in the most cynical corporate environment, asking questions — and getting answers! — is the best, primary way to set the stage for making a decision.

You have to be careful, however, of how many questions you ask, and on what topic. If you ask too many questions, you may find that you’ll just create more work for yourself. Before asking just any old question, ask yourself if you’re willing to do the work needed to answer it…because as the asker, you’ll often be tasked with doing that work. We see this in life all the time, you ask someone “want to go to lunch?” and next thing you know, you’re researching in all the restaurants within five miles that have gluten-free, vegan, and steak options.

I’ve seen countless “staffers” fall prey to this in meetings with managers who’re putting together plans and strategies. The meeting has spent about 30 minutes coming up with a pretty good plan, and then an eager staffer pipes up and suggests 1–3 other options. The manager is intrigued! Quickly, that staffer is asked to research these other options, but, you know, the Big Meeting is on Monday, so can you send me a memo by Sunday morning?

In some situations, this is fine and expected. But in others, conniving management will just use up as much as your energy as possible: it’s always better to have done more research, so why not let that eager staffer blow-up their Saturday to have more back-up slides? Co-workers can also let you self-assign homework into burnout if they find you annoying: you’ll notice that when you, the eager staffer, pipe up, they go suddenly quiet and add no input.

As always, you have to figure out your corporate culture. But, just make sure that before you offer up alternatives and otherwise start asking The Big Questions, you’re read to back up those questions by doing the extra homework to answering them yourself.

One of the more eye-rolling tactics of white collar workers is what I call “fence painting”: an employee somehow gets someone else to do work for them. This can be as simple as coasting off budget, but the more insidious practice is to get other outside your chain of command to do work for you.

Most of us have experienced this: days after The Big Meeting you suddenly think “why am I up at 11am working on this report for Scopentholler? I don’t even work in that division!”

What you, the whitewash-encrusted white-collar worker want to do here is somehow still seem “up for anything” and fully capable, and yet not end up painting Scopentholler’s fences. I suggest assigning “homework” as the first rung of filters. If someone wants your input, or wants you to somehow get involved in a project, come up with some mini-project they need to do first. Have them write a brief for you, put on a meeting to bring you up to speed, do a report about how the regional sales have been going, or otherwise force them to do some “homework.”

Homework filters and prioritizes

Assigning homework does two things:

1. It gauges their commitment to getting you involved, filtering out lazy-delegators. If all this person is looking to do is get you to do their work, it’s highly unlikely that they’ll do additional work. Mysteriously, the importance of you being involved in this project will disappear.
2. If they do the homework, you get more information (one of the major currencies of corporate culture) and you can better gauge if it’s actually worth your time to get involved. If the quality of the “homework” is good, you’re interested in the work, and it aligns with your responsibilities, then you should probably consider the original fence painting task.

I’ve seen assigning homework cut out a huge amount of fence painting work, for me and others I’ve observed doing this. Also, once it’s known that realize you assign homework, people will stop preying on you: “oh, don’t ask Crantouzok to get involved, you’ll just have to make another deck before she lifts a finger!”

Of course, if you’re pure of heart and mind, you can always just be direct and say “that’s low in my priority queue and not really my responsibility.” But, as with all thriving in BigCo tips here, first make sure the BigCo you’re working in is equally pure of heart and mind.

In corporate meetings, oftentimes one person figures out a problem and comes up with a solution. Equally often, multiple people in the meeting like the re-iterate the point in their own words, adding 5–10 minutes more to the meeting.

Once the epiphany and decision is made, everyone should just close the issue, and move on. No need for people to comment on it more.

For example, in one company I worked for we were discussing a software product name. The project had been called “APM.” But it turns out, it wasn’t an APM product, it was just exposing instrumented metrics in the software. This is, in itself, incredibly valuable, but not full blown APM. Someone initially pointed out, “we shouldn’t call that APM,” and everyone agreed.

Then 3 other people chimed in with their retelling of this point, basically embellishing and rephrasing the point. In most corporate meetings, and I’d argue in the never-ending meeting of Slack channels and email, there’s no need for all that extra talk after a realization and decision is made. Someone needs to pipe up and say “what’s the next issue?” or close out the meeting.

A kingmaker in the making.

I’ve talked with an old colleague about pitching a developer-based strategy recently. They’re trying to convince their management chain to pay attention to developers to move their infrastructure sales. There’s a huge amount of “proof” an arguments you can make to do this, but my experience in these kinds of projects has taught me that, eventually, the executive in charge just has to take a leap of faith. There’s no perfect slide that proves developers matter. As with all great strategies, there’s a stack of work, but the final call has to be pure judgement, a leap of faith.

“Why are they using Amazon instead of our multi-billion dollar suite?”

You know the story. Many of the folks in the IT vendor world have had a great, multi-decade run in selling infrastructure (hardware and software). All the sudden (well, starting about ten years ago), this cloud stuff comes along, and then things look weird. Why aren’t they just using our products? To cap it off, you have Apple in mobile just screwing the crap out of the analogous incumbents there.

But, in cloud, if you’re not the leaders, you’re obsessed with appealing to developers and operators. You know you can have a “go up the elevator” sale (sell to executives who mandate the use of technology), but you also see “down the elevator” people helping or hindering here. People complain about that SOAP interface, for some reason they like Docker before it’s even GA’ed, and they keep using these free tools instead of buying yours.

It’s not always the case that appealing to the “coal-facers” (developers and operators) is helpful, but chances are high that if you’re in the infrastructure part of the IT vendor world, you should think about it.

So, you have The Big Meeting. You lay out some charts, probably reference RedMonk here and there. And then the executive(s) still isn’t convinced. “Meh,” as one systems management vendor exec said to me most recently, “everyone knows developers don’t pay for anything.” And then, that’s the end.

There is no smoking gun

If you can’t use Microsoft, IBM, Apple, and open source itself (developers like it not just because it’s free, but because they actually like the tools!) as historic proof, you’re sort of lost. Perhaps someone has worked out a good, management consultant strategy-toned “lessons learned” from those companies, but I’ve never seen it. And believe me, I’ve spent months looking when I was at Dell working on strategy. Stephen O’Grady’s The New Kingmakers is great and has all the material, but it’s not in that much needed management consulting tone/style. (I’m ashamed to admit I haven’t read his most recent book yet, maybe there’s some in there.)

Of course, if Microsoft and Apple don’t work out as examples of “leaders,” don’t even think of deploying all the whacky consumer-space folks out like Twitter and Facebook, or something as detailed as Hudson/Jenkins or Oracle DB/MySQL/MariaDB.

I think SolarWinds might be an interesting example, and if Dell can figure out applying that model to their Software Group, it’d make a good case study. Both of these are not “developer” stories, but “operator” ones; same structural strategy.

Eventually, they just have to “get it”

All of this has lead me to believe that, eventually, the executives have to just take a leap of faith and “get it.” There’s only so much work you can do — slides and meetings — before you’re wasting your time if that epiphany doesn’t happen.

The transformation is complete.

If this is your bag, come check out a panel on the developer relations at the OpenStack Summit on April 28th, in Austin — I’ll be moderating it!

Hey, I’ve not only seen this movie before, I did some script treatments:

Chief Executive Officer John Chambers is aggressively pursuing software takeovers as he seeks to turn a company once known for Internet plumbing products such as routers into the world’s No. 1 information-technology company. … Cisco is primarily targeting developers of security, data-analysis and collaboration tools, as well as cloud-related technology, Chambers said in an interview last month.

Good for them. Cisco has consistently done a good job to fill out its portfolio and is far from the one-trick pony people think it is (last I checked, they do well with converged infrastructure, or integrated systems, or whatever we’re supposed to call it now). They actually have a (clearly from lack of mention in this piece) little known-about software portfolio already.

In case anyone’s interested, here’s some tips:

1.) Don’t buy already successful companies, they’ll soon be old tired companies

Software follows a strange loop. Unlike hardware where (more or less) we keep making the same products better, in software we like to re-write the same old things every five years or so, throwing out any “winners” from the previous regime. Examples here are APM, middleware, analytics, CRM, web browsers…well…every category except maybe Microsoft Office (even that is going bonkers in the email and calendaring space, and you can see Microsoft “re-writing” there as well [at last, thankfully]). You want to buy, likely, mid-stage startups that have proven that their product works and is needed in the market. They’ve found the new job to be done (or the old one and are re-writing the code for it!) and have a solid code-base, go-to-market, and essentially just need access to your massive resources (money, people, access to customers, and time) to grow revenue. Buy new things (which implies you can spot old vs. new things).

2.) Get ready to pay a huge multiple

When you identify a “new thing” you’re going to pay a huge multiple of 5x, 10x, 20x, even more. You’re going to think that’s absurd and that you can find a better deal (TIBCO, Magic, Actuate, etc.). Trust me, in software there are no “good deals” (except once in a lifetime buys like the firesale fro Remedy). You don’t walk into Tiffany’s and think you’re going to get a good deal, you think you’re going to make your spouse happy.

3.) “Drag” and “Synergies” are Christmas ponies

That is, they’re not gonna happen on any scale that helps make the business case, move on. The effort it takes to “integrate” products and, more importantly, strategy and go-to-market, together to enable these dreams of a “portfolio” is massive and often doesn’t pan out. Are the products written in exactly the same programming language, using exactly the same frameworks and runtimes? Unless you’re Microsoft buying a .Net-based company, the answer is usually “hell no!” Any business “synergies” are equally troublesome: unless they already exist (IBM is good at buying small and mid-companies who have proven out synergies by being long-time partners), it’s a long-shot that you’re going to create any synergies. Evaluate software assets on their own, stand-alone, not as fitting into a portfolio. You’ve been warned.

4.) Educate your sales force. No, really. REALLY!

You’re thinking your sales force is going to help you sell these new products. They “go up the elevator” instead of down so will easily move these new SKUs. Yeah, good luck, buddy. Sales people aren’t that quick to learn (not because they’re dumb, at all, but because that’s not what you pay and train them for). You’ll need to spend a lot of time educating them and also your field engineers. Your sales force will be one of your biggest assets (something the acquired company didn’t have) so baby them and treat them well. Train them.

5.) Start working, now, on creating a software culture, not acquiring one

The business and processes (“culture”) of software is very different and particular. Do you have free coffee? Better get it. (And if that seems absurd to you, my point is proven.) Do you get excited about ideas like “fail fast”? Study and understand how software businesses run and what they do to attract and retain talent. We still don’t really understand how it all works after all these years and that’s the point: it’s weird. There are great people (like my friend Israel Gat) who can help you, there’s good philosophy too: go read all of Joel’s early writing of Joel’s as a start, don’t let yourself get too distracted by Paul Graham (his is more about software culture for startups, who you are not — Graham-think is about creating large valuations, _not_ extracting large profits), and just keep learning. I still don’t know how it works or I’d be pointing you to the right URL. Just like with the software itself, we completely forget and re-write the culture of software canon about every five years. Good on us. Andrew has a good check-point from a few years ago that’s worth watching a few times.

6.) Read and understand Escape Velocity

This is the only book I’ve ever read that describes what it’s like to be an “old” technology company and actually has practical advice on how to survive. Understand how the cash-cow cycle works and, more importantly for software, how to get senior leadership to support a cycle/culture of business renewal, not just customer renewal.

7.) There’s more, of course, but that’s a good start

Finally, I spotted a reference to Stall Points in one of Chambers’ talks the other day which is encouraging. Here’s one of the better charts you can print out and put on your wall to look at while you’re taking a pee-break between meetings:

That charts all types of companies. It’s hard to renew yourself, it’s not going to be easy. Good luck!

Figuring out the market for PaaS has always been difficult. At the moment, I tend to estimate it at $20–25bn sometime in the future (5–10 years from now?) based on the model of converting the existing middleware and application development market. Sizing this market has been something of an annual bug-bear for me across my time at Dell doing cloud strategy, at 451 Research covering cloud, and now at Pivotal.

A bias against private PaaS

This number is in contrast to numbers you usually see in the single digit billions from analysts. Most analysts think of PaaS only as public PaaS, tracking just Force.com, Heroku, parts of AWS, Azure, and Google, and bunch of “Other.” This is mostly due, I think, to historical reasons: several years ago “private cloud” was seen as goofy and made-up, and I’ve found that many analysts still view it as such. Thus, their models started off being just public PaaS and have largely remained as so.

I was once a “public cloud bigot” myself, but having worked more closely with large organizations over the past five years, I now see that much of the spending on PaaS is on private PaaS. Indeed, if you look at the history of Pivotal Cloud Foundry, we didn’t start making major money until we gave customers what they wanted to buy: a private PaaS platform. The current product/market fit, then, for PaaS for large organizations seems to be private PaaS

(Of course, I’d suggest a wording change: when you end-up running your own PaaS you actually end-up running your own cloud and, thus, end up with a cloud platform. Also, things are getting even more ambiguous at the infrastructure layer all the time — perhaps “private PaaS” means more “owning” the PaaS layer, regardless of who “owns” the IaaS layer.)

How much do you have budgeted?

With this premise — that people want private PaaS — I then look at existing middleware and application development market-sizes. Recently, I’ve collected some figures for that:

• IDC’s Application Development forecast puts the application development market (which includes ALM tools and platforms) at $24bn in 2015, growing to $30bn in 2019. The commentary notes that the influence of PaaS will drive much growth here.
• Recently from Ovum: “Ovum forecasts the global spend on middleware software is expected to grow at a compound annual growth rate (CAGR) of 8.8 percent between 2014 and 2019, amounting to $US22.8 billion by end of 2019.”
• And there’s my old pull from a Goldman Sachs report that pulled from Gartner, where middleware is $24bn in 2015 (that’s from a Dec 2014 forecast).

When dealing with large numbers like this and so much speculation, I prefer ranges. Thus, the PaaS TAM I tent to use now-a-days is something like “it’s going after a $20–25bn market, you know, over the next 5 to 10 years.” That is, the pot of current money PaaS is looking to convert is somewhere in that range. That’s the amount of money organizations are currently willing to spend on this type of thing (middleware and application development) so it’s a good estimate of how much they’ll spend on a new type of this thing (PaaS) to help solve the same problems.

Things get slightly dicey depending on including databases, ALM tools, and the underlying virtualization and infrastructure software: some PaaSes include some, none, or all of these in their products. Databases are a huge market (~$40bn), as is virtualization (~$4.5bn). The other ancillary buckets are pretty small, relatively. I don’t think “PaaS” eats too much database, but probably some “virtualization.”

So, if you accept that PaaS is both public and private PaaS and that it’s going after the middleware and appdev market, it’s a lot more than a few billion dollars.