Working in IT, I’ve been talking about unstructured data for years.  We know it’s growing faster than data in databases, we know much of it is machine-generated, and we know there are several emerging technologies to help manage it.

But one of my Achilles’ heels at work is having never been on the customer side of the table in enterprise IT.  I’ve been talking with customers for 15+ years about storage and data management, but I have never been the person actually responsible for it.

In the past few weeks, however, I’ve realized that I have a major unstructured data management problem in my own life – and it’s giving me a taste of what IT management struggles with on a massive scale.

Let’s just consider two important types of files in my life: my music, and my photos.  For a few years, I’ve been syncing every song and every photo to the cloud (for music, first iTunes, now I’ve moved to Amazon; for photos, Google).  So I don’t have a storage space problem, and I don’t have a portability problem – everything is accessible from each of my devices.

The music is organized by artist and by album.  And the photos are organized by date (and sometimes by trip).  This works ok when I know what I’m looking for and it’s aligned to these structures.  For example, these types of things are easy to find:

• Pictures from our trip to Prague and Budapest
• The Tori Amos Little Earthquakes album
• The photo I took of Curt Schilling at the Red Sox Parade in 2004
• Let me Clear my Throat by DJ Kool

But there are times I want other kinds of things, and these are nearly impossible to find:

• The best 5 photos of my daughter since she was born
• All the photos of my dog
• 30 songs I like from different artists that I haven’t listened to lately
• A playlist-style playlist of good songs to work out to.

For music, I do have a few other options – I have Amazon Prime, so there are a lot of playlists of music I may or may not otherwise have in my library that i have access to.  So, I recently chose to listen to a playlist called “90’s Alternative Rock” and it was like being transported back to college.  It was exactly what I wanted.  But that was a kind of lucky hit.  And what about something as effective like that, but with my existing library that I have acquired and culled over the years?

I can see why people hone Pandora stations and stop buying individual songs or albums.  But even if that worked for me (and I’m not ready to give up my music library just yet) I can’t do that with my photos.  Google’s been doing a nice job with “highlights” and with making animated GIFs and collages from my photos, but even those aren’t as focused as what I can get from music.

I could tag every photo (and song, I suppose, or at least put songs on playlists) to help with this. But I don’t always know when I take a photo (or tag a photo) the ways in which I might want to look for it.  I could tag all the people in photos, but how would I know that I would have wanted to tag something as “outside” or “old apartment” until I want to retrieve it that way.

I would love any suggestions you readers have about solving either of these problems, but mostly I’m enjoying the parallels between this and enterprise IT.

Last week I was fortunate enough to work remotely – from my parents’ house in Florida, to be

View from my remote office last week – note the reflection of the blinds in the glass – I really was working inside!

exact.  Work is much more palatable with palm trees.

I had a few meetings scheduled back in our Cambridge office during the time I was in Florida, so I did some by phone and some by video chat.  I use Facetime pretty often so my daughter can talk with her grandparents, but it had been a while since I used them for professional meetings.

Here’s what I learned.

1. Video calls have come a looooooong way.  There still may be a little turbulence in logging in and getting set up but they’re nothing like the choppy and garbled experiences I remember.  (We used Google Hangout)

2. I liked video chat far more than I liked voice calls.  One day I had two meetings with the same group of people, and did one in each format.  So much more effective to be “in” the room – I could see responses better, which is the obvious benefit everyone mentions, but I could also better understand when was the socially appropriate time to contribute my thoughts.

3. It’s silly to join a video chat and then not appear via video.

4. There’s no sense in joining a video chat and then making it a screen share so you don’t see any video.  Get the person or team to send you the presentation and then have both windows open (the preso and the live video stream of the room)

I was pleasantly surprised at how effective video calls were – a technology I’ll definitely rely on again in the future.

A few weeks ago I wrote about why I shouldn’t work at a startup – the tl;dr version is that I’m risk-averse, skeptical, and I like firm answers to things.

Of course there are good reasons for me to be here, and one of them crept up last week.

We’ve been having a series of sales and marketing leadership meetings to formulate our FY2015 strategy.  One of the hardest parts of this exercise has been examining our FY2014 activities and analyzing what went right and what went wrong.  Sure, it’s easy to sit through your colleagues’ presentations of their years’ worth of work and critique, but it is not so easy to present one’s own year, and acknowledge the shortcomings.

One of the things that has surfaced is some gaps between functions.  Nothing fatal, but just some places where someone could have noticed that “oops, nobody’s doing that and we should” or “huh, how will this process work?”

And this is where I am valuable – but I can also get myself into trouble.  I immediate look at all those instances and think “should I have been the one to do that?” and “I know how to do that, maybe I was supposed to have thought of that.”

And that, dear reader, can make a person nuts.

So I need to have a gauge, something that helps me calibrate whether that was within my universe or not.  Which is tricky – I never want to have a “that’s not my job” response, but I also don’t want to take on everything (or feel like I’ve failed when I don’t.)

At Dell, it was easier – I would just take a step back to think, “is this something that belongs in classic product marketing?”  and then figure that as an overachiever I would do 20% more.

But this is #startuplife.  It’s not my job to just do 20% more than the “classic” role.  It’s my job to be part of building this company and its story and its processes.  So that calibration is harder. It’s more like “is this something that belongs in classic product marketing?  or does it belong to a function that doesn’t yet exist here?  or am I the best person here to do this right now?”

It makes for a job that right now is pretty big.

When our Keurig coffee maker breaks (which I think will be in the next week) mrDiva and I will probably buy a new one. I know it’s about to break because it’s displaying the same symptoms our previous four Keurigs had before they broke irreparably. Yup, this is going to be our fifth Keurig in ten years. While a few of those were warranty replacements, we paid for most of them.

Why do we keep buying a product that is clearly low quality? It’s not because we think of it as disposable. Actually, when I pay $75-$100 for an appliance, I expect it to last more than 2 years. My parents had a cheap coffeemaker that lasted what seemed like my entire childhood.

So why, oh why, do we keep buying replacements? Because it is otherwise a perfect product for us.  Here’s why:

• It requires zero cleaning.
• It makes one cup of coffee at a time, which means I can have decaf and mrDiva can have regular.
• It requires very little maintenance.

Plus, as another incentive, I have about $100 of k-cups in my pantry right now (some because we’re nuts about trying weird flavors and some because I needed a 5^th Subscribe and Save item a few months ago on Amazon) – this stuff is sticky!

Mark Zuckerberg said, “if you’re building a product that people love, you can make a lot of mistakes,” and I think that’s a great insight. I used to think of it in the context of a startup – as you are finding product/market fit and iterating past your MVP, you can mess up as you learn things.

But this is a more interesting case – I’m totally willing to settle for a product that isn’t meeting one of my basic requirements (coffee uptime!) because it is otherwise so compelling. And the cost of switching (the investment in k-cups and the time to research) just isn’t worth it.

So, here we go again. Another year, another new coffee maker.

At the supermarket I used to go to, there was a sign hanging in the deli area, ostensibly for the benefit of the staff, “Make a raving fan.”  It was a reminder to offer customers (like me) the first slice of meat or cheese so I could be sure it was exactly what I wanted.  I’m not sure I was a “raving fan” of the deli department, but I did like the sample.

This weekend, I had another experience where someone wanted me to be a raving fan: my nail salon.  (Had enough of sports-related business metaphors?  Read on.)

Every other weekend I get my nails done.  It takes about an hour, and I agonize for at least 10 minutes over the color.  Most of the staff is from Vietnam, and their English ranges from passable to conversational.  They’re all very nice.  The owner is extremely friendly, and makes an effort to know every customer by name, which means she keeps hundreds of names in her head – and is almost always right.

This weekend, Kim was doing my nails.  Kim’s English is pretty good, and we chatted about my daughter and her daughter.  When all the filing and cleaning and buffing was done and it was time to put on my chosen color, there was something wrong with the polish.  I don’t know if it had chemically separated or what, but it wasn’t coming out the right color.

Kim immediately sprung into action.  She brought over three different colors and put one on each of three of my fingers, and let me choose what I wanted.  She choose great options and I immediately liked one.  She verified after the second coat that I definitely liked the color.  She told me that it was similar to a color she knows I have chosen in the past.  Then she took the glitter coat I had chosen and applied it more times than is usually done so it really showed up and looked great.

As she was putting on the glitter I thought, “wow, she’s doing this as if it were her own daughter’s nails, or her own nails.  She wants this to come out looking great.”

It was the opposite of the tuna bagel place I used to go to, where I’d look at a sandwich and wonder if the person making it would actually eat it.  It was the opposite of the coffee places I go to where if there is no “medium” size, I’m on my own in ordering a cup.  It was someone wanting to solve my actual problem and provide great service.

As we seek to be customers’ “trusted advisors”, how do we transform that from being a hackneyed, elusive goal to an actual role we can play?  I can remember Dell’s top customers saying that they felt like their sales teams were literally extensions of their own teams – the relationship was so frictionless, and added so much value, that they felt like Dell’s salespeople were members of their team.

This is a hard goal, surely, but one to aspire too.

I’ve been a Car Talk fan for decades.  My parents weren’t big NPR listeners, instead preferring one of the AM talk radio stations, or one of the news stations that had “traffic on the twos.”

However, every Sunday we’d drive to Brooklyn from NJ to see my grandparents, and during that drive, we’d listen to Car Talk.  In fact, when I listen to Car Talk now, I swear I can smell Freshkills Park, at that time a garbage dump.

Ray and Tom, whose voices I still find indistinguishable – well, distinguishable, but not identifiably belonging to one or the other of them – were like an Italian mechanic version of my dad.  They made the same kinds of jokes, laughed at the same kinds of things, and, being roughly his age, made a lot of similar pop culture references.  They also approached problems the same way my dad does.

Reading Tom’s obituaries, I’ve learned how much those guys influenced what public radio is today.  Even Ira Glass, the patron saint of public radio, agrees.  But what strikes me the most about them is how good they are at troubleshooting.

For someone technical, troubleshooting is one of the most important skills to have in your arsenal.  And within troubleshooting, I include things like being sure you know what the problem is, separating confounding variables, getting actual data rather than perceived impressions, and understanding how repeatable problems and solutions are.

Tom and Ray were great at this.  They were great at zooming in on the crux of a problem and quickly figuring out the root cause – or at least forming one or more hypotheses and testing them out.  They’d ask great questions and probe at symptoms and request specific information – exactly how to do problem solving.  They’d also keep each other honest – reminding each other when they were drawing a scientific conclusion and when they weren’t incorporating all the information they had.

They were funny, down-home, as-Boston-as-they-come mechanics, but they were also strong disciples of the scientific method.  (Likely from the many science degrees they held between them, eschewed by their big laughs and thick accents.)

One responsibility I had in my first job was for tech support.  I was pretty good at the methodology of it, but I didn’t have the subject matter expertise to actually draw any conclusions.  So that was the other thing about these guys – they knew everything about cars.

I know that it’s radio, so it’s likely they had some manuals or, later, Google in front of them, but I like to think that they rarely used them.

I had a great week at NetApp Insight with two of my colleagues this week.  We had many, many conversations with interested customers and partners, and spent hours each day telling our story and explaining how Infinio is unique.

Many customers were interested to see a demo – what does it look like to manage the product on a daily basis?  what kind of information about performance can I get from the screens?  I like to demo (partially because our UI is so good – we’ve discussed signage that says “our UI is our booth babe”).

But there is a risk with demoing – once I get into the demo, my ability to have someone’s undivided attention wanes.  People are mesmerized by the screen and often only half-listen to what I am saying.  It’s good because I can understand what their questions are and what they’d like to see, but it becomes a shift in the conversation to a shared screen rather than a shared conversation.

The exception to this is the international community.  There were many people at this show from Asia – China and Korea to be specific – as well as South America.  While their English was far better than my ability to speak any foreign language, it was often not good enough to understand what “distributed deduplicated global content-based server-side cache.”

In these cases, the demo was crucial to selling our value.  Without language and conversation to carry me, the product did a good job of showing what it did.  While it didn’t explain the underlying technologies or the technical differentiation, demoing to an audience who doesn’t speak fluent English gives us a common experience.  It helps fill in some of the words that might not be on the tip of their tongues.  Often I got a lot of questions during the demo once there was something to point at or ask about.  Demoing shows what the solution is – what space it is in, generally what kind of benefits it provides.

It was a great reminder of how universal technology can be – not just a screen, but things like charts and graphs and data visualizations – and how they transcend basic spoken language.

I’m in Vegas this week for NetApp Insight.  It’s been a few years since I was last in Vegas, but there were several years when I was here pretty often, between EMC World, Dell sales kickoff, and before that Interop and Comdex.

Yesterday as I was headed to the convention center, I went down an escalator and was struck by a huge sense of deja vu.  The feeling grew as I walked through the hallway, which had concert posters from the MGM Arena.  Except it wasn’t deja vu – I had been there, on that escalator, headed towards the convention center, a few years ago.

That was at Dell Sales Kickoff, it was the conference when we skipped evening events one night to take in the Cirque Du Soliel Beatles show.  Of course, that wasn’t the first time I had a moment like that – when I got off the plane I had an immediate desire for a hamburger, no doubt a homage to a former boss of mine who always went straight to Fatburger upon arriving in Vegas.  When I saw a taxi line, I remembered meeting Andrea Bocelli in line for a car service once time.  And every time I open a hotel room door I think for a moment of when I was “accidentally” upgraded to a presidential suite at the Bellagio my first time here.

Vegas is funny like this for me; it’s a place that – despite its continuous development – feels the same year after year.  So I can reflect on different points in my career that I’ve been here and what I felt like –

• Excited but nervous going to my first major industry tradeshow and first time at Vegas
• Curious to attend a sales kickoff when the company was redefining strategy
• Shocked culturally to be at a major male-dominated vendor conference
• Nervous to staff a partner’s booth and unsure if I know their technology well enough to be there
• And now, proud to represent Infinio, and interested to learn more about this partner’s community.

Viva Las Vegas.  As for my memories of this trip – what happens here…you know the rest.

That’s a clickbait title, I admit it.  I like working here at Infinio and it definitely feels like I belong.

But I am not a classic entrepreneur; my mind doesn’t work like great startup people’s minds work. Don’t get me wrong, I have some characteristics that are great at a startup – I’m creative, hardworking, willing to jump in to anything, comfortable learning in front of others, and a little bit irreverent.  I’m equally facile in technical and business environments.  Maybe most valuable, I’m invested in working on any interesting problem that comes my way.

I didn’t set out to work at a startup.  Infinio just happened to be the place where I felt the most comfortable.  I liked the people and the culture and the fact it was accessible by public transportation.  I have a background in storage and I wanted to leverage that.  But had I not ended up here, I probably would have ended up at a medium-sized established software company.

There are many, many good reasons I shouldn’t be at a startup: I’m (usually) incredibly risk-averse. My husband is the risk-taker in our family, and he’s already at an early-stage startup.  I value work-life balance or blend or whatever it’s being called these days.  I am trained as a mathematician and an engineer – to learn the rules of a system, exercise them to determine their boundaries, and then work within them.  I don’t like change and I don’t like uncertainty.

I can see these characteristics come out in interactions I have here.  Usually one of the most optimistic people I know, here I’m always thinking, “That won’t work” “We can’t pull that off” “Nobody will buy that from us” “We can’t support something like that.”  It’s unnatural for me to think disruptively.  I’m asking for unrealistic levels of certainty to do “clean” product marketing. I’m looking for a short-term, mid-range, and long-term vision that I can build a marketing story around.  And it just doesn’t work that way.

When I first worked at Dell, I remember being beaten in the field over and over by EqualLogic. Sales management knew that I had worked for a reseller and represented EqualLogic, so they asked me to provide some insight on its Achilles’ heels.  And I had nothing.  Sure, EqualLogic wasn’t a perfect product and there would have been compelling reasons for a customer to choose Dell’s branded EMC gear as an alternative, but I couldn’t help but just say, “It’s a good product, it’s very hard to compete against.”  And that’s not very enterprising, it’s not very entrepreneurial.  But sometimes I can have a pure black-and-white meritocracy view of the world, and that’s hard to shake.

A few weeks ago, I wrote about how I was able to change my Myers Briggs type and I think this is going to be that kind of transition.  The opportunities that will be open to me if I can change my frame of reference in business to a broader one that accepts grey and “maybe” and luck and possibility is large.  Plus, it’s fun.

I thought I’d come and learn “how to do product marketing” but that has been just a small amount of my education here.  Don’t get me wrong – it’s taken a lot of time and I’ve made a ton of mistakes. But more of my energy is spent on “how to think like an entrepreneur” – that things are possible and we can succeed and the market might actually exist.

I am grateful to work with people who think bigger than I do, who make bigger bets more naturally than I do, and who take bigger risks more naturally than I do.

Because I’m learning to do all that, too.