Thoughts on Enterprise Software

The Fall of Work Passion: Job vs. Work

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This is my first opinion piece. Looking for constructive criticism, debates, theories, and the likes to improve. Please be kind ūüôā

I’m fortunate enough to have access to some incredible analysts through my day job at Workfront. We get to share war stories, opinions, ideas, and broader concepts that push our thinking on what we need to do next for our products and how the market views us.

Within these briefings, there are a lot of unique data points shared from various research, surveys, and the like. In a recent briefing we did, there was one particular statistic that resonated with me and is something we’ve been trying hard to figure out how to influence. Ready?

Just 9% of the professional workforce feels like their work matters and that they actually care about what they do.

Another way to say this is that 91% of the workforce really doesn’t care about what they do. They just show up, do their job, collect a paycheck, go to the bars and drink, then wake up and repeat. It’s a depressing cycle that lacks inspiration, passion, craftsmanship, and pride.

Have you experienced it? I’ll be the first to say that I have. Hilariously enough, I felt more pride and satisfaction when I did landscaping or construction. It’s interesting because at the time I felt like I hated what I did. However, I recently stumbled across an amazing and thoughtful piece from a group of folks I follow called Epsilon Theory. The piece was called “In Praise of Work” and calls out something that I had dabbled with mentally but they more aptly described than I could. Highly recommend reading the whole piece.

The most interesting portion of the piece to me was that they claim there is a difference between your job and your work. For them, one of the key differences is that your work is holy. What they mean by holy is that it is a place for refinement, exploration, and ultimately ownership. If you have a hobby that you’ve been cultivating for a long time then you know what it’s like when you “get into the zone” when working on it. It’s a manifestation of holiness that captivates your being. It encapsulates your passion and desires to craft something incredible. That is their argument: your work is holy.

On the other end of the spectrum is your job. Your job is akin to the day-to-day responsibilities and resembles an accounting-like state. You declare how busy you are as a means to accounting and tallying how important you are you are to a company. In their own terminology, they call this the “workism”. Others may call this the “hustle”, “grit”, “grind”, whatever. You see it plastered on Instagram pages to get people motivated about their lives, to follow their dreams and that working your ass off will enable you to get that private jet you’ve so wanted.

Definitions: Your job is the accounting methods you use to report up your importance. We spend most our time doing jobs. Your work is where you leverage your unique skills and craftsmanship to create incredible experience. We spend hardly any time here.

Looking at the former description for jobs, it pushes us down the path of showing our importance so that we get more money or move up in rank. We do that so we can get closer to independence from our job.

What I find funny about all this is that for those that don’t have, they want; for those that have, they seek elsewhere. In a weird but interesting Joe Rogan interview, Dan Bilzerian, who is a wealthy and famous poker player, described why he felt like he (and the rich) need to constantly purchase “things” or create experiences. If I’m paraphrasing correctly, he says that those experiences are generally shallow and don’t provide meaning. In a funny way, it’s a lonely world being at the top because most of what these folks appear to experience is fake. Can you imagine a life where everything you do, your being, your facade, is just so damn fake? You can’t escape it. Maybe most of us are already there with our jobs.

We see this in my job today with the folks that I do user research on. Through deep inquiries, we ultimately find out that most don’t really care about their job but they keep on the act because it’s required by their bosses to move up or make more money. Those are the two primary drivers: breadth of ownership around their job or money. Employees want more ownership because when they are granted ownership, their job becomes more of their work – a passion point. Conversely, employees seek more money in order to become independent from their job so they can focus on their work (ever heard the phrase “when I retire, I will {fill in the blank}?).

What it unfortunately comes down to in modern day work is likely not that the work is boring (this could be a separate topic itself), it’s probably closer to the idea that employees aren’t granted the ability to have more ownership. They have helicopter managers, bad managers who only care about optics, managers who don’t allow for mistakes, managers who yell, managers who care more about the powerpoint than the outcomes. We’ve all experienced this to a large degree in our careers where we had restricted ownership over the entire experience we were working to create. We’ve all tried to take on the broader experience role multiple times only to be told “that’s not your area”. We then try to influence only to find out that the “other side” has as much apathy about their work as a rock does to the wind: zero. This is because they were in your shoes before and experienced the same thing. Ultimately, they were beaten into submission because their managers structured the work in such a way that it hindered experience ownership. For you, you finally get frustrated enough that you start to trend into their camp of apathy because you feel powerless. The cycle continues and we achieve the “9% of workers actually care about their work” statistic.

When you change the employees titles, responsibilities, and areas of ownership to focus on a broader experience, their mentality changes. If you remove the ego from the workplace and create a truly collaborative team setting, that’s when people ditch their job for their work. It’s largely why you tend to find such high functioning startups in the very beginning that end up making it. Sure, there’s managers and a decision hierarchy. But what is ultimately different is that there is a central tenant that is generally around creating the best experience for a customer – and it’s everyones job to achieve that. Everyone is customer support, sales, development, marketing. We all share the same mindset and goal because we have been both enabled to by the company work structure and incentivized to do so. Where it all starts to break down is when you get to that tipping point of size where you feel like you can’t accomplish the experience you want to deliver without restructuring the work – thus starting the decline from work to a job. You get managers with MBAs that have been taught think in a specific way or inside the box with their accounting methods to show leadership they are doing the “right thing”.

But surely there are companies that have succeeded at scale that haven’t transitioned to just having jobs, right? I believe the answer is yes and the one that I keep hearing as the closest to being work is Hubspot. I’ll also caveat this in that this is just my limited exposure to a variety of companies. Hubspot touts a leadership and management model that they call Servant Leadership. And it operates exactly as you would expect. The management in the company hires the brightest minds they can convince to work for them and compensates them as such.

From there, they GTFO of their way.

With servant leadership, your job as a leader is to help align the teams under a central tenant or goal and then allow them to craft their work in the way that they see best fit to achieving those goals. As a manger, you serve them in the capacity of helping them avoid the pitfalls, stay on target with their goals, unblock them, and ultimately coach them to the point where they are so good that they could go get a job anywhere. Except that they don’t, because everywhere else is a job and what they have right now is their work. They and their team members are enabled to own the experience. They get excited because when they succeed, it’s truly because they did it. When they fail, the feel like they have the ownership to make the right changes to influence a better outcome.

To my knowledge and my networks knowledge, Hubspot lives by these principles and it has served them well. It generates outside of the box thinking where they say how can we and what if instead of we can’t because.

Making work matter can’t come from the company you work at if the employees aren’t empowered to have ownership.

Even further down the rabbit hole is something much more challenging which companies struggle with on a damn near definitive basis: a vision that stands the test of time. Most companies have poor leadership vision that lacks something worth working for but definitely warrants something to do a job for. These companies ultimately attempt to counteract their lack of vision through bullshit benefits and culture fluff, such as beer on tap, ping pong tables, free food, and the likes. These are great recruiting techniques but dramatically fall short once the new employees see past the facade and experience the true colors of the company. It’s in large part why newer generations of workers (eg. millennials) jump ship every couple years for a different job: they’re searching for purpose in their work. They would rather hope that the grass is greener on the other side than sit and watch their current pasture turn all sorts of weird colors – but none ultimately becoming green.

Now, I understand the previous paragraph is a bit of a blanket statement but my intention is to convey a general sentiment of the newer workforce.

I’ve had many discussions with my colleagues about what it actually means to change the way humans work, how we can enable digital disruption for enterprises, and what it would take to change that 9% statistic to maybe even 25%. We’ve come to the conclusion that we cannot realistically change that number with a tool, product, or platform but can only create proxy measurements to something relative to “employee engagement”. By showing the number, we hope that we can raise the alarm of lack of employee engagement but at the end of the day, we’ve come to the conclusion that there are really two fundamental issues contributing to the lack of happiness in the workforce: colleges and managers. Funny enough, we think they’re intertwined.

It’s no secret that I’m not a fan of colleges. In my opinion, they are a glorified place to get a stamp on your education passport but rarely provide any value within the first 4 years for most schools. The general elections and rotational classes degrade critical thinking to general platitudes that don’t reward separation of thoughts and discussion. It’s an accounting system to see whether you can do “jobs” and “activities” as opposed to thinking about creating better outcomes. I’ll end my rant there…

What colleges don’t prepare managers for is actually managing work and people. They don’t teach leadership at an effective level and, from general polling, the folks with the strongest or most confident personalities tend to become managers (which isn’t always a good thing). If we distill it down, business schools at universities teach compliance to archaic operating models. What’s worse is that we graduate these bright and ambition minds with the false assumption that their degrees will help them stand out and, worse, that they actually learned something of significance that makes them valuable in the field. The harsh reality is that they are not adequately trained to do work – let alone jobs. They get hired with bright, starry-eyed mindsets only to be beaten down by the management at large to just “do their jobs” and fall in line because the presumption is that they haven’t had enough experience to jsutify having a balanced opinion. Straddled with an insane amount of debt, these students generally do one of two things: they decide to get more “educated” and get a masters or MBA only to accrue more debt or they are beaten to submission and stay in the same type of role for years to come.

The false assumption coming out of MBA schools is that these individuals can lead a team. Now, while there are some that are stellar at this, I would posit that this is likely more of a personality trait in which the MBA provides targeted focus for those personalities. What I think most MBAs ultimately receive is a framework for thinking inside the box in fairly safe ways that ultimately don’t lead to a vision people are willing to follow which, in turn, means their employees experience a lack of leadership. New employees coming under these new MBA wing end up experiencing a manager rather than a leader in which we’ve come full circle to – yep, you guessed it – employees work turning into a job. A series of accounting and metrics displayed in powerpoint to appease the “management gods” that they are super busy and so very important.

What can we do? It all sounds so pessimistic, complicated, deep-rooted, and difficult to change. And I think that sentiment is right to have! We have a workforce that is straddled with a significant amount of student debt with jobs that they hate in a world that peppers us constantly with a juxtaposition of depressing news with rich aspirational if you hustle hard enough you can be like me Tweets. I believe the answer has a couple of different paths but I’ll lay out what I think is most apt and relevant.

  1. We need to teach, at a very young age, how to be physically social and how to be better storytellers which will start creating better leaders.
  2. We need to encourage the mindset that, in fact, most people should not go to traditional universities and rather opt for vocational schools with deep apprenticeships for craftsmanship.
  3. We need to change the manager mindset that your employees are to do specific tasks for you and that they need to own broader experiences.
  4. We need to stop glorifying the hustle and job-porn social posts and start valuing the work we do.

There’s obviously a lot of unpacking with each of the prior statements which I won’t divulge here. However, each of the statements reflect on where I think we’ve gone wrong and what world we live in today.

We’ve been falsely led into a fabricated sandbox where the puppet masters, perhaps with good intentions, have laid out parameters for the actors in which these parameters are touted as if they are the only way to succeed. In life, there are no guarantees and no one way to succeed. I firmly believe we can achieve a better balance between doing our jobs and doing our work. I believe that some of the jobs we do have importance and that we shouldn’t just throw them away. However, when we glorify our jobs as the only way to move up, succeed, get a raise, or whatever else we need to feel justified in the workplace, I believe that is when we get into (and have been) trouble.

It’s an interesting time to be entering the workplace. I don’t want to discourage newcomers to the world but want to paint a picture of what they may experience and what sort of changes could be made to counteract the pain. I’ll be the first to say that I don’t think I’m 100% right on some of the above. There’s conjectures, some data, theories, and personal experiences across the many enterprises and customers that I’ve worked with. That isn’t to say this is the gospel truth but rather a passage within the truth that we can beat up. I hope we can change the narrative as described in Epsilon Theory’s post to transform our world from a gluttonous job and workism era to one that holds work and experiences into a higher order.

The Balance Between Quality & Speed in Product Development

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I’m going to make some controversial statements in this post regarding product management. If you’re currently a product manager, I’m sure you’ve been peppered with the “do this! don’t do this! you’re a bad PM if you do this! 10x PM’s do this!” rhetoric. Honesty, it’s exhausting. Earlier in my career, I read a ton of books on how to be an effective product manager. What stuck out to me is that these books often pushed opposite agendas – sometimes even within the same book.

Having gone through some of my product management career thus far, I’ve realized that there is no silver bullet to doing a good job. In fact, it largely depends on where you’re at in the lifecycle of your company, the industry, the team you’re working on, etc. These books often write about a set of criteria PM’s must meet. They pain the picture of a panacea outcome if you do these 10 things. That’s never the case.

What I learned early on (and quickly) is that there is a very hard balance between delivering high quality products and delivering them in a very rapid format. These aren’t mutually exclusive but they are very hard to balance. Sometimes they shouldn’t be.

For example, let’s say you’re losing a ton of business by lacking a major feature set. The company has put it off for too long and it’s now a top priority in order to help sales to stop losing in competitive deals. To create a feature parity product would take you a minimum of 9 months. Looking backwards, you know that you’ve lost $900k in the last 9 months to competitors because you lack this feature, so it’s safe to assume that over the course of this entire development of 18 months, you’ll lose $1.8M.

Do you build as fast as possible and ship something “good enough”? Do you go for a high quality product and release later?

Personally, I’d opt to release something that is barely good enough. Something that is almost embarrassing but paints the vision, dream, and demonstrates that we can accomplish the basics of what our competitor can do, refocusing the sale back onto features that you crush competitors on.

On the other hand, let’s say that you’re trying to leap frog the competition. Time is on your side and the feature you’re developing is very complex with a high barrier to entry from a user experience perspective. You know that if you ship early, its going to have little to no adoption which will make iterative testing and development challenging since you could be stuck building in the dark.

Do you build as fast as possible and ship something “good enough”? Do you go for a high quality product and release later?

In this scenario, I’d say build a high quality product with lots of UX/UI iterative testing, prototypes, etc. before you commit to engineering on it. This is going to take a lot longer but you know that by doing this, it’s going to make the adoption a bit easier. Plus, you’re confident you have time on your side since you’re blazing a new path through a different aspect of the market.

My opinion is this: product management is a case by case job description. There is no silver bullet method to building great products because every company is in a different place. A super fast, agile, and “release often” approach may not be appropriate for monolithic, highly audited and complex industries. A PM must understand the vertical and adjust their style to match the most effective form of delivering product in that organization.

This isn’t to say that the paradigm can’t change over time. Often times, it’s the product department helping create ways to be more efficient and deliver products in different ways. However, these things don’t happen over night and require a flexible product management style.

As the title of this post suggests, it’s a constant battle between delivering very high quality products and delivering products very fast to the market. They’re not mutually exclusive by any means, but rarely (in the real world) is the environment setup to enable both to happen.

New York, Paris, London – A Software Development Dilemma

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New York is a well thought out, grid based, highly planned city from the ground up from the beginning.

Paris is a complex city with many organic roads that were built long ago but during the Napoleon era, a few large boulevards were built in order to increase the efficiency and connectedness of the city. A hybrid of planning and organic growth.

London is an organically developed city with curving roads, complex subway systems, and tons of legacy but is still a highly functional city.

In all three scenarios, each city is massive, efficient, has high production, and gets the job done. They were all planned in different ways but achieved the same outcome. New York wanted to be very structured, Paris wanted a hybrid, London opted for an organic route. No one city has it right and each have their own charms, cultures, efficiencies, and issues.

In enterprise software development, we have very similar issues. Enterprise software is uniquely hard to make sweeping changes due to scale, complexity, impact, and cost. In certain cases, adding just a single dimensions to a database can mean hundreds of thousands, possibly millions, of extra dollars accrued in storage costs due to operation scale – not to mention performance impact of query times. When a new product or feature needs to be introduced that has sweeping impact and ramifications for the rest of the organization, it’s often a good idea to take a step back to think about New York, Paris, and London.

Strategically, do you think it makes sense to rewrite 1/4 of the platform? Is there a work around? Should we just build something entirely new from scratch then migrate? Is there a middle ground where we can build a connection? Is that a long term solution or just a bandaid that will hurt us later? These are all questions that go back to the same macro level issues of city planning.

I think most companies start out with a basic plan but rapidly move into an organic model – much like London. The development goes in different directions, workarounds are instituted, compromises are made, it becomes more costly to engineer, but it still works. At some point, this scale can break down in which organizations move to the Paris model.

Moving to the Paris model means creating large boulevards that allow for certain efficiencies while allowing autonomy for organic growth to fit into those boulevards. Sometimes we even dig tunnels to find ways around the boulevards and organic streets, but at the end of the day we still provide connections to the main boulevards.

Then, at some point, the intersection of feature needs and tech debt forces organizations to consider building New York – a new paradigm that offers a foreseeable scalable solution and is well planned from the ground up. We build a basic version of New York and then start to port over all of the features. New York works for a while until we start to see flaws, in which we move back towards feature developments that model London and Paris: organic development.

Repeat a few times and you’ve got software development for the enterprises.

This isn’t necessarily a bad thing at all. Much of the worlds greatest software follows each of these patterns and have proven that no single model is “the best”. What has become very apparent to me is that it’s important to know¬†which model you’re building after. It’s critically important because it highlights specific choices and sacrifices you’re willing to make.

Put simply: be¬†aware of which what you’re doing.

Where I’ve seen these models fail the most is when organizations are not aware of the type of city they’re trying to build, making compromises or features that back them into incredibly costly situations. Now, this isn’t to say that you need to consider this for every feature. I personally think it pertains largely to more macro/strategic development (ie. user permissions, data portability, etc.).

Obviously we will make mistakes and sometimes choose to bulldoze the wrong areas in way of building our boulevards, but the hope is that by being more conscious about these decisions it will help shed light on the long term impacts and make decision making easier.