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A step-by-step guide to becoming a better engineering manager

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The typical job description for many engineering manager roles is action-packed. It is a mix of hands-on coding, technical leadership and decision making, process and project management, product oversight, people management, finding and hiring talent… the list goes on.

In our work, we deal with both technical and people systems: we support individual engineers’ growth; help teams become successful; and make the organization more productive, functional, and innovative. Above all, an engineering manager is a service or support role across these various layers.

Perhaps most fascinating and difficult is the high-level of ambiguity that comes with engineering management. Many problems or questions don’t have straightforward answers. There aren’t absolute answers to what it means to be a good engineering manager either, but there are certain values and guideposts to follow.

In this post, I look at what can shape our thinking about our role as engineering managers and how to effectively support individual engineers, teams, and organizations.

What do engineers need to thrive at work?

It helps to start shaping engineering management roles by understanding what engineers need, and the environment in which they thrive. Research from performance coach and trainer Paloma Medina exposes six core needs humans have (including at work). She calls this research the BICEPS model:

  • Belonging. As humans, we strive to be part of a community of like-minded people where we understand and support each other. We also want to feel as if we are not being discriminated against or marginalized. Belonging is really important to me personally: I love working as part of a distributed team, but I also really enjoy seeing people in person every once in a while. It makes me feel more connected to them.
  • Improvement. We also seek to continuously learn, improve, and grow in areas that matter to us, as well as to our team or company.
  • Choice. We want to have choice, control, and autonomy over important parts of our lives. In one of my previous roles, I took on a lot of work to drive organizational change. But ultimately, the control I had over my domain was limited due to organizational issues – which led me to leave the company.
  • Equality. We want to know that our access to information, money, time, and other resources is fair and equal for everyone – not just for ourselves, but also for the people around us. Everyone’s needs should be treated as equally important.
  • Predictability. We look for certainty, safety, and stability in our lives. We also want goals, strategy, and direction to be consistent – and to not change too quickly. I’ve been leading teams in fast-growing startups for the last couple of years, and when there’s a lot of change happening, it’s a challenge to instill predictability in teams.
  • Significance. Deep down, all of us seek meaning, importance, and status. We also want to be appreciated for our work by people whose opinions mean something to us.

If our core needs are threatened, people resort to fight-or-flight modes of reaction, which are very stressful. The failure to meet core needs has high costs for organizations by harming people on our teams. So how can engineering managers put the BICEPS model into action to help their teams thrive?

Using trust-based relationships to help engineers grow

The foundation of being a good engineering manager is getting to know our teammates and understanding what is important to them. Here are a few places to start building trust within your team.

1. Ask questions

One of the most powerful tools managers have is asking good questions. The basis for doing our jobs well is listening, observing, taking note of what motivates our teammates, and really digging into their responses to our questions. I usually gather questions before I meet with my teammates one-on-one, so I am prepared and I can guide the conversation towards understanding them better.

Over time, I have built a kit of one-on-one questions that I pull out when I need some inspiration for these conversations. Asking questions helps us adjust our leadership style to the people we are leading. It also ensures that they feel understood and heard, which are really important pillars of inclusion and belonging.

2. Be curious

People are full of surprises, and sometimes our teammates’ reactions may be completely different from what we expected. I once received a message from an engineer on my team who was deeply upset about the specific wording used in a product-release note to customers.

At first I did not understand their strong reaction. But when we talked, I learned the engineer had been overruled by someone with more power, making them feel helpless, and threatening their core need for choice and equality.

What managers might perceive as no big deal can be enormous threats to other people. Cases where we’re surprised by our teammates’ reactions are good opportunities to focus on human-centric responses, like giving people the opportunity to talk through their feelings.

3. Connect to the bigger picture

Creating an impact is a very good motivator for all of us, so helping engineers understand how their work connects to the bigger picture (how it helps users or supports other teams) is an extremely important and strategic skill for managers.

While goal-setting frameworks like OKRs can help, it is also crucial to align engineering initiatives with higher-level goals, and connect them clearly with user value.

4. Involve engineers in decision making

Feeling that decisions are fair and equitable is an important component of the BICEPS model. When we make decisions, it is helpful to ask everyone for their opinions first, and take their opinions into account.

It is not always possible to go with what everyone wants. But we can still do a good job at contextualizing the decisions we make, and helping people understand that their feedback was considered.

5. Give feedback for growth

One of the best things we get to do as engineering managers is support engineers’ growth. Give feedback regularly to help the people on your team understand where they are at and grow – by course-correcting where needed, as well as by doing more in the areas in which they are already doing great. Managers need feedback as well: it’s important to regularly ask your team for feedback so you can make adjustments.

6. Coach engineers

Coaching helps people find answers themselves, improves their problem-solving and leadership skills, and increases learning, resilience, and self-management.

7. Sponsor engineers

Think back on your career, and whether you have had a mentor who connected you with someone, put your name forward, and used their influence to make a difference in your career. Be that person for someone else: invest in their growth, lift them up, and put your weight behind their success. Supporting your team’s success can make a real difference for them.

This is the foundation of our work as engineering managers.

Driving a culture of trust and continuous improvement on teams

The next important building block in our work as engineering managers is the team. According to research, high-performing teams need the following elements.

  • Psychological safety. This is about believing that we will not be rejected, and feeling free to express our work-related thoughts and feelings to the people around us. It also means believing that others won’t think less of us if we make a well-intentioned mistake or ask for help.
  • Structure and clarity. Everyone on the team should understand expectations, goals, and accountability.
  • Meaning and impact. High-performing teams find a sense of purpose in their work, and know that their work has an impact.

Luckily for managers, this research neatly aligns with the BICEPS model. All human core needs are represented and have impact at the team level as well. By understanding and responding to people’s motivations, leaders create the basis for teams to express themselves – and provide the structure, meaning, and impact they need.

1. Build trust

The first step in creating structure is building relationships. For our distributed teams at CircleCI, we’ve built different structures to help teammates do that, such as regular pair programming rotations and engineering talks.

2. Structure around how we collaborate

Our engineering department has doubled in size for three years in a row. Over this time, we’ve moved to a more streamlined engineering delivery process for all teams. But we still leave it to the teams to decide how to implement t day-to-day processes, including daily standup meetings, planning sessions, or collaboration. Every team has specific needs, and they know best how to address them.

3. Remove blockers

Structures can also help mitigate the impact of getting blocked at work. We all know how frustrating it is to be stuck. Putting up pathways to help people get unblocked can be really important – for example, setting up regular pair programming rotations, investing in self-serve information access, supporting each other across teams, putting up escalation paths for people to get help when they need it, or helping people support each other through knowledge-sharing.

4. Continuously improve

We can use retrospectives to discuss and improve how we work together. Blameless postmortems are also a great tool to help understand problems and drive towards solutions. Code reviews, mentoring, or knowledge sharing can help team members learn from each other.

The way we talk about learning matters – especially the way we discuss mistakes. These decisions will fundamentally shape the culture of our teams, and determine whether people feel safe or threatened in their core needs.

5. Drive toward alignment

Communicate strategy, direction, and relevant tactical details to your teams – and remember it’s almost impossible to over-communicate these details. Always repeat what’s important.

As engineering managers, we are like mortar: we connect structures, teams, and people. We hold them together, but also identify and fill gaps as needed. Handling ambiguity is one of the most important and difficult aspects of engineering management. For a lot of work in our field, there are no straightforward answers, let alone resolutions.

Our work isn’t so much about us; it’s about the people, teams, and organizations we support. We build structures to help others shine.

Supporting organizational change

Lastly, creating environments in which engineers can thrive is about supporting our organization. We need to use our power as managers to drive organizational change, no matter the size of our businesses.

1. Advocate for change

To be effective as managers, we need to push for organizational change to improve the larger structures around us. For example, we may need to advocate for more clarity around engineering manager roles, have conversations about what engineering management should be like in our company, and determine requirements for hiring engineering managers.

2. Manage up

Managing our own managers is a useful but difficult skill. Driving organizational change also means making sure that our engineers’ concerns are heard at the highest levels, and that we use our power to make sure engineers have a voice in the rest of the organization.

3. Build frameworks and standards

While it is always important to make room for individual needs, structures and frameworks for managers help us hold each other accountable. They also help level the playing field and build in equality for the people on our teams.

On my current team, every quarter we pick some high-priority projects to improve how we work as an organization. Most recently, we’ve worked on our hiring process and incident remediation; last year, we developed an internal career growth framework for engineers.

Growing as a leader

Being a good engineering manager isn’t always a straightforward path; a lot depends on where we are at in our careers and where we are looking to go, as well as the growth stage, size, and needs of our organizations. In our daily work, we hold vast amounts of uncertainty while also trying to make progress.

An overarching theme in my work in engineering management has been growth and improvement. We rarely deal with greenfield projects or are able to build a team or department from scratch. Even when we do, we build on existing structures in our organization. I believe our supporting role largely means helping engineers grow, supporting teams at continuously learning, and helping organizations become better.

As engineering managers, we frequently face questions that don’t clear right or wrong answers. Many years ago, my leadership coach encouraged me to use those kinds of uncertain situations to ask myself, “What kind of leader do I want to be?”

I want to leave the last call to growth and improvement with you (and me): no matter what your role or company is like, work on shaping your approach to engineering management. Get to know the people that you work with, and use feedback to help them course-correct. Build teams that are psychologically safe places, where people find meaning in a shared purpose. 

And use your power and privilege to drive change in your organization. Make people the center and focus of your work, and build on that foundation to create an environment in which they can thrive. Always push to continuously improve. Lead with humbleness, empathy, and lots of curiosity.

Published June 5, 2020 — 06:30 UTC

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Securing €3M investment and thriving during a pandemic — here’s how we did it

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Like many other companies, with the onset of the pandemic, Growth Tribe faced the sudden challenge to either innovate or become irrelevant. This is the story about how we not only survived, but were able to develop a new business model and secure €3 million in funding.

I hope that, by sharing our learnings, we can help other companies facing a similar situation to weather the storm and come out stronger.

Around February 2020 we saw our revenue going down. People started to postpone their courses because they weren’t sure if they’d be allowed to fly anymore or be in a classroom together. It was clear pretty early on that social distancing was going to be a big problem for us because 95% of our learning journeys were based on in-person training. 

On top of that, we had been in the process of closing a significant funding round. The final checks were being made when rumblings of COVID-19 potentially coming to Europe started coming in. 

About 80% of funding rounds were being canceled at the time and we thought to ourselves, “Are we going to be in that 80% or 20%?”

At the same time a key senior employee decided to leave the company. 

That was really when I felt we had hit our low point.

Antifragility 

Every day we had new curveballs coming at us. “What if we don’t get the investment? Can we keep growing? What kind of government support will there be? Do we even get government support? What’s going to happen to everyone at Growth Tribe?”

In hard times, I firmly believe you need to make sure your team stays together. There are two books by Nassim Nicholas Taleb which I find really describe what we’re living through now:

The Black Swan: The Impact of the Highly Improbable which says that if you can’t predict the future, the crisis will always come from an unexpected event. And the second book is Antifragile: Things that Gain from Disorder about how only companies that are adaptable to rapid change will survive and thrive in uncertainty. 

And that’s what we did. 

Crisis management time 

During a crisis, one of the first steps companies take is to make cuts, but startups rarely cut their way to success. They need to grow, especially early stage startups.

So we decided to take a more opportunistic-optimistic view of the situation and start experimenting with product iterations to identify and double down on big bets. 

We got our directors team of six to seven people together and built a war room to tackle the question: how can we embrace this next crisis as an opportunity rather than a threat? We came up with a list of 25 ideas and ranked them based on: 

  • The likeliness of it working
  • Ease of execution
  • How big of an impact it would have

Luckily we had already begun creating a digital hybrid of our classes before the crisis to give us more flexibility. Having all our trainers centralized in Amsterdam meant they were flying abroad to different locations for trainings. But this limited us and wasn’t sustainable from an environmental perspective. 

When some of our classes across Asia started being canceled, we decided to accelerate our transition. What was supposed to happen over 12 months happened in 12 days.

I find it interesting that most corporations are killing innovation and training budgets at the moment, because that’s actually what they need most right now. If you look at some of the articles coming from publications like McKinsey and HBR, they’re all saying now is the time to experiment as fast as possible and spend more money on innovation projects. 

Getting clients onboard 

To make this work, we would have to show our audience something different. We would have to make it really hands on, practical, and interactive.

We quickly began experimenting both online and offline. Here I really saw the power, speed, and brainpower of everyone at Growth Tribe. The team’s reaction was impressive. We ran online smoke tests and high hurdle tests for our bootcamp courses. 

For the corporate side, we had discussions with every single one of our corporate clients until we had some sort of letter of intent or quote saying there was buy-in from them to move their learning experiences online. The company became an experiment laboratory. 

That took a lot of work. We’re talking: creating marketing collateral, building videos to show what the learning experience would look like, building up the online learning experience, etc. But this gave us the evidence we needed to go forward with this strategy, whether we got the investment or not. 

We started creating studios and, in two weeks, we flipped the whole company. So when social distancing measures were announced in Europe, we had all our courses online already. 

Since the pandemic started, we’ve trained over 500 students. 

Getting investors onboard

When we came back to the investors we were prepared. 

We showed them external reports, data, and graphs. But we were also able to reassure them by showing hard proof of what we had achieved in those two weeks. We had already gotten traction by selling online courses and producing letters of intent. We had already made sure that operations, HR, and our marketing materials were all aligned. 

We also showed them pictures of our new creative studio. And, most importantly, we showed student feedback proving we’d been able to create the same amazing learning experience.

Ultimately, what we were able to show them was that this was actually a great opportunity and we were prepared to seize it by pivoting and adapting rapidly. 

3 tips for surviving and thriving in an uncertain future 

It’s really difficult to predict what will come in the future. Will the spike go up again? Will new social distancing measures be put in place? You don’t know what will happen with the economy yet, so making big plans for the future is difficult. 

The first thing I’d suggest is to stay close to your customers. Before the government lockdown, a lot of companies already started imposing travel bans, which is what first alerted us. In a crisis, even if you’re not selling to them, just talk to your customers about what’s going to happen and how things are moving. 

Second, experiment as fast as possible and trust your teams. We’re constantly experimenting with new products, new delivery channels, and new markets. We’re living in a new reality and when you don’t know what’s coming, the best thing to do is test, try and learn. 

So make sure your team has the tools and knowledge they need to run effective experiments. And trust them. The team was 95% of the reason for our rapid pivot.

Third, spend more time re-skilling your people because the market is going to be different and it’s going to change way faster now. The rise and fall of new technology and changing market conditions will also cause a rapid change in the skills that will be needed. 

Digital transformation is not about technology, it’s about talent. Prepare your company for what could come by preparing your team with the knowledge they need. 

Published July 10, 2020 — 08:00 UTC

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How today’s best business software goes viral

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Capiche is a secret society for SaaS power users, building a new community of people who care about software to make the SaaS industry more transparent, together. This piece was written by Matthew Guay, Capiche‘s founding editor and former senior writer at Zapier.

When Jiro dreams of sushi, you’d hardly imagine him slicing sashimi with an ordinary, dull knife. Nor would you expect Usain Bolt to cross the finish line in shoes you could pick up at an outlet, the London Symphony Orchestra to grab the cheapest violins at the local music store, or Ford to take on Ferrari and win the Le Mans with any random car.

Experts use expert tools. Rigorously tested, finely tuned, carefully built to perform at the highest levels. They’re crafted, built for the most demanding audiences.

Then those best features trickle down, until yesterday’s best is today’s ordinary. In humanity’s pursuit of the best, we build better things, then mass-market them to fund the next best thing.

Along the way, the best, ideal versions of those tools become icons, symbols of victory. You might not need the absolute best shoe, the fastest car, the sharpest knife for your work. But wouldn’t you like the perfection they represent to rub off on your work? And so the best tools become status symbols. The watch that ticked on the moon makes you think you, too, could shoot for the moon, that you’re someone who needs the most exacting tools.

Now it’s happened to software.

Software was the great equalizer. “All the Cokes are the same and all the Cokes are good,” said Andy Warhol, and the same went for software. Gmail works the same on a $200 Chromebook or $2000 MacBook. Excel can track a $1,000 budget or a $100 million portfolio equally well.

But what if software could be better, crafted specifically for the professionals who need it most? How much would the people who email the most benefit from an email app that made them 10% faster? What would investors pay for a chat app specifically for finance? How many researchers would rebuild their libraries in a better notes app?

Thus positional software, an emerging category of software built for expert users with a focus on design and collaboration, adopted bottom-up in organizations, and often priced at a premium compared to existing category leaders. Similar to positional goods, highly valued items that showcase status, positional software are tools people aspire to use, either as experts in their industry or to position themselves as such.

The editor wars

The first best software was built by programmers, for programmers.

One team at MIT wanted a better text editor, and built Emacs. Another at Berkley wanted the same thing, and built Vi. The former was so customizable, it could be anything: An IDE, an email app, even your psychiatrist. The latter was so simple, it looked like nothing at first, with arcane commands required just to edit text.

Yet there was magic in both approaches. Each text editor was powerful enough to give developers superpowers, customizable enough to keep them from reinventing the wheel again, opinionated enough to build a following.

To this day, preferring Vim or Emacs labels you, puts you in a certain class of developers who are picky about their tools, willing to invest time in learning obscure features, and far less willing to consider switching to other tools.

They’re positional software.

The best software for each job

As software ate the world, developers weren’t the only ones demanding the best in software. When everyone’s work is done through software, everyone could use better tools to work at peak performance.

There have always been better tools, software that hit a higher bar. Niche software, things others in the same role and industry might know and tell each other about, but that would be hidden from the wider public. In the grand tradition of Vim and Emacs, they were often cryptic tools with steep learning curves, tools that made sense to invest time to learn if you used them all day, but that wasn’t worth the effort otherwise. Only those who truly need them would aspire to use them.

Then something switched. The best software became the most popular, aspirational tools that people built their identity around and wanted to use. What cooking shows and documentaries did for knives and premium ingredients happened to software.

Today’s Positional Software required a few ingredients of their own to happen:

Used in public

Email software was perhaps the first mass-market tool where you could earn credibility based on the software you used.

Hotmail got the idea right first. Offer free email when few others did, and add a signature to the bottom of every email that suggested you, too, could get free email. That made it one of the first viral software, a trick both the iPhone and Superhuman copied with an email signature that told recipients what sent your message.

Public use is what made software convey mass-market status. You neither gained nor lost credibility by, say, checking email on Outlook Express or Emails or Apple Mail; few knew the difference. Your email address’ domain, on the other hand, announced your software choice to the world, drew a line in the sand, gave you a digital identity.

Positional software uses Hotmail’s trick, letting the world know you use something different, something better. Superhuman indicates it with an email signature; Hey forces you to get a new email address to make sure no one misses it. Figma’s share links, Notion’s public pages, Typeform’s embeds, and Slack’s invites do the same—everyone you work with sees the software you use, and has to use it, too, if they want to collaborate. The Bloomberg terminal was an early example: If you wanted to chat with other traders, you needed Bloomberg. Even less visible software—modern equivalents of Vim and Emacs—can be used in public if you let the world know on social media, something most common with the most opinionated software.

The halo can wear off. You switched to Hotmail to save money, not specifically for a better tool, so with time a Hotmail, Yahoo, Aol, or Juno email address signified you were behind the curve. A Hey email address, today, might say you’re ahead. It’s a delicate balance, one exclusivity helps extend into a moat.

Exclusive

Free email is enticing. Free email only few can get, even more.

Gmail’s launch on April Fools’ Day, 2004, with a better web app and far more storage—leaps over the two things that set Hotmail apart in the first place. Gmail added something to the equation that made it even more desirable: Invitations. Only a thousand people could get in at first, and those could each invite a few friends. That let Google scale the service up over time, and gave a free Gmail account the cachet of an expensive luxury good, enough that people sold Gmail invites on eBay for over $150.

Invite-only bought Google time to perfect Gmail, a trick Google extended by keeping Gmail in beta for the first 5 years it was available. But the real success was in the viral word-of-mouth as everyone wanted an invite to use Google’s latest software.

Exclusivity speeds up the process of waiting for influential users to promote the product. Imagine Gmail without an invite system; some might mention using it, far more would use it without talking about it. The invite system made it exciting when you get to start using Gmail, making you more likely to talk about it—and for your colleagues and friends to ask you for an invite.

Add social media to the mix, and exclusive, invite-only software can quickly make a new product seem far more desirable. You just need to get people influential in the niche your software targets to use the software in public, sharing what they like about it, and the invite requests will start to come in.

Invite-only on its own isn’t enough; the initial buzz around Google’s later launch of Google Wave didn’t keep that product afloat. But it does add allure to software. Today, invite-only is a key launch strategy for everything from Superhuman (still invite-only) to Clubhouse (with an even more locked down invite system), Hey (invite-only for the first couple weeks) to Linear (invite-only while in beta).

Invite-only starts the sharing process. The real work-in-public, though, comes from collaborative software.

Built for you, then your team

The best software in the world doesn’t help if you can’t use it.

When IT teams mandated what software you could use, there was no reason to seek out better tools. Better to invest in getting the most out of the software they authorized.

Then two major things changed. Companies started switching to bring-your-own-device policies, giving you more freedom over the computer and thus software you use, making bring-your-own-software possible. Then, web apps freed software from IT constraints, making new software only a new tab away.

You didn’t have to use older desktop software. You could use the new best-in-breed software in your browser.

These web apps weren’t just utilities you’d use on your own. Increasingly, modern software was built to work together with a team. Perhaps you’d try Slack during a hackathon or with a group of people from your industry. You’d enjoy it, think your team would like it too, and so would go to slack.com and make a new team, and invite your colleagues. The exclusivity appeal would take over again, as others in your company would want into the cool new app, and before you knew it, Slack had swept through your company.

Google Docs didn’t need everyone to switch. It just needed influential writers in your team to start using it for collaborative edits, then to share the document links, and it’d grow from there. Airtable did the same to databases, Figma to design tools, Notion to notes. They were enough better to make the most choosy users switch, got them to work in public, and that sparked bottom-up adoption throughout the company.

But first, the product needed to be enough better to get that first tranche of users to switch.

Opinionatedly different

Here’s to the crazy ones,” said the classic Apple ad. “They see things differently.” That is the defining feature of positional software. They force you to work differently.

Gmail removed folders from email, prioritized an Archive button over delete, forced you to use tags if you wanted to file messages. Typeform showed only one form question at a time. Superhuman hid most buttons, opting to prioritize keyboard shortcuts and the command palette. Figma abstracted away files, blurred the lines between mockups, demos, drafts, and finished work. Hey took away archiving, said inbox zero isn’t important, said 3 folders is enough.

Few are passionate about the differences between PDF editors or domain registrars, say—they either do the job, or they don’t.

Code editors, however, are worth fighting for. Vim and Emacs’ opinionated differences are what make them polarizing. The same goes for modern positional software. They take a stand, say there is a better way of working. That makes them polarizing, which makes them worth talking about, which helps them spread further. It lets them charge a premium for a product built with care.

It’s a virtuous cycle that helps positional software spread to everyone in its niche. They don’t need everyone to use their software, but they do need everyone who cares about the same things they do to use it. You can’t get there by being a jack of all trades. Opinionated features let software be a master of one.

Premium by design

Design, then, ties it those features together.

“Design is how it works,” said Steve Jobs, but better features alone were hardly enough for Apple’s co-founder. The company that taught us what chamfered edges and complications are cares deeply about how their products look and feel. So, too, do positional software.

Vim and Emacs may fall into the design is how it works category, with devotees favoring their raw simplicity. But they’re not turning heads when used in public, not making people wish they had an invite to see what the fuss is about.

Slack was an early leader in the crafted software space. Built from a company that two times had built a game and each time ended up building another product instead, the Slack team surely had great designers in their midst. But they also enlisted an outside design firm to launch the most polished team chat app the world had seen. Team chat wasn’t new; fun team chat was, and design was a key differentiator for Slack, enough that they could charge nearly three times as much per user than their closest competitor.

Positional software pairs a deep focus on features for the most exacting users with an equal focus on the design that will appeal to and work best for them. The chef’s knife needs a carefully curved handle and sharper blade to be worth buying—but it also needs to look the part, especially if it’s to cross the chasm from tool to desirable luxury.

Much of the discussion about Superhuman centers on its price, assuming a $30/month email app is a luxury, a Veblen good. Yet even if the status conveyed an exclusive Superhuman invite is worth the first month’s subscription, that alone is hardly enough reason to continue using the software. Subscriptions if anything align developer and users’ interests, as the latter can choose to leave anytime. Superhuman survives solely on how well it helps those who use email the most. If it makes them better at email, they’ll continue to pay, and talk about it.

Democratizing power features

IRC had been around for decades as an early team chat. Slack added design and opinionated tweaks and turned it into a chat app worth paying more for.

Gmail was built around keyboard shortcuts since its inception. Superhuman taught them to you with personalized onboarding and tooltips, making sure you’d learn them.

Vim and Emacs had features tucked away to make you a more efficient text editor if you took the time to learn them. Sublime Text put those features in a command palette where they were easy to discover.

You could always email design files around, track document changes in Word, update an intranet by hand. Figma, Google Docs, and Notion turned those tedious tasks into a single click, freeing you up for your real work.

Positional software makes its name with unique features and better design. But often it’s not entirely reinventing the wheel. Instead, it’s thoughtfully simplifying what previously were power-user features, making you work faster in ways that were only possible in older software if you took hours to study and memorize. Thus the common complaint that positional software is nothing new, that Slack’s just IRC and Superhuman’s only Gmail with a newer design. The detractors have a point—the features often are there in older products if you dig.

Positional software makes everyone a power-user.

Customizable, within limits

Software can’t gain a patina from wear-and-tear, doesn’t show your hard-earned battle scars of day-in-day-out usage the same way a long-loved tool can.

And opinionated software can never be as customizable as their developer-orientated, open-source, handcrafted counterparts. That’d take away the original insights and designs that make them great.

But you can’t have power user tools without some free-for-all, some area to experiment and make yourself at home. If anything, customization keeps the work-in-public going, as power users want to show what they’ve built from tools others might have originally dismissed.

And thus, positional software typically lets you customize something. Maybe just themes and add-ons, with an ecosystem of third-party developers turning the software into a platform. Maybe with emoji and stickers, consumer-style flair that makes you feel at home. Maybe with custom workflows that force you to think through how you work, make you invest in making the tool your own.

That keeps the virtuous cycle going, where the custom tweaks make it a tool you couldn’t imagine living without, which makes you talk about it in public, which makes others want in, which helps the vendors find someone else in your niche and increases their pricing power as that customer wants their software alone, not any random tool.

And that’s positional software.

A new world of premium software

Software started out enigmatic, mysterious, difficult to understand, gate-kept by obscure terminology and hidden features.

Then it went mass market, where everyone used the same tools, where Microsoft Office was standard and seldom was indie software considered.

And then, as software became the primary tool for everyone’s jobs, not just developers, the same principles that helped developer tools become great were brought to prosumer business software. More esoteric software appeared, tools used by only those with the most demanding needs, with details you’d have to be an insider to appreciate. Mass-market software could serve the bulk of the market; these new software focused on those who need them most.

The best tools signify the value a craftsperson places on time and efficiency. They’re emblematic of the role that craftsperson holds, signify their status and skill. And they’re honed over time to be best for that role.

Today’s positional software does the same. It’s best tools, designed for specific roles, carefully designed to make craftspeople better at their digital work. It’s software that positions you as an expert. It’s priced at a premium, and worth paying for—by those who need their features, and by those who want the status those features convey. They’re spread as digital artisans work in public, share their work, talk about their tools.

And that halo effect can, over time, make positional software the new leader in its field. It still may not overtake the market leader in sales. But it will absolutely influence its entire industry as it occupies the mindshare of the most influential segment of that industry’s professionals.

Published July 10, 2020 — 06:30 UTC

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Work perks are changing — and that’s a good thing

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Catered lunches. Gym memberships. Meditation rooms. Work from home Fridays. 

These are a few of the perks tech companies commonly dangle in front of current and prospective employees. In a COVID-19 world, however, budgets are being cut, people are being laid off and these shiny office perks are no longer within reach

Shelter-in-place orders have accelerated the adoption of remote work by years but it also leveled the playing field to eliminate the work perks that are costly and unimpactful.

So instead, here are some steps I feel companies‘ leadership should take to ensure their employees are taken care of in an impactful way. 

Evaluate current perks, go back to the basics and build from there 

Right now, according to several work-from-guides, having a dedicated workspace at home for remote work is key to setting up employees for success.

Companies like Twitter and Shopify have already provided a stipend or have reimbursed employees for home office equipment, which as career coach Julie Kratz described to CNBC, doing so helps build loyalty among employees

As a CEO, I believe this as well so at TravelBank we implemented a work from home expense policy where all employees are allowed to expense up to $150 each month. The allowance can be used for home office setups, or for those that already have one they can expense groceries, meal deliveries, their internet bill, or other expenses described within the policy. 

In the first month of this new policy, employees have used 100% of their funds which has contributed to employee happiness and further enabled a level of transparency and appreciation within the company.  

Furthermore, costly perks that are nice-to-haves but aren’t being maximized should be reevaluated. For example, gym memberships to physical locations. This is the perfect time to scale back and offer access to digital fitness apps. 

The Peloton app is very popular among our employees and there are other alternatives Fitbod, which uses a training algorithm to build a personalized workout plan, or Aaptiv, which provides unlimited access to thousands of workouts, that can be used on a trial basis.

By using this time to test out more affordable alternatives companies can get a better view into their spend and analyze the use of perks like these and their impact on culture.  

Perks have always been a way to invest in employee retention and happiness. Hundreds of thousands of dollars are typically spent on such efforts but it doesn’t always work out. With budgets being tight and hiring at a freeze at most companies, this is also the perfect time for HR and culture leaders to survey employees about what’s missing and how the company can improve.  

Work-life balance is going to become even more important — listen to your team 

Fortune 500 companies like Google and Facebook have already expressed that they’re expecting to work from home the rest of the year and per a recent IBM survey more than 75%, of the 25,000 US participants, indicate they would “like to continue to work remotely at least occasionally, while more than half would like this to be their primary way of working.” 

A significant portion of small-to-mid-sized businesses won’t be able to transform into a completely remote operation but there will be a more truthful and open discussion about what work-life balance can look like moving forward. Some companies, for example, might adopt WFH Mondays and Fridays while others test out core work hours, like 9am to 3pm to give employees the flexibility they’re looking for. 

At TravelBank we’ve already taken a step forward by eliminating our physical office space and allowing our employees to take home their desks and monitors. 

Another way companies can invest in work-life balance for their employees is by offering digital mental health resources. Employees are not exempt from burning out, even if they are working from home. Offering meditation apps like Calm as a perk shows your team that you care. A small gesture, like sending a plant, also goes a long way. 

According to our own data, startups are using services like Urbanstems to send their employees succulents, which are popular in office spaces and can positively contribute to an employee’s working environment — from simply brightening up their at home offices and improving their focus to enhancing memory.  

More changes are on the horizon 

Companies are not rushing back to setup offices anytime soon; physical office spaces, company culture and on-site benefits are going to look drastically different. Right now, the future of work is being completely reenvisioned. Companies relied on office perks to attract and keep employees happy and productive. Now, with a permanent shift to working from home, employees are going to be looking at companies that provide that level of flexibility. 

According to the previously noted IBM study, more than 40% feel that their employer should provide opt-in remote work options when returning to normal operations, and it’s very likely that a significant number of more companies will jump on board. With these new shifts, expect a boom in more remote indie work tools and others that focus on the employee life at home. 

Published July 9, 2020 — 08:00 UTC

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