The Introvert and the Startup

feetPerhaps nowhere is the phrase “one size fits all”  more misplaced than when talking about work environments and company culture. This is particularly true if, like me, you just happen to be something of an introvert.

At startups with aggressive growth and targets to hit, we try to foster a culture in which people have the opportunity to contribute their strengths and abilities, whilst creating an environment in which they want to spend a significant amount of their time. We also want to have some fun to offset all the hard work.

The creative options and flexibility for doing this at small startups simply can’t be matched in the wider corporate world, so it is no wonder that startups tend to have some of the most enviable work environments and cultures.

But getting it right involves a complex interplay of factors when catering for a diverse workforce, and talented people bring their whole personality to work. Tweak one environmental or cultural aspect to suit certain people or to get results, and you often find you’ve ruined another aspect for someone else. Worst of all, you may even hamper their ability to contribute.

There is perhaps no group that this applies to more than introverts, as many startup environments can be somewhat charged up and geared towards the high-energy needs of extroverts.

introvert, noun /ˈɪntrəvəːt/

A person who is more energised and stimulated by spending time alone or in low-key situations, than with others, and who finds certain group interactions exhausting.

To my amusement, I find it easier to tell people that I’m gay than to admit being an introvert. The former rarely causes a ripple. But the latter is often the start of a grand inquisition: “What’s an introvert?” “Why do you say that?” “You don’t seem like one” “We don’t need introverts here” “You just need to come out of your shell and let your hair down”… All precisely the kinds of confrontation an introvert wants to avoid at any cost. It’s no wonder we usually try to fly under the radar.

It is said that people are hard-wired somewhere on the introversion / extroversion spectrum, or we learn it very early on in life and it can be incredibly hard to unlearn. This has certainly been my experience. But what we are rarely told are the upsides to being introverted, particularly in environments you might think it would be a weakness, such as at startups. Indeed, a mix of introverts and extroverts may be the ideal team configuration… but only if handled thoughtfully.

So what are some of the unexpected strengths of introverts?

  • Leading – Many famously great leaders report being introverts; Bill Gates and Abraham Lincoln among them. Perhaps introverts make good leaders because it didn’t come naturally to us, we had to learn it and tend to have a more considered leadership style that we adapt to the needs of those we are working with. We also have less of a tendency to micro manage, choosing instead to let people exercise their abilities and prove themselves to us.
  • Presenting, Explaining – Strangely, I have no difficulty standing up in front of 200 people to give a presentation or to explain a technology. But after presenting, being part of the audience as a crowd can suddenly seem daunting to me. This is perhaps the opposite of what you’d expect.
  • Listening, Insights – Introverts tend to develop good listening skills. We have a tendency to step back from crowds, or to remain at the edges. We also spend more time processing what has been said to us, less time interrupting and, because we naturally need breaks from engaging, we are more likely to spot connections and insights.

But what do introverts find harder, and what might we need adjusting in work environments and culture so we can thrive?

  • Discussion, not Confrontation – Discussions that turn into confrontations, or environments that verge on being boisterous, can be tough for introverts. We tend to retire rather than engage, feeling shut down rather than fired up. The precise opposite of how extroverts react. When discussions stick to facts, rationales and explanations rather than the raising of voices, introverts can actively and even energetically engage and, as mentioned above, may have an entirely different set of valuable insights to offer. Conversations can still be very animated and productive.
  • Space to Recharge – We tend to need time in which we are likely not to need to engage with others, so we can digest, consider and recharge. We also need the physical space to do that in. If an environment is socially charged non-stop, introverts can rapidly be worn down, drained and become detached.
    Good environments allow a mix of engagement and focus, with meetings and work spaces kept separate where possible. Some would say this limit on engagement is a downside, preferring constant communication instead, but I’d say it naturally timeboxes interaction and forces more considered work to be scheduled. No-one, not even extroverts, can stay engaged, communicative and effective the whole time. Open-plan spaces can be a drain on everyone, not just introverts.

So perhaps the strengths we’re recruiting for in fast-paced startup environments might occasionally come aligned with a personality trait we’ve usually considered to be a weakness: introversion.

Introverts comprise up to one-third of the total workforce, so getting things right for a mix of personality types could be a significant win for startups looking to build great teams and great places to work. And if startups can get this right, the wider corporate world might follow.

Headspace: Perhaps the Most Urgent Thing?

londonNothing of any significance or impact was ever created by a scattered mind.

Great things are not built in a rushed series of truncated thoughts, punctuated by distractions. They are created by getting the headspace to go deep, to stay there a while, and to surface with new insights, structure and conclusions.

Even with a eureka moment, a spark of brilliance or a chance connection, those initial insights take focus and refinement to develop, distill and simplify; to make them usable.

In fast-paced modern work environments, it’s clear that most of us aren’t managing to achieve headspace or to go deep into our work with any regularity. Our days seem like a series of distractions, email, phone calls, chat, meetings and being ever-available. Busy-ness, and particularly visible busy-ness, is a medal we seem to wear with pride.

But it’s likely that we’re barely scratching, then re-scratching, the surface of the work in front of us. We’re probably repeating large portions of it, as we absorb the cognitive switch away and back again. If we’re lucky, we’re gradually making progress in the right direction, though it will be hard-won, inefficient and lacking any real insight or depth. We may find ourselves achieving most of our meaningful work outside of office hours, which implies our work environment isn’t… well, isn’t working.

Most worryingly, we may be killing our ability to innovate, to compete and to deliver value… which is surely why we’re at work in the first place?

After 20 years working in teams, I spent a year working alone on two startup ideas… yet initially I still found it hard to focus. Surely, I had assumed, headspace would be simple to achieve alone?! It seemed that the learned expectation of interruption and the numbing array of possibilities to do other lesser things to get a hit of achievement kept me from focussing deeply for any duration. I had become a busy-ness and achievement junkie. At first, I seriously wondered whether I had some kind of attention deficit problem and so I turned to tools like the Pomodoro Technique to regain my headspace.

I gradually learned to commit to 25-minute periods of focused work, during which I would let nothing else (including my own thoughts and other interests) distract me, and then to take a short break or work on something less involved. Before long, I could crank out 6-10 of these “pomodoros” per day without too much struggle, and my ability to focus on my own returned.

During that year of regular focus, the work I produced felt significant: I made leaps forward, created two products and wrote my own UI framework. These achievements would never have been possible in my usually-scattered frame of mind. All of them were the result of focus and depth… of finding regular headspace.

Even more so in teams, the ability to carve out periods of headspace is key to getting work done together. But balancing it with being available on-demand is also crucial. We simply can’t schedule the needs of other people and the wider team, nor block them out to pre-determined times. But perhaps, after a landslide of unscheduled requests, we can push back a little, pop on a pair of headphones (a visible sign of focus), and get 30 minutes of focused work done before accepting more outside input. Oscillating in this way between being available and being focussed allows a portion of our time to be allocated to deeper work, even if we have to be a little creative and flexible about precisely which hours of the day that ends up being.

Respecting Headspace: It may seem that getting immediate answers from colleagues, and being available to provide them ourselves, keeps a work environment moving at maximum speed. But there is a cost to the team, and therefore to the project, for that immediate answer, paid in terms of the headspace of the person providing it. It may feel as if asking in-person is more productive and that chat or email are inefficient ways of getting an answer, but those tools allow the person providing the answer to crank out a series of such answers during a quick break from other work, and perhaps still within a relatively short timeframe. More urgent interruptions can still take place, but they must be balanced with the permission to block out further interruptions for a period of time that each person chooses themselves. Our headspace and their headspace will rarely occur in-sync.

Deserving Headspace: There is a flipside to this. In order to be allowed to focus, we must also prove ourselves capable of handling those queued requests in a responsive and reliable manner. Ignoring emails and not scanning chat channels for updates occasionally are certain ways to force people to interrupt us with more urgency, to grab our attention and to destroy our focus. If people learn that we will always respond within a reasonable timeframe, they will happily learn to queue non-urgent work for us.

Respecting the headspace of others may improve the output and depth of work produced by the whole team, by reducing cognitive switching. It probably also doesn’t greatly delay the answers our interruptions require, and it can be mixed with much more interactive sessions, standups, meetings and brainstorming to get the best of both worlds.

Headspace in teams, but also alone, isn’t easy to achieve. But what’s clear is that without it, the work we produce and the things we create will be mere shadows of what we’re capable of.

Maybe headspace and our ability to focus really are, somewhat counterintuitively, the most urgent things of all?


Image: (c) 2015, Ian Cackett


Why Time as a Solopreneur Might Make You a Better Team Player

forwardTeamwork: Good. Lone work: Bad.

Or at least that’s how the stereotype drummed into us through education and our careers seems to go. We learn to focus our CVs and resumés on our team contributions, and to downplay the things we achieved entirely alone.

But what if the things we achieved on our own somehow made us more effective the next time we joined a team? What if a balance of both experiences made for better team players?

It’s my experience that teamwork between people who have never known an occasional lone accomplishment can suffer from a few blind spots: Such team members may have an inaccurate view of their contribution and how to tune it, having only ever seen their work as part of a larger deliverable. There’s a danger of feeling like a full four-wheel contributor, whilst actually running on three wheels and being unaware how much your contribution leans on the work of others. People who have never known personal wins can see a team project as their only chance to demonstrate their abilities, and may be over-invested in personal outcomes rather than team outcomes, safe in the knowledge that they can shine elsewhere or next time.

So what do I mean by lone accomplishments? Lone accomplishments could be a product (software, hardware, anything), a piece of art, training materials, blog posts, or a book. Anything you actually launch, publish or deliver to an audience, for which the entire deliverable depends on you, and for which you have no backup or other input to assist. Anything for which there is no scapegoat once you deliver it; it is yours, good and bad.

I’ve done this twice, with software products of my own. They were far from a commercial success, but the lessons learned were worth more than the time I spent and the salary I forfeited in those months. Since then, I’ve gone back to teamwork in startups, and really appreciated the perspective that my lone achievements have given me.

So what do lone accomplishers bring to a team? How can lone work strengthen and define you?

  • People with lone projects under their belt tend to have a more accurate view of their own strengths and weaknesses, and an appreciation for the roles others perform in a company.. because they’ve probably filled them at some point, albeit probably rather clumsily. Most former solopreneurs will have noticed how they couldn’t possibly fill all those roles alone… and will appreciate that it is only possible to cover them well in a team where a variety of skillsets are present.
    For me, as a software engineer, I now have a great appreciation of the other roles involved in startup life: Marketing, PR, design, QA, Ops, etc. Prior to undertaking my own projects, I probably had a dismissive or inaccurate view of those roles.
  • People with lone projects under their belt already have personal “wins” in the bag, so they don’t feel the need to act as if the next team project is their own pet project or chance to shine. This makes conversations more about a team win, rather than a personal win, less religious, more exploratory, and more practical.
  • People with lone projects under their belt tend to appreciate the difficulties of building something entirely alone, and therefore the need for others. The mature lesson from this is a willingness to delegate… and truly delegate, giving people a long leash and adjusting it appropriately. Knowing I can’t do it alone, but might be able to achieve it with others, makes me value the contribution of others and the need to delegate effectively.

Why is lone work a rarity? Aside from the widespread celebration of teamwork, we probably shy away from lone work because we know it will truly define or break us; there is no middle ground, and so we fear it. Through it, we will either discover, once and for all, that we can lean into a challenge on our own, or that we don’t (yet) have what it takes. Unlike teamwork, there is no scapegoat, no fallback, no-one else to blame. This is a hard reality to face.

But I’m convinced that every day we put off an attempt at lone work, is a day we never really understand what we are capable of; both alone, and in terms of our contribution to a team.

I’m convinced that, particularly in industries that involve building something (software, hardware, arts), we should exercise our lone capabilities on a regular basis, and at least once a year. It’s an ongoing eye opener on who we are, what we’re capable of, and therefore what we each bring to a team.

Far from being a red flag when hiring, lone work — when properly learned from — could be the thing that truly makes a strong team player.

Sipping from the Firehose: The next Challenge for Social Media?

firehoseDespite my often tempestuous relationship with it, I love social media. Everyone’s a publisher; individuals and businesses alike.

If you want a platform to say something, you’ve got it. With the click of a button, your content is out there. The potential reach is tantalising, and we all religiously know how many friends and followers we have. Publishing is certainly cathartic and feels productive.

But there’s a problem we’re overlooking: Social media is ineffective for finding and consuming content.

Even when it reaches our devices and screens, there is simply too much to consume or it is unstructured, often interwoven with irrelevant and sponsored content. It is well known that a tweet has a very short lifespan, after which it is almost entirely unlikely to be read, hence a plethora of tools to help us schedule tweets to increase their audience. Due to the way they are presented to us, Facebook posts last longer, but our news feeds have grown exponentially and we seem less willing to scroll through it all.

Worse still, we no-longer even see everything that’s published with us in mind as the audience, because algorithmic filtering is now common, particularly on Facebook.

What does this mean? No-one’s really listening. Well, certainly not the size of audience we expected. The tantalising reach of social media — which basically means your content reached a device or screen — is misleading at best. We aren’t focussing on genuine reach; meaningful consumption of that content.

Even when content reaches its intended audience… their attention span is often scattered, knackered, insufficient by that point to absorb it, because they are drowning in other content. A page view means nothing if it lasted 2 seconds, or they scrolled on by the summary and didn’t even click. A “like” or a “favourite” may not mean they actually read the content, which is surely what we really wanted?

Attempting to sip from a firehose probably isn’t the best way to consume content, and surely publishing on social media is intended as a two-sided affair? We’ve focussed so-far almost exclusively on publishing itself, because it’s by far the easiest angle to tackle. We’ve constructed the firehose.

Isn’t it about time we did something for the consumers of all that content? After all, we spent time crafting it, so we want it to find the right audience and have an impact on them when it reaches them?

Is making social media consumable again its next great challenge?

The Great Offline

yorkshire-landscapeWell, not entirely offline. I didn’t actually spend New Year in a cave. But I did decide to spend the last two weeks of 2014 away from most forms of social media: Facebook, Instagram, Twitter. Basically anything I felt I was over-using and could do with a break from.

It seemed a good time, from 18th December until 1st January, to remind myself what the world is like without those sites and that minute-by-minute urge to “contribute”. Aside from the usual seasonal socialising and some much-needed down time, I planned to focus on other projects and prepare — at a more leisurely pace — a few lengthier blog posts.

After the first two days of the self-imposed social media break went by, it became clear that I needed to widen the scope. The first sign was the recruiter who messaged me on LinkedIn but who then took three replies from me to convince that I really, really only wanted to talk to him in January. Then there were the emails from folks wanting to arrange work-related drinks in the final week before Xmas. So, whilst I still checked my email once a day, and promised myself I’d reply if anything urgent came up, I decided to leave the rest there in my inbox, unread other than their subject line, until 1st January.

The relief at dropping the social media frenzy for a while and letting email pile up was rather unexpected, palpable and amazing. I rediscovered a slightly-less-connected world and, strangely, one in which I felt more deeply connected to real things: Face-to-face encounters weren’t interrupted by Facebook’ing, phone calls had my full attention, meals cooked at home didn’t get uploaded pictorially to Instagram. They just got eaten. I know, how refreshingly retro!

There were also other benefits: This blog post, to my delight, is easier to write without the constant distraction of inbound social media. I also drafted a longer software-related post for LinkedIn next week, the flow of which seemed to have eluded me until then but which came easily during the break from the constant notifications. I got my head around a new product idea that I’d been failing to define beforehand, and which I now found the focus to think deeply and easily about.

By unplugging from the distractions, and yet still remaining online in other ways, I regained a degree of that longer-term focus required to cultivate ideas, respond at-length, react appropriately and digest the articles and news that I was still choosing to read. Regaining that focus, albeit briefly, gave me a real sense of what social media and always-on email is doing to us. It’s somewhat scary what we’ve lost without even noticing, and how short-term and reactionary we — and hence our lives — have become.

Of-course, now the two weeks are over, I’m back in the social media world and my inbox has been tamed again, I realise I must have missed things whilst I was away: The constant commentary on every news story. The social status bingo of everyone else’s Xmas and holiday pics. The reactions and counter-reactions to every domestic stress and strain of the season. Minute, by minute,… by online minute.

Yeah, on second thoughts… perhaps I didn’t miss that much really.

Happy New Year!

The Biggest Barrier to Doing Good Work

hands-on-keyboardFor me, the biggest barrier preventing me from doing good work is the strange notion that I should be producing my best work all the time. It is simply not possible.

This self-imposed expectation and lofty standard is what creates the feeling that, if I do some work now, it won’t be good enough or I won’t be sufficiently productive. So I beat myself up and I don’t get started, when getting started  is the only thing that’s actually required.

I’ve learned that when ideas and work are tough — as anything worth doing surely is — all that is required is spending time with those ideas and with that work. Going back to it repeatedly, developing it a little more, lifting it a little closer  to where it needs to be. It won’t always be productive, but doing this frequently is necessary. Without spending regular time in that work, it won’t magically become what it is potentially capable of becoming: My greatest work, or simply the next ball of screwed up paper to hit the waste paper bin. And it really doesn’t matter which.

What matters most, and the real urgency, is progressing this piece of work towards its logical conclusion. There can be no urgency to have a great idea, because that just won’t produce one.

Knowing that I’m engaged in the right process, and that this is all that’s required, helps me to get started and stay engaged. The rest will come.

More Of The Same: The Own Goal of Online Advertising and Recommendations

cartI can’t be alone in feeling that most of the online advertising I see, and most of the “recommendations” I receive from online retailers, are just plain dumb.

Last week, I purchased hand towels for my flat. And now the retailer is showing me recommendations for hand towels. A month ago, we bought new office chairs at work. And now when I visit most news sites, I see adverts for office chairs… in-fact, the very office chairs we just bought.

What’s so dumb about this? I am being shown the very last thing I’m going to be interested in buying right now. When I  just purchased X, I am highly unlikely to want to purchase X again any time soon. In-fact, I will probably buy anything but X.

What would be cleverer? What goes with X? What compliments it, or what did other people like me who bought X go on to buy subsequently?

I bought hand towels, so how about showing me bath towels, face flannels and other bathroom items? We bought office chairs, so how about showing us office desks, printers or stationery items? Things that surely have a higher conversion rate and that we might actually be interesting in buying now.

The problem is that it’s harder for retailers and advertisers to make those leaps and to write performant engines to do that. It depends upon meaning and context, rather than a quick match. It relies upon having a great deal of anonymous data about each purchaser, each viewer of adverts,… and people similar to them.

I worked for two years in online advertising, on the advert selection engine used by a particular platform, and I know how hard it is to even begin to raise the bar and make better decisions about what to show, even with adequate data and clever modelling. It is far easier to go with targeting broad demographics, or repeating specific past purchases.

People are also understandably reticent about data being gathered about them, even anonymously. And yet, without that anonymous data, recommendations and adverts will always be somewhat dumb.

What might the reality be? A person buying office chairs may buy them because they are setting up a new office (like us), or because their already-over-equipped office is expanding and they just need 20 more, in which case they may indeed purchase more of the same again soon. A person buying towels may be setting up home for the first time, or they may just be replacing worn out towels in an already over-stuffed flat (like mine).

Understandably, recommendation and advertising engines go for the easy win and the ultimate own goal: More of the same. Rather than engaging us, they come across as unintelligent and reductive. The easy win for them, is an annoyance for most consumers.

I guess they fear that when data is sparse, clever recommendations may be way off the mark. I am always amused to recall the Amazon recommendation (“People buying this item also bought…”) after I purchased a battery charger: Most of the recommendations were for packs of rechargeable batteries (pretty good). But the bumper box of condoms — perhaps a subsequent purchase by a very small sample… maybe a sample of one! — was amusing, but not particularly useful, and probably an embarrassment to Amazon.

I believe we, as software engineers and data scientists, can and should do better. Any advertising or recommendations platform solving this problem, or even improving it slightly, will have a real edge over the others out there.

Meaningful, compelling advertising and useful recommendations. Anyone up for that challenge?! 🙂

The Imposter at the Keyboard

handI’ve often talked, and joked, with a former colleague and friend of mine about Imposter Syndrome: the belief that you are a fraud just waiting to be found out, and that your prior accomplishments are the result of luck and timing rather than genuine ability or skill. Though rarely admitted, it seems to be rife in the software industry, particularly amongst those who are actually outwardly very successful. In-fact, I’m convinced the industry probably unintentionally causes this genuine psychological phenomenon.

Firstly, let me say that I am not a trained psychologist. I just find it interesting that this phenomenon seems to crop up regularly in discussions with industry colleagues and seems to be suggested, by way of implication, even when it isn’t openly acknowledged as a factor.

The sheer range of skills that software engineers could employ in our working lives leads to the obvious implication that no single engineer can be competent in all possible skills. There are simply too many to even be aware of them all, let alone regularly use them, let alone to be competent in them. Therefore, it is just a hard fact that most capable engineers will lack a significant number of skills that are considered desirable or current at present, and that this is not a reflection of their worth as engineers. As an engineer, if you look at the set of all possible software languages / skills / disciplines, you will currently be lacking a large number of somewhat recent, marketable, relevant and possibly desirable skills. Even if you actively learned 10 of the most bleeding edge ones this month, it is fairly likely that you would still be lacking some new and desirable skill 6-12 months down the line – probably the ones required by the new start-up you’ve just heard about and would love to work for. Such is the continual progression of our industry. This is also, however, what draws many of us to software engineering as a career.

And so we specialise, or we pick an area, through necessity and practicality. But what’s interesting is that, because of the grey lines between areas, we are forever discussing which skills we have, which we lack, and accounting for our level of competence in them. This mental accountancy exercise, and the introspection it brings, is ongoing. We know that the skills we picked today will become dated tomorrow and that each skill has a shelf life.

The answer to the skill competency question is never clear-cut. One person’s “senior python developer” is another person’s “intermediate python developer”. Even a senior person may have focussed on a subset of the overall skill, such that they have a blind spot in the precise area that a project requires. Java developers often suddenly discover they lack sufficient knowledge of threading and concurrency and, most capable developers use this discovery as an opportunity to learn, and to fill in that knowledge gap. There is an endless “Am I good enough at skill X?” going on. At least, in the heads of most genuinely capable engineers. I’m sure there are others who never give this a thought, which is also why I believe that Imposter Syndrome may be more prevalent amongst genuinely capable folks; the ones who think “How am I doing? What could I improve?” on a regular basis.

I suspect that bravado also gets in the way of healthy introspection. Many engineers are reticent to acknowledge the lack of a particular skill, seeing it instead as a form of weakness. And in a world where only the best get hired, who wants to admit what they don’t know? So discussions about skills are somewhat externally skewed, leaving an individual wondering whether they are, in comparison, somewhat lacking.

The path to becoming competent in a new skill is often difficult, and there is the usual Catch-22 of being unable to get on to a project requiring Skill X until you have demonstrated Skill X… on a previous project. As hiring managers, we tend to “body shop” engineers based upon skills and keywords, rather than on potential. And so we spend our personal time acquiring the required skill, demonstrating it on a side project, and somehow trying to segue from newbie to competent. There is a natural push to appear competent, perhaps before we genuinely are. Couple this with the fact that an employer will always be able to find a pool of available candidates who already have Skill X, and the urge to upsell our own skills is almost justifiable. And so it is natural to wonder whether our own hype meets the reality of our abilities.

The final contributing factor is feedback… or rather the lack of timely, honest feedback. I have rarely seen a struggling engineer told, in a timely manner, precisely the areas in which they were seen to be lacking such that they had an opportunity to improve and turn the situation round. The consequence of this is that we all wonder what folks think of us. Really think of us and our skills. It’s rarely said aloud. Again, a cause of introspection but this time not a healthy one. Perhaps if we encouraged a culture in which those difficult conversations actually took place, rather than being endlessly postponed or referred to behind the subject’s back, engineers would believe they had a firmer grasp on whether their skills were considered appropriate for a particular job. I’m lucky, I don’t seem to have been that guy… yet, to my knowledge… but I’ve known several who have heard way after the fact how they unfortunately missed the mark.

In conclusion: I think that if we acknowledged the need to specialise, to pick up new skills, to be a newbie in those skills for a while, and also learned to give honest (and sometimes difficult) feedback to one another, we might find the causes of Imposter Syndrome in our industry were greatly diminished. Until then, I suspect it will be, rather perversely, the more capable engineers who suffer from it the most.