Project Management for Startups

In large companies, project management is a must; in startups, it’s a radioactive “hot” potato. Large companies have dedicated project managers and sometimes even a Project Management Office (PMO). Small companies like ours don’t have one and we’re pushing 60 employees now after 18 months. Eventually, it’ll make sense to have a full-time project manager, but until then we want to stay agile so we get by using software, process, and face time.

Use the Right Software

When our Product-Engineering team consisted of CEO, CTO, and two engineers, email was our issue tracker and a whiteboard contained our roadmap. That worked well. Soon we hired a few more engineers and email proliferated. Pivotal Tracker (PT) became our issue tracker (still free then!). PT is simple, light, and an engineering team’s dream–a place where only engineers could hang out. We upgraded to Google Spreadsheets for our roadmap so we can do more sharing and simple Gantt charts. Once we hired some product managers, added a QA team, and started developing many projects at once, it was time to swim in the Olympic-size pool: Jira. Besides being created by a hilarious bunch, Jira does everything. That’s part of the reason we resisted using it early on, since we didn’t want to fill out so many corporate-y fields like “hours worked” (::shudder::). As for our roadmap, it broke Google Spreadsheets and I grew tired of the “aw, snap!” pages. I’m experimenting with a few tools and so far I like Asana and Smartsheet. Find what works for you now.

Evolve Your Process But It’s all About Face Time

We tried to add only as much process as we needed over time. You start out with a fast track from feature conception to release. When you have two people who work on a project, you can sit down and have a heart to heart, nod heads, and then start coding. When a product manager has to convey thoughts to a few developers and a few QA–this is a small team still–details get lost in translation. Not only that, conversations may happen between members of the team that aren’t shared with the rest of the team. Let the frustration and angst begin. For a while, we went with the Product Requirements Document (PRD) approach, which is very monolithic. We’ve since moved away from that. Recurring meetings get moved around and their titles and agendas change. We went from 1-week to 2-week releases. Processes should change when the team changes or when the needs of the team change. It all comes down to getting a bunch of people to share ideas and work together efficiently. All this software and process is meant to cheat time–time to talk to one another face-to-face that is very hard to come by.

 

How to Find a Technical Co-Founder

Finding a technical co-founder is like online dating: too many guys and not enough women, except you skip the engagement and jump straight to the wedding. Often times, what’s really being asked is “How do I learn about starting a company?”. Check out the title of this hugely popular Quora question: “I am a creative guy with a startup idea. Where is the best place to find a rockstar developer to bring it to life?” There are 35 answers and it has been viewed 19870 times. The wording of this question reveals a troubling conceit–the idea that once you have an idea, all you need is to hire a few monkeys to code it up–then profit! The world is richer and more complex than that, my friends.

1 is the Loneliest Number

Apple had Steve Wozniak, Google had both Larry Page and Sergei Brin, Facebook had Mark Zuckerberg. It’s hard to build successful technology companies without a strong technical co-founder. You really need the wide range of talents from a Marketer, Product Manager, and Designer–it just so happens that the 1+1 combo of a business founder and technical founder can condense this set of skills into two people. With freelancers and advisers, you can keep the team size to two longer, but you’ll be hard-pressed to find a single person that does it all.

Be Realistic

Be honest with yourself first so you can be honest with others. Rate yourself on a scale of 1-10 for this role. Figure out what strengths you bring to the table and what’s lacking. Are you ready to be part of a 1+1? Most likely, this means you’ll be solely responsible for the business side of things including marketing, sales, legal, etc. Should you find a co-founder or should you join a startup to learn some skills first? If you’re not a superstar business guy, you will not get a superstar technical guy to work with you, so have realistic expectations.

Make Friends

Highly sought-after women generally don’t need online dating. A great engineer will have six-figure offers from Google and Facebook on the table. For them to pass on those jobs is like ditching a millionaire for a struggling writer. You better be Ernest Frakking Hemingway carrying a dead lion you just killed with your fountain pen. I suggest you make friends with as many technical people as you can. Go to meetups, conferences, Startup Weekend, etc. Make connections on Twitter and through your extended network. Meet your neighbors who may be trying to build the next Instagram (engineers tend to tinker too much and ideate too little). At some point you’ll realize why the term “rockstar developer” is so passe. If you need some technical advice, introduce yourself on Twitter–I go by @mankindforward.

Why your engineering team needs Vagrant

One of the first things I told our CEO when I joined as the first engineering hire was to buy every engineer a 15″ Macbook Pro. I wanted to have a consistent development environment for my team. I created a Google Doc and at first I ran through this How-To personally on every new machine for every new hire. The last 3 or 4 hires were given this doc on their first day and their setup time became part of the “How quickly can I setup my dev box” game. The record is 4 hours but he had most of the dependencies setup. The longest was two days.

It’s All Fun and Games Until Someone Upgrades

In the last 18 months, Apple has changed the processors, memory, and countless other aspects of the 15″ Macbook Pro. OSX has gone from Snow Leopard to Lion to Mountain Lion. Ruby has gone from 1.8.7 to 1.9.3, Rails has gone from 2.3 to 3.1, and I can’t keep track of all the versions of gems that have changed. The development world–it changes fast. How bad could it be, really? Well, I include 4 different manual “patches” in that doc of mine to make mysql work. The working patch depends on whether you have 32-bit or 64-bit OSX, your version of Xcode and mysql, whether you used a tarball or a dmg, whether you use mysql or mysql2 gem, etc. Lately, I just tell new hires to try everything until they find something that works. Even for packages installed via macports, certain version of ports don’t install properly. Some of these can be fixed by editing the portfile with information culled from the Interwebs. Other times, people just give up and use the homebrew version. This is us at 10 engineers.

Remove Doubt

Development and debugging can often lead to situations where you try to find what is different about a working scenario and a broken one. If a test passes on my machine but not on yours, I don’t want to say “it could be because you’re using Rails 2.3 vs 3.2 or Ruby 1.8.7 vs 1.9.2” or god-forbid “it could be because you’re using Windows”. Ideally, I would like to say “it’s because you forgot to pull the latest code” or  “your custom configuration file is not consistent with mine”. The more differences between one environment and another means the more variables to consider–follow the rabbit down the hole.

Abstraction FTW

Just as rvm helps engineers manage Ruby versions and bundler, Ruby gems, Vagrant helps engineers manage their entire development environment. With the concept of “boxes”, an engineering team can build Virtual Machine images to suit their every need. Want to onboard a new hire? Give then a computer and have them load your team’s starter box in 5 minutes. Want to roll out security updates to all 500 of your engineers? Script everything up using Chef or Puppet and have everyone download a new box. Want to test how your app would run in Ubuntu rather than Gentoo or OSX? I just did that while writing this post. When do I really need vagrant? For small teams (2-3), you’ll probably live without Vagrant. However, if you want peace of mind or plan to scale, check it out now.

Every Startup Needs a Gong

This is our third gong. Our first one was a few inches in diameter and sat on a desk. Our second one is about six inches in diameter–a mini version of this beast, which vibrates your soul if you stand too close. Gongs are a meme at Badgeville–a unique story about our company just like “Team Punishment” and Iceland. We hit the gong whenever sales closes a deal and the size of the deal determines the number of gongs (and now also what size gong you hit). Other companies also does this for sales. I hear New Relic gongs and sends a mass email to the entire company when a client goes premium (awkward and funny story around that). I love the gongs because they’re a tangible reminder of progress. As an engineer living in a world of 0-downtime releases and in the past weekly or even daily releases, there’s no party to commemorate the mailing of CDs with your software. Somewhere out there, some VMs turn over in a dark, temperature-controlled room and your SaaS product has been updated.

Gongs are one of the many ways companies develop culture and character. Our name is “Team Punishment”. The origin of the name is oh-so-random but it’s stuck nonetheless. Every quarter we design t-shirts to commemorate the evolution of “Team Punishment”–recent ones featured images from the Godfather and Scarface. I remember one quarter we had one w/ a japanese phrase translated as “team with no worthy enemies”. As we’ve grown to over 50 employees and moved 4 offices and now occupy a fifth across the street, it’s the little things like gongs and team names and backstories that pass on the culture, the essence of the company. The space-time continuum in a startup is compressed–years feel like months and weeks feel like days. It’s very easy to get caught up in Getting Stuff Done (GSD), but it’s these tiny details that help tell the story of your company.