My Huffington Post Article: From Dungeon Master to SCRUM Master

My latest post on Huffington Post is “From Dungeon Master to Scrum Master: 15 Software Development Lessons from Dungeons and Dragons” and is a bit of a revamp of my D&D article from here, but geared towards SCRUM mastering and managing Software Development teams. You may find it fun and kitschy or you may find it dumb. I’m kinda’ ok with both (I’m learning that I can’t make all the people happy all the time). A sampling of that article:
I started playing Dungeons and Dragons in about the 5th or 6th grade. I didn’t get good at it for a while, but once I did, I didn’t play much longer (insert reference to “The Best Days of My Life” here.) Dungeons and Dragons taught me a few lessons that I didn’t realize would turn out to be great life lessons, until I was much older. This childhood game taught me life lessons that I would eventually apply to the business world – more specifically, the world of software development – and I know I’m not alone. In fact, there is a distinct possibility that many a developer got their start scoping out character sheets, and many a Scrum Master began as a Dungeon Master.
Here are a few of the lessons I took away from those carefree days. And yes, this image is from a box set sitting on my table at home. Don’t judge.
1. Build a great campaign, and if the game is good, expect your players to break it. 
In software, we design workflows. Then, users take routes we never thought possible. You build a product, sell the product and potentially service the product long-term. Maybe it sells, maybe it doesn’t – but if you’re not ready for the sales to happen, you won’t sell that much. How much work do you put into building a campaign, or game, in Dungeons and Dragons, if the characters are just going to go right off your script? How much effort do you put into building a business if the customers are just going to buy something from you that is completely different than what you thought you were going to sell? These are the same questions, and there’s no right answer to either (although there are many wrong answers). Understand that when momentum strikes, if you don’t have a good campaign built that is flexible, you won’t maintain that momentum. And if you haven’t thought of all the various routes a user can take around your software, you’re going to have a bunch of lost paladins mucking around in swamps with no monsters!
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20 Lessons About Business I Learned From Dungeons & Dragons

I started playing Dungeons and Dragons in about the 5th or 6th grade. I didn’t get good at it for awhile. And once I got good at it, I didn’t play much longer (insert reference to “The Best Days of My Life” here). Along the way, I learned a few lessons that until I got older, I didn’t realize were great life lessons. I also learned a lot that helped me later in life in the business world. Here’s a few you may or may not agree with (and yes, the image is of a box sitting on my table at home:).
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  1. Build a great campaign and then if the game is good, expect your players to totally break it. In business, you create a situation where customers give you money. You build processes, procedures, marketable packages, and teams. These prepare you for the massive onslaught of all the moneys that are going to come in. You need to be able to build a product, sell the product, and potentially service the product long-term. Maybe you sell it, maybe you don’t. But if you’re not ready for the sales to happen, you won’t sell that much. How much work do you put into building a campaign, or game, in Dungeons and Dragons, if the characters are just going to go right off your script? How much effort do you put into building a business if the customers are just going to buy something from you that is completely different than what you thought you were going to sell? These are the same questions, and there’s no right answer to either (although there are tons of wrong answers). But understanding that when momentum strikes in a game and if you don’t have a good campaign built that is flexible, you won’t maintain that momentum, is key.
  2. If you have to stop the game to look up the rules, your momentum is lost. Games got way more fun as we better understood the rules. When you have to stop and look something up, the attention of the gamers can get lost on things like potato chips. Similarly, the attention of the market is lost when you have to stop a business transaction to review contracts, train employees, rebuild processes, and reengineer product. The better all employees are trained, the more likely they will respond quickly and appropriately to the market and not have their attention wander when you have to look up how to properly figure out what saving throw is required to keep from getting crispy from the breath of a red dragon.
  3. Have fun! There’s not much reason to play Dungeons and Dragons alone. If the game isn’t fun, you will invariably not have many people come back for a second or third campaign. In business, employees need to be engaged. Products and companies these days need to have a personality. Sure, you might make a great widget, but if it isn’t fun to come to work and make, sell, or support that widget, then you’re going to have a much harder time getting those things done. Fun brands, like fun games, drive engagement – and engagement amplifies your spend.
  4. You gain experience incrementally, but it shows in bursts. In Dungeons and Dragons, you gain experience points for doing things. When you accumulate enough, you go up a level. At that point, you might get a higher score for an ability, you might pick up proficiency with a new weapon, or you might get more hit points. Heck, according to your character class, a lot of cool stuff can happen. I find that in business, we slowly work our way towards a new level. We learn lessons along the way (like a Level 1 Cleric learns not to tackle a blue dragon alone). I was recently in a meeting where someone said that a department had reached a new level. In business, you kinda’ work your way there, learning lessons, training staff, expanding, contracting, etc. But all of a sudden, you realize “holy crap, we can now cast fireball spells!” When did it happen? Sometimes you don’t even know… But it’s usually obvious to everyone that a gap was closed, a threshold crossed, and it’s time to start building momentum for the next level, tackling more difficult monsters, arming up with better weapons, and maybe even picking up some new NPCs along the way!
  5. To sell, you need to be confident. When it’s your turn in a game, you may talk as your character would (I’ve heard some of the worst accents ever in these games). The more confident you are, the more the game is immersive. Without confidence, a Dungeon Master is likely to get walked all over. Most jobs in a company have way more of a sales component that most employees want to admit.
  6. Some players are just going to be more engaged than others, no matter what you do. Different people want different things out of a game of Dungeons and Dragons, their jobs, and this life in general. When I was taking MBA classes at Cornell, they referred to this as different people having their own motivators. These motivators influence how impactful various initiatives are. For example, some respond well to financial incentives. Others to social interactions or pats on the back. Some players have a math test the next day and are going to miss a game. Others are ridiculously into the game. Just because you put a lot of work into developing a campaign doesn’t mean that others are going to be into each and every game. Everyone will have more fun if the expectations for engagement with a given initiative are tempered and any involvement is looked at positively.
  7. Don’t dominate the game. Everyone should have a say in how games go. There’s going to be natural alphas in any group. But try and give everyone ample time to play and talk about what their character is doing. And if some people don’t have that much to say, that’s fine. Just routinely return to them and give them the opportunity. This is how a game, meeting, brainstorming session, town hall, etc can be run. If one player is dominating the game, it’s a great idea to step in and keep them from doing so. How you go about doing so will become a skill that you hone for decades. And try not to be that person. Another skill you may hone for the rest of your life…
  8. When the 20 sided dice goes missing, it was probably the paladin that took it. Yup, stop blaming the thief. The person who prefers to play a Lawful Good paladin might just be living vicariously and might not be the eagle scout everyone thought they were. Don’t jump to conclusions when things happen in the professional world. Gather all of the information. Especially when there’s an accusation to be made. When you’re trying to isolate a problem with a process or product, perform your due diligence. Root cause analysis, etc. Of course, you’ll need that 1d20 back eventually the game is to go on…
  9. You are invariably going to outgrow the game. People don’t stay in the same position forever. You need to build a growth path. You don’t want your level 5 Drow Elf Ranger to stay level 5 forever. You want to be prepared for how the game will play out with higher level characters, and maybe even keep a funnel of lower level characters and employees who can work their way up into higher positions. And when a player decides to leave the game, you need a succession plan. It’s easier in Dungeons and Dragons than in business. Sure, you can switch classes, just like employees can switch departments, but it’s a pretty linear path for most in the game. In the real world, everyone will have something different they want out of a job and it’s the job of a servant leader to help them get there, even if it means helping them soar to new heights at another organization. It’s best though, if you can provide a growth plan that keeps your awesome people in house, of course… But sometimes a player’s going to go off to college. Maybe they’ll come over and take over as the Dungeon Master when they come home though. So stay in touch. Also stay in touch because you just plain like them and want to be friends…
  10. Morale is optional in Dungeons and Dragons, but not in the business world. Morale was a slightly more advanced feature for Dungeon Masters. Basically, if a creature or retainer fails morale check (2d6), it will disengage from a battle and retreat. If it sucks to work at your company, or on your team, your employees will do the same. If you don’t work on morale, you won’t find yourself with talented employees for long.
  11. What happens when you turn a bag of holding inside out? Some things, you’ll never know. But, you can’t wait until you know every detail in business. You see, the cost to gather tooooo much intel can outweigh the opportunity cost of jumping into something. Every now and then you have to trust your gut. But, when you do, maybe turning that bag of holding opens a black hole and ends the game, or maybe it takes you to a whole new level.
  12. It’s about the journey, not the destination. Sure, you could rush through a dungeon, or a forest of kobolds in record time. But why? Killing all the kobolds is going to get you experience points, which add up until you get to the point where you can tackle golems and orcs and dragons. At work, try and be thorough. I find that I can get 90 percent of a project done in no time. That last 10 percent is the hardest, and where I learn the most. It’s also where the polish can be seen by others. You obviously need to complete projects, but it’s the journey towards all of your goals (the projects, the learning, etc) that really matter. And if you’re rushing through everything, it will show. Plus, there’s usually a low chance you’ll get some kind of magic item off a kobold…
  13. Eventually, your fighter has to work on more traits than just strength. The easiest character to play is usually a fighter. You’re just kindof a tank. You can walk into a room and fight and kill monsters. In Dungeons and Dragons, each character has a number of different abilities. These include things like Dexterity, which helps a thief to pick locks and all characters to avoid getting hit. There’s also intelligence, wisdom, constitution, charisma and strength. Each class of character will need different abilities to be higher than others. And as you level up you receive adjustments you can add to abilities. Naturally, a player will work on the abilities for their class first. For example, if you have a fighter, you’ll increase strength and constitution (which gives you more hit points), or if you have a thief you’ll work on dexterity. But, as the character progresses, you’ll invariably work on different abilities to unlock more advanced features of your class. The same is true at work. Let’s say you write code for a living (which many consider the magic-user of the business world these days). Eventually, you may choose to manage a team, become a scrum master, or manage products. For each of these, it will greatly help if you’ve dedicated a little time to working on your charisma ability. So while public speaking and management classes might not seem all that awesome for a code monkey, well, they will suit you well later in the game of your career.
  14. The more junk you have the slower you move. Each item that your character finds in the game will weigh you down a little. Eventually, when you find items, you’ll have to choose what you carry and what you leave behind. And sometimes, you’ll find yourself leaving behind things that you fought huge battles with monsters to attain. It’s hard to let go of things, but sometimes you have to. At work, you might have projects that you want to continue with but have to let them go to move into a new position. You might have equipment that you love but can’t keep. You might have data on your computer (or phone or iPad) that’s just wasting space. Keep in mind, that there’s a weight to that data, even if only mentally. Learn to let things go. Sometimes the character simply can’t move to the next room with a massive bag of treasure on their back.
  15. Energy draining monsters are the worst! As mentioned earlier in this article, once you reach a certain number of experience points (pretty much double from the previous level up) you get to move up in levels. However, occasionally you find undead monsters that can drain experience points from you. Ghosts, ghasts, ghouls and other monsters are the total suck. They can set you back pretty far. And sometimes permanently. We all know people that just suck the life right out of you at work. They always talk about how they tried an initiative and the initiative didn’t work, so they don’t want to try anything else. They always go back to the good old days and these days everything sucks. These energy draining attitudes must be vanquished. Regrettably, in Dungeons and Dragons, that often requires magic items. Positivity and strategy are the magic weapons in the corporate world. Results speak for themselves, so they are the vorpal sword of the board room!
  16. The best business happens in a pub. Yup, you’re not gonna’ buy that crazy Staff of Wielding in a regular-old blacksmith’s shop. Instead, sometimes you do your best business in a bar. Or a golf course. Or at church. When you’re in these places, be you, but don’t be afraid to let business happen where it happens!
  17. Teams need to be diverse. A party of 6 fighters really isn’t going to make it far. Nor 6 clerics. You need a couple of fighters, a cleric (to heal everyone), a magic user (maybe an elf), a thief (likely a halfling), etc. A well rounded adventuring party is key to the success of a campaign. The same is true for many teams at work. Different experiences and different backgrounds bring different ideas and perspectives. And bring everyones game up a notch. Of course, sometimes your half-orc rogue will spar with your paladin. But the team is better for having everyone together.
  18. Sometimes you have to retreat. A 4th level barbarian walks into a bar… It sounds like a joke, until it ends “and get shot with lightning by a level 36 drow lich-king. A/B testing, pivoting, fail fast. Have an open mind. Be creative, but if your initiatives aren’t working out, get out of the bar, before you get lit up. Having said that, let things play out. Sometimes the lich-king just hits you with a riddle and might give you treasure rather than have you dual it out. Modern business acumen is to try things, let initiatives play out, but be prepared to change course. Don’t be afraid to admin that you were wrong. This is a common trait of people who are right a lot.
  19. The best loot is free. I guess it’s according to how you define free. Organic growth is always best when possible. Buying customers, buying products, buying teams, etc are all problematic in their own way. Sometimes you do those things so that you can get to market quicker. But when you go into a dungeon and try and take on a stretch goal of killing yourself a giant spider, you’ll get rewarded by great loot. That +2 longsword will do you well. And it’s better to get it that way than to get it in a store.
  20. Sometimes you get a critical miss, sometimes you get a critical hit. In Dungeons and Dragons, if you’re trying to stab a monster, you roll the dice to see if you hit it. There are certain numbers on a dice that might have your character inflicting extra damage, because you hit an artery or something like that. There are other numbers that might cause you to actually stab yourself. There’s a certain amount of chance to everything we do. Maybe a critical miss is to get fired by your biggest customer for something you had no control over. Maybe a critical win is to have your largest deal ever come in during the last couple weeks of a year so the year ends historically awesome sauce. Maybe you ship software with a huge bug. Maybe you have some widgets made and they fall off a cargo ship on the way from China. I’ve seen it all. Sometimes things backfire. The best plan, have a backout plan. And be prepared for the critical hit pushing your business forward a year or two with one deal. If you don’t try, you might not get it!

SMIME in OS X Lion

In a previous article I showed how to get and install an SMIME certificate. Now let’s look at installing it into Mail. It’s really, really hard. First, open Mail. Then, click on the Mail menu and select Preferences. Then click on Accounts. Then click on the account you got an SMIME cert for. Then, in the TLS box, select the certificate you want to use. Next, go to compose a new message. You will see the little disclosure triangle to the left of the From dialog. Click on it and then check the box for the lock and the icon to the right of that, meant to look like a Beholder from Dungeons and Dragons. Beholders see well, so they can see if you’re the person who really is the person allowed to send the email. The lock encrypts email (provided you have a certificate for all recipients) and the eye of the beholder icon signs messages. Once you’re happy with your checkboxes, click on OK. Now, in your new email message, use the icons. Sign or encrypt. If you don’t have a certificate for a user, have them sign an email and send it to you. When you read their email you should then have their public key in your Keychain. Now, take your 100 sided dice and take the rest of the day off (after all, you just figured out how to make email more secure for your company). Also, you may notice that in these screens I’m using MobileMe certs. If you use the System Preferences pane to install MobileMe into your account then you’ll be greeted by the cert automatically being installed into your keychain for you. So for MobileMe users, you don’t even need to go get a 3rd party cert. I also use this on my work email, but didn’t want to put those screens in here (after all, I did misplace my tin hat and would hate to get hax0r’d by government goblins before I can track it down).

Dungeons and Dragons

I walked into my office and caught people playing Dungeons and Dragons.  It brought a smile to my face.  I haven’t played since I was in the 8th grade (or 7th) but I remember those days fondly, with Rob, Jason, Steve, etc.  And seeing that my office is as geeky as it should made me very happy.  It was on a Saturday, btw, so they weren’t playing D&D instead of working.  🙂