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CIO 101 for Entrepreneurs

This morning I got to share IT infrastructure, business strategy, and business
architecture tips and recommendations with some local current and future entrepreneurs at The Capitol Post in Old Town Alexandria. Capitol Post is a great organization focused on inspiring Veteran entrepreneurs to find professional clarity and scale those visions. They offer several great things, including a cool co-working space right in North Old Town Alexandria, classes, and a startup accelerator program.

Here are the slides and strategy template I went through with the group this morning, helping entrepreneurs deal with IT. We talked about:

We talked about how IT for non-technical entrepreneurs can be like personal finance for non-financial people — it’s very important, but it’s hard to motivate yourself to invest the time you need to understand it, make some solid plans, automate it, and then move on to creating value.

It’s been a year since I last taught at Capitol Post (https://mikehking.com/2015/09/11/talking-technology-bunker-labs/), and it’s great to see how much they’ve grown (the office is beautiful and their getting ready for their next cohort to go through the Bunker Labs DC accelerator.

I Draw on a Whiteboard for a Living

While it’s a gross oversimplification to say that I draw (I use the term “draw” loosely) on a whiteboard for a living, it’s amazing to reflect on how much of my time is spent using a whiteboard for all kinds of things (most of which are incredibly valuable to the work I’m doing). I can tell I’m spending a majority of my time on the whiteboard while at work, because my smartphone pictures are about 25% whiteboard pictures and 75% pictures of my adorable son (and beautiful wife).

As a Chief Technology Officer, I end up using the whiteboard for all kinds of things, like:

Facilitating solution architecture discussions and development with subject matter experts (technical experts) and people who understand the needs of our customers, creating things like Concepts of Operation (ConOps), system architectures, and unifying proposal roadmap figures
Outline and storyboarding proposals before we start digging into these (This is key — just like software engineering, you need a plan/architecture before anyone writes any code)
Creating product backlogs and release plans, where I sometimes throw in some painter’s tape and sticky notes so I don’t have to keep rewriting the user stories when I move them between releases/sprints
Creating user interface wireframes (whiteboards are great for this, because they force you to focus on the big picture — just like using a Sharpie to sketch these on paper, instead of a pen)
Creating process map and flowcharts with process owners, trying to define current and to-be business processes (and sometimes trying to map the value of different steps while refining)
Sketching out tables to validate content structure before going off to create them in a tool like Microsoft Office or Confluence

That said, I want to be clear that the pictures of my wife and son are much cuter than my whiteboard pictures.

March 8, 2016 0

Engineer Grandpas are Pretty Cool

My grandfather, a NASA engineer who worked on telecommunications systems for many of the Apollo missions was always coming up with things I never saw anyone else doing. Some of that came from having engineering education and skills, but much of it came from a willingness to learn new things — he was never intimidated to do something new.

He loved telling the story of his father wanting to keep squirrels off his grape vines, so he
ran electrical wire through the trellis the vines were on, and put a button by his back door. When he pressed the button, it would give the squirrels a zap and they didn’t come back to try new grapes. (Apparently you could tell which squirrels were new to the neighborhood, because each squirrel tried to eat his grapes exactly once.)

When my father was in college, his 1960’s VW Beetle was having significant engine

problems. My grandfather didn’t want my dad worrying about the car when he should be focused on school, so my grandfather bought a mechanic’s book on the VW bug and over a weekend he rebuilt the entire engine in his garage and brought it back to my dad. I heard this story while helping my grandfather adjust the spark plug timing on an old 1970’s Plymouth in his driveway — it was a fun afternoon learning how engines run.

My grandfather came over to our house when I was a kid to help us hang a bird feeder in our backyard. Instead of some more boring options, he came over with a bow and arrow (pretty cool way to show up at your son’s house), fired an arrow over a tall branch with a rope attached, and used the line to hang the birdfeeder with an anti-squirrel dome over it, far enough from the tree that the squirrels couldn’t jump from the ground, tree, or branch to get to the food. We had that birdfeeder for at least 15 years, and a squirrel never managed to get on it.

My grandfather installed counterbalancing weights on strings and pulleys for all his sliding screen and glass doors, so you could open and close them with a tiny touch — it wasn’t necessary, but it was a constant touch reminder that with a little effort, creativity, and patience, you can do some cool stuff (and this was long before you could Google, YouTube, or Quora search something).

March 4, 2016 0

Buy a Sandwich and Support Christian Student Athletes

I’m excited that, for the first time, the eight Jersey Mike’s Subs shops in Northern Virginia have selected NOVA Fellowship of Christian Athletes (FCA) to partner with for the month of March, as part of their annual Month of Giving. Every year, Jersey Mike’s stores pick local charities to partner with for the month.

Every day in March, everyone who buys something from a participating Jersey Mike’s store will have the opportunity to add a dollar or more to their order, to donate to FCA. While that’s exciting, the big day is Wednesday, March 30 — on that day, 100% of the day’s sales (every single dollar) will be donated to FCA from these 8 stores. So if you’re a fan of FCA’s mission of ministering to student athletes and coaches, please put in some big catering orders or bring all your friends on Mar 30!

Buy some tasty sandwiches from these Jersey Mike’s stores this month to support FCA’s great mission to invest in student athletes and coaches across the NOVA region:

(And if you’re excited to find other ways to support FCA, please ask me about their Fellowship Dinner, coming up on Sunday, April 24 in Falls Church. It’s a great every year to hear how God has blessed students and coaches connected to FCA.)

March 2, 2016 0

Don’t get Stuck in the Past, Present, or Future

As I’ve gotten older, I’ve realized how each person has different tendencies. Some of us are introverted. Some are analytical. In addition to personality axes like introverted vs. extroverted, thinking vs. feeling (see Myers-Briggs); people often have a tendency to either live in one of these times instead of balancing their time among them:

Past – Looking back at what has happened in your life, learning from mistakes and reflecting on what happened and what they learned about themselves through those experiences
Present – Engaging in the present, connecting with people and experiences as they happen
Future – Looking down the road and making plans, setting a vision and goals for your life

Each of these perspectives is important in moderation, but people sometimes get into trouble by being too focused one view — they can get stuck reliving the past (they miss life entirely, always looking behind them), living only in the moment (reacting to the present without looking down the road and making any plans) so life happens to them instead of creating the life they want, or only focusing in the future, so life passes them by while they make and refine plan after plan. Don’t get stuck in only one of these — make time to look at all 3.

To quote the cinematic classic Spaceballs, which is almost partially relevant to this discussion:

Colonel Sandurz: Try here. Stop.

Dark Helmet: What the hell am I looking at? When does this happen in the movie?

Colonel Sandurz: Now. You’re looking at now, sir. Everything that happens now, is happening now.

Dark Helmet: What happened to then?

Colonel Sandurz: We passed then.

Dark Helmet: When?

Colonel Sandurz: Just now. We’re at now now.

Dark Helmet: Go back to then.

Colonel Sandurz: When?

Dark Helmet: Now.

Colonel Sandurz: Now?

Dark Helmet: Now.

Colonel Sandurz: I can’t.

Dark Helmet: Why?

Colonel Sandurz: We missed it.

Dark Helmet: When?

Colonel Sandurz: Just now.

Dark Helmet: When will then be now?

Colonel Sandurz: Soon.

Dark Helmet: How soon?

February 26, 2016 0

Breaking the Rules at the Local Airport

You don’t always have to play by the rules

My father often used boldness (be confident), candor (you’ll be surprised what people will agree to when you ask plainly), and creativity to find ways to get some amazing deals and create fun adventures for my sister and me.

He would go into car dealerships who were offering something like a free picnic set if you would test drive a car, and explain “Look, I’m not going to buy this car. We can go on a test drive if you’d like, but it’s only going to prevent you from selling to someone else who comes here.”

Long before the tragedy of 9/11, when I was probably 8 or 9 years old, my father took me to the small, local airport in Manassas because I was a big fan of airplanes. Normal fathers would have hung out, watching the planes take off and land with their child, and have a great afternoon. Not my dad — he walked right up to the air traffic control tower with me, knocked on the door, and asked if we could come up and watch the planes and the controllers while they directed traffic. The man who answered the door was surprised (I’m guessing normal people didn’t randomly knock on the door and ask), but he welcomed us up — it was an awesome experience as a child. My father later brought me back to the airport and persuaded a local pilot to let me sit in his plane while he gave me a tour of every control and dial.

These were powerful experiences as a child, realizing that there’s a whole world of adventures that are available to you if you ask. Adventures that aren’t listed on the official brochure.

February 24, 2016 1

Organizational Operating System Upgrade?

I’ve started reading Brian Roberton’s book Holacracy, which talks about an organizational
management approach focused around self-organization and protected autonomy. It’s an interesting attack on the base assumption that we should build companies in the traditional, top-down approach where a CEO directs leaders who direct other leaders, through layers and layers of business leaders. Holacracy is the first non-traditional approach I’ve seen to business architecture (designing a company) that is cohesive and specific. Managing teams with a methodology like Agile Scrum is powerful, but Scrum doesn’t scale to an entire organization, without armies of Scrum of Scrum Masters. Early in the book, Brian lays out this metaphor of a business having its own operating system (including the org chart, business processes, etc.):

…the operating system underpinning an organization is easy to ignore, yet it’s the foundation on which we build our business processes (the “apps” of organization), and it shapes the human culture as well. Perhaps because of its invisibility, we haven’t seen many robust alternatives or significant improvements to our modern top-down, predict-and-control “CEO is in charge” OS. When we unconsciously accept that as our only choice, the best we can do is counteract some of its fundamental weaknesses by bolting on new processes or trying to improve organization-wide culture. But just as many of our current software applications wouldn’t run well on MS_DOS, the new processes, techniques, or cultural changes we might try to adopt simply won’t run well on an operating system built around an older paradigm.

Brian describes an entire methodology, like some of the prescriptive ceremonies and roles you see in Agile Scrum; which I’m still wrapping my head around. The core tenets of independent, autonomous roles seems incredibly powerful, because it seems to make companies much more scalable. And it reminds me of the core factors that Daniel Pink identified in Drive as what employees wants in their job:

Autonomy: People want to have control over their work
Mastery: People want to get better at what they do
Purpose: People want to be part of something that is bigger than they are

Holacracy’s concepts explained in 107 seconds: https://www.youtube.com/watch?v=MUHfVoQUj54

February 23, 2016 0

Life Advice from a Man of Many Skills

My dad was full of lots of great advice — he was raised by polar opposite parents, a reserved NASA engineer and a high-energy, life-of-the-party mother who was always a great hostess. His wisdom comes from a diverse career that includes working at McDonald’s, selling microwaves when they were first available, selling real estate, teaching sixth graders, working in the tax industry (H&R Block), providing customer service at Home Depot, delivering car parts anywhere they were needed, and mentoring teenagers who made some bad choices early in their life:

Prepare for big purchases long before you need them: I remember going car shopping when my father when I was about 12 years old. Our car was running fine, but my father wanted to know what car he would buy if one of our cars died suddenly on us; so he wouldn’t have to rush into a decision. And I think he was excited to try to convince the salesmen that his young son was really the car purchasing decision maker, which was pretty amusing.
Whenever I was competing in something, my father was quick to find ways for me to observe others to learn what to do, and what not to do. When I was taking swim lessons, we’d go early and watch other kids jump off the diving board. When I played sports, we’d come early or stay late to watch other kids play. When we went to the boardwalk at a beach, we’d want other kids play carnival games to figure out if you could win and if so, what the trick was. My father is also always quick to ask recommendations and tips from people, like waiters at restaurants (“What’s your most popular dish? What’s your favorite?”)
Think through the total cost of ownership of things — he loved to remind me that he thought dual exhaust was so cool when he was shopping for his first car, but his father reminded him that he’d have to buy twice as many mufflers when they failed. And those 17″ allow wheels means your tires will just cost that much more to replace.
“There’s no such thing as extra credit in this house“: You might think this means we didn’t have to do extra credit when it was offered in school. You’d be wrong — this meant that extra credit in any form, when offered, was required; just like completing all our required assignments.
Never be a afraid to try: I remember several times as a child where my dad would encourage me to do something that seemed impossible to do or win. In elementary school, there was an annual egg drop contest where kids would build contraptions to protect an egg that was dropped from an extended fire engineer’s ladder. My father encouraged me enter both the standard category and the category where the entire egg-holding-contraption could only be made from toothpicks and glue. It sounds like a crazy mission, but we created a football-looking thing with a little egg compartment, and I was the only kid to even try to make anything for that category. It’s a great lesson to teach: You can’t win if you don’t show up and try

Growing up, my dad loved to quote Mark Twain — it was frustrating at the time, but I appreciate him reminding me:

When I was a boy of 14, my father was so ignorant I could hardly stand to have the old man around. But when I got to be 21, I was astonished at how much the old man had learned in seven years.

February 18, 2016 0

Work on your life, Not just in it

I was chatting with some friends recently about making time to reflect on your life, and making time to really connect with close friends, digging into each other’s lives. It stuck me that the concept of ‘You need to work on your business, not just in your business’ (paraphrased) from The E-Myth is very relevant to both business and your personal life. Gerber is making the point that entrepreneurs often get mired in the distractions of doing day-to-day things (operations) without making time to build a business (strategy, business architecture) — things like enabling the company to scale by defining strategic objectives/plans, processes, expectations, etc.

Just like that, it’s all too easy for me to live my life in a reactive mode, trying to work on the next crisis, both in my job at at home, without taking time to sit down, reflect, think about my priorities and objectives, and what types of mental models/worldviews are informing those goals. In your life, don’t forget to make time to think about your life — whether it’s in a structured way (e.g. creatingyourlifeplan.com, livingforwardbook.com) or just taking time every month or quarter to reflect, journal, and dream about what you want to change in your life. Companies are much better at strategic planning than most people are (though certainly not perfect Holacracy Bicycle Metaphor ).

February 16, 2016 0