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Reflections on technology, business, and life

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:

  1. Autonomy: People want to have control over their work
  2. Mastery: People want to get better at what they do
  3. 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

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:

  1. 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.
  2. 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?”)
  3. 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.
  4. 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.
  5. 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.

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.comlivingforwardbook.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 ).

Make your Life Easier by Converting Decisions into Systems

You have a fixed amount of decision making each day (see Wired article, Conserve Your Willpower, It Runs Out), so it’s incredibly valuable to automate the unimportant decisions so you can focus on the valuable ones.

So carve out some time to reflect on what takes your time and energy, and what your goals are; and then invest energy in creating and sustaining systems, instead of trying to make new decisions constantly:

  • President Obama reduces daily choices like which suit to wear and what food to eat, so he can focus on important decisions
  • Personal finances – Ramit Sethi’s great blog post explains how you can automate your monthly savings and investing, so you don’t need to spend time each month managing it
  • Create weekly and daily routines around how you eat — think about how grocery shopping and weekly routines can set your week up for success or failure regarding food (see Scott Adams’ blog or Tim Ferris’ 3 minute breakfast recommendation)
  • I have a weekly work routine where my colleagues share our top priorities for the upcoming week each Monday as a way to communicate priorities, identify ways to help each other, and hold each other accountable (check out Execution:  The Discipline of Getting Things Done)
  • When I come home from work, I put my work shirt on the right side of the closet so I don’t keep wearing the shirt day-after-day (it’s one less thing to remember early in the morning)

How to Copy Photos from Apple Photos to Google Photos with Correct Dates and Times

I recently wanted to copy a large set of photos (over 10,000) out of Apple Photos (Mac-based photo management application/database) and save them on a USB hard drive so I could import them to Google Photos (cloud-based photo management service).  I did an export of all the photos out of Apple Photos, which saved the date and time information in the EXIF metadata, but not in the file metadata itself.  Here’s how I solved this (which I’m sure isn’t the most elegant solution), using a Mac:

  1. I found this thread, which explains how to use a few different tools to accomplish this, on photo.stackexchange.com
  2. I downloaded jhead for my Mac
  3. jhead for the Mac doesn’t support recursive (e.g. -r) calls, so I needed to consolidate all the images from sub-folders and sub-sub-folders — I did that using this command on the Mac terminal using this command “find ./ -name ‘*.jpg’ -exec cp ‘{}’ ./ \;“, which I found on this forum http://ubuntuforums.org/showthread.php?t=1385966:
  4. Then I deleted the folders and sub-folders, as I don’t need them for organization (I just want to get the photos backed up into Google Photos)

Talking Technology @ Bunker Labs

I spent some time at Bunker Labs DC, part of Capitol Post, in Old Town Alexandria — it’s an exciting place to be.  Bunker Labs is a startup accelerator (like Y Combinator or TechStars) focused on helping Veterans start and grow and new companies.  Their first class of startups is graduating in December 2015 and it’s exciting to be around several entrepreneurs as they are building brand new companies.  The first class of startups include:

Bunker has been hosting a Summer Series (which still has some exciting classes left if you’re interested) with free training for entrepreneurs in the DC-area — it’s a program you should check out if you’re a small business leader, entrepreneur, or future entrepreneur.  The upcoming classes are listed at Capitol Post Summer Series

I’m excited that I go to to be part of their series — I spoke yesterday about technology strategy for entrepreneurs, including how to pick technologies, develop associated processes, develop your technology goals, and define your enterprise architecture.

Here are the materials I presented to the class:

How to Pick IT Systems for your Small Business

If you’re the CIO, Director of Technology, IT Person, or Only Person (Solopreneur) at your organization, here are 5 areas of questions areas to consider when determining if a specific IT system or process would align with your small company’s needs:

  1. Alignment:  Does this system align with your business model (how you do business) and your current infrastructure?
  2. Lock In:  Would this system lock you (Vendor lock-in) into this vendor or system long-term?  Could you export your data and move to another system as you grow?
  3. Investment-worthy:  Is this system worth the investment of money and time (your time, your employees’ time, your customers’ time?
  4. Get Traction:  Would this system get traction with your employees and/or customers?  Does it align with how you do business, or would you spend your time forcing people to use it?
  5. No Huge Risks:  Are there any significant risks (red flags, deal-breakers) that should drive you away from this system? (e.g. cyber security, loss or productivity, removes future options you want)

align-framework

Shameless plug:  If you’re interested in learning more about setting up the technology for your company, or future startup, check out this free class I’m teaching next week (Thursday, Sept 10, 2015), sponsored by Capitol Post, in Old Town Alexandria:  Technology 101 for Entrepreneurs (How to Choose to the Best Systems for your Business).

How does a CTO Spend Time?

I’ve recently realized that I’ve been drawing a similar pie graph several times recently, explaining how I spend my time as a Chief Technology Officer (CTO) at a small business.  I thought I’d share for those interested in how I spend my time juggling the demands of CTO across various company priorities.

CTO_time

If you’re interested in learning more about small business CTO activities, including technology strategy when you’re too small to have a dedicated CTO, check out this free, upcoming training in Old Town Alexandria, sponsored by Capitol Post, that I’m teaching next month (Sept 2015):  Technology 101 for Entrepreneurs (How to Choose to the Best Systems for your Business).

The Kindle’s Best Feature: Seeing all your Highlights on one Website

The Amazon Kindle is great and it’s incredible it was introduced almost 8 years ago.  I realize it can still be a controversial topic for hard-core readers regarding whether paper for e-ink is better, but for anyone who doesn’t own a Kindle or does and doesn’t know about this feature, the best part of a Kindle is being able to see all your highlights from all your books in one place online at:

Some of you may already realize this, but it’s incredible.  The ability to be able to go back and review everything that resonated with you when you read it is incredible.  Sure, if you underline or highlight tangible, real-paper books; you could go through your old books on the shelves — but no one ever does.

Being able to scroll through a feed that shows the books in the order you last read them, and the highlights are incredible — here’s an example:

Screen Shot 2015-07-19 at 9.55.30 PM

While I don’t use this feature as much as I’d like to, I love the ability to scroll through and see what struck me in a book I was reading recently or years ago.

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