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.



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

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)


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.


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).

How to get Started with CMMI

Capability Maturity Model Integration (CMMI) is a process maturity model focused on helping organizations mature how they create things (CMMI for Development), provide
services (CMMI for Services), or buy things (CMMI for Acquisition).  The predecessor to CMMI, CMM, was created back in the late 80’s and early 90’s due, in part, to systemic issues with software development in support of Department of Defense projects.

CMMI often gets a bad wrap for being a bureaucratic, paperwork-heavy set of compliance checklists that doesn’t help anyone and is really annoying.  While it certainly can be, if you focus on using it to make your processes better (and not just check the boxes to get a rating) it can be a great way to mature how a company operates.  I’ve been really impressed with how powerful it can be, especially for small technology companies where processes are not formalized, and project teams depend on heroes from each team, with prior training and experience to ensure project success.

CMMI can be a very valuable investment, that transforms a company into one that has projects that are more predictable and lower risk, and an organization that is continually improving; but the investment isn’t small (think on the order of $100K).  Some of the big cost areas are:

  1. Sending people to take classes in CMMI
  2. Allocating people’s time toward planning, creating, and training process development and improvement
  3. Bringing in consultants to coach and support process improvement
  4. Bringing in a Lead Appraiser to formally assess an organization for compliance to CMMI

If you’re interested in pursuing CMMI for your organization, I’d caution you that it’s a big undertaking, and you shouldn’t pursue if it you’re just doing it to try to be impressive to potential clients or get the ability to bid on work that requires CMMI.  If you don’t buy into the idea of investing time and money into making processes better, you’re going to spend lots of money making everyone’s life worse at your company

If you are excited about making that investment in how your organization runs (very much working on your business instead of in your business, see E-Myth Revisited), make sure you take your time in selecting people to support your pursuit who are great at what they do and bought in to how you do business.  If you’re a big Agile development shop, don’t work with someone who has “taken an Agile class or two” — you want to work with people who really know your business model and business perspective well.

Some recommendations:

  • Take the 3 day Introduction to CMMI from a great teacher — someone like Bill Smith, who makes CMMI interesting and engaging
  • Go to a CMMI conference (SEPG) if you can — this is a pretty small community, so it’s a very accessible community to go to one conference and get to chat with the thought leaders and meet companies like yours
  • Get a hardcopy of the CMMI book for the constellation you want to pursue (e.g. CMMI for Development) and actually read through some of it.  It’s a big intimidating book, but the introductory content and the overviews of each of the practice areas is pretty accessible.  You’ll want to keep a copy of this and mark it up as you learn more about it and how it relates to your business.
  • If you get consulting support (which is critical, unless you have a CMMI pro on your team), shop around and really interview them well to understand their style, areas of expertise, and level of experience — I’ve been really impressed with consulting from thought leaders like Broadsword, who know the Agile-CMMI intersection very well (and their senior leaders, such as Jeff and Ross put out great blog and webinar content), and great appraisers like Frank Koch who really help companies understand what CMMI really means for a company like theirs
  • Don’t try to “do CMMI” in a vacuum from other parts of your organization — any other process improvement activities, such as ISO 9001, back-office process development, or overall organizational process architecture should be integrated (or you’ll have to spend more energy integrating them later)
  • Don’t over-engineer — it’s important to avoid letting technical people create too much process instead of focusing on the most valuable process improvement work
  • Ask questions — the CMMI community is full of people who want to help people make their companies better

Small Business Cyber Security 101

Way back in 2009, NIST released a 20 page document that is a great set of fundamental
recommendations for small business cyber/information security.

There’s certainly many more things you should be doing, but it’s a great place to start if you’re an IT Director or CIO at a small business and you’re not sure what you should be doing to secure your company’s information and systems.

There’s plenty of ways to spend money on shiny cyber security software and devices, but this is a great foundation to build your company’s defenses on before start buying Intrusion Detection Systems or hiring Penetration Testers or Social Engineers.

Fire and Forget: Difference Between A Vice President And A Janitor

The military classifies some missiles as “fire and forget” because they don’t need to be missilesmonitored after they are fired.  Great leaders are like this — their boss can give them an objective and know they don’t need to follow up over and over to ensure success.

This concept is incredibly important in your career as take on more and more responsibility.  Junior team members are expected to work hard and be guided by leaders to support the team.  However, there is an inflection point where the the value people add to the organization separates based on those who work hard and those who will ensure success.  It’s great to be someone who works hard to support the team, but it’s a whole different level of value to an organization when someone can be trusted to accomplish an objective without needing oversight.  This doesn’t mean you shouldn’t check in with your boss, or ask for advice or mentorship, or request in-progress reviews (IPRs) or other meetings to touch base — it means that your boss sees you as a person they can “fire and forget”:

This type of high-value leader doesn’t wait for someone to check on them if they have questions or obstacles (they analyze and solve them, or they ask for help, or they bring recommendations to someone for validation)

Business Insider wrote a post several years ago about a related quote by Steve Jobs:  Steve jobs explained that the difference between a janitor and a Vice President is that a janitor can have excuses for not getting their work done, but a VP is responsible to succeed, regardless of obstacles.

“Somewhere between the janitor and the CEO, reasons stop mattering,” says Jobs, adding, that Rubicon is “crossed when you become a VP.”

In other words, you have no excuse for failure. You are now responsible for any mistakes that happen, and it doesn’t matter what you say.

Invest time and energy and become a leader that people can trust to get things done when you say you will, without oversight or reminders.

Ideas at the Intersection of Agile, Startup scaling, Business Process Management, and Organizational Design