Lessons Learned by a CIO

Lessons Learned by a CIO


Everyone we meet is either a blessing or a lesson in that we can learn from them.  I’ve been blessed abundantly by meeting wonderful people in my career and my life.  I have also learned many lessons from others whose paths crossed mine during nearly 40 years in IT.  I kept a journal of lessons I’ve learned framed into two categories: “Things to do when I become a manager” or “Things to never do when I become a manager.”  I hope you will find some of these lessons interesting, and noteworthy.


Lesson 1 – Recruit Leadership Talent

You will face many hiring opportunities in a management position.  Some of your needs will be technical, some will be administrative.   All will require Leadership.  Learn to recognize leadership skills.  Ask interview questions that provide insight into the leadership nature of your candidates.  Of course you will cover the basic technical content.  However, strive to understand them as a potential replacement for you.  You can’t get promoted until there is someone waiting and ready to fill your shoes.  Here is my favorite interview question:  “Would you rather be the best player on a mediocre team, or a mediocre player on a Championship Team and why?”  The answer is meaningless.  The “Why” tells you everything.  Are they looking to contribute and learn?  Do they want to mentor and grow?  Or do they want to coast and let others carry the load?


You also need to identify Leadership Talent on your existing staff and nurture it.  Give visible projects, provide the necessary resources and keep distractions away.  Help them be successful.  And when they succeed, tell everyone what they accomplished.  My unofficial job description is simple: make my boss and my staff look as good as possible.


Every staff has its complement of HIPOs, LOPOs and POPOs.  HIPOs are your High Potential employees.  Grow them and reward them handsomely.  They are the future management team for your company.  LOPOs are the Low Potential employees.  You need them too.  These are the ones that may not want to manage but are happy in the trenches making everything work.  Notice that I never mentioned competence.  I assume you will only hire competent people.  Potential is a function of ability to advance and grow.   So what are POPOs?  Pardon my language, but these are the employees that are Passed Over and Pissed Off.  They can be HIPOs or LOPOs.    Their continued career growth could depend on how you mentor them.


Lesson 2 – Mentoring

Mentor continually.  Programs that assign mentors for the first few months are simply onboarding exercises.  Continually look for ways to make your direct reports better.  Continually look for flaws to correct.  Treat them like your children.  Parent them.  Encourage, teach, praise and sometimes correct them throughout their entire lives (careers).  Be their role model.


Lesson 3 – Look at Everything Through Other People’s Eyes

I am firmly convinced that most IT Executives would rather be right than successful.  When presented with an opportunity, many CIOs see the potential risk and the effort needed.  Look at each opportunity through the eyes of the requestor.  They are coming to IT for help.  Be helpful from the beginning.

  • Look at every application request through the eyes of the user that will spend their days working in that application. Engage them.  Let them drive functionality.  Give them the bells and whistles up front.
  • Look at each Helpdesk request through the eyes of the requester that is struggling to get their job done with broken technology. Technology always works for the CIO.  Your team will see to that.  Not every employee is so fortunate.
  • Look at your projects through the eyes of your team that missed a lot of family activities to make sure they hit YOUR date.
  • Look at failed projects through the eyes of your owners. Take responsibility for failures.  I send many emails of apology.  We are all human and we make mistakes.  Admit them and learn from them.  The lesson can be expensive and unfortunately the final exam occurs before the lesson.


Lesson 4 – Thinning the Herd

This might sting a little but: STOP FIRING PEOPLE!   Firings rip at the fiber of your company’s culture.  It violates the employer/employee relationship.  But most importantly, it breaks down the “Circle of Safety”.  Simon Sinek, in his book Leaders Eat Last describes the Circle of Safety in terms of how the US Military Operates.  If you have not yet read it, read it immediately.  Military personnel risk their lives for each other because “They would do it for me.”  They trust each other.  We need to act the same way in business.  Protect your employees and their families.  Hire better.  Spend more time getting to know your future coworker.  We did a marvelous job at American Textile when we hire new employees.  We team interview.  All Sr. Executives interview candidates.  We debrief.  We discuss.  We do not hire until we have consensus.  Firing an employee means YOU hired the wrong person or did not mentor sufficiently.  Terminating is easy.  It is much harder to correct the problem.  Parent them.  (Hmmm, another parenting reference)  You would never send a child away for misbehaving.  Correct, encourage, discipline, teach, and mentor.  Take the time to understand the root cause of the behavior and fix it.  There are only two scenarios when termination is appropriate:

  1. Malicious, felonious behavior – If an employee sexually harasses or assaults another, you have no choice but to protect your company and terminate.
  2. Malicious, gross insubordination – If an employee refuses to follow policy or do their job despite repeated insistence and formal discipline, you need to be fair to the employees that are working hard for you and terminate. This is not so much you dismissing as their career suicide.


Lesson 5 – Keep a Sense of Humor

As a CIO, you are responsible for all technology.  I feel personally responsible for anything that has electricity or data running through it.  To break the tension I approach everything with a sense of humor.  Taking away smart phones and blocking web sites make you unpopular.  I display a sign in my office that reads “Lightning Rod of Hate”.  It is, of course, to poke fun at myself for being the “bad guy” that all CIOs must be occasionally.  Make time at every staff meeting for humorous anecdotes.  Laugh at jokes made at your expense.  You know the ones, “everything can be fixed by turning it off and back on.”  Stop taking yourself so seriously.


Your takeaways are: Recruit Leadership not just Technical talent, mentor your team continuously, see through your users’ eyes, protect the Circle of Safety, and for heaven’s sake learn to laugh at yourself.