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Five Leadership Lessons From Former Bosses

Over the past 16 years I have had a chance to work for more than 12 different bosses. While some have been better leaders than others I’ve tried to learn from each of them. Below are five leadership lessons that I’ve picked up from them and subsequently been able to use with my teams.

  • Retain Talent – Go out of your way to retain your good people. Make it personal and include the family when possible. One of my star players shared with me that she had dinner plans with her husband for their anniversary. I called ahead to the restaurant and bought them a bottle of wine with the message “Happy Anniversary and thanks for all of your hard work.”
  • Success Metrics – Use team success metrics to motivate your team and create a strong culture of driving to success rather than some arbitrary stopping point like a release. As we’ve written about before don’t confuse product releases with success. Identify and start to measure business metrics that the team can understand and rally around. Determine what to measure based on the drivers of revenue and cost of your business. Share these metrics with your organization and celebrate success and dig into areas where you are falling short to identify a get-well plan.
  • Guiding Principles – Empower your team with guiding principles that help them to make day-to-day decisions. Similar to architectural principles, guiding principles empower your team or organization to make decisions on their own. Have the team help develop them and make them visible. Revisit them on a regular basis. This especially helps during times when you need to drive mindset change. You will be surprised at the questions and conversations that come up as you drive to calibrate on mindset shift.
  • Poor Performers – Do not ignore your poor performers. Use these three axes to evaluate employees performance. If the problem is performance, attempt to help the employee by coaching and mentoring. If the problem is behavioral or if they don’t respond to coaching, you need to manage them out quickly. Depending on your organization, it may be difficult to manage poor performers out but this is not an excuse to ignore it. Poor performers can be a drag on the team, poor behaviors can be cancerous. And don’t forget they are a reflection of your work as well.
  • Feedback – Give feedback to your team members frequently and in real time. Don’t wait until the annual review to give feedback. Gen Y and Millenniums are more accustomed to instant feedback and communication. That means you may have to adjust your style as you work to coach and guide your direct reports. Utilize all available communication medium to praise. Send them an email recognizing them for their actions and tie it to the positive impact it had on the business or the team. Leave them a voice mail. And of course the good old fashioned in person or one by one conversation works well. You will soon seen the positive motivation you inject into your team.
  • Business KnowledgeUnderstand the business. The only way for you to be successful is to be able to speak and work with other business executives, which means you need to make the effort to understand their roles. Block off your calendar to sit with peers to see what they do on a day-to-day basis. The path to a CIO/CTO role is by being a great partner to the business.

Hopefully you can use some of these with your teams or at least make you aware that you should periodically look back for lessons learned. Often these lessons learned make great one-on-one topics for junior managers interested in improving their leadership.


Two Important Leadership Tests

Somewhere in the mix of my father, the United States Military Academy and the Army I learned two important self tests for leadership: the “Man in the Mirror” test and the “Would I” test.  While I am human and have failed these tests and their exacting standards from time to time, I think they have on balance served me well.

The Man in the Mirror test is:  Can you look yourself in the eye (in the mirror) after you’ve made this decision?  The question is profound and very powerful.  It alone, if asked at the appropriate time, might keep you from making otherwise foolish ethical choices and poor leadership decisions.  Would it have kept Lay and Skilling, Maddoff or Kozlowski  from  violating their fiduciary responsibilities?  While I can’t answer this question, I do believe that if a person is “on balance good” and hasn’t succumbed to greed induced sociopathic behaviors, then this test will help keep them straight if asked at the appropriate times.  As we’ve written before, building tests such as these into your daily routine can help you from taking the long journey of small steps towards unethical behavior.

The “Would I” test is much more focused on the concept of “Leadership by Example” that we discuss in The Art of Scalability.  This test is also simple.  You just ask yourself “Would I be willing to do what I am asking this person to do?”  Maybe you are asking someone to work during their anniversary.  Perhaps you are asking someone to skip a child’s sporting or school event.  Maybe you’ve just given them some last minute assignment that will cause them to work all night, like completing a presentation for you to give at a conference tomorrow.  “Would I” is not an excuse to be lenient on people, or not to hold people to aggressive standards.  Rather, it is a test to determine if you are truly meeting the expectations that you hold of those around you.

In one respect, the “Man in the Mirror” and “Would I” tests fly in the face of concepts such as Strengths Based Leadership.   They exist to keep us from failing due to shortsightedness, a lack of introspection and aggressive or excessive egoism.  They are rooted in the concept that we sometimes fail because we fail to see how our actions will be perceived or acted upon by others.  Leaders are humans, and leaders make mistakes.  The “Man in the Mirror”, if employed often, helps us to avoid dangerous ethical pitfalls and the “Would I” test helps us avoid burning out our teams.

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4 Types of Organizational Cancer

Don't allow cancerous employees to ruin your organization, product and company. Treat and excise these tumors quickly.

I’m a cancer survivor.  Not the kind of biological cancer that took my mother and some of my friends, but the evil and malicious cancer that mutates and destroys the people and performance within an organization.  I’ve learned through my personal battles with “org-cancer” that you have to act quickly and decisively to excise these “org-tumors” the minute they are detected.  Early detection and treatment are the only way to keep these beasts from destroying your organization, your product and your company.  Here are the four most common types we find in our practice:

The Information Hoarder – This nasty cancerous employee believes that information is power; the more he has relative to everyone else, the more powerful he is.  These cancers don’t like to share information unless it makes them look good. Information that makes them look bad gets secreted away, allowing problems to fester and destroy your product or customer relations.  This employee will provide or expose information only when it meets his or her own needs.  This is an engineer who might not want to share knowledge about a codebase, an executive who only shares metrics that show stellar results and hides those that show problems, or a sales person who refuses to share how he or she has been so successful.  Solution:  Remove this cancer before it grows.  Do not promote this individual and do not allow others in the organization to believe this behavior is acceptable.  As a CEO, this cancer is very dangerous for a board of directors.

The Bragging Hero – As Fish has written before, you should be creating a culture that embraces those who keep problems from becoming crises.  That said, nearly every business has a crisis from time to time and typically there are a number of heroes who help solve them.  You want the type of hero who corrects a situation and moves on without fanfare.  Be wary of the hero who repeatedly trumpets his or her accomplishments.  Often this person can be seen hanging around the Information Hoarders and sometimes they are the same person; an information hoarder who brags about his or her heroic accomplishments.  Solution:  Sometimes this cancer can be “treated”.  Explain the need to reduce self publicity and if you are unsuccessful, excise.

The Gossiper – With all the talk about how much time a company should spend on new products vs maintaining old products, who has the time to invest in morale destroying gossip?   Time spent gossiping by definition steals away from both new product or maintenance time.  This cancer often greets people with “Did you hear about John’s affair?” or “Have you heard about Jeanette’s new boyfriend?”  Let’s be honest – most of us indulge in this behavior from time to time – but I’ve seen people spend an hour plus a day discussing the latest gossip.  You can spot this person because they think they know something about everyone and they aren’t afraid to share it.  Baseless, third hand rumors can destroy the lives of good employees.   This type of cancer shows up in more extroverted professions like project management.  Solution:  You can try to treat this cancer by explaining the effects of their actions on the lives of others.  Most likely you will be unsuccessful and you will need to excise the mass.

The Passive Aggressive Seditionist – This is the cancer upon which the phrase “grin-f&#$er” was based.  This person will say “yes” and make you believe he or she is on your side and “fighting the good fight” all while spreading rumors about you and maybe even making up some stories of his or her own.  They are often seen in the company of Gossipers and sometimes will be the rare but extremely deadly combination of Passive Aggressive Gossiping Seditionist.  Whether of the merged mutant variety or the base type, there is no treating this cancer.  It must be irradiated, chemo’d and excised with extreme urgency.

Make no mistake about it, you have no obligation to continue to employ these mutated employees.  Very often these employees get a lot done, but as we’ve explained in the past it is critically important to evaluate both behaviors AND performance when building a culture of excellence.  “Treating” (counseling) or removing them is the right thing to do, and you can never act too quickly.

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4 Things I Wish I’d Learned as an Undergraduate

I recently had the honor to speak with the CS and IT majors of the USMA (West Point) Class of 2010.  Recognizing that these young men carry an incredible burden for all of us,  I struggled for what I could tell them.  These young men and women, after all, are going to be the tools of our international efforts against terrorism for quite some time to come and in 5 years will likely see 2 combat deployments.  The price they pay for their “free” education is much higher than the one my partner and I paid and larger still than the 99.9+% of the rest of their generation (those that never serve their nation in uniform).

I settled on trying to pass along four things that I wish I had learned in school – before the Army and before becoming a civilian.  These aren’t four things that I wasn’t taught mind you.  I may have been taught some of them, and at any rate the burden for learning should really be placed upon the student – especially in college.  These are four things that I wish I had recognized, retained or learned on my own; four things that would have made my Army and civilian life much easier.  Here they are as I discussed them with elements of the USMA Class of 2010:

1)      Moral and Ethical Challenges Occur Frequently – More So Than You Might Think

It doesn’t matter if you are in the Army and parts for your dead-lined vehicle magically appear overnight or you are reviewing the use of company assets and find that people are using company assets for personal use – potentially in violation of company policy.  Sometimes even people who are on balance “good” make ethical mistakes.  And make no mistake, there are morally bankrupt people committing unethical acts at an incredibly high rate all around us.

Most of us, quite honestly, are ill prepared to address ethical issues upon graduation.  Many schools barely touch the subject.  Even the service academies, with their strict honor code, too often paint topics as black and white rather than the spectrum of blacks, whites and grays that occur in the real world.  As we’ve written in the past, the journey to moral bankruptcy isn’t one giant leap, but a series of small steps.  Draw lines in the sand early in your career so that you know you are heading in the wrong direction as you progress.  Build a support group of people who will tell you the truth and help guide you should you start to go astray.

2)      Smart People and Terrible Teamwork Equals Crap Technology

Intelligence is only one of many independent variables (inputs) resulting in the dependent variable (output) of overall team performance.  Behaviors of individuals within the team are another equally important independent variable.  Leadership and culture are important moderators of this equation.  It is possible to have brilliant jerks, incapable of getting along with anyone, who completely destroy the output of the team.

We should reward people on their accomplishments and their ability to work as a team.  Intelligence is great, but we simply don’t pay people for being smart.  Who cares if you are smart if you can’t either get something done or alternatively destroy team morale and throughput?  Consider using this 2×2 matrix presented within The Art of Scalability to evaluate the individuals in your team for both behaviors and accomplishments.

3)      Leadership is about EQ – Not IQ

Our frequent readers will also remember this from our postings abroad.  As Malcolm Gladwell has indicated within his book Outliers, all of the evidence points to the notion that the most successful leaders have some minimum IQ.  But IQ alone is not sufficient to be a successful leader.  The greatest leaders have high emotional quotients, often considered a combination of social intelligence and emotional intelligence.

Two of the world’s foremost experts on the topic of leadership and social and emotional intelligence, Richard Boyatzis and Annie McKee have written two wonderful books on this topic:  Primal Leadership and Resonant Leadership.  In keeping with our theme of 2×2 matrices, here is Richard and Annie’s representation of commitment and emotional quotient.  The Y axis indicates how mindful the leader is of himself/herself (emotional intelligence) and how mindful they are of others (social intelligence).  The X axis indicates their overall emotional tone towards others.  Successful (aka Resonant) leaders have on balance a positive emotional tone and are in touch with themselves and their teams.

4)      It’s All About Performance

See my brief discussion of the model for success.  Superior performance, I argue, is measured as improving long term stakeholder wealth.  This might be emotional wealth in the case of some non-profits or financial wealth in the for profit world.  This means getting things done on time, on budget, in an ethically appropriate manner, with the right quality and meeting the expectations of stakeholders.  Time and experience are just moderators to this equation; they only help performance.  Independent variables are intelligence, drive, commitment, behaviors, etc.  Look to build the right teams with the right behavior at the right time.  Don’t get tied up in how much “experience” people have.  I’d rather have a dedicated person with 5 years of experience than a lazy person with 20.


Speak in Terms of Objectives – Not Actions

Have you ever been in a position where a project you were managing was late or over budget? Have you ever supported an application that had a customer impacting service outage? How did your boss respond to these issues? Did she say something like “I want a review of our quality strategy” or “I’d like to see our application rollout strategy”? Maybe they asked for something even more nebulous and less connected to the issue at hand like “Show me our site and product integration strategy”. Huh? What does that mean?

It’s easy for managers to react to incidents and problems by requesting that certain actions be taken by a person or team. The problem with such an approach is that it feels like a punitive action to the people from whom the action is being requested. Maybe the group or person needs to receive performance feedback, but by asking them to take an action you are not really giving them feedback. If your goal is to both provide feedback and ensure the underlying issue is corrected then provide candid performance feedback and explain the desired goal of the corrective action.

Great leaders understand intuitively that they should speak in terms of desired end states and then ask for plans to achieve those end goals or states. Another approach is to use the Socratic Method and ask your team what an appropriate end goal should be, whether they’ve achieved it and how they should correct their approach to achieve that goal. The first is probably the best approach when the team is overwhelmed or you are in the middle of a crisis. The latter approach is best for higher performing teams who have simply hit a “bump in the road”.

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VP of Operations

One of the most common questions we get from individuals is “what is the path to becoming a CTO?” We posted about this before and focused on the skill sets required as opposed to the path to get there.  We highlighted 1) good knowledge of business in general 2) great technical experience 3) great leadership 4) great manager 4) great communicator and 5) willing to let go.  This time we’re going to one of the jobs that is often a stepping stone to the CTO job.

The VP of Operations is the person who leads the Technology Operations or Production Operations team.  This team has responsibility for running the hardware and software systems of the company. For SaaS or Web2.0 companies this is the revenue generating systems. For corporate IT this is the ERP, CRM, HRM, etc. This team is often comprised of project managers, operations managers, and technical leads. As the head of the Operations team the VP of Operations has responsibility for monitoring, escalating, managing issues, and reporting on availability, capacity, and utilization. Incident and problem management as well as root cause analysis (postmortem) are some of the most important jobs that their team accomplishes. In order to perform this role well the VP of Operations must have good process skills, a strong leadership presence, able to remain calm under fire, and goof overal knowledge of the system.

The VP of Operations is often also responsible for the Infrastructure team. This team is usually comprised of system administrators, database administrators, and network engineers. This team procures, deploys, maintains, and retires systems. As the head of this team the VP of Operations has requirements for budgeting, balancing time between longer term projects and daily operations on the systems. This team understands the system holistically and are often the most useful when performing scalability summits. In order to perform this role well, the VP of Operations must have a good understanding of each of the technical roles that this team is responsible for, including the databases, operating systems, and the network. This doesn’t mean in order to succeed in this role a person must be able do each of these jobs but they do need a good, solid understanding in order to converse, brainstorm, debate, and make decisions in each of these technical realms.

If you compare this list of skills that we mentioned at the top of this post with those mentioned as necessary to succeed as the VP of Operations you’ll see they overlap a good deal. Great technical experience, great leadership, and great management skills will serve you well as the head of operations and will also go a long way to developing most of the skills you will need as a CTO.

We’re approaching the end of the year, a time that many people and organizations use to reflect on what they have accomplished and what they want to accomplish next year.  A good idea as part of your personal growth is to use the list above and score yourself as honestly as possible in terms of skills.  If you’re missing some of them make sure you have some goals in place that help you acquire a few more of these each year. Do this and not only will succeed one of the important jobs that lead to the CTO job but when you do arrive at the CTO position you will be one of the successful ones.

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Resonant or Competent?

What type of boss or employee would you rather have, one who is in tune with the team or a competent one? While we usually don’t have to make that extreme of a choice it is often the case that we are faced the decision of keeping or letting go a manager or employee who is technically excellent but difficult to work with. Sometimes this is our boss and we have to decide as an employee whether to stay or not. Two theories on leadership that I’ve come across recently have me debating this question. The first is Extremis Leadership from Colonel Thomas Kolditz who is a professor at West Point. The second is Resonant Leadership by Richard Boyatzis and Annie McKee. Dr. Boyatzis is a professor at Case Western Reserve University, Dr. Annie McKee is the founder of the Teleos Leadership Institute, and both are co-authors with Daniel Goleman of the bestselling book Primal Leadership.

A simple blog post cannot fully explain either one of these leadership theories and while they do offer generally different perspectives on leadership there is also a great amount for which they complement each other. I encourage you do investigate and read each book but I will provide a quick positional overview that can spark our discussion. Extremis Leadership essentially states that in crisis situations three characteristics of leaders stand out, competence, trust, and loyalty, in that order. And that competency is by far the most important when people feel their lives are on the line. This is to such an extreme that competency can supersede the individual’s rank, which as you can imagine in the military is pretty strong words. There is a promotional video on his site that shows some of the principles that he espouses put into action as Col. Kolditz takes someone through their first parachute jump. The term Resonant Leader, was first introduced in Primal Leadership and refers to a person who is in tune with him or herself, and the people they work with. They create a sense of resonance in the workplace, so great work can be accomplished. Resonant Leadership explains that mindfulness, compassion, and hope are the key elements to enabling renewal and sustaining resonance in leaders that produce quantifiably better results. Additionally they prevent the leader from burning up and becoming dissonant.

An easy way to compare these theories is using our 2×2 matrix that we usually use to explain our “Seed, Feed, and Weed” approach to leadership. In case you haven’t gotten a chance to checkout the rough cuts version of the book we have an expanded section on this concept of identifying the right team members to reward, coach, or encourage to pursue other job opportunities. Below you see how we have overlayed the theories on the axis that they most strongly relate to. Obviously both strive for the upper left quadrant as their goal but each has a dominant axis in which they utilize to get to the upper left.


Having been a part of many crisis situations, including some where people’s lives were on the line I can see how competency can momentarily trump all other characteristics. However, a leader who has produced dissonance in the organization over many weeks, months, or years before the crisis can and probably will be ignored exactly when they are the most useful in spite of perhaps having the best plan.

I would put up with a boss or employee who was extremely competent but difficult to work with for a short period of time to get through a crisis. But having to work with someone for any extended period of time would cause me to discount the value of their competency and remove them from the organization. To me there is an inflated impact rate over time. For every day I have to put up with a person, rather than enjoy their resonance within the team, the value of their competency gets diminished.

As much as I’ve pointed out the differences between the two theories there are many overlaps. For instance, the Resonant Leader is required to display competency but additionally must be able to foster resonance with themselves and their teams. The Extremis Leader displays trust and loyalty among their team in addition to their unflagging competency. I think the answer for all leaders is yes to both. From what used to be the Army’s eleven Leadership Principles, notice the first two:

  • Be tactically and technically proficient
  • Know yourself and seek self-improvement
  • Know your soldiers and look out for their welfare
  • Keep your soldiers informed
  • Set the example
  • Ensure the task is understood, supervised and accomplished
  • Train your soldiers as a team
  • Make sound and timely decisions
  • Develop a sense of responsibility in your subordinates
  • Employ your unit in accordance with its capabilities
  • Seek responsibility and take responsibility for your actions

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Principles of War as Applied to Business Leadership – Part 1


Many authors have previously described the relationship between business and war and we believe that the most successful businesses approach their operations as would General Douglas MacArthur when he claimed that “In war, there is no substitute for victory”.

Carl von Clausewitz offered several tenets of war in his essay “Principles of War” and later expanded upon those in his book “On War”.  Many armed forces throughout the world have taken portions of these tenets and adopted them for their own use.  This post is the first in a two part series relating the 9 US Armed Forces Principles of War to your everyday business activities, strategy and tactics.  The 9 US Principles of War are Objective, Offensive, Mass, Economy of Force, Manuever, Unity of Command, Security, Surprise and Simplicity.  We will discuss the first 5 in this post and the next 4 in a subsequent post.

Objective.  The US Armed Forces definition is to direct every military operation toward a clearly defined, decisive and attainable objective.  We think this is pretty self explanatory and includes concepts about which we’ve previously blogged such as the need to set aggressive but achievable goals.  The most important aspects of “Objective” as applied to your business are for your goals to be clearly defined, well understood, measurable and attainable.

Offensive.  The military definition is to seize, retain and exploit the initiative.  The business definition here is found by looking at what Offensive implies – specifically that it’s all about time to market and getting the right features, products and services out and adopted first.  Being first offers the best chance at achieving virility within the market, and creating a viral marketplace or product is the military equivalent of seizing the high ground.

Mass.  The military definition is to mass the overwhelming effects of combat power at the decisive place and time.  Mass here in military terms is different from the concentration of forces which may not be desirable.  Combat power refers to all the aspects of military power from infantry and armor, to field artillery and other combat multipliers. The business equivalent is to ensure that your business units are aligned with your greater business objective and that they are contributing to it properly.  Your technology, product, marketing and finance teams should all realize and be contributing to the core objectives necessary to win your business battle.  If you wish to win quickly, they cannot be marching to separate agendas and they should not be fighting with each other.

Economy of Force.  This one can be confusing, but within the military definition is a reference to “No part of the force should be left without a purpose”.  The military definition also hints that every part of the force should be used in the most effective way possible.  Goals and objectives are again part of this, but more importantly you should be able to answer the question of whether you are using the right team for the job at hand.  Not only should you ensure that every organization has a purpose directly relating to your most important initiatives, you need to ensure that they are the best team to have those specific goals and objectives.  Client Services and Customer Support teams might be useful in helping to QA new products but allocating them 100% to such an endeavor is probably not the most leveraged use of their time.  Conversely, forgetting to include Customer Support or Client Services in any product rollout is a failure to employ a very important part of your “combat power” in achieving product success.  While its useful for engineers to understand customer needs and complaints, allowing more than 5 to 10% of their time to be taken up by such activities is a costly endeavor relative to your future product needs.

Maneuver. Place the enemy in a position of disadvantage through the flexible application of combat power.  This one relates to how flexible you are in your product delivery lifecycle, and whether you are set up to respond to your competitors actions in the marketplace.  This IS NOT an argument that you should abandon products in flight and constantly change your strategy.  Constant change in strategy is a clear indication of a management team incapable of defining a winning path and it’s a early indication of likely future failure.  You should be flexible, and changing features or making course corrections a few times a year is appropriate.  Ensuring that your product delivery processes allow you the flexibility to change (with the additional cost that implies) is critical to success.  But constant change is not a strategy – it’s a recipe for disaster.

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