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Evolution and Journey of Becoming a Great Leader

There is a significant difference between management and leadership.
  • People follow managers because they have to.
  • People follow leaders because they want to.

Leadership is demonstrated through numerous behaviors. I will cover in detail the behaviors that I believe are typically shown by the majority of strong leaders. Leaders naturally exhibit many of these behaviors but can also learn certain behaviors.

This article will take a different approach than the other "leadership" articles. It takes a no-nonsense approach to leadership by looking at the top traits of a strong leader. Somewhat terse but to the point, it is designed for people who want to understand the difference between managing and leading. It is also designed for seasoned leaders who want a refresher on key leadership qualities. Enjoy reading!

Chapter 1 – Courage at All Costs
“Courage is the management of fear, not the absence of it”.
-- Rudy Giuliani

When you think about the leaders that you respect, you will notice that they exhibit courage. A willingness to take on the tough problems, go against the grain when necessary and take risks in order to do the right thing.

Exhibiting courage will draw your supporters closer and impress your non-supporters when handled properly.

Keep in mind that there is a fine line between courage and stupidity.

Pick your battles wisely and make sure to think through the scenarios of what could happen when you do challenge the status quo. Courage without planning is foolish. Do not confuse rudeness or arrogance for courage. Sometimes people try to mask their insecurity with arrogance which on the surface looks like strong self-confidence. Do not increase your rudeness or arrogance in an effort to be more courageous. Courage can be displayed in respectful and positive ways.

Courage requires a certain conviction and determination. The hardest challenge in these cases is avoiding the perception that “you are not a team player”. Most people are conflict averse and do not appreciate being challenged. The easiest way to strategically deflect someone who is courageously challenging the status quo is to create the perception that the person is simply a trouble maker. Do not wait until this happens. Use the techniques below to avoid being seen as a trouble maker.

You can increase your chance of avoiding the perception that you are “not a team player” by using the following techniques:

1. Use data to support your conviction – facts that are indisputable help remove the perception that your conviction is emotionally driven and also reduces an emotional response

2. Socialize your idea initially with one person at a time to understand whether you are explaining your position properly and to incorporate their thoughts and ideas – if your position is controversial, do not socialize with a large group until you hone the message first through individual discussions.

3. Find a senior level advocate for your position and then increase the number of advocates by socializing your position in one-to-one meetings.

4. Use external examples from other companies who have utilized your approach – sometimes it is easier to “sell” your position if you can show that other reputable companies use the same approach.

Your team expects you to have courage and take on tough challenges. Lack of courage demeans your status as a leader and undermines the team’s confidence in you.

The better you are at communicating and selling your message, the stronger a leader you will be.

A leader needs to be able to convince others that their strategy or vision is correct. Convincing others is easy if you have strong communication and influencing skills. You can develop your communication skills by joining groups such as Toastmasters. There are numerous classes and training associated with influencing since it is a critical skill in business.

The most convincing messages are the ones in which the person who is sending the message truly believes in the message. People are insightful and can quickly perceive insincere messages – you will not be fooling anyone. At the same time, people love to be entertained and naturally gravitate towards entertaining speakers. Do not forget the common tools related to persuasive speeches including humor, passion for the subject, eye contact and vocal variety. It is evident if you say the same words in an entertaining manner versus a monotone manner, you will make a greater impact.

Chapter 2 – Custom Style
Leadership is not about adopting someone else’s style. It is about developing your own style. You can however learn how to improve your leadership style by observing others – regardless of whether they are good or bad at leadership. Observe others for their approach to leadership. Build your “leadership toolkit” by reading, listening and discussing leadership with others. From these discussions you can craft your own “hand-crafted” leadership style.

Over time your style will morph and evolve as you pick up new leadership skills. If you are learning new approaches, you will find yourself saying, “Hmm, that’s an interesting approach. I am going to try that next time.”

Just like a custom suit or jacket, your leadership style should be tailored to you. Leverage your unique traits to develop a leadership style that works for you. You may really admire someone else’s leaders approach but that does not mean their approach will work for you - the worst thing that can happen is that you will come off as disingenuous. You have seen these people who try to adopt a style that simply will not work for them. For example, they may see a very vocal and charismatic leader and say, “Wow, I really like their style. I want to be like that.” But if their fundamental personality does not support that style, their attempt to adopt that style will be unsucessful.

The strongest business leaders are actually quite diverse in terms of styles and approaches. We hear and read about the leaders that are gregarious, charismatic and outspoken (Larry Ellison, Steve Balmer, Scott McNealy) but there are many who are less charismatic (Lou Gerstner, Scott Cook, Anne Mulcahey). They all can handle difficult situations, make tough calls and demonstrate phenomenal leadership but their styles are very different. Take heart in the fact that you do not have to be the loudest, most vocal person in the room to be a great leader. You may gain greater notoriety and greater exposure faster if you are a loud-mouth, but it does not make you a better leader than someone who is more cerebral.

If you do not understand yourself, it is difficult to understand and effectively coach others. I strongly recommend spending time throughout your career trying to better understand your strengths and weaknesses. The best way to start is through a joint exercise with your team on personality types. Programs like Myers-Briggs, Colors and ID help you identify your natural personality or approach – the approach that you naturally gravitate towards.

Going through one of these personality identification programs with your team (take a half-day or full-day) helps people better understand themselves and helps them better understand others. We forget, over time, that others react differently than we do to certain situations based on our personalities and approaches. The better you understand yourself, the better you will be at creating a leadership style that matches to your natural personality.

Focus most of your time and effort leveraging and building on your strengths. Parlay those strengths to gain greater and greater opportunities and challenges in your professional career. Understand your weaknesses and make some effort to address those weaknesses. Do not ignore your weaknesses – spend some amount of time throughout your career attempting to improve. However, your strengths are an asset that you should leverage and improve also. If you analyze why you have been successful, it is due to a special skill or approach that you have. Ensure that you are in positions during your career that allow you to showcase your strengths.

Hire a team that compensates for your weaknesses. We will discuss this approach in more detail in Chapter 3.

Chapter 3 – The Team is Everything
Your team is your success. Consider this – you are never any better than the worst person on your team. Ok, this is not exactly true but weak team members can cause substantial damage by reducing the credibility of the overall team which negatively affects team morale. Sometimes you can be successful in spite of the weak team members but they will increase your risk of problems.

Strive to get rid of the weak, grow the folks with potential and reward the super stars. Invest your time in developing your team - always, always make time for your team. The team is your number one priority.

Do not confuse “weak” with the most junior folks on the team. Weak in this context can be defined as the folks that do not respond to coaching and do not have much in the way of potential. They are the ones that everyone senses would be better off somewhere else. They do not fit and in many cases cause more damage than good.

Managing out the weak people on your team is a win-win opportunity. Removing fundamentally weak people from your team is appreciated by the folks with high potential and the super stars. Most of the time, the team is fully aware of the weak players and is wondering why you are not dealing with them. Realize that the team has discussions about the weakest folks. Why aren’t you? I can answer that with a simple answer – it’s easier for you just to ignore them. Like most people you may avoid performance discussions because it makes you uncomfortable. You may be conflict averse.

Get over it. To be an excellent leader you have to be able to give both praise and constructive coaching. Start by leveraging your one-on-one discussions with your team members to interject some coaching and not just discuss the status of projects and programs.

Often times, the weak folks know they are weak; they are unfulfilled and are dragging the other team members down – at worst, poisoning the team with negativity and complaining.

The weak are always willing to point out the problem and have no ability to suggest a solution to those problems. Often they can tell you the company history of every single problem in gory detail but have no suggestions to solve those same problems.

The other category of weak people is much more difficult to deal with – they are the folks who have no self-awareness. They do not know they are weak and think that the problems are due to someone else or some other situation.

These weak folks exhibit the classic “victim” mentality.

If you determine that a person is fundamentally weak, do not just move them to another group. Do the right thing. The approach of moving them to another group is almost always a cop-out taken by the manager in order to avoid terminating the person. You might be moving the person because you do not want to live with the fact that you were the one that caused them to “lose their job”. Trust me when I say that they ultimately will be better off at some other company with potentially lower standards or simply a different culture..

Invest in people who have potential and invest in the super stars. Spend the majority of your time ensuring that the best team members are praised, recognized and rewarded. Take extra special care of the super stars – this does not mean pay them more and treat them like royalty. The last thing you want is a group of prima-donnas.

Taking care of the super stars means empowering them, rewarding them and perpetually challenging them.

The strongest team members want to continually learn and grow – they hunger for new challenges and new learning. As a matter of fact, if you do not perpetually challenge them, they rapidly will become bored and will eventually look for something else to do. Some options to challenge them include the following:

1. send them to an external conferences and ask them to report back to the team on the findings from that conference; challenge them to develop relationships with folks from other companies to share best-practices and lessons learned
2. challenge them to improve the way the team operates – challenge them to identify process and policy improvements for the team
3. have them meet with the senior folks from other teams and challenge them to build a collaborative partnership with those folks
4. identify soft-skill or hard-skill opportunities for improvement and focus on one for a couple quarters
5. ensure that they have mentors – folks that they trust and that they can have open and honest discussions with – folks that can provide constructive insight and feedback

The super stars expect you to coach them – to give them insight and feedback on how they can improve and develop.

The super stars realize that they are not good at everything and are looking to you to help them identify weaknesses. They are typically very competitive. The super stars are motivated to develop professionally and expect you to coach them so that they can improve. If you are not doing this, they will not see you as a top leader. Coaching in the case of the super star can be something like this:

  • After the fact - “I really like the way you handled the situation. The only change that you could have made was this... Let’s talk through the results if you had taken that approach.”
  • Before the fact - “So you will need to drive to completion of this program. Here are some ways that I can think about getting it done. Let’s talk about each one”.

Empower the folks with potential and especially your super stars. This means giving them enough leeway to take risks and make mistakes.

Managers control, while leaders empower.

Assure your team members that you will help them if they make a mistake which then allows them to take risks. The command-control style of management is not leadership and only creates robotic employees incapable of making decisions based on their own judgment. For the folks on your team with experience and more seniority, give them general direction but allow them to figure out the “how”. Tweak their approach by providing feedback and suggesting options – avoid detailing how to solve a problem even for the junior folks.

A common problem that I have seen is the situation in which the manager or director is not acting in their expected leadership capacity. Here is an example of what happens: the manager is not acting as a leader but instead as a project manager. The manager is micro-managing, way too deep into the details and not providing critical direction. This is the manager as a “glorified project manager”.

The result is that the project managers are confused about their role and are caught in between the team and the manager. The team starts by-passing the project manager in some cases since they have to get the manager’s approval on everything. The manager misconstrues this behavior and starts believing that the project manager is not capable of doing their job when in actuality it is their own behavior which is causing the problem.

The subtle effect of these types of situations is a team in which there is a perpetual discussion about roles and responsibilities. The team is constantly meeting to discuss and define each person’s role. Typically the project manager instigates these discussions in an effort to stop the manager from micro-managing. Sadly these discussions often never meet their objective because the manager does not change his or her behavior and thus there is a negative, perpetual ripple effect through the team.

How can you change the micro-managing manager:

1. Attempt a discussion of roles and responsibilities at least once
2. I found that an effective tool to stop negative behaviors like micro-managing is personality-type identity tools like Myers-Briggs, Colors, etc. Work with your HR representative to coordinate a half-day or full-day session to identify and discuss personality-types. This sometimes proves to be a good way for people to become more self-aware and identify their own propensity to micro-manage.
3. If you have a good relationship with your micro-managing manager, give them the direct feedback that you feel that they are getting into too much detail. Ask them why they feel that they need so much detail and try to understand if there is a trust or confidence issue. Sometimes just bringing your feeling to the table can open the eyes of the manager.

The best leaders that I have met take personal pride in seeing others succeed. They genuinely want to see their team members develop professionally and are motivated to see that those team members are rewarded for their excellence. Those same leaders will reward the super stars financially and reward them with higher-level positions. Inwardly-focused managers are naturally driven to see themselves succeed, typically ignoring their team members.

Leaders realize that the success of their team members is a reflection of their leadership capability.

The leader is a person that can grow and develop talent and enjoys seeing others become successful. This is a sign of greater maturity and self-confidence. If you take as much pride and excitement in seeing your team members succeed as in your own success, you will attract top talent. If you have no examples of people that you have developed, you are not a leader. If no one credits you for their professional growth, you are not a leader.

Developing your team members takes time and effort. This typically means meeting with your team members individually and discussing strengths as well as opportunities for improvement. If you get into the habit of doing this regularly, it will become a comfortable and natural habit.

Managers fear losing their jobs. Leaders are looking for the next opportunity.

Leaders are perpetually thinking about succession planning. They look for the next successor in order to ensure their ability to take on more responsibility or different responsibility. A manager that hordes information in the false hope of retaining “job security” exemplifies the worst possible trait – that of purposely not developing their team to falsely protect their position.

Leaders will always put the company’s interest ahead of their own. Sometimes this leads to decisions which require the leader to give up part of their team or reduce their responsibility. Strong leaders will ultimately regain more responsibility.

Good leaders have a strong following inside and outside their own team. They have a positive reputation that precedes them.

An easy way to spot a strong leader is to find the person who many others proactively seek out for guidance and direction. It will not be evident on the surface who these strong leaders are since they will not typically publicly applaud themselves. If you have managers reporting to you and they are continually being sought out for advice from others, make sure you support them in providing the time for mentorship to others. If that same manager is being asked to provide mentorship to many people outside of their organization, that manager has been able to build a strong reputation and is exhibiting strong signs of leadership. This is another sign of strong leadership – if people are seeking you out who you do not know but they have heard of you; your positive reputation is drawing people towards you.

If you yourself are not being sought out for your opinion or guidance, you probably are not seen as a true leader. What is your reputation?

Good leaders have teams that will happily walk through fire for them.

Top leaders have teams that will do anything for that leader. Why is it that strong leaders have teams that will happily do anything for that leader? Leaders will not ask their team to do something that they would not do, they fundamentally take care of their team, challenge their team, speak openly and honestly, and put the team members’ interests ahead of their own. Leaders are genuine and the team can discern between being genuine and putting on a fa├žade.

Good leaders can easily attract and retain top talent.

In any company, you create a reputation over time. The better your reputation, the more likely you are to be able to retain and attract talent and therefore the more successful you will be. So, working backwards, to be successful you need a talented team and to have a talented team you need to attract and retain top tier folks which requires a strong reputation.

I am perpetually amazed by managers that either have no reputation (ie – no one really knows them) or have a bad reputation. These same folks wonder why they cannot attract top talent. Don’t kid yourself – most people care about who their manager is and will do some ‘background checking’ when interviewing for a position in your team. People talk – they share information. If you act like a manager and not a leader, you will have great difficulty building a top tier team (assuming people have free reign to move around within your company).

The most talented people prefer to work with other top-tier people.

Average teams attract average talent and top teams attract top talent. Smart, motivated people fundamentally want to work with other smart people from whom they can learn. No top-talent person wants to sit with the C-team and are smart enough to know that the quality of the team is a reflection on them. Great teams do not accidentally happen – they are a sign of a strong leader.

Build a team that helps you address your weaknesses. This means diversity.

This sounds easy but runs against the grain for all of us. Why? Because it is human nature to want to surround ourself with people that have the same beliefs, approaches and values. Be aware that you need to proactively counter this natural tendency in order to build a diverse and robust team. People that can compensate for your weaknesses are typically different from you and you will naturally have an aversion to hiring them unless you internalize the benefit of doing so.

A diverse team is a strong team. A diverse team is sometimes more challenging to manage but the payback is substantial – higher likelihood to come up with different solutions, ability to proactively determine future impacts of decisions, ability to better partner with diverse customers or clients.

Chapter 4 – Think Positive

No one wants to follow someone who is negative. It’s a fact. If you are a naysayer or a “glass half-empty” type of person, you will have serious trouble ever being regarded as a real leader. Imagine the person who inherently says, “Everything is broken, nothing works, and there is no solution.” They are depressing and they drive people away. I prefer and recommend realistic optimism – this approach does not resist telling it like it is, even if the news is not good. But hand-in-hand is the attempt to find a solution and drive to that solution with enthusiasm and positive energy.

The realistic optimist can balance challenge with a positive, “can do” approach which people want to rally behind. Everyone wants to overcome tough challenges – it is the competitive nature that we all have in us. People take pride in “doing the impossible”, in fixing problems that seem insurmountable. The realistic optimist can identify and analyze the problems that exist but not get bogged down in negativity.

The forever optimist is sometimes as bad as the pessimist. The forever optimist cannot rationally deal with tough situations and is often unrealistically optimistic – either underestimating the challenges, complexity, time to address the problem, dependencies and/or politics. They can be dangerous in terms of over-promising and under-delivering.

Amazingly, most pessimists do not realize that they are perceived as pessimistic. They often believe that they are striking a balance between realism and optimism. Think about it, if the pessimist realized that they were a perpetual downer, wouldn’t they attempt to change their behavior? Sadly, people fail to give feedback to these pessimists and they are unaware how they are perceived. Your duty as a leader is to help them realize that they are not striking a balance and let them know what the perception really is.

I give the following advice to people who are perceived as pessimists but feel they are balancing optimism with realism:

1. Start and end meetings or discussion with a positive perspective. At the end of the meeting something like, “There are obviously challenges but we’ve got the ability to overcome them.” Use your own words, of course. The point is to leave people with a positive, uplifting final message which starts the process of changing perception.
2. Once a week, meet with your manager to role play through a specific scenario from that week. As an example, walk through a meeting or discussion and as accurately as possible relay your exact words. Ask your manager to give you a sense of what they would have said and done.
3. Be careful about your body language. Whether you like it or not, slouching, facial expressions like rolling your eyes, the way you talk and nervous habits can be perceived as negativity. Ask your manager and at least two other people that you trust for honest, direct feedback on these.

Leverage the techniques above to change the perception that people have about your negativity.

Chapter 5 – Strategic Vision with Execution
True leadership requires the ability to think strategically and to have vision. Managers are good at executing what they are told or what obviously needs to be done. Leaders derive the future through a variety of means and then create a strategic plan that will prepare them for the reality of the future.

You can develop strategic vision over time. I typically coach people to think about the following:
1. What trends are occurring that will have an effect on the business in the future?
2. What do we need to do today to be ready for that change?

Developing strategic vision as a skill requires research, reading and discussion. Through analysis of trends you can start the process of determining what the future might hold. I sense that the biggest barrier that people have with developing the skill around strategic vision is that they are apprehensive about guessing the future.

Keep in mind that no one, no matter how sure they may appear, knows what the future will hold. With enough research and analysis, your guess is as good as theirs. Possibly it is the fear of taking a risk or being wrong which factors in to people’s reticence to guess the future. Once you get over this apprehension, you can start developing your own interpretation of what will happen over time.

The IT industry is constantly changing. Years ago it became evident that the IT professional would need to increase their business acumen in order to reach a higher level of partnership with their business partners. This realization caused some IT professionals who saw this trend to fundamentally shift their approach to professional development. Instead of focusing the majority of time on hard skills like technical acumen, IT professionals started developing their soft skills like communication and negotiation, and increasing their knowledge of business process. Those IT professionals recreated themselves proactively based on their impression of what would happen in the future.

Leadership requires that you look into the future, make an attempt at determining the coming changes and then prepare your team for those changes. Your ability to proactively respond to upcoming changes will help your team be ready for change and give them time to adapt. Managers often find themselves in reactive mode, buffeted about by changes that they did not anticipate. Unfortunately the team members pay a price for this reactive response versus a proactive approach.

Chapter 6 – Take Responsibility
Leadership requires that you take responsibility for yourself and your team. A strong leader owns up to mistakes and missteps, and understands that mistakes are part of risk taking. Sadly we all have had experiences in which people who are responsible for a mistake do not take ownership.

Walking away from responsibility or pointing blame at others will damage your reputation. It is always better to take responsibility which people perceive as strength. By modeling accountability, your team will also be motivated to model accountability. Over time, accountability will become rooted in the team culture.

Innovation can occur in a variety of ways. I will focus mainly on process and technology innovation.

Leaders must push and invest in innovation.

Perpetual Learning

Ability to Change and Adapt

Ability to Deal With Ambiguity


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