Leadership is an oxymoron

July 18, 2010

Having spent a lot of time with entrepreneurs through EO, my personal angel investing, and playing poker with a bunch of them, I’ve found some consistent lessons that are useful for folks who are looking to improve their leadership skills.  It’s strange, but they seem to be oxymorons.  Here are some lessons that have challenged me:

1.  The best leaders seem to have a strong enough ego that they don’t need the recognition and can easily pass all the credit to a team member or team.  They see the big picture and the vision of where the company is going, but realize that they do not need to take the credit.  They actively seek out recognition and use it to motivate their team and are content with pushing the spotlight on everyone else.  The converse is true as well, they can and are willing to take criticism and deflect it from the team.  They possess an ego that doesn’t need stroking and can take punches when necessary.   You’d think a leader would want to take credit, but the opposite is true. 

2.  Leaders rarely have to dictate.  They surround themselves with competent and motivated people.  They attract the best talent.  The best leaders lead by asking questions and allow the team to own the answers and the ideas.  They realize dictation rarely secures buy-in.  They allow team members to arrive at the same conclusion that they’ve already arrived at.  This is such a difficult skill, but the most effective leaders are capable of leading their team to own their ideas.    You’d think a leader would have the best ideas and dictate every action their team members should make, but the opposite is true. 

3.  Effective leaders aren’t looking to be served, they are looking to serve.  They realize by enabling team members to succeed and removing roadblocks scales the business significantly.  Helping team members realize their own personal goals motivates them to do things beyond their potential.  Giving and serving are passionate drivers for the most successful CEO’s.  You’d think a leader would be looking to be served, but the opposite here is true as well. 

4.  Leaders let people go.  There are people that just aren’t a great fit, most leaders try to adjust, motivate, and invest in the poor performers or the unmotivated.  The best leaders adjust, motivate, and invest in the best performers realizing that companies scale on the backs of the best performers.  I have a tough time with this as I build human relationships – friendships – and it’s often difficult to make the move of letting them go.  More often than not, the poor performers will find relief that they are let go so that they can pursue something that is more meaningful or within their skill set.  The best leaders let go of poor performers quickly and invest the majority of their time on the best performers.  You’d think the best leaders are capable of turning around poor performers, when in reality, they are the best at getting the most out of their best performers.   

5.  Leaders are humble.  I love interacting with CEO’s that are always trying to learn, pushing themselves to improve personally and reinventing themselves.  I’m always thirsty to learn something new from a restaurant waiter to a first-time entrepreneur to a retired businessman.  The more I’m involved in businesses, the more I realize that I don’t know.  Meeting an entrepreneur in El Salvador who has no education, no strong upbringing, and leading a successful business is extremely humbling and inspirational.  The best leaders know they still have a lot to learn.  Knowing that you don’t know much is always a good place to be in becoming an effective leader.   You’d think a leader knows everything, in actuality, the best leaders realize they are always in need of more knowledge. 

I realize that there are successful leaders that do exactly the opposite of what I’ve described, but I’d argue the majority of successful entrepreneurs that I’ve had the privilege of meeting with have many of the traits that I’ve described above.  Do you agree?  What other traits do you see in successful leaders?

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Comment by Jon Bach
2010-07-18 07:29:43

Great post as always! The only point I have a hard time with is #4. Some of my best employees are ones that didn’t look like they’d work out at the beginning. It took them time to grow into the position, or I had to try them somewhere else. I remember feeling like I was “pushing through” a wall against the recommendation of my managers. If these employees were mediocre today, that would be one thing. But they are some of my best! Maybe it just comes down to making sure leaders do not make snap judgements about who the poor performers are, despite the pressure found in the fact that point #4 is spot on once you know for sure about their ability to perform.

Comment by Classes Subscribed to comments via email
2010-07-18 08:16:08

Fantastic post, Andy — regarding #2, how have you developed that skill? I wrestle with the same issue of ‘dictating vs. eliciting conclusions/direction’. I know the latter is significantly more motivational, but sometimes the questions just aren’t there, or even with the right questions, the answers aren’t forthcoming. You could say “well then you don’t have the right team”, but I don’t think that’s the case at all — sometimes folks are so heads-down on the problems that they’re individually working on, that’s it’s extremely hard to expect the broader answers.

Any advice appreciated.

Dave (Schappell), founder of TeachStreet

Comment by P Russell Subscribed to comments via email
2010-08-10 13:59:00

In my opinion the best way to learn how to do #2 is to be patient and ask a lot of questions you already know the answers to. Often times the best conclusion will surface through enough inquiry. Each situation is different and requires minor adjustments, but ultimately you have to let go and let the person draw their own conclusion lining up with yours. The cliche “you can lead a horse to water, but you can’t make him drink” has some truth to it. This process provides others a valuable learning experience and when a boss dictates (those who dictate are not leaders) the course of action, it robs the other person of that learning experience.

2010-07-18 11:05:17

I really feel like #2 and #4 are what hit it home. I try to surround myself with competent people that know MORE than I do and can manage themselves. This allows me to be the grease on the team and really make things move. I convey a direction and they work out the details. If they can’t do that, they’re probably not the right fit.

Comment by Glenn Kelman
2010-07-18 17:47:40

Great post Andy. You mention the ability to attract and motivate great people, and perhaps it deserves more prominence. To me, it’s the most important measure of a leader…

Comment by Jonathan Washburn Subscribed to comments via email
2010-07-19 20:38:50

You summed up what it takes to be a great leader perfectly. I’m sure I’ll reference this post for years to come!

Comment by John Kitover Subscribed to comments via email
2010-07-24 15:03:47

I’m going to implement these changes this week! Thanks for the great advice as always Andy! – Regards, John

Comment by Ben Greene Subscribed to comments via email
2010-08-02 09:01:45

@Dave Schappell – I think the key to learning how to bring others to your point of view, as opposed to dictating your decisions, is acknowledging to yourself that you have the responsibility to explain your actions and decisions to those you are leading. If you can acknowledge this, it becomes necessary to invite others to engage in the logical process that lead you to your decision, and the most effective way to do this is to lead others down the same logical path that you followed yourself. In this way you 1) lead people to see things as you do, 2) teach them how you approach decision-making, and 3) give yourself the opportunity to learn from your team and, if necessary, change your decision.

Great article, thanks for writing! –Ben Greene

Comment by Thos003
2010-08-02 14:46:55

Was that intended to be “my personal angel”? That would actually be appropriate if you were subscribing to your own ideals and thus giving credit to a personal angel rather than a self thought up, personal angle. =)

Great observations. Effective leaders serve and thus through their genuine care and concern for others they are supported by those that know them. Making it easier for them to say, “follow me” and truly lead because they have those that willing follow.

Comment by Thos003
2010-08-02 14:51:55

Sorry didn’t catch that as angel investing, but the analogy still works. So we will call it a happy accident.

Comment by Cary Bergergon
2010-08-06 19:27:43

#4 is spot on.

No need to try an polish a turd!

Comment by Nick
2010-09-02 18:52:38

I totally agree with these 4. I work in an industry where there are defined “leaders.” Quite often those “leaders” are not the actual team leaders. Instead the team members who show respect, humility, enthusiasm and an unqualified desire to resolve our cusotmers are often the real leaders.

One of my bosses recently said something to the effect of: You can tell who the leaders are based on foot traffic. True leaders are the people others go to when they have an issue or question, not the people who have leadership titles.

Comment by Surrey Locksmith
2010-11-07 20:42:14

Re #4 – I like to invest in the top performers. If I can make a 5% improvement in a top performer then I get more than if I make a 20% improvement in a poor performer.

Comment by James Loperfido Subscribed to comments via email
2011-08-21 17:35:14

Andy, your article resembles “Good to Great” by Jim Collins. Strongly recommend it if you haven’t read it already.

Comment by E. Anderson Subscribed to comments via email
2014-03-02 22:50:09

I wish I’d found this article a few weeks earlier. It is great information that I could referenced in my Leadership and Organizational Change course! I see so much of myself in this article!

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2015-09-04 21:07:54

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