At some point in a career every manager has his authority challenged.  Typically the challenge comes towards the beginning of a new relationship with an employee.  But if it is not successfully dealt with, it can last for years. These encounters come in different forms and with varied methods.   Such contests are completely demoralizing and can leave many managers with self-doubt and asking themselves why they are in management in the first place.  Learning to deal with the undermining of these challengers is a survival skill of a Street Smart Leader.

First, let’s define when a challenge is a problem.  It is perfectly acceptable for people to challenge your ideas and methods in a professional and respectful way.  You should promote an open atmosphere which encourages vigorous and passionate debate regarding the best strategies and practices for your business. Healthy combative interaction in the arena of ideas makes them stronger and increases the likelihood of their success. A good Leader will learn to facilitate these discussions with astuteness and confidence in order to get the most out of a high performing team.  We are also not talking about someone who just makes a mistake and is out of line.  A good leader takes the higher road here.  He pauses the conversation or activity, creates an uncomfortable moment, then continues and let’s this one pass. 

When someone questions your authority on an ongoing basis, they are purposefully sabotaging your existence. They are rebuffing your ideas on the basis of rejecting your rightfulness to oversee them.  For whatever reasons they have decided, “You are not the boss of me.”  But you are and they just don’t like it.  Maybe they believe they should be the boss or maybe they want you to prove yourself or maybe they just have psychological blocks. Regardless of the reason, they are planning to undermine your effectiveness.  You are in Street Fight!

Their number one weapon in this battle is your inaction.  They are counting on the presumption that they are too clever, or that you will avoid confrontation, or that they can build an unassailable coalition.  They plan to diminish your power by ignoring your authority. They are counting on you forfeiting your power and allowing them to subsist.  Power is not lost it is relinquished. 

This point was driven home to me years ago while I was attending a charity dinner event.  The draw that evening was that business leaders were able to enjoy dinner with Professional Athletes at the table while we watched the program.  I am not one who is easily star struck, but still I attended as a part of our Executive Team.  Not knowing who he was, I found myself sitting next to Pete Vuckovich.  I quickly read the program and realized he had been a Cy Young Award winning baseball pitcher who had played in the World Series.  As I saw those at my table engaged in lively conversations with these sport’s idols, I wondered what I could say to Mr. Vuckovich.  I was far from a baseball fan and not really interested in his celebrity.  However, I didn’t want to miss an opportunity with a real Pro who was once at the top of his game. 

After some awkward silence as dinner was being served, I finally leaned over and asked, “Pete, do you mind if I ask you a question?”  He graciously smiled and replied, “Sure. Go ahead.”  I continued, “Have you ever stood on the pitching mound … against such a formidable opponent, who was on such a hot hitting streak, that you didn’t want to throw the ball?”  Mr. Vuckovich began to transform in front of my eyes.  As he lunged to within four inches from my face, his 6’4″, 220 lb frame and full Fu Manchu moustache took on an intimidating and intense bearing.  His eyes were penetrating and his posture was snarling like a charging bull on the brink of losing self-control.   Seconds seemed an eternity. He almost began shaking when he grabbed my arm and squeezed.  Then without raising his voice, almost in a whisper, he bursted, “Why would I be afraid.  I’m the one with the f—ing ball!”  Later I learned how Pete Vuckovich was famous for his intensity and competitiveness.  That night I learned what it meant to not resign your power.

Not if, but when, you find yourself in this predicament there are a couple of overall guidelines to follow.  Most importantly, you must remain “cool-headed”.  You cannot become emotionally reactive and let the perpetrator push your buttons.  You are in a battle for credibility and the fastest way to lose it is to over-react to a situation.  Be committed to defeating your challenger, but make sure you let them escalate each level of the interaction.  It is never long before such a contest enters the public square, so your boss will be evaluating your actions.  He will be watching to see if you are in any way “going after” the employee to settle your own grudge.  It is important for you to demonstrate the truth of your reluctance to participant in this conflict.  Make sure you are on solid ground. 

When someone is continually challenging your authority they provide many opportunities to make themselves look bad.  You don’t have to take them on at each one.  Wait for the battles where you are on firm unquestionable ground.  Be patient and be right – chose winning conflicts with which to discredit your opponent.  In truth, it is difficult not to be emotional when under this kind of attack.  It is personal but your emotions will work against you.  This is a time to “out-think” your opponent.

Usually their tactics fall into one of two general buckets: Direct Confrontation or Indirect Manipulations.  If you are to defend against these tactics, you must be able to recognize them and counter attack with veracious action.

Direct confrontations take several forms.  They include obvious hostile behaviors such as rudeness, inappropriate complaining, sarcasm, and insubordination.  Less visible, but just as aggressive, are the plots of backstabbing and gossip which are designed to build a collective resistance.  Direct confrontations are usually exploited by the arrogant.  They believe they are either “untouchable” or that they will gather support from others which will corroborate their bad behavior and disentangle you.  They are bullies and they are counting on you to avoid the confrontation.

As a Leader, you need to meet this confrontation head-on.  The trick is to do it in a way that is non-confrontational.  They are baiting you with their bad behavior and setting the trap.  The mistake many managers make in this situation is to react and take the bait.  They make a spectacle of the situation drawing the attention to their own behavior.  The over-reaction replaces the bad behavior as the topic among employees, peers and their boss.  Instead, you must have a plan thought out and be ready to execute it in an ultra-professional way.

Let’s look at a few examples of the Direct Confronter:

1.)    Take the person who challenges your authority in a meeting with sarcasm or anger.  You are sure this is no mistake and you have been waiting for it.  Instead of taking the bait, you stop the meeting with silence and allow that uncomfortable moment to sit with everyone and then continue the meeting.  Just before the meeting adjourns, while everyone is still seated, you look directly at your offender and calmly say, “Dennis, I’d like you to stay for a few minutes.” Be prepared, for he will most likely tell you how he can’t because he has something urgent to do.  With your eyes focused on his, tell him this will only take a moment and to please sit down. Watch everyone’s faces as they get up leaving Dennis sitting in the room.  Then you handle Dennis’s misconduct in an ultra-professional manner.  With no emotion, you point out how his behavior was unacceptable and that it will not be tolerated in the future.  Let him know if it does happen again, he will be asked to leave the room immediately.  If this happens again, you are on very firm ground and can begin replacing Dennis.

2.)   Having successfully shut Dennis down in a way that curbs his public grandstanding, you can next expect Dennis to concentrate on building his collective through backstabbing and gossip.  Backstabbing is most effectively put into play by going around you to your boss and complaining.  Nothing can be as upsetting as when you realize this is going on and your boss is listening to your adversary behind closed doors.  In today’s world of “open door” policies this is a predictable route for them to take.  Well since it is predictable, you will have a plan.  Whether or not your boss initiates a discussion with you, let him know you think it would be good for the three of you to get together and discuss Dennis’s unhappiness.  Dennis might relish the opportunity to “take you on” with the boss.  But you have chosen you battles carefully and you are going to focus the conversation on the indefensible – Dennis’s behavior and not on your ideas or style which he disagrees with.  Through your preparation, you make certain this meeting is about him.

After a few such interactions the Direct Confronter will lose credibility and will recognize your authority and the personal cost of challenging it.


Those who use Indirect Manipulation characteristically rely on “Passive Aggressive” tactics.  These tactics will usually manifest themselves as helplessness, procrastination, stubbornness, bitterness, moodiness, or deliberate and repeated failure to accomplish requested tasks for which one is responsible.  They do not disagree or confront you.  Instead they wear you down with friction and attitude.  They wage their war with deliberate actions of resistance which, individually do not justify a response from you.  With these employees you find yourself terribly frustrated and insecure.  The good ones are masters at making you think there is something wrong with you as a manager.  They accomplish their jobs proficiently enough to make any application of your management over them seem trivial and as if you are picking on them. 

Learn to recognize the manipulations of the Passive Aggressive employee and prepare yourself to again deal directly with them.  Let’s look at some passive aggressive situations:

1.)    Many passive aggressive employees constantly test your will by not following policies and procedures, but still get the job done.  They don’t agree with the rules and they are not going to follow them.  When you call it to their attention, they’ll say they forgot, or they will try and improve, or they don’t see why it is such a big deal, but okay.  Just like their confrontational counterparts, they are baiting a trap for you.  They have set you up for a false choice.  You either become upset with them and appear completely irrational by making a big deal over such a small thing or you let them off the hook not wanting to deal with it.  They are very good at knowing where the line is drawn and running right up to it.  As a Leader you must take on the passive aggressive with a deliberate, constant, non-wavering campaign.  You need to move the line back.  Keep your responses proportional and do not over react.  This doesn’t mean you let things slide.  You risk looking aggressive if you go after everything at once.  So again, pick your battles and fight them.  Concentrate on policies that are already being followed by everyone else without a problem.  This eliminates any controversy on the right and wrong of the matter.  Find several areas that you are going to enforce “every day”, from everyone, even if it kills you.  Set deadlines and follow-up on them.  You must “break” your passive aggressive employee methodically, consistently and relentlessly. Without any emotion, excitement, or drama. 

2.)   Once they lose this battle your passive aggressive will most likely fight back with a bad attitude.  Since they are passive in their choice of weapon they will not be openly disgruntled.  Instead they will choose moodiness, sulkiness, irritability or the like.  Even worse they may try apathy or setting up others for failure.  All of these are unacceptable and should be dealt with immediately.  A serious conversation in your office with them will fix it for a week.  They will be dismissive and defensive and they will again test your will.  Do not let them get away with it.  As uncomfortable and upsetting as these meetings are for you, rest assured, they are hell for the passive aggressive.  If they persist in forcing you to meet with them again and again, begin taking notes of the conversations right in front of them.  Make it clear that you would rather not escalate the situation, but if they insist on it, you are prepared to win.

If you are constantly dealing with authority challenges, you need to take a strong deep look at yourself and ask if you are the problem.  Otherwise, you must be prepared to take on the occasional Underminer.  They are dangerous to you, your team and your company.  They focus attention on themselves and detract from the goals your team is working so hard to accomplish.   Take notice, everyone is aware that the game is on and they are watching how you deal with it.  They are evaluating your Leadership capability in these situations.  If you can conquer adversity without becoming emotional and reactionary, your team will respect you.  Take your victories with grace and silence.  There is no need to showboat or strut.  Everyone has noticed what just transpired.  Remember no one wants to follow a Leader who can’t stand up for himself when he is right and win!  Play it Street Smart and as Pete Vuckovich taught me – don’t relinquish your power.  You’ve got the Ball – KEEP IT!