The Destructive Advisor: When a Leader’s Closest Ally is Her Undoing

Why do otherwise promising leaders hitch their wagon to an anchor?

Being an effective and ethical leader is exhausting. It requires constant effort and a strong group of allies and advisors (i.e., other leaders). When you’re desperate or feel like you’re drowning and someone tosses you a rope, you can be so eager and grateful for the gesture that sometimes you don’t notice when it’s a noose.

When a leader gets hooked on a destructive advisor, it’s toxicity grows. The leader can put so much faith in the relationship that other relationships start to suffer. Other would-be allies, intending to alert the leader to the problem, are seen as a nuisance; people who are just getting in the way.

As the leader pushes his team away, he becomes increasingly dependent on the destructive advisor. When it feels like more and more people are out to get you, it’s increasingly reassuring to have that one person on your side. You know he’s on your side because he keeps showing you all those other people who are out to get you. Soon you have no one left but the person who is destroying you. (You may have seen this play out in someone’s personal life as well.)

Here a two stories that may sound familiar to you that illustrate how a destructive advisor gains power.

Story 1

The department lead, Agnes, has her go-to guy, Hal. When it comes to transactional work, he seems to be the master. It appears no one else can do what he does. And Hal makes damn sure it stays that way. Hal constantly laments how overworked he is. He exhibits his workload physically so all the world can see the demands put upon him. His calendar is like a sliding block puzzle, forever shifting, rescheduling, and cancelling. When he is offered help, it never goes well. The offer is either rebuffed or the good Samaritan fails miserably. No one, it seems, is capable of understanding the intricacies of the tremendous demands Hal faces on a daily basis.

Agnes buys it hook line and sinker. The dread of losing him is so consuming that she doesn’t see the misery that Hal creates all around him. He can’t collaborate. He refuses to explain in any form how he takes care of his end of a process. And although he insists that it’s everyone else that just doesn’t get it, the work that he produces ranges from inadequate to incompetent.

Story 2

Margaret is intent on ferreting out the dysfunction and incompetence in the office. She spots when mistakes are made and eagerly notifies her boss, Paul. Paul is grateful for the discovery and aghast that such things could be happening under his watch. With apparent support from the Paul, Margaret confronts the offending parties and interrogates them about their deplorable practices. She gives the impression that Paul is questioning their ability to do their jobs. Margaret takes it upon herself to closely monitor everyone under the dark cloud of her suspicions.

Paul admires Margaret’s tenacity and ambition to clean house and get things in order. When he needs information, she gets it. Or at least incessantly harasses people to get the information. What would he do without her, he wonders. Never mind that she is essentially terrorizing the rest of the office. Never mind that she is creating massive dysfunction and inefficiency. All Paul can see is that Margaret uncovered wrongdoing and therefore she is indispensable.

Spotting Iago

Unlike the destructive advisors in Shakespeare’s plays, in the workplace a leader’s destructive advisor may not be deliberately trying sabotage the leader, which makes it that much more difficult to spot. Not only does the leader believe the destructive advisor is doing the right thing, so does the destructive advisor. A destructive advisor believes she is the leader’s and the organization’s greatest asset. It’s a sort of spell both parties fall into in this toxic relationship.

Here are four ways to break the destructive advisor’s obfuscating spell.

  1. Listen—truly listen—to the entire team, and never let one person be your barometer for the wellbeing of the organization. It often takes a lot of courage to go to the boss to express your concerns, so when someone actually musters it, the boss should take it seriously. Yes, there are people who are a little too eager to gripe, but that doesn’t necessary mean their concerns are unfounded. If you, as the leader, are using one person to interpret how the whole team is functioning just so you don’t have to deal with it, you are failing as a leader.
  2. Look closely at how your closest ally treats other people. The personality they present to you, may not be the personality they present to others. Don’t make excuses for abusive or unfair treatment. Justifying bad behavior as your ally being firm or other people’s misperceptions or over-sensitivity is not OK. No one, much less a leader, should ever tolerate  anyone being treated badly. Full stop.
  3. Spotting when things go wrong is relatively easy. Fixing them is slightly more difficult. The part that takes real skill is working with the people who own those processes and treating them with respect and dignity they deserve as the problem gets resolved. If your advisor can’t do that part, he either needs to be developed so he can, or removed from that role entirely.
  4. If it looks to you as if one person holds all the knowledge for how to perform a key function, that’s a problem. It may not necessarily be the destructive advisor’s fault that a process isn’t transparent, but, as the leader, it sure as hell is your fault. You cannot allow one person to monopolize so much institutional knowledge that they that can use it to hold the rest of the organization hostage.

Leaders should respect the hard work and expertise of their team. They should be grateful for their contributions and let people know how much they are appreciated. But when someone crosses the line and starts to use that expertise against the organization, you need to put an end to it definitively. That could mean helping that person see that they are doing harm, or, failing that, helping that person transition out of the organization.

Leaders need allies. No one does it alone. Just proceed with caution. Trust is important and it should extend beyond your closest ally.

+ https://www.cnbc.com/2017/12/28/top-technology-stories-of-2017-softbank-facebook-bezos-and-bitcoin.html

The Slow Boil: Why We Shouldn’t Shy Away from Politics When Discussing Leadership

Some people, I have found, are displeased when we mix politics with talk of leadership. Readers who feel this way, I surmise, just want to stay focused on what they know to be an important subject without having to wade through someone’s political opinions to get to the point. They want to be free to talk business and share knowledge of their profession without slipping down the dark hole they suffer through every Thanksgiving with their relatives. There’s also this element of liking what someone is saying about leadership only to learn that he voted for the other guy that can be a real buzzkill.

I get it, I really do. But I also disagree that we shouldn’t mix leadership discussion with politics, and here’s why.

Government and the private sector are conjoined (sometimes in ways they should not be), and running a government involves politics. To try to extract politics from talk of leadership would be negligent. We don’t pretend to be able to talk about economics or history without involving politics, nor should we with leadership.

The political world is filled with highly visible leaders who make critical decisions that sometimes have a global impact. We are able to see the effects of their leadership and decision-making on a massive scale and that helps those of us who study leadership learn from them and point to them as examples of what to do and what not to do.

No, it’s not entirely objective, and yes, there is a way to report on politics and government without picking sides. Once upon a time, the news media was rather good at this. But leadership theory and development is not necessarily about staying dispassionate (sometimes it is, but not always). More often it’s about getting passionate, angry, excited, or scared and then doing something about it. More to the point, leadership development is about getting people passionate, angry, excited, and scared enough to take take action. And that means getting people out of their comfort zone.

While some of us might wish leadership was pure science, it is not. There is a lot of opinion involved with the study and practice. People will disagree with methods and even outcomes. For instance, Scott Pruitt, Betsy DeVos, and Ben Carson were appointed to the president’s cabinet in the hope that they would bring down the offices they are leading (EPA, Education, and HUD respectively). One might therefore argue that they are effective leaders because their intentions are being realized. But as Barbara Kellerman teaches us, when we talk about good leadership, we need to consider ethics as well as effectiveness. My opinion would be that, by evaluating them on both criteria, they are disastrous leaders, and I could have a pretty rousing discussion on the subject. Others may not agree, but if we’re going to discuss leadership and learn from each other, we’re going to have to be OK with disagreeing. In fact, we’re going to have to venture into areas where we know there will be disagreement. That’s how we learn.

When teaching leadership, people like to lean on sports metaphors because there are clear winners and losers and no one’s going to get too offended when they hear a story about Vince Lombardi or Red Auerbach. Those leadership lessons play it safe (for the most part).

But many of those anecdotes are a bit shopworn and sometimes pretty shallow in terms of leadership theory and analysis. We need to be willing to go out on a limb—sometimes making people feel uncomfortable—in order for them to understand the underpinnings of leadership. What’s more, we need to be willing to point to poor leadership when we see it because calling out bad leadership is just as important as calling out good leadership.

The alternative is complacency. If we’re not clear about what bad leadership is and explicit about who those bad actors are, we start accepting it as normal. By not calling it out, we are allowing it. It slowly destroys our standards and when it comes to leadership, the corrosion of standards is catastrophic.

The bar keeps getting lower and we don’t notice it. Slowly the caliber of leaders descends until we look up and find ourselves awash in leaders who are toadies, nincompoops, and assholes.

When we don’t point out bad leadership when we see it, we start thinking that it’s perfectly acceptable for people like Scott Pruitt to be in a leadership position.

It’s not acceptable. It’s wrong and it’s tremendously damaging. And if we’re going to discuss leadership and get better at it, we need to be screaming that from the rooftops.

While leadership worship needs to stop, we also must have increasingly high standards for our leaders. We don’t get the likes of Devin Nunes into positions of leadership because our standards are just too high. They are there because the standards are too low. And every day they hold positions of leadership, the bar gets lower.

We need to continually improve leadership, constantly striving for better. It is an issue that is just too important to be bashful about.




A Simple Way to Improve How Your Work Gets Done

There’s a lot of information out there about the importance of creating workflows and documenting processes. Process outlines and checklists are incredibly important for cross training, consistent and accurate service, reducing error, and continuous improvement. A lot of smart folks are giving great advice on the subject, but it can also be intimidating. For many situations the methods they provide for documentation is overkill. You don’t have to be a Six Sigma Black Belt to articulate a process or create a useful checklist. Here’s a really easy way to at least get you started.

  1. Write out the triggering event — This is the thing that starts the whole process rolling—a customer orders an item, the boss requests a report, a client walks in the door, etc.
  2. Write out the final successful outcome — The end of the process when you can call it complete—a customer receives the order, the boss gets the report, the client walks into her appointment, etc.
  3. Write out the first thing that must be done after the triggering event — The very first thing you have to do after the triggering event to get the process rolling.
  4. Write out the last thing that has to be done before the successful outcome — Your final action before the process is complete.
  5. Fill in two to six actions that must be done in between —  You’ll need to spend some time thinking about these. These are the broad strokes. The things that are critical to the process, but not all the granular stuff that might or could happen.

You will be able to completely document every single process conceivable in this way.

Just kidding. Of course you won’t. Don’t be ridiculous. But it will help a lot of people get what they do out of their heads so they can check their effectiveness, let their boss and coworkers know how they do their job, and create a record for succession planning. The hardest part is figuring out those broad middle steps.

This is not one of those complex flow charts with scores of if-then scenarios. If you need to do one of those later, this will help you get there, but this isn’t that. This is great for creating checklists or simplified workflows. Here are some examples of where it will help:

  • When you’re out of the office, someone else can step in to take over
  • When you’re first learning a process and you need to remember the critical steps
  • When it’s imperative to get the process right every single time

Atul Gawande’s book Checklist Manifesto shows just how powerful creating checklists can be. It can save money, improve engagement, and save lives. It’s a big return for just a little investment.

Try it. It could have a tremendous positive impact on how you get things done.


The Rise of Horseshit Leaders

What the hell is happening? We can look back at centuries of what makes good and bad leadership. Our culture is rife with leadership programs, courses, and institutes. Books on leadership rain from the sky. We are obsessed with leadership.

And yet in virtually every industry and institution today we can find numerous examples of absolute horseshit leaders and they only seem to be multiplying. Harassment, abuse, negligence, corruption, and incompetence are commonplace everywhere from Silicon Valley and Wall Street to higher education and government. We can’t shake it. It’s gotten so bad that the current “leader” of the free world exemplifies every one of those problems mentioned above and so, so many more. He is, in fact, a paradigm of a horrible leader. Of course it’s not just the Oval Office. The word “kakistocracy” is becoming a normal part of our lexicon.

How did we get here? 2 big reasons.

1. Plutocracy

Good and ethical leaders want to contribute in a positive way to their community and society. In a plutocracy people in positions of power are self-serving. They have no interest or motivation to help others.

Jane Mayer’s book Dark Money details the rise of an extremist political ideology that greatly advantages the grotesquely wealthy elites. Money buys power, a malignant brand of power that serves no greater good. It’s end goal is only to acquire more power.

While plutocracy refers to a government run by the wealthy elite, it stems directly from a corrupt relationship with the private sector. Quarterly myopia and the race to the bottom shows us just where some corporate leaders’ motives lie—not in long-term progress, stability, and service to community, but in quick accumulation of wealth and power.

Wall Street was once a financial service industry. That is, the financial industry’s mission was to serve the public in order to maintain sustainable growth and productivity. Now it is purely self-serving. The People serve Wall Street so that the industry can accumulate wealth and power at an unimaginable level.

Qualifications, experience, ability, or moral obligation be damned. The name of the game is money, and that means getting people with money in positions of power so that they can acquire more money and power. Again, malignant power, which is a zero-sum game. Someone has got to lose. In this case it’s the general public.

When this happens, the people in positions of power are thieves. They have no incentive to be sound leaders. And because anyone they might report to are of the same mind, there is no accountability. It makes for a highly hospitable environment for horseshit leaders to thrive and multiply.

2. Cronysim

Sound leaders want to develop other leaders and they seek out potential leaders based on merit. Cronyism cares nothing about who would make a sound leader. It’s all about people in positions of power wanting their own kind around them.

Cronyism goes hand-in-hand with a plutocracy (crony capitalism is plutocracy’s key ingredient), but it can be more insidious. It’s not just macro-cronyism where entire industries like Silicon Valley and Big Pharma grease each other’s palms to strengthen their domination. It’s the cronyism that happens on a smaller scale that is perpetuating bad leadership. Horseshit leaders hire and promote horseshit leaders. Because they are often narcissists, they see what they think is the right stuff in people who resemble themselves, and this results in propagation of lousy leaders.

This is rampant in higher education where people are put in powerful positions with no experience or qualifications for leadership whatsoever. Instead they are deemed leaders based on their academic pedigree and how much they resemble their faculty peers. And once they land in those lofty administrative positions, they are virtually untouchable barring some criminal act.

In all kinds of industries, people regularly get hired into powerful positions and given ungodly amounts of money from VCs to lead new ventures based on things like their association with people in positions of power. (Why in God’s name would anyone in their right mind give money to someone like Jared Kushner?)

If you’ve held a job for more than a couple years, you know how this works. Someone in a leadership position likes the cut of some schmuck’s jib and they’re advanced to the C-suite. Out of cronyism or sheer laziness the people who have no business being leaders become just that. They say, the devil you know is better then the one you don’t, but the problem is he’s still the goddamn devil.

This glut of poor leadership is not unprecedented. Not by long shot. (The early- to mid-20th Century was pretty tough period, for instance.) And there are in fact some inspiring leaders out there today. Knowing that we do sometimes actually learn from history and that good and ethical leaders are more powerful than their lesser counterparts, let’s all hope that the tide will turn. Let’s do more than hope, actually. Let’s work tirelessly to hire, promote, and advance good leaders into powerful roles, expelling horeshit leaders to the margins where they belong.


Introverts, Extroverts, and Being Out of Your Comfort Zone

I loved the movie The Omega Man when I was a kid. Charlton Heston is seemingly the only man left in the world. He spends his days scavenging the city for goods (sometimes really good goods), and every night he barricades himself inside his fancy house to protect himself from the apocalyptic mutants known as The Family that ravage the Earth. He’s safe outside in the daytime because the mutants cannot tolerate bright light, and at night he lights up his urban castle with klieg lights to keep them away.

I felt like that was a pretty sweet deal. Sure the homicidal monsters outside the fortress walls were a nuisance, but it seemed like a small price to pay to not have to ever deal with other people. It was the ultimate version of locking yourself in your bedroom and putting on headphones when your relatives or parents’ friends came over.

During breakfast, I used to build a less robust fortress around me made out of cereal boxes to block out anyone who might dare try interacting with me during the most miserable meal of the day.

I know what you’re thinking: Sounds like you were a real loser as a kid. But I can assure you, I still am.

I felt the same way about Tom Hanks in Castaway many years later, when I was ostensibly a grown-up. It just goes to show you, I thought, even after a horrible tragedy like that plane crash, something good can happen like being stranded on a deserted island. And your sole companion, Wilson, is so refreshingly unencumbered by speech.

Some people have a hard time interacting with other people and prefer being alone with their thoughts. They are often referred to as introverts when their backs are not turned. Lately they have been getting a fair amount of favorable attention partly, I think, because of the popular book Quiet, and also because of the Internet. (It’s a lovely medium for introverts. You can just scream into the ether then run away and hide.) And while I am all for people extolling the virtues of my people, one should be cautious about excusing away one’s behavior with “That’s just the way I am.” Yes, find the strength in who you are, but beware of complacency.

Growth is hard. It comes from forcing yourself to be uncomfortable. This is true if you want to be really good at math, writing, painting, or making small-talk at a cocktail party. Some people may have an earlier head start with certain disciplines, so it seems to come easily to them, but that doesn’t mean you can’t develop it because it doesn’t come naturally to you. If you want (or need) to be good at something, you have got to put in the time and effort. You’ve got to work at it and build up the skill. As Mihaly Csikszentmihalyi teaches us, as your skill increases with highly challenging activities, your anxiety decreases and arousal and even joy (or “flow”) increases.

Building a coalition, creating a supportive social network, meeting likeminded and not-likeminded people, even casual interactions are incredibly important not only for professional growth but the human experience in general. It’s comforting behind those cereal boxes, but sometimes being comfortable is not the best thing for us. Believe it or not, generally we all feel better when we’ve had some level of social interaction. It’s important to make the effort to have an exchange of ideas or present your own thoughts and discoveries for the same reason it’s important to grow in other disciplines that will help you make a positive impact and have a fuller life.

The same holds true for extroverts. Although some may not see their aversion to introversion as a shortcoming, it certainly can be. An introvert’s opportunities to develop social acuity are abundant and painfully clear. Extraversion, on the other hand, is often assumed to be everyone’s aspiration. Introversion is perceived as lacking something while extroversion is an abundance of that same thing. What is there to develop when you are what everyone else wants to become? But of course one can just as easily rely too heavily on extraversion: flitting from one meeting to the next, booking lunches every day, constantly being on the phone with someone, and never taking a beat to just stop and think (or not think) on one’s own. There is power and goodness in solitude.

For a kid growing up in Minnesota with dozens of cousins who were talented performers and gregarious (shall we say) orators anxious to bring me into the fold, The Family in The Omega Man resonated with me. After a few decades of perspective, I can see now that while I still may not want to be one of the mutants, there is good in them and putting up barriers (made out of klieg lights and razor wire, cereal boxes and books, or iPhones and video games) is not productive. Reach out. Talk to other people who are not like you. There is life out there to live (on your own and with others).

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