What’s the difference between a good leader vs. bad leader? What do good leaders do differently?

It’s an essential question every leader must ask themselves.

~ Jason Evanish from,

“What do good leaders do differently?” They ask themselves that question. It’s a good article (an actual article, not just a wee listicle) worth glancing at simply for the first graphic which should make you chuckle and stick with you.

I want to ask the next question: What do effective leaders do differently? Because I’m emphatic that it’s possible to be a good leader—even a great leader—but end up not being effective. Great leader, great goal, and yet… sometimes failure. There are also some horrific examples of bad leaders who manage to be extremely effective. It really feels like the quality of a leader and the effectiveness of a leader aren’t interdependent. What’s up with that?


Easy versus hard

Those things are easy now. They might cost more than we’d like, but you can put them on a check-list and they’ll get done. What’s hard now is breaking the rules. What’s hard is finding the faith to become a heretic, to seek out an innovation and then, in the face of huge amounts of resistance, to lead a team and to push the innovation out the door into the world. Successful people are the ones who are good at this.

~ Seth Godin



Most see excellences as some grand aspiration. Wrong. Dead wrong. My two cents: Excellence is the next five minutes or nothing at all. It’s the quality of your next five-minute conversation. It’s the quality of, yes, your next email. Forget the long term. Make the next five minutes rock!

~ Tom Peters



And in the end, cynicism is a lousy strategy. Hope without a strategy doesn’t generate leadership. Leadership comes when your hope and your optimism are matched with a concrete vision of the future and a way to get there. People won’t follow you if they don’t believe you can get to where you say you’re going.

~ Seth Godin


On leadership

Conflicting opinions. Confusing data. Unexpected developments. Interpersonal conflict. We sometimes miss the bliss of the vision and despair. I’m not sure I can do this. You respond immediately, “It seems an impossible thing. Of course it’s hard, but we are going to do this together and I’ll explain how.”

~ Rands from,

There’s an array of skills that a leader has to master to be a good leader. Explaining things is one of those skills. Everyone who knows me even slightly, knows I’m great at explaining things. But as I try to lead more, I’m realizing that no, actually I’m a mediocre—possibly even a poor—explainer. I’ve recently realized that vastly too much of my explanations are about attempting to control other people’s reactions, (or their opinions,) to what I’m suggesting.

“Take this jacket. It’s lightweight, water proof and will keep you dry if we encounter rain. And rain is likely on the mountain we’re setting out to climb. I once went without such a jacket, and I wound up wet and miserable. The color also happens to be one you normally like, and it looks good. It’s got lots of pockets, which are all taped and the design of the flaps keeps water out.” (Alas, a decade ago, that explanation would have also unpacked what “taped” means, and why it’s a desirable feature.)

But that’s way too much information, all intended to convince the listener. It’s a sign of attempted consensus building. It’s all hedging. It’s all me sharing the reasons why you too would make the same decision—to bring this jacket—if you too had all the information and perspective that I have.

A real leader would say, “This is the correct jacket to take, considering the weather we are going to face when we climb that mountain.” Because then, if it turns out it is in fact not the correct jacket, then I’m on the hook for that error. Which is exactly where—on the hook that is—a true leader should be.



People think that leadership is something that just happens. One is anointed a leader. One is promoted to leadership. One is born into leadership. And of course, this is not the case.

~ Ryan Holiday from,

Holiday is most famous for his work raising awareness of the ancient, but still very apropos today, philosophy of Stoicism. (Not to be confused with the very different english word, “stoic.”) But this article is all about leadership. It’s a wonderful survey of guide stars. I’m particularly fond of the idea that a leader doesn’t make things worse.

My bias towards taking action… my urge to make a change to make things better… far too often I make things worse. If my life had an omniscient narrator, there’d be a lot of scenes that start with, “Here Craig forgot a hard won lesson. Despite not having a clear idea how to help, he still put his two cents in.” (Cue slow-motion footage of car crash unfolding. Cut to black. Roll end credits.)



Being asked to generate this kind of realistic solution requires letting go of the childlike fantasy in which one can have all upside and no downside. It requires really digging into an issue, developing a depth of understanding that goes beyond drive-by feedback. As the officer quoted above observed, by mandating that any critique be coupled with a counterproposal, Ike’s policy “made for more careful scrutiny and analysis.”

~ Brett McKay from,

Not long ago I thought that this arrangement—requiring realistic solutions be provided when criticizing current ones—was unhealthy. I thought that it also led to people generally not speaking up when they saw a problem. But I now see that there are two different scenarios: raising issues and providing criticism.

“Always bring me problems,” is an important policy. It encourages people on a team to speak up when they see something they believe is a problem. The team then benefits from everyone’s perspectives, a culture of openness and honesty is created, and even when mistaken less-experienced people learn from their practice at assessment of problems. This is a different scenario than the one of criticism.

One of the hallmarks of constructive criticism is that it provide alternatives. In this scenario it is not sufficient to simply point out flaws or problems. To encourage deeper understanding each person must be challenged to find an alternate proposal. Doing so requires each person to understand the goal and the realities which constrain the possible courses of action. This type of constructive collaboration, where criticism is of the idea and not of the person, is where teams can really multiply the impact of the individuals’ efforts.

To put it as a spin on acting improvisation: Where improv instructs us to avoid, “no,” preferring, “yes, and….” Constructive criticism requires, “no, and….”



All outcomes are manifestations of forces that are at work to produce them, so whenever looking at specific outcomes, think about the forces that are behind them. Constantly ask yourself, “What is this symptomatic of?”

~ Ray Dalio from,

This is pretty much the zero-th rule of being a rational agent. (But that doesn’t mean it doesn’t bear repeating.) The post from Parrish is simply a long list of quotes from Dalio. It’s a great list, and it’s assembled in the context of leadership skills. This one, (quoted above,) in particular speaks to me; speaks to me like a drill sergeant. “What is your dysfunction?!” Anyway.

Once I started practicing being rational—yes, emotions are real, they are important, they get their due… But once I started intentionally practicing using rationality as a tool I made huge strides in self-improvement.


Bias to action

The full definition of leadership that Badaracco gradually unfolds through literature in the course is: “Leadership is a struggle by flawed human beings to make some important human values real and effective in the world as it is.”

~ Martha Lagace from,

I’ve mentioned bias to action previously, but I don’t recall having every connected it to one of Machiavelli’s best-known quotes, that fortune favors the bold. (Click through for more context.) Here I’m struck by Badaracco’s choice of, “effective,” as a critical feature of leadership. Certainly without action, there can be no efficacy. (And, yes, using my words totally counts as action, thank you.) Leaders are by definition out in front. That means acting first, and that presumes being capable of acting. If my bias is towards inaction, (gather more data, think about it more, however you want to mince those words,) I cannot be a good leader.