Kyle Downey

Managing Pandaemonium: Leadership Techniques from Hell

(Previously published pseudonymously, 25 May 2019)

One of the guilty pleasures of Milton’s Paradise Lost is the appeal of his central character; even though you know you should not be rooting for him and his band of fallen angels, Milton sets up the unfallen angels for a greater Fall: they lack the appeal of Satan’s unruly crew, Jesus is a milquetoast, and God himself is at best peripheral. Satan is one of the original anti-heroes: he’s the Tony Soprano of the underworld, and Hell is his New Jersey. To achieve this, Milton does something interesting: he paints a picture of an effective leader with the most unlikely, demonic form.

We need to start with definitions first. Management & leadership are commonly distinguished as iterative improvement and effective running of the status quo vs. the enabling and shaping of transformational change. The reality is any effective leader shuttles between these two modes constantly, but we are going to focus on Satan’s leadership here. But what is leadership?

In Leadership Without Easy Answers, Ron Heifetz’s 1994 classic on leadership studies, he struggles with this question. He points out that our gut feelings about great leadership are often vague (what is charisma anyway?) or tend to confuse effective persuasion with leadership; it’s too easy to end up with a definition that includes both acknowledged great leaders and demagogues. “When influence alone defines leadership, Hitler qualifies as an authentic and successful leader: he mobilized a nation to follow his vision. Indeed, he inspired millions of people to organize their lives by his word.”

So Heifetz sets forth to introduce values into the definition:

First, the definition must sufficiently resemble current cultural assumptions so that, when feasible, one’s normal understanding of what it means to lead will apply. Second, the definition should be practical, so practitioners can make use of it. Third, it should point toward socially useful activities. Finally, the concept should offer a broad definition of social usefulness.

As he states it later: “socially useful goals not only have to meet the needs of followers, they also should elevate followers to a higher moral level.” He introduces the idea of “adaptive work,” the work that must be done for the community to respond to a changing environment.

You might think that Satan’s prior conviction for trying to overthrow Heaven or subsequent plotting to corrupt all of mankind would be disqualifying, and you’d probably be right. Ideally our definition of “socially useful” should be expansive enough to cover the good of colleagues, shareholders, communities, the environment, future generations, and more. But let’s put that aside and limit our definition of the followers and stakeholders just to Satan’s former army, now downcast:

… he with his horrid crew

Lay vanquisht, rowling in the fiery Gulfe

Confounded though immortal: But his doom

Reserv’d him to more wrath; for now the thought

Both of lost happiness and lasting pain

Torments him; round he throws his baleful eyes

That witness’d huge affliction and dismay

Mixt with obdurate pride and stedfast hate:

At once as far as Angels kenn he views

The dismal Situation waste and wilde,

A Dungeon horrible, on all sides round

As one great Furnace flam’d, yet from those flames

No light, but rather darkness visible

Serv’d only to discover sights of woe,

Regions of sorrow, doleful shades, where peace

And rest can never dwell, hope never comes

That comes to all; but torture without end ….

Something here has to change, and quickly, which means we are in the mode of leadership. Satan pulls together the full toolkit, starting with the simplest resource, himself.

Executive presence

As a life-long introvert, I tend to weight executive presence much less. More often when the subject comes up with a direct report or a mentee, it’s because someone’s previous manager gave them advice to work on his or her executive presence with no explanation of what this means and no concrete advice on what behaviors he or she should change. But while most of success is showing up, how you arrive does matter: the Devil wore Prada for a reason.

Milton’s Devil arrives, finally landing on a firm spot in the middle of the lake where his “horrid crew” have fallen, “all [their] Glory extinct, and happy state / Here swallow’d up in endless misery” — yet he rises up:

Forthwith upright he rears from off the Pool

His mighty Stature; on each hand the flames

Drivn backward slope their pointing spires, & rowld

In billows, leave i’th’ midst a horrid Vale.

Then with expanded wings he stears his flight

Aloft, incumbent on the dusky Air

That felt unusual weight, till on dry Land

He lights, if it were Land that ever burn’d

With solid, as the Lake with liquid fire.

And what an arrival! Satan is still armed from his battle in heaven, a shield thrown behind his shoulders, his towering spear a support as he makes his painful way across the fire, and you feel his size and presence in the detail as he stands among his fallen angels. He is not just huge and impossible to ignore — he’s gorgeous:

… the superiour Fiend

Was moving toward the shore; his ponderous shield

Ethereal temper, massy, large and round,

Behind him cast; the broad circumference

Hung on his shoulders like the Moon, whose Orb

Through Optic Glass the TUSCAN Artist views

At Ev’ning from the top of FESOLE,

Or in VALDARNO, to descry new Lands,

Rivers or Mountains in her spotty Globe.

His Spear, to equal which the tallest Pine

Hewn on NORWEGIAN hills, to be the Mast

Of some great Ammiral, were but a wand,

He walkt with to support uneasie steps

Over the burning Marle, not like those steps

On Heavens Azure, and the torrid Clime

Smote on him sore besides, vaulted with Fire;

Nathless he so endur’d, till on the Beach

Of that inflamed Sea, he stood and call’d

His Legions, Angel Forms, who lay intrans’t

Thick as Autumnal Leaves that strow the Brooks

Not everyone has great physical presence; entering a conference room with a massive spear perhaps sets the wrong tone nowadays; and none of us gets to speak with Milton’s poetry. But Milton pauses here to really set the stage for Satan’s great speeches with good reason. We are meant to not just absorb Satan’s ideas, but to feel his presence in the midst of the fallen angels he aims to lead.

In my mind, presence is a combination of physical charisma, dress, non-verbal cues and confidence. Like the Supreme Court’s definition of pornography, you know it when you see it, but it can take many forms. The most powerful form of presence comes of light expressions of confidence, which anyone can learn: the joke you will tell at your own expense; the side comment with a touch of edge; the choice to press your point or the confidence to just let a criticism stand and pass it by.

Building software, writing a complex contract or planning a budget is not like making a chair; the people you are working for sometimes do not really understand what you do and cannot tell the difference between a good job and a great job, yet they still need to make a choice to put the responsibility in your hands. And so they make the call based on their past experience with you or what they know of your reputation, if anything, plus non-verbal cues. You need to bring your expertise and deliver, but before you are even allowed to deliver, someone needs to trust you can do it. I worked in technology on Wall Street, and I can tell you the right answer when a head of a trading desk asks you “are we going to be all right in these market conditions?” is not “I don’t know” or an incoherent mumble. The right answer is: “absolutely, and here are the five things we did to make sure it all goes smoothly.” And when the shit hits the fan anyway because of the sixth thing you forgot to do, you calmly take responsibility, explain how you will fix it, and list out what you’ll do to make sure it never, ever happens again.

I once heard a particularly harsh executive comparing someone who had been in a meeting to a houseplant. This was not a comment on his choice to wear a tie and “dress like the job you want” or whether or not he made sure to speak up: this was about the real substance of presence, the stuff that makes people remember you were there, which in turn serves to amplify your best ideas. That manager lacked presence, and so he was less able to influence and get his ideas not just heard, but followed.

Don’t be a houseplant. Strap on your titanium Laboutins, swing an asbestos scarf across your shoulders, and walk across a lake of fire to higher ground. The confidence you carry matters more than the cost of your clothes or the expression of your eloquence.

The call to action

Once risen from the lake, Satan surveys the rest of his fallen soldiers and calls them up:

He call’d so loud, that all the hollow Deep

Of Hell resounded. Princes, Potentates,

Warriers, the Flowr of Heav’n, once yours, now lost,

If such astonishment as this can sieze

Eternal spirits; or have ye chos’n this place

After the toyl of Battel to repose

Your wearied vertue, for the ease you find

To slumber here, as in the Vales of Heav’n?

Or in this abject posture have ye sworn

To adore the Conquerour? who now beholds

Cherube and Seraph rowling in the Flood

With scatter’d Arms and Ensigns, till anon

His swift pursuers from Heav’n Gates discern

Th’ advantage, and descending tread us down

Thus drooping, or with linked Thunderbolts

Transfix us to the bottom of this Gulfe.

Awake, arise, or be for ever fall’n.

The response is immediate: “They heard, and were abasht, and up they sprung.” What’s notable is how Satan started here. He did not appeal to their anger or greed, and he touches only lightly on their fears, pointing out that if they stay down for too long their pursuers could take them down. He is not scolding them or insulting them; he. In fact he seems at pains to offer up some more innocent explanations: perhaps they are just resting after battle, for instance, or maybe stunned from the fall. He is trying to inspire adaptive behavior while at the same time is very clear about the dire situation they find themselves in. Taking our common understanding of the Prince of Darkness, he could have easily taken his great spear and made a example of a demon or two and hollered at them to get their lazy asses in gear. That he does not shows he understands it’s more important to fix the situation and help his army than to just vent his anger and frustration — and that by so doing, he’s more likely to get them moving.

He spake: and to confirm his words, out-flew

Millions of flaming swords, drawn from the thighs

Of mighty Cherubim; the sudden blaze

Far round illumin’d hell: highly they rag’d

Against the Highest, and fierce with grasped arm’s

Clash’d on their sounding shields the din of war,

Hurling defiance toward the vault of Heav’n.

Emotional openness

A damaged Satan stands before his vanquished army, and initially Milton focuses on how even all the scars of war have not entirely dimmed him. Returning to presence, Satan, standing “like a Towr” is the center of the encircled warriors, who “half enclose him round.” But what’s interesting is where Milton goes next, before Satan’s speech starts:

… he above the rest

In shape and gesture proudly eminent

Stood like a Towr; his form had yet not lost

All her Original brightness, nor appear’d

Less then Arch Angel ruind, and th’ excess

Of Glory obscur’d …. Dark’n’d so, yet shon

Above them all th’ Arch Angel: but his face

Deep scars of Thunder had intrencht, and care

Sat on his faded cheek, but under Browes

Of dauntless courage, and considerate Pride

Waiting revenge: cruel his eye, but cast

Signs of remorse and passion to behold

The fellows of his crime, the followers rather

(Far other once beheld in bliss) condemn’d

For ever now to have their lot in pain,

Millions of Spirits for his fault amerc’t

Of Heav’n, and from Eternal Splendors flung

For his revolt, yet faithfull how they stood,

Thir Glory witherd. As when Heavens Fire

Hath scath’d the Forrest Oaks, or Mountain Pines,

With singed top their stately growth though bare

Stands on the blasted Heath. He now prepar’d

To speak; whereat their doubl’d Ranks they bend

From Wing to Wing, and half enclose him round

With all his Peers: attention held them mute.

Thrice he assayd, and thrice in spite of scorn,

Tears such as Angels weep, burst forth: at last

Words interwove with sighs found out their way.

Three times Satan tries to speak but cannot because he’s crying. He is so moved by not only the sight of his former army, but by the realization that “[m]illions of Spirits” had been “for his fault amerc’d / Of Heav’n, and from Eternal Spendors flung / For his revolt, yet faithful how they stood.” Satan is guilty and grieving. He does not hide this either: he pulls himself together and then starts to speak.

A former manager once told me that one of the leader’s jobs is to moderate and re-interpret emotion for his or her team. It’s not a stoic role: we must acknowledge sometimes that the situation is not good and even show the effect it has on ourselves. But because that “half-encircled” group around us is taking cues on how to feel about the situation, we need to moderate that emotion: clip the highs and elevate the lows. Here Satan shows that it’s OK to let some emotion out, and he likely gets credit from his assembled ranks for having the courage to show it and then overcome it. Put another way, Satan models how to process the situation effectively, and adapt to “this dire change.”

Consensus-building

After Mammon crafts the great capital of Hell, Pandaemonium, Satan’s crew gathers within, and “After short silence then / And summons read, the great consult began.” That word choice, consult, again reflects what Satan does not do after his call to action: he doesn’t start by telling everyone what to do. “Satan exalted sat, by merit rais’d / To that bad eminence” so he’s clearly in charge here, but his very first act is to listen:

… With this advantage then

To union, and firm Faith, and firm accord,

More then can be in Heav’n, we now return

To claim our just inheritance of old,

Surer to prosper then prosperity

Could have assur’d us; and by what best way,

Whether of open Warr or covert guile,

We now debate; who can advise, may speak.

But we already know Satan’s preferred course of action. Even before Mammon built Pandaemonium, Satan showed his preference for guile, and hinted at his later plan to go to Earth (“Space may produce new Worlds”). He speaks at length, and only at the end concedes that “these thoughts / Full Counsel must mature.”

Henceforth his might we know, and know our own

So as not either to provoke, or dread

New warr, provok’t; our better part remains

To work in close design, by fraud or guile

What force effected not: that he no less

At length from us may find, who overcomes

By force, hath overcome but half his foe.

Space may produce new Worlds; whereof so rife

There went a fame in Heav’n that he ere long

Intended to create, and therein plant

A generation, whom his choice regard

Should favour equal to the Sons of Heaven:

Thither, if but to prie, shall be perhaps

Our first eruption, thither or elsewhere:

For this Infernal Pit shall never hold

Caelestial Spirits in Bondage, nor th’ Abysse

Long under darkness cover. But these thoughts

Full Counsel must mature: Peace is despaird, F

or who can think Submission? Warr then,

Warr Open or understood must be resolv’d.

Subsequently multiple demons speak: Moloc urges “open Warr” for he is “[o]f Wiles / More unexpert”; Belial slyly “with words cloath’d in reasons garb” says he’d be for war (“[a]s not behind in hate”) but … guys, seriously, it’s probably a really bad idea after the way we all nearly got killed; it could be much worse the second time around. He proposes they stay in Hell instead: he “[c]ounsel’d ignoble ease, and peaceful sloth” as Milton describes, showing what he thinks of the idea. Mammon continues the counsel for peace, pointing out that they could re-make Heaven in Hell if they wanted:

As he our Darkness, cannot we his Light

Imitate when we please? This Desart soile

Wants not her hidden lustre, Gemms and Gold;

Nor want we skill or art, from whence to raise

Magnificence; and what can Heav’n shew more?

Our torments also may in length of time

Become our Elements, these piercing Fires

As soft as now severe, our temper chang’d

Into their temper; which must needs remove

The sensible of pain. All things invite

To peaceful Counsels, and the settl’d State

Of order, how in safety best we may

Compose our present evils, with regard

Of what we are and where, dismissing quite

All thoughts of Warr: ye have what I advise.

And that seems to get a lot of traction. What Beelzebub calls “the popular vote” to become “Princes of Hell” holds the room for a while, but Beelzebub pulls them back, returning to Satan’s original theme of corrupting Man as the better approach, for “[t]his would surpass / Common revenge, and interrupt [God’s] joy / In our Confusion ….” And finally it’s resolved without Satan ever having argued his point:

Well have ye judg’d, well ended long debate,

Synod of Gods, and like to what ye are,

Great things resolv’d; which from the lowest deep

Will once more lift us up, in spight of Fate,

Neerer our ancient Seat ….

In fact, Milton suggests that Beelzebub was a plant, arguing Satan’s point for him: “Thus BEELZEBUB / Pleaded his devilish Counsel, first devis’d / By SATAN, and in part proposed.”

Satan thus demonstrates several effective strategies for driving change: he frames the discussion; he gathers views and listens first, giving even views strongly against his own a chance to be heard; and in pushing his army toward a more adaptive response, and away from the easy but potentially dangerous course, he tilts the table a bit by having a trusted partner argue his case for him. This is not an authoritarian approach, but it’s not a democratic one either: it’s more like a process of going from an idea to a plan, and ensuring everyone comes along with the idea, even those (like Mammon) who might prefer another approach.

In the end the only question that remains is who will go to Earth, and carry out the plan, and this gives us Satan’s final example of effective leadership.

Servant leadership

Robert Greenleaf’s idea of “servant leadership” aligns well with Heifetz’s concept of leadership: He asks: “Do those served grow as persons? Do they, while being served, become healthier, wiser, freer, more autonomous, more likely themselves to become servants?” The servant leader shares power, and “the leader exists to serve the people.” And sometimes this means getting down in the trenches.

Satan asks for volunteers to go to Earth:

… who shall tempt with wandring feet

The dark unbottom’d infinite Abyss

And through the palpable obscure find out

His uncouth way, or spread his aerie flight

Upborn with indefatigable wings

Over the vast abrupt, ere he arrive

The happy Ile; what strength, what art can then

Suffice, or what evasion bear him safe

Through the strict Senteries and Stations thick

Of Angels watching round? Here he had need

All circumspection, and we now no less

Choice in our suffrage; for on whom we send,

The weight of all and our last hope relies.

It’s a dangerous and important mission, and the response is … crickets:

This said, he sat; and expectation held

His look suspence, awaiting who appeer’d

To second, or oppose, or undertake

The perilous attempt: but all sat mute,

Pondering the danger with deep thoughts; & each

In others count’nance red his own dismay

Astonisht: none among the choice and prime

Of those Heav’n-warring Champions could be found

So hardie as to proffer or accept

Alone the dreadful voyage ….

Finally, Satan, knowing that the good of his army depends on this potentially fatal mission, takes the role of the servant leader and volunteers himself:

But I should ill become this Throne, O Peers,

And this Imperial Sov’ranty, adorn’d

With splendor, arm’d with power, if aught propos’d

And judg’d of public moment, in the shape

Of difficulty or danger could deterre

Me from attempting. Wherefore do I assume

These Royalties, and not refuse to Reign,

Refusing to accept as great a share

Of hazard as of honour, due alike

To him who Reigns, and so much to him due

Of hazard more, as he above the rest

High honourd sits?

Satan doesn’t berate his army for not volunteering, nor does he pick some hapless soldier to go and take the risk. He acknowledges that since he did not “refuse to Reign” then “Refusing to accept as great a share / Of hazard as of honour” ill becomes him. In short, he understands that with great power comes great responsibility, and that even applies to the Prince of Darkness. And so our servant leader turns to go, “with thoughts inflam’d of highest design, / Puts on swift wings, and toward the Gates of Hell / Explores his solitary flight,” on a mission to help his people. In the end, it’s hard to find fault with him, despite the significant downer of the whole forbidden fruit business, because he leads so well. Go forth and help your demonic horde: the greatest pleasure of leadership is not the recognition, the palace or the throne, but the honor to serve.

CEO & Co-founder, Cloudwall Capital