Henry VIII as CEO

Dotty Schaffer, August 19th, 2015

In my line of work I am priv­i­leged to know many extra­or­di­nary lead­ers. Now and then I run into one that I call Hen­ry, usu­al­ly when I’ve been asked to replace him. 

Prince Hen­ry of Eng­land wasn’t raised to be king. He was a spoiled child, whose moth­er and grand­moth­er dot­ed on him. He was hand­some, well read, musi­cal, spoke sev­er­al lan­guages, could sing and dance, and write poet­ry. He loved joust­ing, and excelled at all sorts of sport. The child Prince Hen­ry was the delight of every­one at the court. Then, at 11 years old, his broth­er Crown Prince Arthur died and Hen­ry was next in line to be king. At 17 he was crowned, mar­ried his brother’s wife, Queen Kather­ine, and things went South fast. You know the sto­ry: he dumped Queen Kather­ine after 22 years of mar­riage, chopped the heads off 2 of his 6 wives — as well as the heads of any­one who got in his way or dis­agreed with him.

Enough about the old Henry, let’s discuss how to spot a Henry today

  • Hen­ry can be bril­liant and charm­ing and daz­zle in an inter­view.
    He talks more than he lis­tens. His expec­ta­tions can be unrealistic.
  • Hen­ry hires weak peo­ple.
    He likes peo­ple who tell him what he wants to hear, and if they don’t, off with their head (think Thomas More).
  • Hen­ry is inca­pable of win-win nego­ti­a­tions.
    It’s his way, or the high­way. (When the Pope refused to annul his mar­riage to Kather­ine, he had him­self declared Supreme Leader of the Church).
  • Often a Hen­ry will man­age his team hub-and-spoke style.
    He avoids reg­u­lar­ly sched­uled team meet­ings. He has all the answers, and he doesn’t want to hear from you.
  • Hen­ry takes cred­it for every­thing.
    In Hen­ry VIII’s court, he always won every joust, every card game, and every sport. See a pat­tern here?
  • Hen­ry doesn’t like crit­i­cism, input, or shar­ing the spot­light.
    You’ll rarely see his team pre­sent­ing at Board meetings.
  • He fails to see his own faults and no one will tell him the truth.
    As Hen­ry VIII became obese, the men in his court padded their dou­blets so he would not seem so huge.
  • If some­thing goes wrong, it’s your fault.
    Thomas Cromwell’s down­fall was because he arranged the mar­riage to the not-so-pret­ty Anne of Cleves. After the mar­riage was annulled, Hen­ry put Thomas’ head on the block.
  • Hen­ry trusts few peo­ple with the excep­tion of a cho­sen bul­ly.
    Car­di­nal Woolsey and Thomas Cromwell played that role for Henry.
  • Short tenure is a pat­tern under Henry’s lead­er­ship.
    At least you can get a new job and not put your head on the block.

Hen­ry VIII is a fas­ci­nat­ing fig­ure from his­to­ry. In the busi­ness world today, he still makes an appear­ance from time-to-time as a prob­lem for his court and country.

Know any Henrys?

Dotty Schaffer

Partner, Lonergan Partners

Specialty: Public Company Boards


[email protected]

Dotty Schaffer Portrait