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Why do some newly-hired executives & senior managers at your startup (or bigco) fail spectacularly?

A thread of archetypes
-The One-hit Wonder
-The Tailwind Catcher
-The Hand-in-Glove Fit
-The Smooth Operator
-The Me-First Optimizer
-The Interview Genius
-The Pedigreed Royal
🔻
At times, companies small & large hire senior managers or executives with much fanfare.

After months (or years) of searching for & courting The One, the deal is closed.

As a CEO or executive, you’re feeling excited, hopeful, & if you’re being honest, a little proud of yourself.
Company-wide email announcements are sent to create hope & optimism with the troops: “... they've managed 1000s of people, have 25 hobbies, 7 dogs, ...”

It might even be a PR event, with the obligatory Techcrunch or Recode interview.

And yet too many of these don’t work out.
While there perhaps as many reasons for this phenomenon as there are flavors of ice cream, here’s one of the leading reasons: the leader is fundamentally flawed & your company was unable to detect this in your hiring process. You might have known in your gut, but failed to act.
And while one could write a whole book on this & related topics, here’s a crash course that should improve your chances of detecting a potential mis-hire. If you are a rank & file team member, this should help you understand why fancy executive Bob was DOA.

An archetype survey:
The One-hit Wonder

Has had one spectacular success that made them famous (Valley-famous, not NYTimes-famous) or rich. Everything else has been meh.

Detecting:
Probe deeply into "past successes". Ask why they think X, Y, Z were successes (often spun that way but are really not).
The Tailwind Catcher

Has had many successes but they’re due to “right place right time” factors not skill e.g. aligning with growing verticals/companies.

Detecting:
Mainly evaluating role-specific skills (future), less of “tell me about a time when X, Y, Z..” questions (past).
The Hand-in-Glove Fit

Seems perfect because they spike on 1 or 2 skills that your org uniquely values. But otherwise they have glaring role-specific gaps.

Detecting:
Catch yourself “falling in love” (hard, I know), don’t over-weigh the advice to “hire for crests not troughs”.
The Smooth Operator

Is very impressive mainly due to charisma, has been successful in many places (since charisma works like a charm), comes across as "very executive-y”.

Detecting:
Test for core “technical” skills required for the job, look for signs of over-confidence.
The Me-First Optimizer

Actually very competent, capable of doing a spectacular job, just one glaring flaw: extremely self-centered, will sacrifice team, company, etc. for self.

Detecting:
Gives self too much credit when talking about past successes, backchannel references.
The Interview Genius

Knows all the theory of the job, interviews like a boss (top 5%). Has very few past successes. Often suffers from inability to take action.

Detecting:
In-person job-relevant exercises (don’t do take-home). Unlike The Smooth Operator, references will be meh.
The Pedigreed Royal

This is W2 Royalty. Superb background: Ivy League, White House, Volunteer Work, Big 5, etc. Can be quite competent, just will miss the high expectations

Detecting:
Might not be a bad hire, just keep expectations in check, don’t fill up your C-suite with them
That’s it for today.

I don’t think I’ve shared anything revolutionarily new here.

But it’s my hope that these archetypes & this lexicon can be a bit helpful in avoiding what can be very costly hiring mistakes.

Feedback, questions welcome (reply below / DM).

All the best!
👍🏽
Trying something new.

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