So this is a niche post on a niche issue, but I think an important one because I see it creating real problems all the time.

The Arrogant Chief of Staff that is empowered to make big decisions, but goes rogue and makes bad ones.  Or at least, lacks the life experience and maturity to make good ones.

Three recent examples from just the past few weeks:

Example #1:  CEO of $10B+ Public SaaS Company’s Chief of Staff Never Follows Up

A little while back, a CEO of a $10B+ Public SaaS Company that I love asked if we could partner on something for SaaStr Annual.  I said Of Course, and was passed on to their Chief of Staff.  The other day, the CEO asked me if the partnership was still happening. I told him I’d followed up twice with the Chief of Staff but heard nothing.  And now it was too late.

Example #2:  More Minor, But Bumping Podcast Guests — Without Telling Them

While a much minor minor than the first example, I think it’s common enough to be worth telling.  The other day I was asked to join a podcast as a favor.  The day was packed but I did rearrange my whole schedule and day to help.

I fired up the Zoom and the browser, and waited and waited.  Nothing.  No email, no nothing.

I emailed the team and was told by the Chief of Staff, “We decided to work with other partners”.

What does that even mean?

Example #3:  Top SaaS Company Wanted to Collaborate with SaaStr on a “StartUp Day”

Now this would be a ton of work for us with no direct benefits, but I loved the CEO and wanted to help.  We agreed, and were passed on to the Chief of Staff.  And just … crickets.  No response, no nothing.  Aha.  I was genuinely shocked a COS wouldn’t even respond once when asked directly in email to do something seemingly important by the CEO of a public company, but they didn’t.

My Only Point is This:  I Know You Need Leverage, But Just Make Sure Your Chief of Staff Isn’t Going Too Rogue

We all want that magically right-hand person that can just Get Sh** Done for us.  I need one myself.  But most folks can’t really operate at that level.  And many Chiefs of Staff are really still early in their career, and don’t actually have the life experience to make the right judgment calls on things.  And sometimes, perhaps even oftentimes, that title “Chief of Staff” goes a bit … to their head.

I really do see this a lot.  I don’t take it personally.  I’m just sharing this post as it’s more common than CEOs realize.  Get the leverage, get the help.  Just make sure that Chief of Staff is actually giving you leverage.  Not just making poor decisions or hiding things.  Or just not getting them done.

And experiences from a few others:

“The problem is even more upstream than that. Many CEOs don’t know what a CoS is, let alone a solid grasp of how best to leverage them. So if this is the case and they hire one, it’s already a house of cards. I know of founders hiring Chiefs of Staff with no job description, in which case, it’s more useful to light your money on fire and make some s’mores.”  — Zaharo Tsekouras, Chief of Staff Recruiter

“Have seen #1 happen multiple times” David Andersen, Principal Architect, 

“Conversely, I’m going to use this opportunity to shine a light on the very best Chief of Staff I’ve ever seen. Emily Tate moved from the US to the UK to join Mind the Product as Chief of Staff just before the pandemic. Her product-led thinking, her deep empathy for the team and her ability to keep her head (and ours) above water as the pandemic literally destroyed our existing decade-old business was a core part of the firm’s survival and subsequent successful exit (i.e. not a fire sale!) to Pendo. Get your Chief of Staff right, and the unlock is incredible. Quite possibly the single best leader I’ve ever worked with, and sit beautifully across CPO, COO and COS, unlocking value and performance everywhere she goes.” — James Maye, ex-CEO of Mind the Product


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