The Musings of the Big Red Car

CEOs — Doing Tough Things Shoptalk

No tough things for a Big Red Car today, just chores.

Big Red Car here on a big day for chores, accumulated, undone chores. Bah humbug!

Before we head to do our chores, how about a bit of shoptalk for CEOs?

Being a CEO is a great job. Don’t listen to the hair-shirt-of-the-month club and their “it’s lonely, so lonely at the top.”

But, if you’re going to be a CEO, you have to do tough stuff sometimes.

What seems tough the first time, isn’t tough the third time and when you do tough stuff, you get used to and comfortable with doing tough stuff.

Tough stuff, define tough stuff, Big Red Car

OK, so The Boss has worked with CEOs on things like this:

Extricating a co-founder from a management team without the use of guns or knives.

Parting from an endeavor when the endeavor makes a pivot with which one doesn’t agree.

Dealing with a partner whose personal life precludes their further involvement.

Going through a personal upheaval, like a divorce, while trying to keep the enterprise functioning while an ex sics lawyers on you.

Raising money in a tough environment and facing down the end of the runway before rotation speed is reached.

Firing a new hire — always an expensive, critical one — who was perfect at practice and was a first rate shithead on game day.

Emerging from the cocoon of three co-founders to stand atop the food chain and run the business because you cannot build a winning company with a committee.

Telling a co-founder you need to bring in a big league CTO or CMO and watching the hurt pool up behind his eyes.

Staring down the price tag of values and saying, “This is going to be expensive.” Because nobody really has any values until they buy them at full retail. Until then, they’re ideas.

Telling a client — big, important client — you screwed up and trying to regain their trust.

Putting together a board from disparate individuals so different as to make “odd” a compliment.

Scaling so fast one can’t remember the names of the new folks.

Backfilling after a key member of management or the founding team says, “Adios, MFers.”

Working through a down round.

Putting together that first off site meeting with an Anonymous Company Survey in your hand.

Adding top talent to the management team which dooms the long term viability of folks who were there from day one. Outrunning folks’ shadows.

Starting that second, third, fourth gig and knowing what you learned from the earlier gigs informs you you need to do it differently and stop shooting your own foot.

Contracting, not abandoning, a business which is not quite there, yet.

Negotiating an Employment Agreement and not feeling like a beggar with a tin cup.

Telling a big, strategic supplier that you can’t pay their bill this month.

Laying people off.

Shuttering the business while getting the paperwork right for tax purposes.

Telling your frat buddy who introduced you to your wife that he’s not the right guy for marketing.

There’s no mortar fire, no snipers, but it can get intense.

Bottom line it, Big Red Car

The lesson today is not how to fix these things — all eminently fixable — but to tell you once you can do one difficult thing, then other difficult things aren’t so damn difficult. A guy who can get a board to act like adults, will be able to use that experience to run that first off site.

When CEOs get used to doing tough stuff, other tough stuff isn’t so tough.

So, dear CEO, take heart. Not everything will make your heart race, overwhelm your deodorant. You will be able to transfer your experience mojo to other challenges without encountering migraines.

That’s all there is.

But, hey, what the Hell do I really know anyway? I’m just a Big Red Car, y’all, and that’s good enough. Be good to yourself because it may not be a parade out there trying to do good to you and you’re your own drum major.