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.

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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.Monkeys Paw knot pic

14 thoughts on “CEOs — Doing Tough Things Shoptalk

  1. Just reviewed the list. Wowee–the longer I go, the more items on the list I keep encountering. Thanks for the encouragement.

    How about this one: Holding fast on a price point you know is correct, since every other customer (save one prospect demanding to blow it up) cheerfully purchase at that point–with a partner whining that we should cave?

  2. awesome list.
    Biggest mistakes related to these kinds of situations I have seen – DO NOTHING
    On the flip side – OVER-REACTING and making major changes without enough reflection can be worse.
    I observed so much of what I perceived as “DO NOTHING” early in my career, that I don’t think I was ever accused of not taking action.
    The periodic crises that I experienced in two startups were great learning experiences.
    It’s a great test . .do you
    1. freeze up?
    2. freak out?
    3. figure it out?
    After about 10 times, you get pretty good at staying calm and figuring it out. If you don’t get good at it, you probably shouldn’t be in charge.

    • .
      It sounds obvious, but a CEO has to want to be in charge and then has to take charge.

      One does not receive power, one takes power.

      Courage, even in the most desperate situations, is continuing to act when you don’t want to.

      Once you have tasted command, power — there is no other flavor which is as essential and as delicious.


  3. Challenging situations.

    I’ve been in some challenging situations in some organizations: Sometimes what I did was effective and the results good, and sometimes not.

    The situation that would cost me sleep, give my a sick stomach, a bad headache, etc. would be one that threatened serious harm or the end of the company.

    More broadly I see the possibilities as between two extremes, (1) move fast and (2) move slowly, in a sports team context:

    (1) Fast. Pull together the players, practice one afternoon, head into the schedule, and make personnel changes between games and even during games. Upside: Get into the real games right away. Downside: Risk losing nearly all the early games.

    (2) Slow. Carefully select the team members. Have several months of practice, e.g., shirts and skins, have time to train and develop some of the players who do have potential, have time to make personnel changes, scout the competition, have a deep bench, then charge into the schedule of the real games with confidence that can win most, maybe nearly all, the games.

    (1), (2) are extremes and only sports analogies, but maybe they are pertinent. Analogies from other areas of work — military, engineering, financial, legal — are also possible and maybe similarly pertinent.

    My suspicion is that good planning and careful work can make an effort relatively immune to lots of unpredictable but, really, not unusual, exogenous nonsense. E.g., Ike’s Overlord suffered from (A) Bradley’s too little shelling of Omaha Beach, (B) Monty’s too slow progress at Caen, (C) the big storm in the English Channel, (D) the challenges of the hedgerow country, and maybe more, but STILL was successful. In strong contrast, Monty’s Market Garden was planned too quickly and needed a lot of stuff to happen just as planned (it didn’t) or the whole effort would fail (it did).

    My suspicion is that when big disasters hit, the effort had charged forward too fast with vast goals with half-vast planning.

    Maybe I’m being too simplistic and wrong.

    Maybe much of the difference is good leadership: Maybe often really can move too quickly and when stuck in some swamp — bills unpaid, employees leaving, Sheriff coming to lock down assets for unpaid bills, no money for expense accounts, big customers screaming that even the basic billing was both late and badly wrong, some employees close to fist fights in the offices, internal fights with some cliques trying to sabotage other cliques, etc. — use good leadership to get the now barefoot employees to come together (lunch for all from some loaves of bread and a block of sliced American cheese, paid for by the CEO personally), get the work done, and be successful.

    I see the (1)-(2) difference as not just leadership but solid plans, the difference between (A) the stalemate in the trenches in WWI and (B) what Schwarzkopf did to Saddam in Gulf War I.

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

    Quite the interesting challenge, especially the culture shift that comes with it.

    Thanks for the pep talk, you glorious junk of metal….”overwhelming your deodorant” made my morning.

    • .
      The jump from AA ball to The Show is a big leap and not everybody can make the jump. Even CEOs.

      When the guys at the bottom of the ditch were there when you lit the campfire, it’s tough to do and do well as there are no good feelings to share.

      It is real and it happens.


      • What about the issue of loyalty? So, there’s (A) loyalty of the CEO to the members of his founding team and (B) the loyalty of that founding team to the CEO and the company.

        For (A), the CEO doesn’t want to get a reputation that he will too soon be disloyal to people who have been loyal to him. For (B), replacing loyal people with outsiders — the outsiders may be better in this and that but what about their loyalty to the CEO, the other founders, and the company?

        In some organizations in some circumstances, loyalty plays a big role, but maybe usually a CEO needs to emphasize just getting competent people just to get the work done? Maybe.

        • .
          Loyalty and fairness are cousins.

          Loyalty can rub up against one’s fiduciary duty to operate an enterprise solely for the benefit of the shareholders.

          The conflicts are real and, sometimes, irreconcilable. That’s why they’re tough.

          They’re not always perfect answers even when there are perfect facts.

          Loyalty, like respect, is earned. Loyalty, however, does not have a very lengthy shelf life. The day after you resign as a CEO, you will understand this.

          Loyalty, like respect, is a two way street. You get what you give.

          If I could only obtain one, it would be fairness.


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