SOMEHOW I MANAGE. dot. dot. dot. Michael Scott’s Leadership Booze Cruise

RET2082 [Roy Tertman]
7 min readApr 20, 2018


Welcome back to the series where we dive in and try to give a new voice to the various actions of the great regional manager — Michael Scott.

This week we take a look at episode s02e11, Booze Cruise, where Michael decided it’s time to share some pearls with the only people he can make it mandatory for them to attend.

Episode recap:

Michael takes the entire branch to a cruise where they can drink and participate in so called leadership games and lots of metaphors on how to run or save a business. They all go on a cruise (in January) and witness Michael tries to perform some motivational speaking and mainly hogging the mike and fake-sinking the ship until he’s literally handcuffed.

The word ‘Ship’ is the word leadership.

Captain Michael Scott

Don’t get me wrong, as much as i’ve been, seen and heard at/of awful leadership exercises and company empowering retreats — i still think that we should do it, only way different that what Michael did :)

So about all those leadership retreats, seminars, vacations, etc. that you may have been to in at least one your workplaces — why and do we need them?

Leadership training exercises: Fun, Motivation and Education

In small and big workplaces, it is important to leave the comfort zone and go out just because people remove a lot of layers and barriers they otherwise would still have, and its a great opportunity to see other characteristics of the people you spend about 60% of your day.

It should be fun — otherwise you would get the same results as you would if you just did it as a meeting. Also remember what Einstein said about doing the same experiment…

It needs to be motivational — otherwise you won’t be able to see what truly moves and opens your team, and you can actually regress the whole team if you lack motivation as a leader in a leadership exercise.

It should be educational — otherwise you just waisting everyone’s time and probably doing it just to check it off your ‘Must-do’ activities or something. Educational can be lots of things, you can educate your team on the road-map of the company and the deliberations you have in the leadership, you can share something personal about hobbies and stuff like that, or you can take everyone on a mind-opening experience. 90% of the cases where the leadership of the company did something small like a Town-Hall meeting — the team solved their issues same or next day.

Michael educated himself (albeit a really small effort) by attending s short seminar by the airport by the sales team of Tony Robbins.
Tony Robbins is very well known veteran motivational speaker, i have read his book (too long), And Michael will not invest in the whole course and only will go to a promotional 2 hour seminar to get the gist.
And you know what? it’s great! what have you done to make yourself a better leader for your company? at least Michael did :)

Education = Knowledge; Knowledge = Problem solving

Just dont do those stupid ‘old’ exercises — Enough!, Gen-Y’ers dont relate to them whatsoever.

Boat Analogies, ’Cause well, we’re on a boat…

  1. I am the Captain.
    Michael starts with the reason on why he even chose a freezing cruise to begin with — he’ll get to be the captain there by default. Are you the captain of your company? you should be, because eventually when sh!t hits the fan — all eyes will be on you to (almost literally) save everyone and get them to safety, or at the very least, set course.
  2. All in the same boat
    We sure as hell are aren't we? a good captain realizes that it’s all about team collaboration and particularly a small company will need to pull their efforts, skills, motivation, and hard work to pull it off. It’s a good reminder to your team that what and how they perform will make everyone more focused on the road ahead and the destination.
  3. Sales is the furnace. Not the sails.
    According to Michael the most important thing in a boat are the people working in the furnace shoveling coal — is it? i can’t say for sure, but i can say Michael brings up a notion in business that has been fading away in recent years — the important of sales.
    Someone once told me that in any business, you can create whatever it is you want and you’ll probably be able to pull it off, but if you can’t sell it — it’s not a business. That person even went as far as saying that sales is 99% of any business. I give you this scenario, let’s say you have built a manned tour flight to Mars. You got it all figured out, the tech, the business model, the go-to-market and you have the resources to pull it off — still you will need to sell it right? otherwise what’s the point… So Michael tries very poorly to show everyone in the Dunder Mifflin team that the sales department is the most important thing in a boat or a business, and it’s a good place to remind ourselves how it sometimes it is the case.
  4. Sometimes you have to be the boss of fun
    It’s 2018 people, we expect fun in our workplace otherwise we will not stay there (or stay, and perform lousy). First fun does NOT mean friendship, so its not about turning your work environment into the team’s personal life, but it is a great way to bring some more of the person behind the employee out.
    Google did slides in the office (wrong), FB does campus parks (great) and i’ve seen companies who take a 3 day extreme trip (because that’s a sure way to strip people of their masks and barriers), it all comes down to how can you make your team see what they do most of their day as also fun — it is scientifically proven that its a mind game — fun makes better workers. So the next time you think about spending some of your budget on fun activities with your team, dont skimp and put some thought into it, it will be worth it in more ways you can imagine…
“Dancing is a form of ancient communication” — Michael Scott
  1. If the boat is sinking — what do you save?
    This one is hard to discuss in just a paragraph, what do you save when things get hard? which they will.
    Michael declares it’s sales and profit centers which are of course the revenue source for almost any company, while that’s not necessarily true for everyone, the exercise is great. Do it with your team, see how they will behave if they had to make hard decisions, it can also make it more sympathetic with your role as a leader, and sympathy towards a team member makes a person a better team player.

Epilogue: Captain in desert storm

The actual captain in the boat was captain Jack, a former marine who did a tour in Desert Storm. It was a brilliant way the writers showed just how Michael is off in his methods.

Since this series is all about showing how Micheal Scott’s management styles are relevant in 2018, i thought it’s relevant to capture true leaders and what they can bring to a company.

Recently, i read on opinion article about how the Israel tech scene has forgotten the qualities combat soldiers bring to the table when it comes to leadership, and how only super-tech people are thought to be great leaders. I read it again after finishing this post and you know what — that episode captured that notion very well. Of course i can’t compare Michael to super-smart tech people, I’m just saying leadership is the most important thing in any company, so be sure to remember that everyone can be a leader, and a great leader puts his team ahead of them in any situation, And great leaders come in a ll shapes and forms :)

Have a great weekend, see you next time.



RET2082 [Roy Tertman]

i write stuff 'cause my therapist told me its good for my mental health, She was right! …. Aggressive Blader | JBC | XCCV 🕺 i do Biz Dev & Strategy for SaaS