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Rule 38: Work politics is chess, not checkers

Posted on March 14, 2024March 27, 2025 by Duncan Zaves

The higher you climb in an organization, the more you need to think through each person’s motivations. Most people are very self-serving, as they should be. We aren’t working in a utopia – we are being paid. Everyone you interact with is building a career, influence, and ultimately power and job security. If you play by simple rules and always look to do the right thing without thinking through the impacts of those decisions on others, sooner or later someone will rip you apart. Do not expect people to do what is right by the company, or even what is right. They will first do what is right for them.

So I’ll keep this advice short – You need to think ahead and think through not just the work, but the motivations of the people involved.

Sooner or later you will come across people who are just bad actors. They’ve built up their power and have no desire to help, take on extra responsibility, or even do the things they are paid to do. Here is a short collection of advice on dealing with people that need to be dealt with:

When you shoot, make sure you kill them:
It’s usually best to play the long game with a safe approach – basically, help people discover the truth about the bad guys and weaken their power base until there is nothing left for them at the company. But sometimes you have to be more forward. Just remember, if you attack someone – in a meeting, to HR, to their boss, whatever…. always remember, a wounded animal is the most dangerous. If you take your shot, make it count.

On character assassination:
Similarly, if you take the low road and stab someone in the back, make sure you hit a vital organ. Frankly, I save the low road for very special cases – usually when they wield much more power than I do. The low road will destroy your reputation and is actually much tougher to do without harming yourself and the company. It is almost always better to stab them directly in their face and just make a thing of it. The better Pro will win.

On handling your own team:
You are only as strong as your weakest link and carrying bad people hurts your good people. So here’s a tip – Don’t fire someone slowly. Don’t be the nice guy. Don’t let it linger. Just shoot them – Once in the head, two in the chest and be done with it. You aren’t doing them a favor wounding them and letting them bleed out, and you certainly aren’t doing yourself a favor letting them linger on… limping around… bleeding all over the place.

Is it better to be feared or loved?
Both.

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