A Leader’s Reflection on Sh*tty Coworkers

Parsing the difference between “could have done more” and “should have done more.”

Photo by Quino Al on Unsplash

Good leaders often look at their failures so they can learn from them. They care about the teams they lead, hoping to show up big and inspire others to do better. They’re often self-reflective, analyzing each step they’ve taken, and trying to figure out how to personally grow and minimize making the same mistakes they’ve made in the past.

Even with all of that reflection, sometimes leaders fail.

Sometimes leaders deal with team members who simply refuse to do the work. Other times, they have higher-ups who are petty, devious, or can’t be bothered to do any real work and sabotage the work from above.

While there’s a lot of strategies to try and work with these troublemakers, one things I hear a lot from leaders looking back on these situations is: “Could I have done more?”

I often respond to this question with a question of my own (as coaches tend to do): “Would the cost of doing more have been worth the change?”

If the answer is yes, then this can be a learning moment and it’s time to deconstruct what went wrong. Where were the shortcomings?

How might you have shown up in a way that would be more effective to enroll this person into your vision of teamwork?

What was holding you back from making that change?

There are many ways of reflecting on this, especially if you felt like the cost was outweighed by the benefits of creating change. But what if the answer is that it wouldn’t be worth it?

Then you have to leave the failure with the other person.

As a good leader, it is often hard to blame the other party. As a leader, your personal integrity and willingness to take the blame are usually the attributes that inspire others to follow your lead. But in cases like these, you need to know when it is right to lay the blame on the other party. Communication and teamwork are two-way streets. While you can be one of the greatest leaders in the world, not everyone will be on your side, no matter what you do.

Think of the great leaders in history. No matter who you’re thinking of, they were great not just because they inspired a mass of people, but because they did it in the face of another mass of people who disagreed wholeheartedly.

Martin Luther King Jr. was never going to win over the guy who shot him. Winston Churchill was not going to enroll Hitler on his side. Julius Caesar wasn’t going to get Brutus to back down.

Like I said, sometimes you have to leave the failure with the other person.

If we look back at the original question of “Could you have done more?” the answer is almost always yes. It is true — you probably could have done more.

However, the upward limit of martyrdom is pretty high and there is almost always the potential to have “done more.”

You could have worked a 100+ hour week and prioritized work over everything else. You could have kept trying to engage with your problematic co-worker and subjected yourself to hours of verbal abuse and gaslighting. You could have spent all your money on gifts to bribe your way into their heart to the point that you don’t have any money to pay rent. You could have called a team meeting and then dramatically cut off your hand and screamed “this is my dedication to the team, all I ask is for you to do your damn work!”

But should you spend extra time, energy, monetary resources, and/or limbs to win over people who might just be diametrically opposed to you and your beliefs and goals, and probably are never going to change regardless?

I think we both know the answer to that.

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