Difficult conversations don’t come natural to me. I was brought up in Minnesota by my Irish Catholic mother who taught me to be polite and never criticize, condemn, or complain.

However, the ability to provide and receive substantive criticism—early and often—is the most important skill of a design manager. As the director of design at Flexport, this became evident to me when the percentage of my time managing people surpassed 50%.

In a quest to improve my ability to provide substantive feedback, I developed a framework for growth, which is my guiding compass. It comprises 4 quadrants which are divided by the polls of positivity/negativity and vapid/substantive feedback.

Negative Feedback

Both negativity and positivity are infectious. Negativity causes destruction. Positivity produces growth. If positivity is represented by the words “Yes and,” negativity is represented by “no but.”

No matter how great life is, humans find the capacity to complain. Misery will always find company. There is a certain pleasure people get from tearing things down. However, the end of this road is filled with loneliness as negativity ultimately pushes people away.

Transforming a negative criticism into a positive one will always better the thing or situation being criticized. However, positivity often provides a false sense of progress and hope, especially when the critique lacks substance. Vapid optimism is probably worse than negativity in this respect because the person receiving the feedback might continue with a bad idea or situation.

The phrase “If you don’t have anything nice to say, don’t say it at all,” should be changed to “If you don’t have anything substantive to say don’t say it at all.” Empty words—whether positive, negative or somewhere in-between—are never helpful. However, “I love it,” or “this is stupid,” is often the beginning of the path to a substantive critique. Our visceral feelings should be explored to derive the substance from our subconscious to be later articulated.

Words that are worth a damn belong in this section. Whether stated negatively or positively, providing substantive feedback is the fuel to create change. The provider of feedback should always aim for clarity of thought.

This is by far the worse quadrant. Examples of criticism that belong here is “this idea will never work,” or “this is stupid.” Avoid this quadrant by thinking through feelings. Intuition and gut reactions should be interpreted and refined into a rational argument tailored to the specific audience.

“I really love…,” or “the colors pop,” belong in this quadrant. Most of the time endearing praise is harmless if more substantive feedback comes later. Endearing praise often comprises the positive parts of the “shit sandwich,” which is a technique used to deliver criticism by wrapping it in praise.

Some people are just negative, and that’s okay as long as their feedback is on the substantive end of this quadrant. The destructive forces of negatively delivered feedback can be a catalyst for a new direction. Sometimes a new direction is what’s needed.

I think of this compass whenever I provide critical feedback, and aim for substantive ideas positively delivered. I hope this framework helps you improve your ability to have difficult conversations and provide critical critique.

Also, check out OhApollo, a web app I am working on with Cody Krainock during weekends that aims to strengthen digital critique for design teams. Sign up, and I will send you a link to the private beta. I would love to get your constructive feedback.

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