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For most of us, this creates a double bind. Speak up too loudly or assertively and you’re seen as the problem. Rely excessively on “being nice” and you not only fail to get results, but you’re also frequently left feeling resentful.

So how can you give the gift of truly listening, paying attention to, or interacting with individuals or groups that you would normally write off?

There is a middle path between aggression and avoidance. While it usually doesn’t come naturally to most of us, there is a way to start and stay engaged in a challenging conversation. And instead of causing anger, frustration, or bitterness, these interactions can actually help you grow, see new perspectives, and develop deeper relationships.

Here are eight things to keep in mind when sparking or engaging in a challenging interaction.


What you think and feel is an important part of who you are, but it’s not the sum total. A pattern of personal overidentification with a core mission is an occupational hazard for those working in NGOs, nonprofits, and socially responsible business organizations. Make the conversation about the issue, not your need for validation or approval.


Active listening is a practiced skill, and is often the first thing that gets fried when the heat is on. Emotional filters and cognitive distortions kick in, and next thing you know, you’re firing back a response based on what you’re sure you heard, without any awareness of how your biases and interpretations are coloring it. Make sure you can accurately reflect what is said to you.


Sometimes, the best way to get your point across is to ask the right question first. This creates an opening, as opposed to something to defend against. Of course, you must be authentic in seeking to learn. While it is important to put your principled point out there, you also need to see if you can create space to understand the other person’s.


Wouldn’t you like a dollar for every time you made an assumption that turned out to be incorrect? You may think you have the same information — and that you’ve interpreted it in the same way — as others (isn’t this what “rational” people do?), but letting go of your certainty can help you avoid being certainly mistaken.


Emotional reactions are an essential part of our humanness. However, when reactivity gets the best of you, it can derail your ability to connect and stay connected. One clue is when others you trust provide you with the feedback that you were “triggered” by something — meaning that the force of your response was not appropriate for the situation at hand. You can’t surgically remove your triggers (because they’re based on old patterns), but you can change the wiring behind them. Otherwise, when you “lose it,” the other person feels perfectly justified in believing that you are the problem, and can deny any responsibility on their part.


We’ve all gotten ugly at times. We’ve all allowed our sense of right and wrong to create such a sharp edge that we cut off the possibility of understanding and being understood. But when you talk down to someone from a high horse of righteousness, you forget that you’re also dropping a few turds in the process. You are no better or worse than your adversary, and it’s good to keep your common humanity in mind (and in your heart).


Our first tendency when confronted with opposition is to: a) find fault and place blame with the other, b) state our logical and rational talking points as if they were obvious — and then repeat them more loudly if they’re not accepted, or c) shut down or walk away. If you can actively repress your swift judgment and ask, in a genuine way, “Really? Help me understand why you see this so differently,” you may discover that you actually have some common ground that you would have otherwise missed.


“What?” you may be thinking. “Give up the fight?” No. Take a clear, principled stand, engage with compassion, and do the best you can. If you’re going to be upset if it turns out a certain way, you’re most likely setting yourself up for frustration or disappointment. All you can do is try your best, so don’t beat yourself up or denigrate the other person. It may take a second conversation, a different approach, or another day.

When all is said and done, embrace healthy conflict as an opportunity for growth. You don’t have to like it, but each time you move through conflict by assuming that the other person has positive intentions, using your best skills, monitoring your own emotions, and considering it ongoing practice, it increases your resiliency and optimism for the next time.

And yes, there will be a next time — life and work are a series of challenges punctuated by periods of relative satisfaction. With better tools and awareness you can experience less stress, and more meaning and fulfillment. And you can still be a fierce, but humble, agent of change.

Flip Brown is the founder and owner of Business Culture Consultants, a Burlington, VT-based Certified B Corp that helps individuals and organizations experience more meaning, fulfillment, and results. He has a background as a furniture maker, ski industry executive, psychologist, nonprofit program director, and musician. He is the author of “Balanced Effectiveness at Work: How to Enjoy the Fruits of Your Labor Without Driving Yourself Nuts.” He loves his job.

Flip Brown

As principal of Business Culture Consultants in Burlington, VT, I serve as a catalyst to help good people in great organizations experience better results and deeper satisfaction.