‘Difficult Conversations Can Deepen Bonds’ by Harry Chang – September 2020

Harry Chang

Harry is currently a Realtor with Compass in Palo Alto, California, and loves what he does, especially since he works with his best friend, Charlene – who also happens to be his spouse and life partner. Prior to real estate, Harry had a fruitful career in finance, consulting, private equity investments, and corporate management. He left his last role as an Executive Vice President of Li & Fung in 2015, because he had promised Charlene he would leave his globe-trotting job when his younger child left for college, and he kept his promise.

Harry has been in the Bay Area since 1988, when he transplanted from New York to attend Stanford Business School. The sunny climate, the great outdoors, and the diversity of people and cultures served as strong draws to keep him here, and he hasn’t looked back since. In addition to work, Harry volunteers his time with various organizations, including serving as Chair of the San Francisco Lodge of FF Fraternity, the oldest Chinese fraternity in the US, and interviewing for Yale College and Phillips Academy. Harry is a former Director of Yale’s alumni interviewers for the Peninsula region and was a founding Board member of the Association of Asian American Yale Alumni.


Most of us have more than a few good friends. We enjoy each other’s company, having nice meals together, playing games, and oftentimes having thoughtful discussions. Sometimes we help a friend through a difficult time – parenting problems, issues with a spouse, or an illness. During these rough patches, friendships can grow deeper as we offer comfort, love, and support to our friends in need. There are other times when our relationships may hit some turbulence and we avoid talking about the cause of the rough air. My proposition in this posting to Billy’s friendship website is that rather than avoiding the bumps, making the choice of engaging in difficult conversations can deepen the bonds of a friendship or other relationship that may be meaningful to you.

I would like to share two personal examples:

A long time ago when I was a second-year business school student, I was in a class that included a time-consuming group project, and everyone in the group received the same grade on the project regardless of individual effort. One of my very good friends was a member of this project group and he usually came unprepared to our meetings and hardly did any work. One of my core values is to be fair and considerate to others, so I felt strongly that my friend was being extremely inconsiderate of his fellow group members. This feeling steamed inside me throughout the quarter, yet I didn’t do anything about it. Finally, at one of our evening meetings, I called out my friend for his lack of preparation. I tried to talk in an objective manner and voiced my feelings, rather than attack my friend, but it still was a very strained discussion. To my friend’s credit, he pulled me aside after the meeting to talk further and we ended up talking for a few hours until well after midnight. It was definitely not an easy discussion – we were NOT shooting the breeze – but we ended our talk with a tight hug and not only did we remain friends, our friendship got stronger as a result of this difficult conversation.

My second story is both work-related and personal. My boss (who also was and is a good friend) and I had to endure a very challenging stretch at work, commuting weekly from the Bay Area to New York for a few months, as we were trying to save a company from bankruptcy. During this time, we were eating breakfast, lunch and dinner in the office, oftentimes returning to our apartment in the early morning hours. Adrenaline was high, as was stress, and morale was very low. Towards the end of this difficult assignment, I wasn’t feeling great about my relationship with my boss, because he wasn’t communicating like he normally did, he was curt during our discussions, and he just seemed angry with me. Under the circumstances, I didn’t blame him at all, but because the tension between us was bothering me, I finally broached the topic over a late dinner. I tiptoed into the discussion, because this was definitely a sensitive situation, but I was clear in my intention and I voiced how I felt. My boss didn’t hold back and laid out exactly why he was upset with me; the tension between us was definitely real, not imagined. For what seemed like a long time, we talked about our respective feelings and our own perspective on the situation. At first, the tension was as thick as the spicy curry sitting on the table, but in the end the air was clearer and the haze had lifted. We understood each other and we respected each other’s perspective. Instead of letting this tension simmer and fester, and hurt our relationship, we talked through this difficult and sensitive issue. The result was a stronger, not weaker, bond.

I’ve had a few other tough discussions, not just the ones above. I like to share a few lessons learned from my experiences with difficult conversations:

Confront difficult situations, don’t avoid them. For many of us, the easy thing to do is nothing, but avoidance doesn’t resolve differences and, more often than not, simply makes the situation worse. Whatever bad feelings there are will fester and, without meaningful dialogue, both parties just think the worse of the other. Inaction causes a self-fulfilling prophecy, because our negative thoughts fill the communications vacuum.

Difficult conversations don’t need to be confrontational. Take your emotions out of the equation and conversation, understand the other person may have a different perspective, and respect that other perspective. A lot of times when we go into these tough discussions, we go into attack mode, thinking we’re right and the other person is wrong. This mindset will just make matters worse, so don’t do it.

It’s okay to allow yourself to be vulnerable. Share your thoughts, your perspective and, especially, your feelings. Instead of labeling or judging the other person’s actions, talk about the impact of those actions on you. There’s no right and wrong, or good and bad, about how you feel, but when you say something like, “What you did yesterday was bad,” you immediately put the other person on the defensive.

Focus on a mutual understanding of the issue, and move the conversation towards a resolution that meets both persons’ needs. Remember that your goal isn’t to simply “get the issue off your chest,” but to work together with the other party to reach a meaningful (it doesn’t necessarily have to be amicable) resolution.

From my personal experience, when I’ve engaged in difficult conversations with friends, our bonds got stronger and the relationships became more meaningful. On the work front, difficult conversations have resulted in mutual respect and understanding, and a tighter team mentality. So when you’re confronted with a tough situation, think twice before you turn your back on it. Dealing with controversy and sensitive situations proactively and with purpose will strengthen your relationships, both personally and work-wise.