by Amy Alpert

The first hard conversation I can remember initiating was in third grade, when I was new to my elementary school. I walked up to another third grader, who to me was cool in every way. We were lined up to leave music class and she was in line with me. I did not practice what I was going to say. I just launched into “Hi Suzy, I like the games you play. Do you want to be friends?” She ended up my BFF.

The second hard conversation I can remember having was not hard in the traditional sense but was very important. My sister Danielle and I are seven years apart, which made our relationship complicated for a while. However, when I was in my early 20s and out of college, we went to Hilton Head Island on a vacation with my parents. Danielle was still in high school and we were not really connected, as I was an adult and in my mind she was still a kid. But we ended up in the ocean together resting on rafts, just talking. We met each other where we were. We did not worry about what our relationship had been. While we did not openly discuss or evaluate our relationship, we allowed ourselves to reveal our true selves to each other and, most importantly for me, I allowed myself to see her in a different light—as a mature, smart, and kind person who was awesome and who I needed in my life. I cannot imagine my life without my sister and I am so glad I was able to reveal my vulnerabilities to her rather than maintain a distant older sister/younger sister relationship.

My third hard conversation was with my boyfriend (now husband), Gideon. I had just come directly from Barnes and Noble, where I had read books encouraging me to assert myself. Self-help books are like bibles for me, and I was suddenly emboldened to get answers about our relationship. I knew he really liked me, and I was annoyed (especially after reading the books) that he was playing it cool. I encouraged him to reveal what he was really feeling and we both opened up to our vulnerabilities. His playing it cool was silly and my waiting for him to determine our future was equally silly. He still teases me about that conversation, but I just pat myself on the back for pushing us to do the hard stuff.

My relationship with him was what propelled me into having hard conversations more regularly. The safety of our relationship and the importance of it, urged me to put the hard stuff on the table and, as Brené Brown says, “rumble with vulnerability.” I continue to have to put the hard conversations on the table with Gideon and he is never happy about it. He is often “shocked” and “caught off guard,” but I guess that is the point. He can’t know what I am thinking, so I have to tell him, no matter how difficult it is. As everyone who is married knows, marriage goes through ebbs and flows. I can often attribute an ebb to our avoidance of the hard conversations or our inability to rumble maturely. But our marriage is guaranteed to strengthen if the conversation is productive.

I have also had several tough conversations with my best friend, Nealy, over the last 16 years. I had never “worked on” a friendship until I met Nealy, and I really think being married has helped. If having tough conversations and being vulnerable is a skill, then my husband has helped me develop that skill, and I now try to use it in relationships that are important to me. Luckily, Nealy is equally invested in our friendship and we both feel safe having hard conversations. We have learned that avoiding the conversation does not make the problem go away and having the conversation—while incredibly difficult at the time—is what keeps our relationship real, reciprocal, and strong.

For any long-term relationship, there is no way to avoid hard conversations and expect to grow and remain authentic. Life throws too many curveballs and if all is going well, we are growing and changing and evolving, too. It reminds me of the solar system: Not only is the earth turning on its axis, but it is also circling the sun. Relationships do not occur in a vacuum, so if you are not having hard conversations, you are probably not responding to your reality. Sometimes I think it’s really amazing that we can maintain any long-term relationships at all!

As a coach, I need to have hard conversations with clients as well. Of course, they are different, and don’t involve quite as much emotion, but I need to sometimes say what I see and push my client to question things they have not considered before. It is also reciprocal—sometimes I am not on the right track and my client needs to shake their head and say, “No, that’s not it.” The client/coach relationship can be vulnerable, and it also needs to be safe. We both need to be able to throw things out there, rumble with them, and then figure out next steps.

Having the courage to work on my relationships, reveal vulnerabilities, and open up to what happens is one of the skills I am most proud of. I am so grateful that I have found people in my life brave enough and invested enough to figure things out and share this journey with me.

The conversations start here. Join us in the Positive Psychology Coaching Fundamentals course. Le’s start talking!

Amy Alpert

Amy Alpert

Amy Alpert, a graduate of the Certificate in Positive Psychology, is a solutions-focused coach with a practice based in positive psychology. A former human resources executive at Goldman Sachs, she holds a master’s degree in organizational psychology from Columbia University. This article was originally published on Amy’s blog at