Uncomfortable Conversations

If I only knew then what I know now, you know? You might say that a person's success in life could be measured by the number of uncomfortable conversations they're willing to have. The only thing more cringe worthy than having an uncomfortable conversation, is dodging one. If I had a nickel for every time I felt uncomfortable, I’d be living on a yacht somewhere exotic. I’ve always wanted to do great things, and I learned very early on that this would mean I was going to spend a lot of time uncomfortable and possibly alone. Everything comes with a price, and that was a risk I was willing to take.

We tend to do whatever it takes to avoid feeling negative emotions and discomfort, because we are naturally programmed for pleasure and to seek happiness. I know I used to think this was the easiest road especially when it came to communication. Facing an issue head on with the potential to hurt someone else’s feelings, pass. I remember I would get knots in my stomach in situations like when it came time to ask for a raise or bring up any kind of controversial issue at work. I actively avoided every situation possible if I thought it would make me feel anxious or make me look bad.

We convince ourselves that sweeping things under the rug is the easier approach, but I think that’s a contradiction because it’s the smallest things we avoid that can build up, fester and eventually become unmanageable situations when they’re not handled properly.

You might say that a person's success in life could be measured by the number of uncomfortable conversations they're willing to have.

Some of the uncomfortable conversations I’ve experienced have gone horribly wrong. Conversations such as terminating an employee, or a client criticizing one of my team members, or worse, my boss. I’ve always been able to hold my composure, but my challenge was what to do when the person I am speaking with loses theirs. Human nature when we are in a position of discomfort is to turn either silent or violent. Our instincts immediately tell us to go into defence, so this can cause us to become dismissive and resistant to feedback. I was always the silent type when I felt I was being bullied or attacked, until I found my voice. As a young person in a leadership role, this was an area I found very challenging. But over time I realized the more uncomfortable situations I could stomach, the stronger I would become in my role, and as a person. Once I reached the executive level, the stakes were always high, so I didn’t have the option to avoid uncomfortable anymore. Eventually I let go of trying to do it “right” because I knew each conversation would be a learning opportunity. Even when my voice shakes.

I was managing people my parents age when I was 19. I had worked my ass off, proven myself to be a leader and I had made it known that I was hungry to climb up the ladder. I have always been well beyond my years so I knew I was qualified. But, I was not comfortable because I was in fear that all they would see was the young girl—this is called imposter syndrome. Anytime things got hairy I felt huge discomfort. Simple things, like when staff would challenge the schedule I made, or worse, my decisions. There were many times I caved because I hadn’t learned how to handle those situations yet and I would question my instincts at times. There was no real training or coaching at the time, the only option was to sink or swim. I was determined, but not only that, after you allow yourself to be walked over enough times, you get smarter (and pissed off).

Hospitality is an industry for only those who have thick skin because it is impossible to please everyone, and the expectation for perfection is extremely high. It is the industry to receive feedback. You hear it from all angles— your boss, owners, staff, clients, managers, cooks and stewards. Dealing with difficult clients, high profile Chefs and owners for so many years helped me grow a HUGE pair of…

…thick skin and to not take things so personally. If I could say to those who challenged me to the highest level along the way (even the ones who made me feel like shit), I would thank them from the bottom of my heart in the most genuine way possible regardless of friction, tears or feedback that I may have deemed as hurtful or wrong at the time. I would absolutely not be where I am today without them being so difficult and I will be forever grateful. Thank you.

I landed my first Director position when I was 25, which came with a whole other bucket full of uncomfortable challenges I had never encountered. I hired friends a couple of times because I thought they would have my back in setting me up for success, navigating through leadership and just helping me shine in general. Never hire your friends if you are going to be their direct report. For the simple reason that as a leader you are going to be held accountable to make really tough decisions and you need your friends to be available for you outside of work more than you need them in the office. Unfortunately, I lost a couple of friendships along the way because I didn’t know how to use my voice effectively. One of my least favourite lessons learned to date.

In today’s world of technology and the remote office, we are becoming more and more uncomfortable having face to face conversations, especially the tough ones that matter the most. We differ to email and text messages. It’s easier to have hard conversations when you have a screen to hide behind and in my experience, people feel more comfortable flexing their muscles when they don’t have to look at you in the eyes. I’ve been guilty of that myself, but now that I’m comfortable I have some rules. If there are more than 3 emails on the same topic, we meet for a conversation. If we are working in the same room or building, don’t send me an email. If I receive an email demonstrating emotion or frustration, I pick up the phone. If you don’t answer my call, the only electronic reply that you’ll get from me is, “call me when you have a chance and we can talk about your email”. Technology removes emotion, and that is a very big problem with society today because it dehumanizes the experience of having a conversation and truly resolving issues.

I have learned to anticipate some potential challenges and feedback, so a lot of times I’m able to get ahead of situations rather than be in a position of reaction. You have to find the courage to seek these uncomfortable conversations out while they’re simmering rather than wait for them boil over, otherwise it becomes pure damage control. Through my own mistakes and discomfort along the way, I grew into my own leadership style, as well as my own person in my life. I found my voice and every day I am becoming more self-aware. Today, even if a conversation takes a turn or doesn’t go as intended, I no longer freeze up. I think before I speak, and I am now confident enough in myself to recognize when something is about me and when it is about the other person.

Compassion and empathy are crucial, so here’s some advice. First of all, don’t go in thinking the worst because usually we are mis predicting how bad it’s going to be. Once the gloves come off, it is important to remember, whether you like it or not there are at minimum, two sides to every story.

It is not in our best interest to make assumptions about someone’s way of thinking or their intentions. If you want to truly find resolution you have to genuinely make an effort to understand the other persons point of view. You need to walk into the room ready and willing to compromise (check your ego at the door) and make suggestions for possible solutions, rather than becoming defensive and place blame on the other person. If you approach the situation with a list of complaints, the conversation will feel like an attack. Allow the other person the time they need to talk without interrupting them. This can be very difficult if you do not agree with what the other person is saying, or if you feel offended, misunderstood and frustrated. If this is the case, take really deep breaths and count to ten.

Regardless of how good you think you are at avoiding these crucial conversations, you are most definitely going to find yourself here at some point. Sometimes it’s an important and unavoidable talk with a loved one. Other times, it might be a simple talk that becomes an intense conversation and quickly turns hostile. Complaining to anyone who will listen is easy, finding the courage to actually say or do something about what’s bothering you is not.

By actively avoiding confrontation, you may feel good in the moment, but you ignore the future. These conversations are going to feel awkward, but I am telling you right now, you will always feel better after you speak your truth. I empower you to get comfortable being uncomfortable because that is where the magic happens. Having the courage to feel the fear and do it anyway is a special kind of growth that never comes with regret. You are more fierce than you think!