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The importance of being uncomfortable

Caroline Drucker
May 12, 2015 · 6 min read

Why hard news can sometimes be the best news.

Lessons can come from the most unexpected places. As I packed my bags to leave Berlin after nearly 15 years, I expected a lot of overwhelming emotions. However, amid the gooey happy feely missives were emails from people I didn’t expect to hear from. They came from people with whom I’d had truly difficult conversations. Conversations that I remembered as being awkward and had filed away in the far back of my mind along with getting hit in the head with a frisbee in front of my entire 10th grade class. I took a breath in each time I saw the sender list in my inbox. But the anxiety was moot. Those emails from people with whom I’d had difficult conversations? They were thanking me.

One of the women who reached out to me was someone I didn’t give a job to. She was just the wrong fit — too senior for the role, indeed I’d wondered why she had applied in the first place. She was a friend of a friend who I deeply respected so rather than just outright reject her, I met her for lunch to let her know that it didn’t make sense to interview. I did not want to go to that lunch, I would have gladly done my business travel receipts, heck, anyone’s travel receipts rather than sit down with an unemployed stranger and tell them I didn’t have a job for them. But I went. I quickly let her know why her profile wasn’t right for what we were looking for, but also spent some time talking with her about her CV and her job search. Listening to her, it was quickly apparent that she’d had a really bad experience at a company that was negatively impacting her perspective. I told her that she was undervaluing herself by applying for roles far too junior and not focused around her strengths, that it takes two to tango and that a bad work experience can be as much about the employee as the employer. OK, I don’t actually remember saying this. All I remember was being nervous about the lunch and that I ate linguini with pesto (I think). She remembered it all. She wrote me the following: “In all seriousness, without that lunch 2 years ago, I’d probably have put an end to my career and be living in a small community somewhere in Bhutan right now.” Had I been selfish and shied away from having a tough conversation face to face, the lunch would have never happened, she’d be in Bhutan probably making a great contribution but also probably filled with a lot of “What if’s.” Sorry Bhutan, but plus one for the London tech scene who gained a fabulous addition.

Another thank-you was from someone who I had actually confronted. It was someone who wasn’t appreciating a relationship that I thought was built on mutual respect. I’d done a lot of favours, and while I didn’t expect much in return, I did expect a thank-you. I didn’t get any. My inner scardy-cat told me to just avoid the person for the complete rest of my life and not do them any more favours. Simple as that. However, this person was at the start of their entrepreneurship journey, and while I was seriously pissed, I also cared about their future. We need strong female entrepreneurs, and if she carried on like that, she wouldn’t win any friends for the long battle ahead of her. Though I knew what the right thing to do was, I didn’t want to do it. So I outsourced the decision by asking someone, someone I admired so much that whatever she said, I had to do! Of course, her advice was to confront immediately, but to do so quickly and calmly and then move on. So I did. And it sucked. As a Canadian I have to suppress the urge to apologise for apologising. Confronting someone is about the last thing I’d like to do. But I’m glad I did. That person had no idea that she’d forgotten to say thank-you. She was not being intentionally rude, she was just so caught up with the haze of early success that she hadn’t taken time to take stock. No one else had stopped to give her a quick reality check and she was incredibly grateful. And even better, we mended the relationship.

Most surprisingly, an email from a former team member that I managed arrived. She was a challenge, to say the least. I knew she was incredibly talented, whip smart and extraordinarily dedicated, she just lacked experience and specific training. We did not see eye to eye and I dreaded our 1 on 1’s — as she was so intelligent, she was able to dispute issues in quite clever, tiring, actually exhausting ways. I could have let her carry on as she wanted to (you’d be surprised how many managers’ mantra is “give them enough rope”) but I needed all the manpower I could get working at full capacity, especially someone with so much promise. So I bit the bullet and faced down our 1 on 1’s each week, working away at all the areas for improvement. Being honest, not beating around the bush and feeling like I was losing a battle every single time. When we reshuffled our org structure, I took on a new area and the team member reported to someone else. From afar, I watched her take on leadership roles and excel. And I didn’t think I had much to do with it, she was part of another team where she seemed really happy and fulfilled. Until I announced my departure, and she wrote to say “Having had you as my manager was one of the best things that could happen to me. Not only did I learn a ton from you, but I grew professionally and personally.” I was, to say the least, gobsmacked. I’d had no idea. Again, my memories were of frustration, not of a blooming professional relationship. This was a far cry from Diane and Alicia (if you don’t watch the good wife, you’re missing out), but somehow, consistent constructive feedback paid off.

We all know that it’s important to be honest with each other. It’s one of the first things we learn as children, right up there with “share” and “play nice.” But honesty is hard. We spend a lot of time trying not to be uncomfortable. That means that we often tell white lies or avoid disclosing the full truth to avoid being uncomfortable ourselves or making someone else uncomfortable. Sometimes we stop listening to someone telling us about their idea or personal story because we suspect it just won’t end well. We doubt our own and others’ abilities. I say we, but that’s a faulty assumption — there are probably lots of brave, intelligent people who never do this. But I know that I’ve done these things plenty of times, more than I’d like to think about. Again I’ll say it, honesty can be hard. Yet the biggest growth can come from hard conversations. While I hate them, they do help foster a backbone (thus getting me closer to acheiving Katherine Hepburne’s aplomb). But what really mattered were the giant steps those women took. Each conversation was a tiny effort on my part in comparison to the jumps they made. They took the reigns and flourished and I am proud to have been along for the ride, if only for a few moments.

So face the fear. If you think it’s the kind, right thing to do to say something someone may not to hear, do it. It may be difficult to decide out how to deliver tough news: how to be kind yet still get the message across? How to be compassionate yet real? Believe me, you can do it. Just be thoughtful. You may be deeply underestimating the strength of that person, not to mention the impact you can have. You’re stronger than you know, and more importantly, so are the people you come into contact with.

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