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The Power of the Awkward Conversation


The Power of the Awkward Conversation

This article is based on a speech given by Scott Simon, founder of Voicebox Karaoke, at the 7th Annual EO Talks: Experience, Shared. You can watch his whole talk here.

Telling someone they screwed up a project. Telling the team that you gave them bad instructions and now they have to redo all the work. Giving someone a “needs improvement” performance review. Having to put two people in a room and help them hash out a dispute.

Leadership is filled with hard, awkward, uncomfortable conversations. Even when you’re on the giving end of the bad news, chances are you’re not having a good time. It’s not a topic many people like to talk about, but we’re going there. 

That’s because one of the keys to confident leadership is knowing not just how uncomfortable it is to be the pointer, but how much harm it can cause you and those you care about. And how, when it comes to business, biting your tongue could mean hanging on to an employee or situation that just doesn’t work — all because you just don’t want to deal.

Bottled-up feelings can lead to bad situations that drag on for ages, but boy are we a stubborn lot. Scott Simon, founder of Voicebox Karaoke, said it best: “Never underestimate the days, the weeks and the years that someone will endure suffering just to avoid a 5-minute awkward conversation.”

The life experience that brought him to this realization was a tough breakup with a longtime girlfriend that happened because he spent too much time inside his head and not enough time communicating his concerns to his partner.

What was he ruminating on that whole time?

Outcomes. What might happen if he said something. What might happen if he didn’t. If his words would hurt his girlfriend. If his silence hurt worse. And perhaps most important, whether he could admit to failure. But he was too afraid, so he couldn’t say anything. And he didn’t until it all came out in one big “I’m leaving.”

What does this have to do with business? 

While it’s important to understand that a boss/employee relationship should not function like a personal relationship, the psychology behind the hesitation to speak up is the same. And when that 5-minute awkward conversation with an employee (or a manager) is avoided in the workplace, it can lead to days, weeks and even years of keeping someone in the wrong role, creating bad vibes with the team and decreasing the productivity of everybody involved, all while your team watches you tip-toe around what everybody else is thinking.

The wild thing is, even as we avoid the uncomfortable conversation we need to have, it saves us absolutely none of the pain of having it. We think that because we’re not addressing it, it’s not happening. But in the meantime, leaders have the entire conversation, the whole fight, a thousand times … they just do it in their own minds. Think about the last time this happened for you and you can probably remember how the whole fight set up shop in a part of your head where it ran on loop for weeks, or months, or years. 

Scenarios, What Ifs, and What to Do Instead
When you internalize stress, you create a landscape of different scenarios and outcomes that live entirely between your ears: “If I tell her she’s not delivering on her job description, will she leave? If I ask my boss for a more flexible schedule to pick up my kid from daycare, will I eventually get fired?”

If this line of thinking goes on for too long, it can quickly send you straight down the “what if” rabbit hole. 

Fortunately, leaders can train themselves to escape these traps. One way to keep yourself out of the quicksand is to look for this pattern of “smile and nod” in yourself and those around you. When you see it, don’t jump on the “What am I going to do about this?” train. Instead, just say how you feel in that moment.

I am disappointed in her work. I really want my boss to appreciate me. I don’t feel like this job is the right fit. I don’t feel like this employee really wants to be here.

Feelings? Double ick. But in these types of situations it can do the trick for two reasons: One, expressing the concerns now will get you out of the hypothetical future. And two, expressing feelings is what starts to connect you back to the people around you.

Still, though. “I feel” statements should be reserved for a psychiatrist’s couch, right? 

Not if you can express it in the form of three other little words: “I am confused.” 

The Gift of Confusion
If life is a collection of facts and the feeling those facts create, then confusion is what happens in the space between when things don’t line up quite right. Here’s an example:

Peter is a great employee, and I love having him around the office. At the same time, though, I’m really disappointed in his work. At the same same time, I don’t want to feel like a failure as a boss.

Or, from another perspective:

I look up to my boss, and want her to be really impressed with my work. At the same time, though, I don’t feel like I’m being set up to succeed. At the same same time, I don’t want to feel like a bad employee.

If you just start with “I am confused,” that opens the door to conversation (and, party bonus, doesn’t even include the word feel.) Yes, it’s going to lead to a 5-minute awkward conversation, and no, it’s not a cure-all. There could still be pain and hard work ahead, but the good thing is that you’re no longer doing it alone.

This isn’t just important for the workplace. It’s also important for you as a human being, because those potential years of pain will build up slowly over time, maybe so slowly that you don’t even realize the damage it’s causing. It’s like the concept of “death by a thousand cuts.” Stress leads to emotional, mental and physical distress. And it’s the thief of joy.

So here it is, in three steps: the plan to break out from the exhausting circles leaders run around in their own heads. 

  1. Accept that how you feel is real. Maybe something doesn’t feel quite right. Didn’t feel right yesterday, either. Your instinct is likely correct, which means you’ll need to take action. If you find yourself arguing with your feelings, that’s a good trigger to know you’re in this step. 
  2. Listen to your thoughts: “Maybe tomorrow I’ll have the insight that will solve this problem … maybe tomorrow I’ll look at my employee in a new way and see his value … maybe tomorrow a meteor will destroy Earth and I won’t have to deal with any of this. (Wouldn’t that be a relief?)” and acknowledge that they are confusing and conflicting. 
  3. Get out of your head and say it: “This doesn’t feel right. I am confused. Here are my thoughts.”

Once you get through the awkward, you can look forward to days, weeks and maybe even years of connectedness, peace and progress.

Related Content:
Mediation Part 1: Defining and Diagnosing Employee Disputes
Mediation Part 2: Ways Employee Mediation Could Fail
Mediation Part 3: How to Handle Employee Disputes
How to Fire Someone


If life is a collection of facts and the feeling those facts create, then confusion is what happens in the space between when things don’t line up quite right.

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