4 Strategies for Conquering Awkward Situations (in Business and Life)

When was the last time you were uncomfortable? Not like there's-a-tag-in-your-shirt-that's-scratching you uncomfortable…I'm talking about socially uncomfortable. That feeling where you want to crawl under something or at the very least avert your eyes because you can't bear to meet the eyes of the other person. You might look back and cringe over the moment because it was just so uncomfortable or the way you handled it was just…bad.

  • Did someone ask you that dreaded, "So, what do you do?" question?
  • Did you have to have a discussion with someone on the topic of money?
  • Did you have to stand up for something when you knew you were going against the majority?
  • Did you make a faux pas so bad you wish your could erase the memory, Men In Black style?

This topic always makes me think of that deodorant commercial where the cute 20-something is at a work party with her boyfriend. She sees him standing at the refreshments table, walks up and flirtatiously smacks his butt then he turns around and it's her boss wearing the exact same outfit as her boyfriend. I'm shuddering just thinking of it!

Now think of one of those moments in your life (bonus points if it was in your biz). Do you have a super uncomfortable moment in your mind? Tell me- what happened as a result?

Was your life in danger? No? Did you almost lose your home? No? Did you business go under? No? Do you get what I'm getting at here? The point is that we're all conditioned to be almost deathly afraid of awkward and uncomfortable situations.

I'm not saying that you should go up and smack a random person's butt tomorrow- I'm just saying that sometimes the biggest leaps you can make in your business are just on the other side of an uncomfortable situation.

Some obvious examples:

  • Raising your rates and having to approach your current clients about it
  • Having straight forward sales conversations
  • Approaching big names about collaborations
  • Nominating yourself for an award
  • Speaking in front of a big crowd

Think back again to the awkward moment you were thinking of before. What could have happened if you handled it perfectly? Best case scenario; what was the potential? I'm willing to bet there was serious potential for you to either look awesome, feel awesome, or just grow as a person (bonus points for revenue potential!).

Huge opportunities disguised as potentially awkward moments pop up all the time. Tough discussions and being put on the spot come with the territory when you're running your own business so it's time to get prepared for the situations.

Here are a few simple strategies you can use to prepare for and shine in awkward high-stakes moments:

Ask for more time

I know that I get flustered when I am put on the spot. It's okay to need more time- sometimes we are the ones pressuring ourselves to come up with a quick answer. If it's appropriate in the situation, you can say, "Wow, thanks for asking, that's such a great question. Would it be okay if I get back to you on that? I want to be sure that I can give you the best answer/explanation and I don't feel quite prepared to do that this moment." As a bonus, it makes you look even better because it shows that you care about accuracy and quality.

Say your peace, then shut up!

One of my good girlfriends taught me this years ago and I’ve heard it time and time again since then. Silence is your friend! This is particularly true in negotiations or when discussing rates or rate changes. When we are have uncomfortable conversations, we all seek to make the situation more comfortable, perhaps subconsciously. So, what do we find comfortable? Words, noise, chatting, small talk, filling the space so no one has to deal with what’s right in our face: the uncomfortable topic. My friend told me the story of a friend of hers who was negotiating her new salary and was asking for significantly more than the initial offer. When they asked what number she was thinking, she told them and then was silent. An uncomfortable amount of time went by where there was silence on both sides because both were aware that whoever spoke first “lost.” Finally, the company’s HR rep spoke first- and she got her much higher rate. Although it was an uncomfortable silence (she said it was almost unbearable and felt like a solid minute of silence), she didn’t lose the opportunity and I can damn well bet the people that went toe-to-toe with her in the negotiation respect her for sticking to her guns and negotiating like a champ. Silence is golden. Say your piece and then shut up!

Prepare ahead of time 

If it's possible, get your head together before the potentially awkward situation. I do this by thinking through every possible rebuttal, response, and reaction. There are some situations in which you may be unable to predict how things will unfold but the vast majority of the time, you can anticipate possible outcomes. Once I think of all possibilities, I plan how I will handle each of those situations. Need to fire a client? Think through all potential outcomes and consider reaching out to your network to find out what people in your trusted inner-circle have encountered in similar situations. Ask for their hindsight advice. Think through every possible situation, role play your points and rebuttals, and prepare yourself. You'll feel a million times better going into that conversation than if you were just to wing it.

Employ humor

I love using humor in tough situations when it's appropriate and won't minimize or undermine my stance. As a general rule of thumb, this is helpful in lower-stake situations. In the right situation, I think it's funny to bring attention to the awkwardness of that situation because it eases the tension. You will know when it is an appropriate time to throw in a little one liner but always be prepared to smile, laugh at yourself, and realize that everyone is human. I've seen this work really well when someone is speaking in front of a group and fumbles their words or forgets what they were saying. So make light of it, address it head on, laugh at yourself, and move on. Everyone will appreciate your humanness.

As humans we naturally shy away from uncomfortable situations, even if there's nothing to lose- even if we won't feel any pain other than maybe a pang of embarrassment or momentary emotional dissonance. There's no way to eliminate our self-preservation instinct (and we shouldn't want to!) but I know that if you actively use these strategies, push yourself outside of your comfort zone, and confront uncomfortable situations head-on you stand to gain so much.

What's one thing you've been avoiding because it's uncomfortable? What strategy are you going to implement today to confront it?

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  1. Thanks– this is timely content for me personally as I am getting ready to meet with an important contact.

    During our introduction, the individual managed to make a joke out of my response (I did not say anything funny), leaving me feel uncomfortable. Maybe it was their way of breaking the ice, but made me even more nervous then and now.

    Since I interact better through written communication (i.e. time to think and weigh responses), it takes effort to achieve effective communication verbally. The points that you mentioned help and I will keep them in mind.

    • Steph Gordon says:

      Hey Jennifer,

      I understand communicating best through written word, I am the same way. Are you an introvert? Sometimes I find that introverts really shine in writing because they’ve had time to sift through their thoughts and formulate what they are going to say. It’s great to know that about yourself and conversely even more important that you embrace strategies #1 and #3 above, “Ask for more time,” and, “Prepare ahead of time.” For me the preparation ahead of time is particularly helpful.

      Also, another thought that came to me when reading your note was regarding the contact who used humor in a somewhat strange way. Recently I heard someone say that we judge other’s actions but we judge our own intentions. So, basically we take someone else as the face of their actions but we give ourselves the benefit of looking beyond what we’re doing and understanding where our heart is. You seemed to have considered this, but perhaps the other person was also a bit nervous and was trying (unsuccessfully) to lighten the situation but ended up making it worse!

      No matter what, the fact that you are gearing up for an uncomfortable situation means you are clearly on the verge of some sort of shake up in your life. Good for you and good luck! xo

      • Thanks for your reply, Steph.

        Yes, I am very much an introvert. I know it and I accept it.

        However, as much as awareness of what an introvert is and what makes them special has grown as of late, the world is still made for extroverts. Working for myself allows me to work and interact in a way that is more conducive to my strengths, but of course, not completely. For those times, I have to prepare as much as I can and go forth. 🙂

        Thanks again! Have a great day!

      • Ooh, love that quote about judging other people’s actions and our own intentions! Such an interesting point!

  2. Devon Smiley says:

    Preparing in advance always comes in handy – it’s much easier to enter the difficult situation with a few options in your back pocket for how it will play out. This, combined with facing these situations regularly will help you build a nice internal database of mini-scripts that you can use in any situation. With time, it becomes natural – rather than a tad rehearsed. Practice, practice, practice!

    • So true! And funny that you should mention mini-scripts, because we are working on putting together a package of One Woman Shop approved scripts for handling tough or awkward business situations!

    • Steph says:

      Devon, yes ma’am! You’re so right that it helps to have a few options in your back pocket. Plus, like you said, after a while you get to be a natural and can be a bit better on your feet. I think handling tough situations with grace is like anything else: It gets easier with time and practice. Thanks for your two cents, Devon. You know I always love hearing what you have to say!

  3. Emma says:

    Honestly, sometimes the most awkward and bothersome thing is when YOU ask YOURSELF a difficult question such as “What kind of a business am I running?”, “What is my niche?” or “What do I love about my business?”. Those are questions that a possible client might ask, and it’s important to establish an answer before the ask it, but when you can’t even answer it for yourself, that’s frustrating! I’m just starting out so its definitely been hard to answer questions like that.

    • Steph Gordon says:

      Emma,

      Wow! You bring up such a great perspective I hadn’t even thought of: self-awkwardness. The awkward really does start with us, doesn’t it?! Having answers for ourself is the most important piece and only then can we confidently approach potentially awkward situations with grace and confidence. Great point, girl!

      I sincerely feel that as we all get further along in our business we are afforded the luxury of time to hash these things out. Starting out can be tough but the fact that you’re aware of the unanswered questions is huge. Good for you.

      Keep on truckin’!

      xo

      Steph

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