How We Trained For Tough (Yet Crucial!) Work Conversations

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When stakes are high, opinions differ, and emotions run strong, that’s what we call a tough or crucial conversation. None of us have ever been in this situation, right?! *anxious laugh* 

That’s exactly why the Copywriting Team at Helen + Gertrude recently read Crucial Conversations, and the leadership team did a training titled “Making Tough Conversations Easy(er).”

Our Copywriting Team is all about the feels, discussing the content, and helping each other apply it to real-life scenarios inside—and outside of work. So we read it book-club style, meeting in coffee shops around Rochester each month. As writers, we, of course, had to name our sessions and landed on the straightforward yet alliterative, Copywriters in Cafés. 

We’d bring an update on what we were talking about to each All Hands meeting so everyone could benefit from the big-picture insights. All Hands is the monthly meeting where the entire agency gets together to go over executive, marketing, financial, and department stuff.  

The Tough Conversations training was done with our super knowledgeable, experienced HR Works rep Robyn Walsh. Not only did we learn from her, but we also learned from each other, sharing some of our own tips to use when approaching difficult or uncomfortable dialogue.

Now that we’ve studied how to have productive conversations that produce healthy results—both internally with our teams and externally with our clients and vendors— Helen + Gertrude wants to share five ways to make these hard talks easier. 

Headshot of Tegan Jenner

“For me, a key takeaway was how important it is to address conflicts as soon as possible. When conflict arises, it's easy to drag your feet on following up or to sweep it under the rug as a one-time thing. But the presentation shed some new light on the bigger impact of delaying addressing areas of conflict.

By addressing conflicts immediately, before they grow into larger pain points, you're potentially saving your team from bigger issues down the line, and you're fostering an atmosphere of timely feedback and communication. Also, since it's so fresh, you have a specific, concrete example to reference, and the details are fresh in your mind.”

—Tegan Jenner, Media + Insights Lead

An image of a human brain on top of half the face of a white man with a beard on top of a red swirl next to "Know Yourself" in a light blue speech bubble on an orange background.

#1 Know Yourself

Take it from the famous-for-a-reason RuPaul, "If you can't love yourself, how in the hell you gonna love somebody else?" The same goes for being aware of our patterns and responses when conversations go south. We’re each wired differently and therefore have different filters created by our unique experiences. We recommend taking the Crucial Conversations' Style Under Stress Test. It'll tell you how often you move toward silence or violence: 

Moving toward silence comes in the forms of:

  • Masking: Understating or selectively showing how you really feel.

                    Examples: sarcasm, sugarcoating

  • Avoiding: Steering completely away from sensitive topics. 

                Example: we talk but only sometimes address real issues

  • Withdrawing: Pulling out of a conversation altogether. 

                Examples: leave the room

Moving toward violence comes in the forms of:

  • Controlling: Coercing others into your way of thinking. 

                   Examples: forcing your views on others, dominating the convo, cutting others off, overstating your facts, speaking in absolutes

  • Labeling: Putting a label on people or ideas to dismiss them under a stereotype or category. 

               Example: “Your ideas are so old-school. Any person with a brain would follow my plan.” 

  • Attacking: WAR! You’ve moved away from winning the argument to making the other person suffer.

                 Examples: belittling, making threats 

Why does this matter? Because silence and verbal violence are the two extremes on a communication spectrum, both of which can shut down dialogue, weaken your relationships, and hinder results. 

Headshot of Matt Kirsch

“How you start a conversation is everything! Even if your intention is completely pure, if you fail to communicate this to the other person at the outset, it’s all for naught.

You have to be completely clear about why you’re initiating the conversation because if there’s a misunderstanding about your goals, this makes constructive communication much harder. Most people go into conversations with the best intentions, but being able to explain these intentions clearly and honestly is half the battle.”

—Matt Kirsch, Senior Copywriter

"Rise" in a dark blue speech bubble beside "Above" in a light blue speech bubble on top of a red swirl on an orange background.

#2 Rise Above

You might be the type of person to put that much-needed conversation off or brush it off, but let me tell you, that actually makes you sick, not just mentally, but physically too! Your immune system weakens, and your rate of survival lowers. The more negative feelings we hold in and the less we express ourselves, well, it slowly kills us.1 

When someone says something you disagree with, two things happen. 1., Two glands on top of your kidneys shoot adrenaline into your bloodstream. 2., Your brain moves blood away from activities it deems non-essential and instead to things like physical fights or flights (running away). 

So areas of the body like the large muscles of the arms and legs get more blood and the higher-level reasoning sections of the brain get less blood. Our biologies literally put us on the defense right away instead of putting us on the path to intelligent persuasion and gentle attentiveness.2 

But if you are aware of this science, you can be better equipped for a tough convo. You'll start to see them less as a fight between polar opposites and more as an opportunity to find a higher ground. Rather than a compromise or happy medium, we call this the “apex.” Genuine dialogue rises above it all and creates something new between two sides, like the apex of a triangle.

Headshot of Amy Sadler

“The importance of how you open the conversation and how you respond was a big point for me. Using 'I' statements (instead of 'you') that leave out opinions and feelings and instead stating the facts as you understand them without assumptions about the reason behind the behavior. Then, ask clarifying questions until you understand the whole picture before discussing solutions.

Ultimately, this encourages a healthy conversation that builds trust and vulnerability as you work together to find a resolution. It also removes blame from the conversation, which is counterproductive and can lead to hostility.”

—Amy Sadler, Creative Services Lead, Production

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#3 Prep for the Convo

Before you meet, gather any documentation or notes for your talking points. Clearly define the purpose of the meeting to the other person. And follow the STATE steps:

  • Share Your Facts: Start with observable actions using “I” language and give examples. This is the least controversial and insulting, and most persuasive way to begin. Help them see how a reasonable, rational, and decent person could think what you’re thinking. 
  • Tell Your Story: Time for our Copywriting Team’s fave part: the feels! What are all of these facts leading you to conclude? What assumptions are you making based on them? Here’s where you describe the impact they had.
  • Ask For Others’ Paths: You’ve expressed your viewpoint. Now let them share theirs. Ask for their facts, stories, and opinions. Give them the benefit of the doubt and try to understand their challenges. Here’s where you talk less and listen more. Pay attention to pitch, tone, and body language, and make them feel heard.
  • Talk Tentatively: Once you’ve reflected on their opinions and feelings, paraphrase their point of view and seek clarification. If you continue your story, use statements like, “Maybe you weren’t aware of …” or “This might just be my opinion …”
  • Encourage Testing: Invite opposing views with questions like, “Do you see it differently?”, “What was your experience?”, and “What am I missing here?” Get curious and engage the other person in helping to solve the issue at hand. Go back and forth between listening, reflecting, and responding until you make it to the apex. 
Headshot of Sammy Boyd

“My learning was how important it is to be intentional and strategic during these conversations. So often, we go into them and kind of just ‘see what happens’ without a plan, which is when emotions can take charge and you can end up with an outcome you're not happy with. So it made me just want to take note of when a conversation will be ‘crucial’ and then make sure I'm being extra thoughtful.”

—Sammy Boyd, Copywriter

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#4 If It’s Heating Up, Step Out

If things are starting to get spicy (in a not-so-great way), step out with one of these techniques to make it safe again. 

  • Apologize: When appropriate, make a statement that sincerely expresses your sorrow for your part in causing pain or difficulty to others. Give up saving face, being right, or winning to gain healthy dialogue and better results. 
  • Contrast to Fix Misunderstanding: Make a do/don’t statement to address the other person’s concerns, which clarifies your real purpose. Example: “I don’t want you to think I’m not satisfied with the quality of your work. I think you’re doing a good job. I do think the punctuality issue is important, and I’d like you to work on that.” 

Headshot of Claire O'Reilly

“It's hard to be self-aware of your communication when you're under a lot of stress and the stakes are high. We learned that responses on the team can vary based on situations and context! How it’s delivered makes a difference, plus, whether the person is in a safe place and has good intentions. Feedback feels genuine when someone has your best interest at heart.”

—Claire O’Reilly, Copywriter

One white woman's smile with a purple speech bubble that says "Show" is next to another white woman's smile with a dark blue speech bubble that says "Gratitude" on top of a red swirl on an orange background.

#5 Show Gratitude

This last one is short and sweet. People usually only remember the beginning and end of conversations. Acknowledge and show gratitude for what they brought to the dialogue. End it on a positive note! 

Headshot of Becca Bellush

“I really liked establishing an agenda before the meeting so whoever you’re talking to isn’t caught off guard and has time to emotionally adjust. And then following up at the end of the meeting with notes and next steps.”

—Becca Bellush, Account Director

When we avoid difficult conversations, we trade short-term discomfort for long-term dysfunction. If you haven’t had enough convincing to take on that tough convo, think about the question: “Do I care enough about this person to feel awkward (for a short amount of time) if it means we'll develop a more genuine relationship for years to come?” For our Helen + Gertrude coworkers, clients, and partners, the answer is almost always a resounding “YES!” And that will help you deliver what you need to say in the kindest way.

Want to know more? These 5 tips are grounded in our human-centered design approach, where we place high importance on growth from the beginning of the process—starting with our people. Fortunately, we’ve seen it time and time again, a healthy culture leads to purposeful work and better results. And while these two trainings were amazing, I know they will not be our last!

1. Ornish, Love and Survival: The Healing Power of Intimacy, 54-56. 

2. Kerry Patterson, Joseph Grenny, Ron McMillan, and Al Switzer, Crucial Conversations: Tools for talking when stakes are high (New York: McGraw-Hill, 2002), 4.

Jill Duff
Creative Services Lead, Copy

Jill is an extroverted and ambitious writer with a passion for taking conflict head-on. She’s working on her 46 ADK High Peaks and 63 US National Parks. If you catch Jill in town, ask her what’s going on in Rochester, and you’ll get a long list of the latest American Advertising Federation Greater Rochester happenings to the newest dive bar around the corner.

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