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Hard Talks Are Hard For A Reason – Five Questions To Ask Before Any Critical Conversation

Written by: Beth Johnson, Executive Contributor

Executive Contributors at Brainz Magazine are handpicked and invited to contribute because of their knowledge and valuable insight within their area of expertise.


A few years into my hospitality career, members of my company’s HR and executive teams asked if I would relocate to London. They were drunk at the time.

Three people talking business in a relaxed bar environment.

Yep, during a conference after-party, these men entered into a critical conversation drunk and somewhat flippantly, asking a question that could affect the trajectory of my entire career. I was stunned into silence. Were they serious? Why were they laughing? Was this a trick?

So many questions crossed my mind but, being young and inept at standing up for myself, I failed to ask them. I simply said ‘hell yeah’ and waited to see what transpired once we returned to the office. As it turns out, they were serious! I happily accepted their offer but also experienced extreme doubt. Not because of my ability to do the job but because of the way they initially presented the offer. These leaders, whom had served for years as my guide and mentor, destroyed my trust and followership with this one action. Not only were they unprofessional but they also made several errors entering into and holding this hard talk / critical conversation. For instance, they:

  • Used cryptic language and provided limited detail.

  • Failed to communicate their (full) intention(s).

  • Seemed oblivious of their inappropriate actions.

  • Disrespected their audience or assumed I wouldn’t question them.

  • Gave no thought to the long-term impact of their words, behavior, and timing.

Upon returning stateside, I learned that they had not been 100% forthcoming. While I had been qualified to take the role and was successful in it, they had also intended to manipulate my personal life. These trusted leaders sought to physically separate me from my beau (who remains my husband to this day) as they believed he shifted too much of my focus away from work.

To say I was angry and disappointed is an understatement. How could these men, with executive privilege and training, fail to be forthright or worse, choose to be subversive? Their actions and choices had long-lasting repercussions. Our working relationship suffered greatly. A job that I had once loved and wanted to advance within had lost all appeal. Eventually I sought other opportunities.

All these years later, I can admit that this had been a ‘hard talk’ for them. Mostly because they were unwilling or unable to share honestly but hard nonetheless. While my understanding does not excuse their behavior, this incident serves as a lasting lesson for me on how not to handle critical conversations.

I mentioned in my last article that few of us learned how to communicate in the workplace, speak to opposition, or stand up for ourselves with grace and confidence. Yet critical conversations – where the stakes are high, opinions vary, and emotions run strong – present themselves almost daily in the workplace.

In my example above, the conversation not only blindsided me but was also quite haphazard. The leaders’ intentions were unclear. Emotions certainly played a central role, though I did not understand why at the time. Nothing about this hard talk was clear and concise, let alone ethical. Instead, it was an example of leaders who did not know how, or chose not, to face the hard talk head-on, in a straightforward professional manner. Moreover, in no way did it set up either party for the greatest success.

Listen, hard talks are hard for a reason. But they do not have to be unprofessional, unkind or incendiary. Of course, there is inherent risk that we may offend, misspeak, or misrepresent. Yet the long-term impact of handing them incorrectly is often worse than being straightforward and honest. Hard talks require preparation, attention to intention, and managing our emotions.

So the next time you are facing a hard conversation, first ask and answer the following five questions. Doing so will increase understanding between parties, grow your followership, and ensure longer-lasting success for you and your recipient.

1. What is My Intention?

The more difficult the subject matter, the more you may be tempted to mask or hide your true intention. Why? Because you are human. Most of us worry about upsetting people or saying the wrong things during hard talks. That worry drives us to limit what we say or avoid direct, straightforward language. We often share only the details that we hope will sway the other party to our side. We tell ourselves that we’re protecting the other person when, in fact, we’re protecting ourselves from their reactions. Another byproduct of limiting detail and hiding intention is that, whether we believe they will or not, the recipient most always senses that something is ‘off’.

In my example, the leaders’ words were right but everything else was wrong. What I felt, but could not identify at the time, was their intention to deceive. To catch me off-guard during a fun event in order to create the result they were seeking. Instead, all they did was sow seeds of doubt and mistrust, which in turn created a snowball of problems that lasted for years afterward.

In the end, if your intention is to leave others feeling less-than, without choice, or controlled, you set up everyone to fail including yourself. Even if the other party doesn’t clearly understand what you are saying, they will feel your message. They will sense that you are hiding something. This is counterintuitive to exemplary leadership, counterintuitive to building robust, innovative teams, and creates very unhealthy cultures.

If, however, your intention is to be fair, honest and find mutually beneficial solutions, your audience will feel it, even if you fail to word your proposal perfectly. Either way, the path your hard talk takes is reliant upon your intention. Remember, wielding power ensures eventual failure. Leadership does not imply control.

2. What is My Mindset?

Before entering a critical conversation, check your mindset. What issues are you bringing to the table? Are you angry or frustrated? Are you fed up or have just ‘had enough’? A negative mindset will negatively affect your conversation. It is OK to feel your feels but set them aside for the duration of the meeting. The greatest leaders possess an understanding of self and are capable of leaving negative emotions at the door in order to bring a success-mindset to the discussion. A positive, solution-seeking mindset will show in your attitude, words and actions. Don’t hide the truth or bottle your feelings, but do be prepared to speak in a positive tone using non-inflammatory, blaming or confrontational language. By doing so you infinitely increase your chance of being heard and engaging in open dialogue.

I recently listened to an interview during which Sandra Bullock reflected on healthy adult mindsets. To quote, she said, “I had to do a lot of work. You can’t point fingers at anybody else. When you become an adult, you point the finger at yourself. I’m lucky enough to live in a time that reaching out and asking for help is readily available.” She goes on to say “I’m constantly working on myself and admitting when I’m wrong, which I do a lot.”

If you are unsure exactly what to say or need to work on your language, attitude or presentation techniques, the very best tip I can give is to seek out three trusted humans in your life, both professional and personal, and ask for their feedback. People who love and respect you, who want you to succeed, who understand your intention to grow, are always the best resource for sharing what they see (good and bad) to help you make enormous strides in your personal awareness and leadership acumen.

3. What Do I Hope to Accomplish?

What is it you want out of this hard talk? How will you define success once it’s over? Will deadlines be set, steps agreed upon to resolve a problem, or perhaps you plan to provide training and ask follow up questions? Overused, generic statements like ‘we’ll be on the same page’ or ‘I showed up for them’ are not enough. Instead, ask and answer these questions:

  • Do I want to establish understanding? Be specific. What. When. How. Why.

  • Do I want commitment and an agreement? Name the terms. Review the timeline.

  • Do I want input or feedback or maybe not? Be honest. Say that up front.

  • Is there a deadline? Call out the exact date and time.

  • Will another people be involved? Identify them and bring them into the conversation when appropriate.

There are 20,000 flavors of success and everyone around you will define their version of success based on THEIR perspective and understanding. In short, the odds are stacked against you at the start. So, before you enter the conversation, know what you hope to accomplish and how you will define success. Share this often throughout the conversation and do not leave anyone guessing or assuming. Ever.

4. What is My Message?

It is imperative that you refine your message before entering a hard talk. Is your message centered around processes or people? Is your message meant to inspire, educate or simply share?

The more task-oriented a message, the more facts, figures, and fine details you should plan to share. The more people-oriented a message, the more of your feelings, thoughts, and experiences you should share. The more high stakes the message, the more attention and time you should give to the message itself and to the responses, reactions and requests from your audience. And, in every single scenario, explain your ‘why’ and leave ample time for open discussion.

My assistant recently reminded me of a basic tool to use when in communication. The K.I.S.S. method. Keep It Simple Silly. This anagram provides a helpful reminder to share your message in simple language using common terminology. It also reminds you not to complicate conversations with needless information that does not pertain to the task-at-hand. Keeping it simple encourages participants to readily speak up with ideas, questions or concerns rather than spend their time deciphering what you just shared.

5. What is My Responsibility?

The best leaders understand that they are responsible to adapt their communication to their audience, not vice versa. Title, status and position do not imply that others must learn to interpret and follow you. It is your responsibility to fix the Communication Highway potholes, not set up the hazards. People are most inclined to follow leaders who accept that responsibility, communicate transparently, and treat them as capable adults until or if they prove otherwise.

For example, I worked for a CEO who repeatedly but quietly called his employees stupid. Of course they weren’t, but he believed that he knew best for everyone and was, in his opinion and in his own words, always the smartest person in the room. When he spoke, no matter the audience or subject matter, he expected everyone to blindly accept and follow. Unfortunately, communicating, team building, and healthy culture were not high on his priority list. He did not accept responsibility for his employees, only his own ambitions. With all of this combined extreme levels of apathy developed in the workplace, which trickled down to the very customers he professed mattered most. Nothing will sink a ship faster than hypocrisy or condescension.

Like it or not, leaders will and always should be held to a higher standard. Employees expect you to understand and honor that commitment. They expect you to be responsible enough to engage in hard talks in a way that make them feel safe, even when the topic is difficult. To be professional, calm, kind and honest. Once you accept that responsibility, you may find that navigating hard talks is not as difficult as you think.

Despite how everything transpired in my own story, I had one of the greatest professional and personal experiences of my life. I returned to the US irrevocably changed. It was also the first of many valuable lessons during my career on navigating hard conversations for which I will always be grateful.

None of us is perfect. No one. We all make mistakes even during the easiest of conversations. We walk away wishing we had said, done, or reacted better. The best we can do is to learn from every interaction and apply those lessons to the next hard talk and the next and the next. Hard talks are hard for a reason but we can make them easier on everyone by identifying our intention, mindset, message, and responsibility all of which is critical to achieving our preferred result. Keep talking. Keep trying. It is worth it.

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Beth Johnson, Executive Contributor Brainz Magazine

‘Culture Concierge’ Beth Johnson partners with gutsy leaders as they flip the script to cultivate and uphold people-first cultures. Beth focuses on 6 core leadership principles, all of which are inextricably tied to emotional agility, conscientious communication, and conflict management. As a leader in both the U.S. and Europe, Johnson reenergized and reorganized multiple teams formerly labeled as disengaged, fatigued, or failing. Beth has always promoted human-centric leadership and her 25+ years of leadership experience has proven that ROI follows.



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