Turn Difficult Conversations to Your Advantage


“They aren’t going to like what I have to say.”

“I doubt this will make much difference.”

“When they hear this, there will be complete chaos!”

“I’ll be fired.”

“I’m going to have to fall on my own sword here.”

“They won’t understand how this happened.”

“Timing is going to be very critical for delivering this message.”

“How can we spin this better?”

“Just rip the band aid off!”

“I will look like a complete idiot.”

“I don’t know how long I can put up with this. Maybe I should just quit.”

“The situation will hopefully resolve itself over time.”


These are some of the statements I’ve initially heard from business owners, leaders and executives when they are faced with a necessary (and difficult) conversation. It is just human nature. We perceive the conversation to have too high of a cost—especially if it doesn’t turn out the way we prefer. All the leadership training in the world, including in the critical areas of empathy, transparency, self-awareness, and accountability, make very little difference when we face a conversation that promises far-reaching, and potentially negative fallout. We drop into survival mode.


Still, we can learn to handle difficult conversations with clients, employees, peers, and key stakeholders, proactively and with remarkable ease. We can even turn those tough talks into a powerful advantage, which, although we might not look forward to them, will at least create a positive impact on us we might never have imagined beforehand.


I coach clients on how to effectively have the difficult conversations that get them the promotion, the raise, the new client, build trust with existing clients and teams when things go wrong, delivers the tough news while still motivating constructive action, and much more. Unlike leadership training, coaching leaders is tailored to their specific personalities, strengths and goals. The result is their brains truly have the opportunity to be retrained through collaborative practice. They build a fresh perspective, loaded with self-awareness and empathy the one-size-fits-all training can’t deliver.


Here are some of the approaches we use that help leaders leverage difficult conversations, instead of dodging them.


Calculate the Cost:


Leverage the high cost of avoiding the conversation to motivate action. Some studies show that the cost of each difficult conversation that is deferred or delayed can cost an organization $100-$5000 per conversation! That is based on reduced engagement, lost business, damaged trust, lowered productivity, and many other measures. But that still feels too distant and theoretical in most difficult conversations. Instead, I encourage leaders to examine what the cost is to them personally when an issue goes undealt with. Mistakes, missed opportunities, miscommunications, stress, distractions, lost income, burnout, and an inability to cooperate effectively are common answers I hear.


What is the cost you are currently paying for the conversation you are avoiding? Be thorough and fearless as you explore. Often we ignore the devil we know out of fear for the devil we don’t.


Be Empathetic First:


Leverage an understanding of the other side of the conversation’s needs, wants and questions to accelerate resolution. When I am writing executive speeches, I invite them to explore the question always in their audience’s mind: What’s in it for me? The same is true in tough discussions. When a boss, employee or client feel their needs are front and center, that a solution is on offer, and a positive, mutually beneficial outcome is possible, even the most disturbing content can be heard more easily.


Rather than focusing on the outcome you want from the dialog, lead with what you believe they want, and then check in to see if you are on track early in the conversation.


What is most important to the other party in your upcoming conversation? How do you know? How can you help them to get that?


Check Your Motives:


Leverage real transparency to minimize argument and obstruction. As a marketer I am mortified at how many people want to lobby their case, omit key facts, manipulate and try to “manage the story” in difficult conversations. Good marketing is about telling the story that connects with an audience empathetically (see above). “Spin” marketing is actually the opposite of good marketing. It is false advertising. The motive of trying to force the other party in a discussion to just shut up and do what you want is far more likely to undo your outcome rather than support it. More so when you misrepresent what brought you into the conversation in the first place. Fear of the whole truth has a distinct odor to it. Other people smell it.


If you don’t believe you can have a difficult discussion with complete honesty, check your motives. The truth will definitely set you free, regardless of the ultimate outcome.


What is you motive in having this conversation? Do you believe in the power of the truth? Or do you want to cover it up and obscure it to appear in a more advantageous light? If you are using manipulation, managing others’ behaviors or marketing your case, then it is time to reappraise your motives.


Turn Rage and Fear into Curiosity:


Leverage your ninja power to become your own hero. Rage (or frustration) and fear are useful – up to a point. They indicate that something is wrong, and that action is required. However, staying in the emotional space of fear or rage quickly disempowers us. We take on the role of a victim, blaming the situation or the other party for our feelings. If it goes on too long many people become depressed or numb. That’s why it is so important to move into a different emotional energy – an energy that is creative and productive – quickly. That energy is curiosity.


When we approach a difficult conversation from a place of curiosity we open up our minds to entertain many possible solutions, rather than just one. We can ask ourselves what “better” would look like. We can assess how we got where we are and if there are different ways to handle it going forward.


What would “better” look like for you on the other side of the conversation? Is there something you could do differently yourself? Are you open to solutions that you haven’t thought of before?


Detach and Listen:


Leverage the power of the pause. In art, music, dance and graphic design there is an understanding that negative space is actually more important that the space where the action happens. Too much action becomes noisy, confusing and repulsive. The same is true of conversations – and especially those conversations where we are dealing with vitally important content.


Creating that space inside a difficult conversation is an art itself. We naturally show up to the conversation with heightened emotions, and a personal agenda. However, when we are aware that that is the case, we can take a metaphorical step back. We can be concerned by what someone says, and not react to it. Instead, we can ask if we understood, and whether they had considered a certain impact of their idea. We can move the conversation forward with combat, but by deepening our ability to hear what the other person is really thinking – even when they are not doing the same. Active listening and detaching from our own volatile emotions is a highly conscious and contagious activity. The result is almost inevitably mutual resolution.


What are your emotions and agenda in the conversation? How can you recognize them, accept them, but not act on them too quickly? What questions could you ask to better understand the other person’s viewpoint?


Ultimately, difficult conversations are necessary from time to time. Instead of seeing them as a thing to be avoided or an obstacle to be overcome, try seeing the ways they deepen your understanding of yourself and others. Explore how they can alter the course of your business for the better. Be open to developing the self-awareness, courage and strength they demand of you. Then expect the best, because you will be bringing your best to the conversation.


If you are facing a difficult discussion, let's talk! I'd love to have a discovery call with you. Let's see if we can make the change you need. Message me, or book the call directly right here.

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