There are few things that instill such fear as the four words: We need to talk

Why is that? What tells us that we should first worry and start assuming it’s for the worst? Our human brains are created with an amygdala rooted in the need to protect us from danger. And even the simplest of questions “Hey, can we talk?” elicits a lightning bolt of fear and uncertainty through us.

But those 4 words don’t actually give any indication of good or bad news. It’s a truly neutral phrase that simply expresses urgency. The concept of “difficult conversations” starts on a similar foot of perceived danger. What makes it difficult and why would I put myself at some sort of risk having this talk? Time to fight or fly my way out of this conversation, right?

Wrong. The real tools required for a “difficult conversation” are based around a plan of how to create something from this talk. How to build an outcome that not only gets you through the exchange but has you looking forward to the next opportunity for a “difficult conversation.”

To that end, there are many different starting points as to what a difficult conversation could be

Perhaps it’s:

  • Someone has a problem with you (or your team)
  • You have a problem with someone else (or their team)
  • Something isn’t working
  • You (or your team) have let someone down
  • Change is coming

Sure, these topics sound less than sunny. Ominous, even. So why would we ever want to have the talk? Why should we force an issue, knowing it might be a tough one? Although each of these topics may begin on an uncomfortable foot, we know that each also has the potential for a positive outcome. By being the voice to initiate the conversation, not only are you already slightly more prepared than if you’d been on the receiving end, you also are able to have a bit of control in how the dialogue kicks off. Being the first to suggest addressing the issue puts the ball in your court. The faster you step in, the quicker you can diffuse any growing tension; keeping news at arm’s length is only going to strain the existing situation.

So you’ve set a time for when this talk will happen. Whether it was requested of you by a client or you reached out with the intention of having this exchange, it’s on the books. 

What do you prepare?

Your checklist for what to bring to a “difficult conversation” is short but significant.

  1. The reason you’re in this call to begin with
  2. The right people
  3. An idea of what a “successful” outcome would look like
  4. A very deep breath

The reason you’re in this call to begin with –> Understanding why this call is happening will help you know how to fully prepare. The context to answer this question likely lives within your team, whether you prompted the call or the other person did. Is communication becoming a challenge? Was a mistake made at some point? Is there massive change happening that will impact you and your team? If you instigate the conversation, laying out the topic for the other party ahead of time will not only help clarify that you see the need to connect, but it also allows them to prepare.

The right people –> Make sure you’re having the right conversation with the right person. If they aren’t able to impact the change you’re aiming to create, it will likely feel unproductive. If they don’t have visibility to the issue, reconsider who you’re directing your message to. As you plan this discussion, clarify the purpose of the conversation to ensure they are bringing or substituting in any person who may need to be part of it. 

An idea of what a “successful” outcome would look like –> Details aside, how do you expect to end the call? With a long-awaited answer? With a list of specific follow-ups for the other person? With a collaborative plan for how both teams will work together? Perhaps the other person simply needed you to hear what’s most important to them. Regardless of the content, your conversation needs an expected conclusion of some sort. 

A very deep breath –> A Buddhist monk once told me that when I felt nervous or worried about having a difficult conversation to focus on a time when I felt similarly nervous and yet it went well. She encouraged me to recall how I felt afterward (relieved, proud of myself, silly for preemptively overreacting, perhaps?) Whatever your method, one of the most important things you can do prior to what might be a tough discussion is taking a nice deep BREATH. 

What do you do in this call?

As you set yourself up for success, there are also behaviors and actions to bring to the call. 

  1. Listen
  2. Be intentionally honest
  3. Verify what’s coming through
  4. Ask open-ended questions
  5. Channel your inner empath

Listen –>  If you’re in a position to be initiating “tough conversations,” you likely got there by speaking up, by leading. But that doesn’t mean you always need to be driving the communication train. It’s been said “No [one] ever listened [their] way out of a job.” We often are too quick to share or redirect, wanting to jump in and contribute. If you often find yourself a perpetrator of conversational narcissism, make time for reflection on how to be a better listener prior to the call. This especially applies to those of us who frequently dominate discussions, feeling very comfortable doing so from our individual vantage points. Listening is about giving space to the silence and letting the other person step in when ready. 

Be intentionally honest –> You may find yourself needing to share some difficult feedback. While “brutal honesty” may not be advised, think about why you need to share this information and frame it as a contextual building block for the bigger conversation. Part of this candor includes standing up when you need to & backing down when you have to. At no point have I said this conversation was your chance to be berated. Or for your team to be thrown on the coals. You have every right to speak up if you feel there is an inaccurate or unfair representation of what’s happening. It is also important to be honest about where you’ve been wrong, if the team has misstepped, or other admissions of guilt. If you’re going to succeed at this “difficult conversation” business, trust and honesty are critical. 

Verify what’s coming through –> There are literally thousands of pieces about “active listening” you could consume, but the primary takeaway from each is the need to be on the same page. Do you hear what the other person needs? Do you get what they’re saying? Remove your own filter and take in what’s being said. And then? Clarify that you’re hearing it properly. This step only takes a moment and can prevent hours of misguided dialogue. 

Ask open-ended questions –> Sounds simple enough, right? But this is actually one of the more challenging elements to master. You are here to learn. As you’re listening to this other person, where might they dig into their ideas or viewpoints? The questions you ask should avoid the “this or that” option, should steer clear of “yes or no” answers, and should encourage elaboration. Your ability to humbly listen only further facilitates that exchange.

Channel your inner empath –> This is likely not the first time you’ve heard of empathy. It’s gained traction as an effective means of connecting with others. Not just hearing them but identifying with what’s motivating them. Their motivation doesn’t need your approval or acceptance; empathy simply allows you to understand how the other person feels and express compassion to them. This can improve your life in more ways than navigating difficult conversations. 

As actor Alan Alda said in his talk about empathy, “The more empathy you have, the less annoying people are.”  Try it, I guarantee you’ll agree.

What should you avoid? 

Not every conversation is about what you’re bringing to it. Sometimes it’s what you check at the door that leads to a more effective discussion, particularly when it may be a bit sensitive, heated, or generally unclear. What should you leave behind?

  1. The need to justify/defend/over-explain
  2. Providing solutions that aren’t yours to offer
  3. Over-talking

The need to justify/defend/over-explain  –> Stephen Covey, renowned for his words on leadership, said “Most of us don’t listen with the intent to understand. We listen with the intent to reply.” When participating in a difficult conversation, it’s easy to want to jump in, cut the other person off, correct them. It’s a very natural impulse to try to change the other person’s perception of the situation. Although you could easily justify that impulse, that inclination is about ego–yours, on behalf of your team. It’s about convincing someone their reality isn’t right.

Instead of going down the extremely unproductive path of defensiveness, consider how you might dissect it. Where is the gap between what you know and what they’re experiencing? Again, empathy, the ability to understand from another’s perspective, will help you recognize why emotions or responses are occurring this way. If you genuinely believe the other person is mistaken in their understanding of the situation, ask if you can provide context. They might reply with “No, I’m not interested” or they may welcome it at which point another step towards resolution has been taken. Either way, leading with the plan to justify or change another’s mind is a road to a disappointing conversation. 

Providing solutions that aren’t yours to offer –> You’ve likely made your way into this role by being a go-getter of some sort. Perhaps a “creative problem solver?” Your enthusiasm for finding and executing solutions may have served you well but before you jump into that mode in a difficult situation, take a beat. Your eagerness to solve your way out of the problem, particularly if it’s pertaining to people or work you oversee but don’t directly work within, may end up biting you in the proverbial tokus. You don’t have to guarantee anything. You don’t necessarily need to provide the immediate solution (if you have it, great, but if you don’t, it’s certainly better that you take a moment than respond inaccurately in the moment. Revise your “what does a successful outcome look like” to address this problem. And when you’ve had time to think deeply on it or even consult with your team, that is when the specific solutions get communicated. 

Over-talking –> You’re here to learn, to empathize, to understand. Constantly bringing your voice to someone else’s place of sharing is a surefire way to leave the conversation with that “successful outcome” totally unachieved. 

And once the dreaded conversation is over? What then? 

Followup right away –> Not just with the individual with whom you spoke, but with your team member(s), too. Looping the relevant folks in on what was covered and what core discoveries you made is a critical element of these talks. If an action plan or deliverable is required, the followup to your conversation may directly impact how soon you’ll need to revisit it again. 

Followup down the road –> The goal of any difficult conversation is to clear the air. And in theory, you’ve done just that. But before congratulating yourself too quickly, identify how you’ll verify that the air stays clear. Mark your calendar with the date and time you’ll reconnect with this person to check-in. Nothing makes someone feel more heard than having a person reach out to say “I’m still thinking about this. How are things now?” So hang up the phone, take another deep breath, and create yourself a reminder for a followup call with them.

Lastly, embrace what you’ve done. You did it! You had a difficult conversation. Remember the story of the monk, channeling the feeling of previous success? This moment is that moment for you. What did you do well? Where do you want to adjust for next time? And how can you take this experience and share it with your team so they’re more prepared for those challenging conversations down their professional roads, too?

Addressing and navigating difficult conversations becomes the path to successful leadership and improved communication. The more you embrace these steps of preparedness, engagement, and followup, the more these “difficult conversations” will become those “nice easy chats” you find yourself looking forward to. 

Helpful resources