9 Powerful techniques for managers to hold difficult conversations

Managers like you are the people having some of the toughest conversations in the organization. You’re sandwiched between the pressure from the management and the pushback from your team. 

Sometimes, no matter what you plan for your team, or how you plan to steer them, you have no other choice but to have difficult conversations with your teammates – be it a review conversation, feedback, or a layoff conversation. These are difficult and have to be handled deftly, or you risk losing a valuable employee who may currently or in the future steer spread the word and send good people your way. 

Chris Voss, a former FBI agent who was the lead negotiator in many high-risk, high-consequence cases says, “During difficult conversations, people want to keep their egos in check, want to be right and win the conversation at any cost.”

This is why you need to wade through the conversation carefully, so you don’t burn bridges, and at the same time, accomplish the agenda masterfully. Here are a few techniques to help you do it right. 

Understand the difference between being blunt and being a straight shooter

One thing people get wrong most of the time is they don’t understand what it’s like being blunt versus being a straight shooter. Being blunt doesn’t take into consideration that the other in front of you is a human, it’s just brutal. But, being honest, and a straight shooter means you’re still going to tell the truth, but give the other person a soft landing. Choosing the latter mindset will ensure you handle the hard conversation effectively while being firm in what you want to accomplish, as part of your job.

Prepare yourself before the conversation

Some people think too much about the difficult conversation they have to have throughout the day, that when they reach the time to talk, they aren’t prepared, or they’re too prepared that they can’t handle the flow if it doesn’t go as planned. Instead, take time to prepare yourself. 

Keep interacting with other people over the course of the day, check in with others, and keep the mental muscles limber, but make sure not to overspend the energy. Some people are nervous talkers – when they have to have a hard conversation at the end of the day, they spend the entire day talking too much to relieve their pressure, which doesn’t bode well for them. Exercise your conversation skills, but don’t dwell on them too much.

Schedule the conversation right so they’re able to pick themselves up after

There’s a common rule in HR – don’t fire someone on a Friday, do it on a Monday. If you do it on a Monday, they still have a whole workweek ahead of themselves to pick themselves up, apply to different jobs, or if they aren’t fired, process the tough conversation as they get on with their workload. If you do it on a Friday, then they’re left wallowing in their thoughts with no means to take any action for the next two days. They’re stuck feeling helpless. 

Prepare them for bad news, but don’t sugarcoat it

Our natural instinct is to care for people around us. Yours is too. When you get to the actual conversation, don’t try to soothe their nerves by enquiring about their family, wellbeing, or chat about the weather or economy before breaking the bad news. Instead, let them prepare themselves for it. 

Also, when you schedule the important discussion, don’t stuff all the major points you want to discuss into the agenda and send them a threatening email. Instead, text, or email them with 1-2 points you want to bring up in the discussion, and tell them that it’s going to be a hard conversation, so they’re prepared for it. It’s not setting a negative context – it’s about being practical. 

Without preparation, there’s a high chance they retaliate and get their defenses up before you even get started. When you give them a heads-up saying, “I want to talk about a few important matters with you. You’re not going to like it, but it’s something we need to do for both our benefit.” When you do this, it takes the other person from a defensive mode into a problem-solving mode. 

Be generous and offer them something right off the bat

Lead with the generosity approach. Show your willingness to show support, or offer them something that’d offer some relief to them. Doing this gives you a positive head start in the conversation and shows the other person that you’re here to deliver a difficult message out of responsibility, and that you don’t have any personal grudges against them. It also helps you maintain contact with them in the long-term, and nurture the relationship.

Switch your tone of voice if the conversation gets heated

When you notice the conversation escalating and feel both of you speaking loud, almost close to yelling at each other, intentionally switch to a lower register – a voice that calms you down, sort of like a late-night FM DJ voice. It helps you calm you down and the other person at the same time. 

It also eases your shift into a positive mindset. This is because the auditory system and the neuro system are deeply connected to each other. Low-frequency sound waves are met with low-frequency firing of neurons. When you speak in a low voice, the other person’s brain entrains to your voice, and they eventually calm down. It comes off as an involuntary reaction. 

State what you observe, instead of assuming their feelings

The person you’re speaking to may glance away from you for a while or look lost during your conversation. Instead of assuming they’re upset worried, or frustrated, gently state what you observe and ask them to validate your assumption. You could say “I notice a shift in you.”, “Sounds like there’s some hesitation”, or “Looks like something just crossed your mind. I’m here to discuss if you want to.” 

When you give pick up on this affective cue and state what you observe, they will be more inclined to correct you if you’re wrong, and in the process let you in on what they have in mind. Correcting someone’s observation is a satisfying thing to do and they’re likely to be candid with you during the conversation. It’s a great emotional lubricant. It also shifts the power dynamic and makes them feel like the driver of the conversation.

Gently revisit what they said if you aren’t sure what they meant

If they’re talking fast, or telling you too many things at once after hearing what you said, it might be hard to process everything all at once. You may be skeptical about asking them to repeat themselves, or saying “I’m sorry I didn’t quite catch that, could you repeat that?”. It shows you’re not paying attention to them, when in fact you are. 

Instead, try saying, “I hear you, and as we speak about this, I’d like to revisit our earlier conversation in relation to the current one, when you spoke about [….], and clarify a few things.” Then you proceed to ask to clarify areas you wanted clarification on. This approach shows you care about everything they say, and want to be crystal clear, instead of just waiting for the conversation to be over.

Handle venting differently

Some people, when given an opportunity, vent or complain all the time. But some people who don’t generally vent out their feelings do so only with the people they trust the most. Either way, when you have a tough conversation and the other person is starting to vent a lot more than you thought, they’re only going to spiral out of control if you don’t take the conversation in your hands. 

Ask to pause for a while, and give them feedback on what it is that’s causing them to vent to you – “Sounds like you’re worried about what to do next”, or “Looks like some resources to help you take the next few decisions will be helpful”. Take an educated guess on what is driving the venting, and ask how you can help out. Remember to not correct, belittle, or invalidate what they’re saying. 

Simply take control of the narrative and offer to help, without letting them spiral out of control. This will help steer their thought process and help them have a productive discussion about the steps they can take. 

Bookmark this blog, and try some of these techniques the next time you plan on having a tough conversation with someone, or when you want to deliver a difficult message to someone. It’ll help you take some pressure off yourself, while also ensuring you don’t damage relationships with the person you’re talking to.