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Can we talk? Tips to build confidence and comfort leading difficult conversations.

One of the topics that repeatedly comes up in my coaching work is helping people see the need for, plan for (and sometimes recover from) difficult conversations.


And I have yet to meet someone who enjoys difficult conversations or who feels particularly confident having them.


Most people report some combination of:

“It feels awkward” “I don’t want to hurt anyone’s feelings/tick them off” “I don’t want to mess up our relationship” “Its my boss [insert other important person here], I can’t say that”



Yet, we know - that the ability to have productive conflict is 100% necessary if we want high-performing teams. In fact, the quality of psychological safety - being able to have the tough but necessary conversations on teams - is widely known as being the #1 driver of team effectiveness.



So, how do you get better and feel more confident having difficult conversations?


Well, as someone who has had a lot of them in my career, I have some ideas.


1. Decide to have the conversation

This might feel like a bit of a “non-tip”, but you have to “do the thing”. If there is a recurring issue that is impacting relationships or team performance, you most likely need to have a hard conversation. [There are a few exceptions to this - where you have other hard choices to make - but that is a blog for another day!]


Having a difficult conversation often means “naming the elephant in the room” - having the exact conversation you don’t want to have. This takes courage. But the risk of not having these conversations is artificial harmony, increasing tension and impacts on performance.


2. Check in with yourself

Before entering into a difficult conversation, check in with yourself. Are you personally triggered by this situation? To be the one leading a difficult conversation, you must be grounded and emotionally-regulated. This requires honesty, self-awareness and an ability to manage yourself. If you need more time - and this happens to the best of us - take it.


3. Plan appropriately

High stakes conversations require thoughtful planning. Give consideration to the appropriate time, place and parties to be involved. There is no specific rule book to rely on here - other than thoughtfulness about the bigger picture context, and the circumstances that are most likely to contribute to a better outcome.


4. Frame the conversation

Take some time to thoughtfully consider how you will “frame” the conversation. For a conversation with an employee, the framing might be that you care about their development and performance, so you need to discuss performance gaps. To a colleague, your positioning might be that you value your relationship, and in the interests of working together effectively, you want to call out some tension you are noticing. In some cases you will need to be more direct: “This is going to be a tough conversation, and its probably one we should have had 10 years ago”.


Do your best to frame the conversation in a way that people understand what is to come, and are open to hearing you.


5. Choose your key messages

Once you have the framing, choose 1 or 2 key themes, messages or requests you want to convey in the meeting. Understand that as humans, we can only take so much constructive feedback before we shut down. If you keep your conversation focused on 1 or 2 key themes, rather than trying to convey the 100s of examples of “infractions” you likely have, your message has a much better chance of being heard. You can also use those themes as your “home base” if the conversation gets off track.


6. Engage curiosity and “beginner’s mind”

Beginner’s mind is when we do our best to enter into situations with a learner’s mindset. With beginner’s mind, we move out of blame, justification and judgment, and into a place of curiosity and trying to understand the other person’s perspective. To practice beginner’s mind, pay close attention to yourself - notice your tendency to want to jump in, talk over someone, justify, rebut or respond versus listening and learning.


[Note - You may not agree with everything the person shares, and there still may be a “bottom line” request to your conversation. But the act of giving someone space to share their side of the story will go a long way to bridging understanding.]


7. Look for commonalities

Its likely that you and the other party see the situation differently, otherwise, you wouldn’t be in the position of having a difficult conversation! That said, if you look for commonalities, you can often find them. Perhaps you agree that you both care about doing a great job for your organization. Maybe you have similar values around fairness or work ethic. Maybe you simply agree that you never want to have this awkward conversation again, so you'll both do your best to avoid it! Try to find the places where you agree, and use those to bridge connection.


8. Co-create agreements and commitments

Wrap up the conversation by ensuring that you both have a common understanding of the take-aways of the conversation. You can ask “what are you taking away from this conversation?”. Be prepared to share what you are taking away and what you will do to support a successful next step.


9. Measure and reflect on what you can control

I sometimes hear from clients that a conversation went “terribly”. Oftentimes these clients are measuring the success of a conversation based on the other person’s reaction, which can involve emotion. Here is the thing - we really can’t control other people’s reactions to difficult conversations. What we can control is how we show up - if we do so with both clarity and compassion. My best advice is measure what you can control (how you show up) and try to let go of the rest.


If you or your team need some help with difficult conversations, contact me at megan@meganmcallister.ca .


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