For Women in Law By Women in Law

So You Need to Have a Difficult Conversation? Here are Some Tips for Gaining Confidence and Comfort

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So you need to have a difficult conversation? Perhaps you need to tell a colleague that they are stepping on your toes? Address some feedback with your assistant? Set some boundaries with a partner?

If you are like most people I know, the prospect of a difficult conversation going sideways is enough to keep putting up with whatever it is you’re putting up with. 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”

Yet there is this nagging that doesn’t go away. It’s impacting your working relationships and your ability to do your work – and you know it’s not getting better if you don’t address it.

That is why having productive conflict is 100% necessary if we want healthy dynamics within our working teams. So, how do you get more comfortable having difficult conversations?


Separate fact from story

Many of us make up a lot of stories about why we can’t or shouldn’t have a difficult conversation. We presume the other person won’t take it well or that they will be upset if we set a boundary. Sometimes that is true and sometimes that is a story we are telling ourselves (and sometimes it’s true, and we do it anyway).

In my former life as a Head of HR for a national law firm, I had many people in my office – staff, associates and partners – saying “why didn’t they just tell me that directly?” after feedback was passed on through a third party. Most people would prefer that we are direct in asking for what we need to have an effective working relationship. Of course, there may be times when you have some pretty solid evidence that it’s not actually safe for you to address feedback with a particular party. If you are in a situation where raising feedback could have real consequences on your career, it’s time to get support from your trusted advisors, whether that is mentors at your firm or hiring an external coach.


Decide to have the Conversation

This might feel like a bit of a “non-tip”, but you must “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. 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 reduced ability to do your best work.


Check in with Yourself

Before entering into a difficult conversation, check in with yourself. Are you personally triggered by this situation? Is this the hill you want to die on? To be the one leading a difficult conversation, you need to 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.


Plan Appropriately

Conversations that have the potential to be high stakes deserve thoughtful planning. Consider the appropriate time, place, and parties to be involved. It’s probably not best to address a tough conversation with a colleague right before a high-pressure event like court prep or if you’re in the middle of dealing with the aftermath of a mistake.


Frame the Conversation

Take some time to thoughtfully consider how you will “frame” the conversation. For a conversation with a staff, the framing might be that you value their support and want to make your working relationship as effective as possible. 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. To a partner, it might be that you care a great deal about being the best co-lead on a file possible, and you want to talk about the best ways to work together for that to happen.

Do your best to frame the conversation in a way that people understand that your reasons for the conversation is to build bridges, not critique.


Choose your Key Messages

Once you have the framing, choose one or two 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 those one or two key themes rather than trying to convey the hundreds of examples of “infractions” you likely have, your message has a much better chance of being heard.


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.]


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 share “what I am taking away from this conversation is X”, as a means of recapping and checking in that you both have the same understanding.


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 – people do have emotions AND 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 in a clear and professional way. My best advice is measure what you can control (how you show up) and try to let go of the rest.


About the Author

Megan (Meegan) McAllister is a certified leadership coach and leadership development facilitator on all things EQ & human-relations related. With a background as a national (Canada) head of human resources for an international law firm, Megan has plenty of insight into the dynamics that exist in law firms, and is passionate about bringing more EQ skills into our high-pressure and high-performance work environments.

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