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5 Tips to Best Prepare for a Difficult Conversation

Posted on May 17, 2016
Kayla DineenWritten by Kayla Dineen | Email author

difficult conversationsAs a consultant in the field of Human Resources, I am often approached for guidance on how to conduct a difficult conversation in the workplace.  I’ve had COO’s come to talk through how to share with their CEO (and boss!) that their contributions in staff meetings are negatively impacting employee morale and undermining their position as COO.  I’ve had employees come to me and ask how to talk to their manager about why they feel overwhelmed and underpaid in their role.  I’ve had friends call me up and ask about best practices for approaching their manager to let them know they will be resigning from their position.  These topics, along with a number of other topics in the workplace, are never an easy conversation to approach and I have found myself consistently providing the following advice in each scenario. Added bonus, these tips apply to those not-so-easy conversations at home as well!

1. Overcome your emotion.

By the time I’m approached for guidance on approaching a difficult conversation the situation, whatever it may be, has almost always escalated to a point of an emotional response by the individual.  It’s important to digest that emotion, understand the root cause of that emotion, and then remove the emotion from the focus of your conversation.  For purposes of your difficult conversation, first apply your focus on the root cause of the emotion and identifying what has transpired and the impact it has made that has triggered you to feel the need to have this conversation. Then focus on your ideal solution or outcome to better whatever situation has transpired.

2. Plan your conversation and know your desired outcome.

I cannot stress enough how important it is to know what you’re hoping to obtain by having the difficult conversation you are preparing for. Maybe it’s a raise, or an agreement on who will conduct the staff meetings moving forward, or maybe it’s an understanding of what you can do better so your supervisor feels comfortable that you are fulfilling your duties and perhaps lighten up on the micromanaging.  Knowing your desired outcome allows you to better plan how you are going to approach the conversation.   Plan out the key message you’re hoping to provide and focus on the facts that transpired, the impact it had on you (or your team, or the company, etc.), and what you’re hoping to gain by having this conversation.

In many cases you may not have a recommended solution and still feel the need to have a difficult conversation about something that is weighing on you. This does not negate the need to plan your conversation, it is still important to think through your key messages and talking points. In this scenario, I recommend starting the conversation by stating that you don’t have a recommended solution and you’re bringing a matter to the other person’s attention in hopes that the two of you can work together to identify a solution. Knowing that you want to work together to determine a solution is in fact a desired outcome of having the discussion.

3. Be Reasonable.

This piece of advice shows up in a few ways:

  • Often times, individuals are upset because they just don’t understand how the other person doesn’t see it the way they see it. It’s important to remember that we all have different backgrounds, viewpoints, pieces of information, and perspectives that all come into play.  Circle back to tip # 1 above, overcome the frustration, and realize that through this conversation you will bring your perspective to the attention of the other individual.  It is not reasonable to assume they know your perspective and can apply a solution if you’ve not shared that perspective with them in turn giving them an opportunity to resolve your concerns.
  • Be reasonable in what you’re requesting through the conversation. If you feel you’re underpaid and are requesting a $20,000 increase (which will likely put you two pay grades above your current job level) that may not be a reasonable request of your supervisor.  I personally like to call out the challenges that I know exist as barriers, and verbally recognize there are likely more barriers that I am unaware of, to show that I understand there are layers of complexity to determining the best path forward.
  • Realize that what may work best for you as an individual may not work best for the team, or organization. Be flexible and willing adjust for the greater good, often we have to find solutions where we meet in the middle.

4. Be Honest.

If you’re going to have a difficult conversation it is important to be honest about what has occurred and the impact it has had on you.  Often times we hope to soften the potential emotional response of the recipient by providing partial information or playing down the impact that it had on us.  This doesn’t allow the recipient to fully understand the root cause of the issue and the full impact to make a fully informed decision about how to best move forward.  If you’ve planned your conversation, and overcome the emotion, you can deliver difficult messages in a respectful and clear way.

5. Do not expect an immediate response.

It is best to allow the recipient to receive the information you have to share and put thought into how best to respond.  Think about how much effort and thought you’ve put into this conversation leading up to it, is it reasonable to assume the recipient will be able to go through all four of the steps above to provide a thoughtful response?  I recommend ending the conversation by setting up a time to follow up to the initial discussion.

6. Bonus Tip: Listen!

Listen and absorb what the other person has to say in response to your message.  Perhaps they can provide clarity on their perspective or intent.  Perhaps they can just acknowledge that they hear you and will provide a response. If you’re too focused on doing all the talking and sticking to your planned conversation you may miss the exact message you were hoping to hear all along.

It’s important to remember you’re not alone if you feel uncomfortable about having one of these not-so-easy conversations.  Following these tips will help you to feel prepared and more confident as you approach your difficult conversation.

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