5 Keys to Navigating Difficult Conversations at Work | Leadership Training for Engineering Managers

5 Keys to Navigating Difficult Conversations at Work | Leadership Training for Engineering Managers

Have you been avoiding that difficult conversation with someone at work?

If you're in a leadership position, you need to embrace the discomfort because addressing conflicts, giving constructive feedback and discussing sensitive topics is a critical skill and it's essential to your professional growth. But there's a good chance you're making it a lot harder than it needs to be which is why I'm gonna teach you simple ways to make difficult conversations go smoother. Stay tuned.

Stay tuned.

Hey everyone, I'm Doug Howard and welcome to my channel. If you're an engineering manager looking to enhance your leadership skills, then you've come to the right place. In today's episode, I'm gonna give you five powerful tips for navigating difficult conversations with direct reports, cross-functional teams, your boss or anyone.

The 5 Steps to Having Difficult Conversations at Work

But before I get too far, make sure you hit that subscribe button and ring that notification bell so that you never miss any valuable insights on how you can increase your productivity and your overall effectiveness as an engineering leader. Let's jump right in.

#1 - Prepare For The Difficult Conversation In Advance

The first tip is prepare in advance. Don't wing it because that pretty much guarantees the conversation will not go the way you want it to. This is because it's very easy to let your emotions influence your message in the moment. 

For example, if this is a difficult conversation or if you're giving someone constructive feedback, there's a good chance this person has been frustrating you and creating problems for you and your team.

On the other hand in the moment when you're giving them the constructive feedback. There's a good chance they're gonna be defensive too. In these types of situations, it's gonna be extremely easy for you to let your emotions take over. It's gonna drive you to pile on nitpicking points and additional criticism that isn't relevant to the constructive feedback you want to give them. All this does is water down your main message, and it makes it less effective. 

To prevent this from happening you need to have a clear end goal in mind, and you need to create a simple plan of attack before you have the discussion with them. Do this by figuring out what specific feedback you want to give them. Make sure you stick to the facts while removing any speculations or assumptions that you can't prove. 

Also, get ahead of any potential roadblocks by taking the other person's perspective into account beforehand. Do this by spending a few minutes brainstorming things like how will they take your message? How do you think they'll react to your message? Why do you think they'll take it that way? What objections do you think they're gonna have? Now you can get ahead of these potential issues by taking them into account. 

For example, if you're worried, the other person is gonna feel like you don't appreciate their hard work, you should lead the conversation by sharing a few compliments about their performance before giving them any negative feedback. 

Now, speaking of the planning in advance, you're also gonna wanna incorporate the next four tips I give you into your plan of attack. But before I get to them, I wanna point out something very important.

If you're uncomfortable with having difficult conversations, there's actually a few specific reasons why you feel this way, and I explain all of them in my episode called Why Engineering Managers And Technical Leaders Struggle With Giving Negative Feedback. If you're interested in checking this out, I'll drop a link in the comments.

#2 - Choose the Right Time and Place for Having the Difficult Conversation

Tip number two is choose the right time and place. This might be the most important factor because poor timing can lead to emotional escalations that quickly become counterproductive arguments, and at that point, you're basically wasting your time. 

Avoid this problem by making sure both of you are in the right state of mind. Pick a time where both of you are calm and open to receiving each other's feedback. This goes both ways, and make sure you budget enough time too, because discussing complex issues and expressing emotions and finding resolutions to these problems, this requires a significant amount of time. So don't underdo it.

You definitely don't want this conversation to feel rushed. The physical location is important too. Make sure to pick a location that's private, comfortable, and distraction free. That each of you can have an open and honest discussion without any interruptions. The obvious choice if you're a manager is to do it in your office with the door closed but if you don't have an office, consider booking a conference room or maybe taking them off site to make it feel a little bit more casual. You can invite them out to lunch or something like that. 

#3 - When you Initiate the Difficult Conversation, Give Them An Out

Tip number three is give them an out. You have to walk a fine line when you're giving constructive feedback to an engineer because most of them take great pride in their work.

It's very hard for them to not take it personally when you tell 'em something negative about their performance. One way to disarm their emotions on the front end of the discussion is by giving them an out. There's a few ways to do this. 

The first way is by validating their perspective. Now think about it. Nothing feels worse than having someone dismiss your thoughts and feelings. So make sure that you're acknowledging their perspective and letting them know that you think their feelings and thoughts are valid. 

For example, if they disagree with your constructive feedback, don't get defensive. Make sure to respond with something like this. Well, I understand where you're coming from, or I definitely see your point, or that's definitely a valid concern. 

By validating their perspective. You're creating a supportive atmosphere and demonstrating that you value their input, which will alleviate some of the pressure that the other person might be feeling during your conversation. 

The second way you can give them an out is by sharing your appreciation with them. It's a lot easier for them to openly receive negative feedback if you start with positive feedback, which is why I highly recommend going out of your way to lead the conversation by sharing a few things that you genuinely appreciate about this person. A good rule of thumb is to have a two to one ratio of positive to negative feedback in these conversations, if at all possible.

The third way to give them an out is admit your faults. Now, this tip is a little case specific, but if you've done something wrong in the situation, even if it was minor, go out of your way to admit your mistake first in the conversation. 

For example, if you're giving constructive feedback to a direct report, you could say something like, I'm sorry, I know I should have done a better job at explaining this before assigning this project to you. Then go into your constructive feedback. 

Now don't do this. If you didn't do anything wrong in the situation, I'm not suggesting that. But if you did do something wrong, don't hide from it, own it. Giving them an out goes a long way in softening the blow when you deliver your constructive feedback and it increases the likelihood of them being receptive to it.

Before I move on, I wanna know what you think the biggest challenge is when it comes to delivering constructive feedback to someone. Let me know in the comments. 

#4 - Frame the Situation as a Positive

The fourth tip is frame the situation as a positive. One of the biggest mistakes managers make is going into the difficult conversation with a negative approach.

This is a big mistake because it sets a negative tone around the entire conversation. But when you frame the conversation in a positive way, where you're emphasizing the potential for growth and mutual benefits, you're setting the stage for a constructive dialogue focused around finding solutions rather than dwelling on problems.

For example, if you're giving constructive feedback to your boss, you should start with something like this. Hey, boss, I'd like to discuss a few areas where I think we could make some improvements that will help both of us out. Are you open to that? 

The goal is to foster a positive atmosphere, so remember to maintain a genuine, empathetic approach throughout the conversation.

#5 - Speak In a Collaborative Tone

Tip number five is speak in a collaborative tone. In difficult conversations, it's easy for the other person to naturally feel like you're blaming them for the problem, even if you're not. This is why you need to make it 1000% clear that you're not blaming them for anything. You can avoid this by creating a collaborative tone around the conversation. So instead of using words like you or me, focus on using words like we, us, and our. Use these words as much as possible. 

Frame this discussion in a way that feels like the two of you are working together to solve this problem. Instead of telling them your proposed solution, focus on asking for their input through open-ended questions like, what do you think we should do here? Or is there anything that would help you with this? Invite them to share their thoughts and feelings about the topic. And invite them to share their thoughts about the conversation itself too. Give them space to express their needs and concerns, and then respond accordingly.

I hope these tips help you feel more comfortable with navigating difficult conversations, but if you're looking for more help, be sure to check out my episode called How to Give Constructive Feedback Without the Stress

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