Navigating Difficult Conversations: Strategies for New Leaders

Dr. Jim: [: 00:00:00

So how do you build a sales culture where you can productively confront and consistently manage difficult conversations? That's what we're going to tackle today. And as usual in our founders feature, we've put Lucas, our fearless host back on the hot seat to help share his insights. Lucas, welcome to your show.

I'm looking forward to this [: 00:01:00

Dr. Jim: This is going to get pretty tactical and I'm looking forward to the conversation because every leader at some point can struggle with setting the tone and setting the expectations and creating the conditions necessary to have the type of conversations that you need to have.

So that you're enabling a high performance team. So this is going to be a very timely and useful conversation, especially when we think about some of the macroeconomic conditions that we're dealing with today and how that can show up in the conversations that leaders need to have with their people.

Now, before we dive in, I want you to get all of our new listeners up to speed on a little bit of your background and your story.

Lucas Price: Two time founder and I've also been a sales leader, had a long journey as a sales leader where I worked at Zipwhip from less than a million dollars in ARR to build the team that took it to over a hundred million dollars in ARR before it sold to Twilio two and a half years ago. So I've been in the founder seat as I am now with Yardstick.

But a lot of my [: 00:02:00

Dr. Jim: the piece of context that's going to be important for our listeners to know, in addition to what you just said, is that you have experience working within B2B tech at all different stages of development. So you've gone from like zero to 100 million. So that represents different stages of organizational development, and it also represents different strategies that you need to use to make sure that you're capitalizing on the capabilities of your people.

ll us a little bit about the [: 00:03:00

So when you think about creating the type of environment where those conversations end up being productive, what are the things that you as a leader? Paid particular attention to you as you were growing zip whip. And as you're growing yardstick.

Lucas Price: A big part of it is creating the type of safe environment where people understand that the feedback is to get better. And so you're being hard on the issues. You're not being hard on the people. And so it's having that kind of trusted environment, open communication, helping people understand that it's a place where there.

You're trying to help them succeed. I also think that, people have different points of view about what's going on. And I think one of the challenging things is you can come in with a point of view to a conversation where with another individual, and they are going to, oftentimes they might try to.

Tell you're [: 00:04:00

There can be this like cycle of I, I'm really having difficulty getting to the truth. And so now, because I've been pushed around so many times, I'm just going to come in really strong and I'm not going to listen to what they have to say. And I'm just going to tell them this is the way it is.

And which creates like a Dr. Jekyll and Mr. Hyde type of relationship with the people on the team. And so listening to that, and understanding and asking questions is like really incredibly important to it, but also, sorting and getting to the truth can be like very difficult.

ends to not have one simple, [: 00:05:00

And like finding that balance can be like very difficult in some challenging situations.

Dr. Jim: There's a lot there that we can expand on. And I'm going to pick two areas of what you said and get some detail around it. One of the things that you said early on in your answer that I really liked was you need to be disciplined in making sure that you're being hard on the issues versus being hard on the person.

So that's a great phrase. How do you do that?

Lucas Price: For me, it starts on day one of working with someone . One of my day one issues. Is, hey, let's talk about what it's like to work together. The types of communication, things that are difficult for you, the types of communication, things that are difficult for me.

ou don't do it and you don't [: 00:06:00

The scope is different than you expected or other things that came up. And so if you come and tell me, Hey, this isn't going to be done on Friday. Now it's going to be Wednesday. I'm probably going to be like pretty understanding about that, unless we really, talked about how important this deadline is or something like that.

I'm going to be pretty understanding about that if you, if Friday comes and goes and it's not done and you never say anything to me about it, then two weeks later comes and it's not done and you've never said anything to me about it. That's where I'm going to be less understanding. And so that's one of my communication issues that I tried to, set that expectation.

communicate with each other [: 00:07:00

And then, when something happens, when this doesn't, when the community to use that same example, when the communication doesn't. Happen, then we can focus on that. We can focus on that. The communication didn't happen. And you know how we fix that going forward, why that's a loss of trust and not, and be less about Hey, you're a bad.

It's not about you're a bad person because this communication happened. It's more Hey, this is my expectation for how we work together. Are we going to be able to keep that expectation? Do we need to change the expectation? So that's one of the ways that you can. You can, set the foundation and then continue to focus on the issues instead of on on, turning into discussions about someone's bad intentions or personal flaws.

with HR leadership. And when [: 00:08:00

And that sounds like really harsh, but it's really clearly laying out your work styles, your expectations, what the job expectations are, and having this two way conversation on day one or early in the process. So you're setting the proper foundation. So I like that concept and I think you and I are on the same page in terms of mapping those things out on the very front end of a relationship so that you're setting yourself up for success and you're mitigating the amount of surprises that you might get.

So that's a day one. Early stage conversation. How do you carry that principle forward so that it becomes embedded in the life cycle of that person that is on your team?

ut I think the part that you [: 00:09:00

And so a lot of times I've had people who've disagreed with me, my thinking on this, but my thinking on it is hey, if there's an employee who's doing low quality work, who doesn't work directly with me, doesn't have a lot of experience with me, I might not go to them and say, this is where your work is falling short.

I might go to their manager and hope that their manager has that type of relationship with them and say, Hey, this is where so and so's work is falling short. Have you noticed it? Am I wrong about this? Are you having a conversation? Are you getting better? And not with the idea of Hey, I'm trying to go behind their back or won't talk to their face or anything, depending on the type of work in, in, specific instances of it, this color is wrong on the website, something like that.

brand? But if there's like a [: 00:10:00

And so I think like the radical candor idea, you have to fit both those pieces together. I'm going to be like very honest about what parts of the work are going well and what parts of the work should be better. But in some situations, I'm not the right person to deliver that honesty and I might need to.

Figure out who is the right person to deliver that because I just don't have the relationship with them because of the way the organization is structured, where they're not going to understand or have this feeling with me of Hey, I deeply care about them as well. Now, the people on my team, my direct reports, I should be building that relationship with them where I'd both they know that I deeply care about them.

And that I will tell them the truth about what parts of their work are really good and what parts of their work could continue to improve.

ong emphasis on building the [: 00:11:00

And I think that's an important distinction to make in general. And it actually got me thinking about one of my favorite books, which is The Challenger Sale. And the idea, or the underpinning of the Challenger Sale is that you need to lead with insight. You need to create a scenario around you where your buyer is thinking about the problem in a unique way.

And allows you to explore that in pursuit of a solution. And that makes a lot of sense. But before you can actually challenge somebody on their assumptions or how they see their worldview, you have to have the relationship first. So I like the emphasis that you made on building the relationship first and making sure that person across from you actually understands that you're committed to their success as a necessary requirement for that candid conversation.

What are your thoughts on my parallel that I just drew there?

ice: Yeah I think that the I [: 00:12:00

And so there is a bit of a, it depends. And. But there are situations, maybe you're placed together and you weren't close, but now you're becoming close and delivering that feedback at the same time. And there are times where it happens in parallel, but it does need to happen in kind of the right quantities and the right mix where it doesn't just feel like here's someone who parachuted and told me everything I did wrong and then left.

and they remove the kindness [: 00:13:00

So when you talk about the right mix of how to deliver the message and how to deliver a difficult message, walk us through what that framework looks like. How do you have these conversations? What should the structure be?

Lucas Price: One of the mistakes that leaders make sometimes is not being totally clear about the parts of The feedback or the coaching about where the employee needs to get better. And, there's a people write sometimes about the compliment sandwich, which is like a compliment and then something you need to improve and then another compliment and the reason and how that doesn't really work and I think, part of the reason it doesn't really work is because the candidate thinks.

ployee is going to develop a [: 00:14:00

He's not really trying to help me. He's just hypercritical. And so how do you fight against the idea of like. All right, being hypercritical all the time on the one hand, and on the other hand, doing the compliment sandwich where the feedback isn't getting clear I've read books and see that seen things where it's like, Hey, the positive feedback that you give people so that they know what they should do more of.

They should get five to six times as much of that as the negative feedback of the things that they need to improve. But the thing that they need to improve should be the last thing that you give them in a conversation, or it should be clear in the comp, so I think trying not to soften it, trying to be really clear about where you want them to improve is like more important than, making sure that every.

things that he's doing great [: 00:15:00

And thoughtful about how to deliver it. Don't soften it. Don't try to make it easy. Because it can end up like not being clear, but also make sure that the employee knows what they're doing really well. Also.

Dr. Jim: So I like how you've positioned that where. You're putting the item that needs to be improved on the back end of the conversation. So it's the last thing that you talk about. The thing that I'm wondering is if you sequence it that way, where the improvement item is on the back end of the conversation, how do you build accountability for results into that conversation?

So in this scenario, you've told me I need to work on something. And oftentimes what happens we know this happens, everybody's busy. And then the next time we talk about it, we're onto the next thing that needs to be sorted. So what can leaders do to build accountability in an action into that area of improvement so that individual is actually getting developed versus just another one of those things that will be forgotten the next week.

Lucas Price: The first thing [: 00:16:00

And then if they agree that's something that they want to work on, if they don't, then obviously there's more conversation to have, if they do agree. Then it's all right, what are you going to do about it? What is your plan for improving this? And once you've started working on that plan, and once you've completed that plan, how are you going to keep me in the loop of how it's going?

putting the emphasis on them [: 00:17:00

Dr. Jim: What if They don't know how to start because oftentimes you can be told, Hey, you need to work on this and I'll sit there and be like I have no idea how to make progress on it. I'm not necessarily in agreement that this is something that I need to work on. So that's a different issue. But let's talk a little bit more about getting them started on the right path.

If probably in a situation where they're paralyzed by the feedback.

Lucas Price: It's something that I'm always willing to brainstorm with them on. And so I'm not saying that all of the ideas for the development plan have to come from them, but I think okay, here's three ideas about what you could do. What do you think of those three ideas?

Oh, I like this one. Okay. So when are you going to try doing that? What do you think you should, what do you think you should do in terms of taking that one of the three? And so it continues to be a conversation and it continues to be like getting them to buy in. And so it doesn't necessarily mean that they have to have all the ideas and they have to figure it out all by themselves.

want to end the conversation [: 00:18:00

Dr. Jim: That's a good framework. And I want to dig in into even more of a challenging scenario with you. So let's put it in context. Let's say you have somebody that's on your team, that's not performing and. It's at the level where, you need to walk through a performance improvement plan and talk through that and build and still work with that person to get them over to the other side.

So you're talking about a really difficult situation. And oftentimes when people hear about pips, they're already checking out. So how do you need to carry that conversation forward? That still as much as you can keeps that person committed with the intent of having them turn the corner and get back to being productive.

, I'm determined to help you [: 00:19:00

And if that's the, your authentic feelings as a manager, then employee. Probably knows it and probably isn't going to stay checked in. And, there are some exceptions to that. There are some employees who have proved their manager wrong over the years during their pit, but that's what happens most of the time.

If the manager says they're committed to helping them succeed. Means it takes follow up actions to help them succeed. Then that's going to keep them engaged. And so a lot of it is it's about, communicating the truth in an authentic way, meaning it and taking follow up steps to show that person, and that's usually what it's going to take to, to keep that a person on the PIP engaged and determined to, to overcome and succeed despite the PIP.

en we're talking about. This [: 00:20:00

Lucas Price: Yeah. That's a great question because these are conversations that those first line leaders, if they're new in the position, they haven't done it a lot before. And so I, I think that asking your manager, asking your leaders. To role play it with you. When you know that you're going into a conversation, it's going to be a difficult one.

p back and forth between the [: 00:21:00

Try to get to the truth of the situation and hot have high standards all at the same time. I think getting that right is difficult and practicing the scenario with your manager with your director beforehand can be really helpful or if you're a director or executive and a manager is walking into a conversation like that, pulling him aside and saying, hey, let's practice this for a few minutes.

Some of the things that might come up. Before you walk into that conversation can be a great help to that manager .

Dr. Jim: Like the fact that that you called out the need of senior leaders to pull aside those managers and go through a scenario and role play. In order for that role play to be productive, what are some of the scenarios or elements of that role play that senior leader should get on the radar of that line manager so that they're well prepared heading into that conversation?

efore and the nature of each [: 00:22:00

And so a lot of it depends on the nature of the conversation, but. Your senior leaders probably had all of those conversations before. And so as a senior leader, if I were doing that, I might write down a few notes on things that been particularly challenging and those conversations when I've had them, and then I would play the frontline employee.

The manager is going to play the manager in the role play, and I'm going to give them, some of the more challenging situations that could come up just so that we can stop and say, okay, let's think about how you'll deal with this if it does come up after we've done the role play.

major things that they need [: 00:23:00

Lucas Price: Yeah. The best leaders have built very strong relationships with their teams and hold their teams to high standards, communicate those standards very clearly and practice the situations that are difficult for you to encounter. I think for some leaders, the difficult situation is showing the empathy.

And for other leaders it's holding the high standards. So if you have someone that you can practice those conversations with beforehand, because you want to make sure that you that you're doing both in those conversations you're building the strong relationships and you're holding very high standards.

Dr. Jim: Lucas, if people want to continue the conversation, what's the best way for them to get in touch with you?

Lucas Price: Yeah, you can find me on LinkedIn. You can also go to our website, yardstick. team. And there's a few different ways to get in touch with me via our website.

nd accelerating growth sales [: 00:24:00

Where a lot of leaders go wrong is that they're not clear in their expectations up front. And that creates this cascade where by the time things are starting to bubble up and go wrong, it's often too late. So if you're looking at setting yourself up for success when it comes to navigating these difficult conversations, you'll be well served by laying out the issues and the process.

eciate you sharing that with [: 00:25:00

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