S2E5: Having Difficult Conversations 2.0

Speaker A: Welcome to People On Purpose, where each episode we explore how founders can navigate building businesses where people and profits can coexist on purpose. When we started to think about the topics that I wanted to talk about on People On Purpose and how they differed from the, uh, over a hundred on the up and up episodes on our feedback, it was really interesting because there are still so many relevant topics that need to be hashed out, discussed that I just simply have a lot of thoughts on, um, that we may have already covered. And I think that when it comes to People On Purpose, the reason that you're here is because we've evolved with you. So probably many of you have been listening since the on the up and up days and, and have grown alongside my business, have grown alongside a lot of our clients and friends and community members and things like that. And a lot of that growth hasn't always been super smooth and straightforward and easy. Um, actually I would say most growth is like the worst thing ever. But at least we got here eventually. Um, and the interesting thing is that I was really cautious because I didn't want to talk about a lot of the topics that come up that we've talked about on, on the up and up because we are just all in such different places of business and we are all in such different phases of leadership. And a lot of what I'm hearing from you guys when you listen to the episodes is the areas that are really resonating now that you didn't anticipate or even that you're not quite there yet in your own business or in your own career, but you're starting to see that there will be a path where you will need to be able to refer back to some of these episodes and these conversations and like really refresh on where you stand on certain things, what your strategy is, how you feel about them, um, or even just some of the skills that we talk about here that we can learn from each other. And one of the topics that just consistently comes up all the time is all about having difficult conversations. Because it doesn't matter if you are a million dollar a year business or a $10 million a year business, or even if you're just starting out and hiring your first couple team members. Difficult conversations are par for the course. You have to be prepared to have them at any given time. You have to be able to be in a calm headspace where you can communicate directly and clearly and people can take home the message that they need to hear. Um, and it's not, it's a non Negotiable that you have to be able to ad adapt and adjust based on how those conversations turn out. And I think that sometimes we as founders get to a place where we have made 3,000 decisions that day. And trying to think about how to cater a conversation that feels like common sense to an employee can feel like a totally different ball game. And one of the things that I really enjoy about working with different types of founders and working with different types of businesses is, is that there are so many different layers of leadership that we have to be able to express and show up as. So they're one of the topics that when it comes down to difficult conversations, that comes up a lot, even in later stages of business, uh, business that maybe doesn't come up early on, is that you are not only the responsible leader for your business and your team, but in many cases, the only way that you can progress your business forward is if you have other leaders on your team that are leading people as well. And your job becomes being a leader to a developing leader, which is a completely different type of conversation than one that you would have with an employee or individual contributor that may need to make some adjustments to their performance or their skillset in order to adequately and basically perform their job at a level that actually moves the business forward. Which it's your job as the leader to be able to oversee all of that progress. When we have had this conversation in the past, it was one of our most popular episodes. And I think what makes it so popular is that difficult conversations can be really broken down into a couple of basic steps in order to make sure that you are executing on them properly. So that episode of on the up and up so still maintains one of the more popular ones that we have. But this episode on of people on purpose talking through difficult conversations is not going to be quite so focused on the execution of those conversations, but more so about understanding your role in those conversations and how to make sure that you're putting yourself in a position to make the biggest impact. Because in many cases, you may not be the one that needs to execute the this discussion, but you do need to be the one that makes sure that it's happening and it's happening correctly. So before we dive into the couple of types of approaches that you can take, I want to talk about why having the ability to do this is so important in, in a business and so important in a leader. Obviously being able to talk through issues, be direct, communicate clearly, um, is all things. Things that we know that a true leader needs to be able to demonstrate. But why does it matter so much when it comes down to being a founder and having conversations with other people that are stakeholders in your team or people that are progressing your vision forward? Number one, it's because there is no other source of greater clarity than from the horse's mouth, so to speak. So even if we create the most beautiful culture, guide the M, most amazing employee policies, the most incredible onboarding, um, and you have the best team agendas, and you have the best team under you, if you show up and your interpersonal skills are in direct conflict with the culture that you're trying to build, then we are not going to be able to bolster anything that could be in disagreement. The culture, as much as we define it, it really does rely on the actions that make it come to life. So being able to fully back your decisions through difficult conversations while also infusing the cultural perspective that is required of your leadership as a founder is super difficult to do and also can be boiled down to a couple of simple truths. The M first is that if you are clear and intentional and direct and honest about what your culture is and what you want it to be, and you make sure that you are showing up in a light that represents that culture every single day, then it won't be difficult for you to find ways to bridge the gap. When there are difficult conversations that need to be had between you and your leaders or your individual contributors, or even vendors or business, um, partners or business coaches or people that you work with, There are opportunities to have friction at so many different points in your day. And oftentimes that friction leads to something better. And so being able to show up with intentionality and clarity and also with a kind of effort, effortless alignment with your cultural perspective is critical to making sure that you are continuously pushing the message forward about what you expect your team to do, how they are to respond to these types of discussions, and most importantly, how your other leaders are going to show up in the same vein. Because if you are showing up fully and intentionally and directly alongside your culture when you are having tough conversations, then, uh, your leaders have to be doing that too, and they're going to learn how to show up by emulating what they see from you. And oftentimes, it's those conversations that you're having with them that are going to contribute to their growth and how that kind of rolls downhill. So, realistically, one of the biggest things that you can do to make sure that you are prepared for this type of interaction at any given moment is not just to define your culture and then live it and breathe it every single day, but it's also to take a little bit of time to look inward at what type of leader that you actually are and how you want to show up. One of the biggest mistakes I see new leaders or new managers make is they had someone that they really looked up to. There's somebody in their life or a manager that really impacted them. There is a coach or a, uh, consultant or even a peer that is kind of represents the type of leader that they want to show up as and they want to be. And basically, they start to, instead of understanding the messaging behind the delivery of their leadership style of this person they look up to, they start to emulate it and mimic it. And what that does is it erodes your authenticity, and it creates an even bigger gap when it comes to having to make quick, agile decisions in an interpersonal space. Meaning that you can't always plan out the difficult conversations you're going to have. Sometimes they're going to land right in front of you, and you're going to have to deal with them right then and there. And if you already have a barrier of maybe not having a ton of experience in this area before, but also that you have been emulating or mimicking someone else's leadership style, you are not going to be able to respond as authentically or effectively or clearly as you can. If you are really in tune with the type of leader that you are, that you want to be, where you see your company going, the goals that you have, and the culture that you're driving. And I think that that's where people get really lost. So sometimes when it feels like things are really overwhelming as a leader, or it feels like things are really impossible, there is so many key priorities pulling you in a thousand different directions, and you're having trouble understanding what's really needed of you in that moment. There are a couple of different pathways to go down. First is to try to get as much off your plate as you possibly can. And one of the best ways to do that is to make sure that you're always doing the legwork to ensure that the leaders on your team are able to show up exactly how you want them to, so that they can help you spread whatever message it is that you need to get out there to the rest of the team in order to pursue any type of agility or changes or pivots that need to be made in your business without a lot of pushback or blowback or just additional friction. If you have leaders on your team that you have not only been able to share authentically with about how you want them to show up for the business, but they're also aligned on the goals and the values that you've set forward and the things that you're driving towards. Then you should be able to give simple directives to your leadership team and have them carry it through, utilizing their own leadership styles to connect with their own team and their own relationships that they've built with them. What we often see, though, is that a lot of leaders feel like they can't put some of these leadership responsibilities on their managers. For whatever reason, having difficult conversations with their teams has become something that they are afraid to put full ownership on their managers for. And that is really why we wanted. I wanted to record this episode and my team and I talked about this on our team meeting because I wanted to make sure that there is a little bit of something different from our more popular episode on Difficult Conversations from back in the up and up days. And again, that episode was all more about execution of these conversations. Whereas now we're talking to founders, and many of you have been in business for many years and you've gotten to the point where there is. It isn't just about how you're showing up as a leader. It isn't just about embracing your goals and your culture and your businesses, um, next steps, and being able to communicate that clearly to the rest of your team. Because while that is very important, the real impact that you are making now is how you are leading the leaders on your team. And how important it is, is for you to be able to hone in on the messaging that you are trying to create to ensure that your team is all moving on the same pathway forward. They're all in the same boat, everybody's rowing at the same pace. We're all moving in the right direction and we're able to rely on each other to help get us from A to B. If our leaders are not able to fully execute on the vision of our leadership, planning our conversations and their responsibilities, then no matter what you do or who you hire, you will constantly find yourself in a managerial administration position. And you will never actually be able to lead the leaders that you've hired. And I say that because there are many opportunities for you as a manager of your leaders, like their direct supervisor. There are many opportunities for you to redirect things that they are bringing to you and to have them take more ownership and onus of them. So if you have someone on your team that is considered a lead, that implies that they have a report under them. If you have a manager on your team, a supervisor or a director, whatever the case may be, implying that there are people underneath them, no matter what, a big part of their job is going to be their obligation to managing and supervising those reports. If for whatever reason you have someone in a position of leadership, but they're not really equipped to be leading or managing another individual, that's where your culture is going to fall apart. Because what essentially is going to happen is you are going to end up being the manager of every single person on your team. Because if they don't have one that is fully established, that is embraced, that is clear, that's straightforward, that communicates effectively, and there is clarity in that leader to subordinate relationship, then, uh, they don't have a leader except for you as the founder, they are going to default to. Not necessarily undermining what their manager might say, but they might overlook things that their manager might say, or their manager might be abdicating responsibility for their progression altogether. A lot of times this happens on accident because the, there isn't a lot of strategy to how tasks are rolled out to team members. And a lot of times there's a lot of growth and we just need to make sure that departments are filled accurately and that work is being done. And that means that there's a couple of different levels in which people function. And it's within those levels that you start to see the breakdown of leadership communication. Difficult conversations have to be embraced and acted upon across the board. Your managers should not only be prepared to do the function of their position, that is creating roi, checking things off a list, making sure that the tasks are getting done, um, and basically reporting back to you about any of their KPIs, metrics or accountabilities that their team is handling, but they should also be prepared and ready to have a difficult conversation at the top of the hat. At the top of a hat. If anybody is to bring them a concern or an issue, they need to be, uh, be just as ready to have a tough conversation, draw lines in the sand, and embrace their managerial duties more so than they would even be doing their focused work or their other type of accountabilities. Because putting someone in a managerial position is not a decision that should be taken lightly. If there is a breakdown in communication on your team, it's usually because all of the leadership is being forced to come from the top and instead of having it inferior, fuse into the culture on the way down the Food chain. What's ending up happening is it's getting watered down through every step because those managers are not necessarily trained or held to, uh, the accountability of fulfilling the image and fulfilling the direction that you are setting within your company. And part of that is because they don't want to take responsibility for some of those difficult conversations that need to be had. I'm going to give a really basic example of this. Um, so we work with quite a few different companies and oftentimes one of the larger conversations that we're having is around paid time off and when people get their vacations approved versus when they don't get their vacations approved. And a lot of that is definitely spelled out in the foundational messaging of the handbook of their company policies, you know, all that stuff that we help them build. So it's helpful to have them refer back to those things. That's why it's really important to have a solid HR foundation even before you are bringing on leaders that you have to manage and lead. But regardless of that, it helps to answer a lot of those questions that could otherwise be put into a gray area. Now the point that I want to make is that oftentimes department heads or leaders are going to be able to be focused on what their department is outputting a lot more than they're going to be worried about if their team is fully staffed. And a lot of this comes with the fact that remote work is so flexible and there are definitely seasons in which everybody is all hands on deck. But a lot of times we can be really flexible with our teams on a day to day basis, which is a great benefit. And our managers probably benefit from leading that way as well. But the problem comes when they become so reliant on the flexibility that comes with the remote culture that they don't draw any guardrails around it. And then they end up taking on the responsibility of their team and then basically just passing off higher level leadership accountabilities up to you as the founder. And the reason that that happens is because there is no strategic bottom up response to management. There is no ownership on an individual contributor level to ensure that people are able to show up exactly as they're supposed to do the job, exactly how it's laid out, and exactly where to go if there's anything preventing them from getting from point A to point B or preventing them from being successful. When we hire our teams, we are hopefully hiring them with the best of intentions to ensure that what they are able to produce is going to help make them more successful in your business as well. And that is often where we start to see the gap. So if there ever is a situation in your company where you feel like you're the one that's always delivering the bad news, where you feel like you're the one that's always rejecting the time off requests, where you feel like you're the one that's always asking where people are and why they are, where they, where they should be, or if you're noticing that there's a delay in maybe productivity or performance or improvement, um, amongst certain members of your team, but you're not 100 sure why it's happening. Oftentimes that's because the ownership of the management of those people hasn't been clearly and fully assigned to the managers or the supervisors that are leading them. Because truthfully, the leadership that you are in charge of are leading your leaders. So you should have only a handful of direct reports that you're managing on a day to day basis to ensure that their performance is matching your expectations. However, that doesn't mean that your expectations for the rest of the team and the functionality of the business as a whole should just be shoved aside, but instead you should make sure that those accountabilities for each individual are coming from the bottom up. So everybody that shows up for work every day shows up, does their job, gets their, you know, basically gets their kudos, gets their performance reviews, they get their compensation analysis. All of these things are happening at a, at a clip that makes a lot of sense to small business. You can tell that people are moving forward, people are moving around the same pace, people are getting promoted around the right times, all of that kind of stuff, those are all, that's all really good evidence that everybody's on the same boat, working together and moving forward. Where we start to see a breakdown is when somebody in the middle, a middle manager, a director, a lead, somebody like that, is not necessarily pushing forward the goals or the cultural perspective that is required of a leader to draw their team forward and keep them moving. So what I'd like to challenge in this episode is that if you find that you're the one that has to make all of the leadership decisions on the team, and you're not understanding why your managers maybe aren't showing up as effective as you thought they would by putting them in leadership roles, then what I would challenge you to do is make sure that your number one, your goals are clear, direct and straightforward, and that everybody knows what they are. If you went to your direct reports, your managers that are under you. And you said, hey, what are our goals for our culture? What are our goals for the company this year? And what do I have working, what am I working on right now that you're supporting me with? If they can't clearly and directly answer those three questions, that's a really solid sign that the communication breakdown is coming from the top down. Which means that you are not adequately representing the image, the vision, the value, the purpose of what everybody's doing every day in a clear enough way that even if it does get watered down through the kind of telephone game that comes with leaders managing other leaders, then you need to reevaluate and make sure that it's clear as glass. And the best way to do that is to quiz, to quiz yourself to go ask those three questions to your direct reports to your managers on your team and if they don't have the answer, it's your fault. It's your responsibility to provide the high level vision and the high level answers in such a clear and distinct way that your managers can take their piece, their expertise, and be able to do the same thing for their team below them. So that everything that they are deciding, everything that they are working through, every conversation that they are having is clearly infused with the messaging from the top down, but with the accountability from the bottom up. And what that should look like is your manager should be able to understand, well, this year we're shooting for X revenue and the major project that you're working on is the expansion of this department and offer. And how I add value to that is by essentially showing up in my job description and hitting these three KPIs and then supporting you. If those need to adjust or change based on our new goals, they should be able to clearly and articulate, clearly and effectively articulate that back to you. It should feel almost exactly like what you would say to them initially if they can't. This is your opportunity to fill those gaps and make sure they're walking away with clarity, not only on what the company is trying to accomplish, but their role in supporting you in that message. From there, they should be able to break that down a little bit further and their team should understand exactly what the company's message and the vision is for that time period, exactly what the goals are for the company during that time period, both culturally and productivity wise. And then they should also be able to see where their perspective, where their role is adding to the value of their leader's responsibility. So if your manager goes, comes to you and answers those questions, and then says, and I help you by making sure that all of our clients bills are paid, their um, contracts are signed, they are working through our onboarding process and they are, um, right on timeline when it comes to providing assets that we need in order to complete the project. If that is their job, then we need to look at how that breaks down for their team. So they should be able to not only have that conversation with the individuals on their team and say, okay, so this is my job we need. I am here to make sure that client contracts are in place, billing is handled properly, assets are delivered, and that we are moving along on timelines to ensure capacity is exactly where it should be and the people under them are going to be able to see clearly what their role is as a direct result of what their supervisor is representing in regards to the overall company's mission moving forward. That should be so clear and straightforward and direct across the board. And it doesn't have to be that complicated. This is a whole other conversation. But within your team, each individual should have no more than three to five metrics or KPIs that they're looking at and monitoring on a daily, weekly, monthly or, you know, quarterly annual basis. They should have consistency in those metrics. And basically what those metrics should represent are their priorities. So if that leader, that hypothetical leader we were talking about earlier, that sounds like their client relations manager in this case, if that leader was like, well, we've got 50 different contracts out and I don't know which ones are coming through and I don't know what's been processed and um, our system keeps breaking down or I'm not getting the reporting correctly or whatever the case may be, then they're not going to be able to accurately be able to put their building block in place in order for you to run forward and ensure that the business is hitting its goals. So their team should be able to see, okay, so my job is to make sure that reports are updated each day, that all of our numbers are accurate and are showing up because. And that are showing up in our bank accounts. That contracts are not only being sent out, but they're also being reminded of them, that we're finding alternative ways to make sure that we're hopping into those conversations with future clients to ensure that we're closing these contracts that we have to set up and we have a really clear and direct path of communication so that my boss can get the answers that they need in order to make quick decisions, especially when it comes to forecasting and projection. Because that's really what we need to see at the top of the. At the top of the pyramid, so to speak. So each of our people on our team should see exactly where they add value in the overall company goal. And where I think things get lost often is in these little things. So not to go back to the PTO thing, but your team members, your leaders and your managers, your directors, everybody should understand the way that work flows underneath them in order for them to get to their goal. When somebody's in a leadership position, it's not just the way that they're, uh, organizing their day or they are producing their material or they are working through their tasks that is important because really, most of their work should be dependent or at least collaborative with the team that's underneath them. So let's just say that hypothetically, in your business, you have all of your paid time off monitored by your coo. And so no matter what department anybody is in, the COO is the one that's in charge of processing the PTO request, putting it on the calendar, and making sure everybody has what they need. This is not the way that it should work. The reason that a lot of companies set it up this way, or they set it up to go through HR or whatever, is because they think of PTO as a task that needs to be completed and documented. They don't think of it as a project planning tool. They don't think of it about it as a labor margin capacity tool. And who should be in charge of the capacity of a team to perform the basic functions of their job in order to get to the vision of the business, the manager that has their finger on the pulse of all of the ways in which their teams work together. In many cases, people will shy away from saying no to paid time off and things like that, or in time off in general, um, because it's an uncomfortable conversation. And especially if you're not a founder, think about it like this. Your manager, they're not a founder. They're a manager. They want their team to be happy. They want their team to show up for them. They want to have good relationships with them. And if we are not providing the tools that they need to have tough conversations with their team around these types of items and tasks to make sure that the company is staffed, that it's working properly, that there is a reason behind the way that our time off works, that our team is reliant on each other. If they're not able to have those conversations, then they're essentially abdicating the responsibility of the functionality of their team to somebody that isn't even playing a role in the success of their teammates and their, their direct reports. So what we need to do is make sure that we are enriching our managers experience to take control and take ownership of the productiv of the people under them with no real reason to be passing off that responsibility to any other leader or manager. They should be so protective of the way that their department functions that having those difficult conversations around PTO or whatever the issue is should come very naturally to them because at the end of the day they're really clear on what the goals, the mission and the purposes of their job on each day to day basis. And they've been able to pass along that message to their team so that they can be on board with the way that those goals are actually shaping out. And one of the most integral ways that we see this go kind of awry is when accountabilities are not assigned to the leaders on the right teams. And so what I want to challenge you with today is that if you're able to take a look at not only making sure that the people that are reporting to you have a really solid understanding of how their role plays into the functionality, the productivity, the projects that are going on, the mission and the vision of the company for that year, not only just making sure that they can answer those clear questions, but also that they can answer questions that come at them that have to be filtered through that lens confidently, directly and in a straightforward way. Because sometimes our managers are going to have to say no. And we can provide the tools that they can use in order to make sure that they are that filter. Because if you don't enforce this, then under every single circumstance where somebody has to get bad news, be told no, get a performance review, be laid off, all these millions of things, every single bad uncomfortable decision is going to have to come from you as the founder and that is not a really functional place to work and be innovative. You have to be able to allow your team members, your managers and your leaders to take full accountability of the productivity of their, of uh, wherever they're functioning within their organization and make sure that they can stand up for it and represent it in a way that makes perfect sense for the functionality of the business confidently, without any kind of guilt or misunderstanding. Number one, have those HR foundations in place so they can do some of the bad cop stuff for your managers. Number two, make sure that your difficult conversation strategy is aligned not only from the, from you down to your managers, but also so that when your managers are having those conversations, you've trained them and helped develop them enough to help them understand what needs to be delivered with clarity and understanding. And often we will see this breakdown big time. Because managers either don't understand their responsibility when it comes to the overarching company goal and they'll forget that within their job description it's not just about their productivity, how much they know about their industry, what they're producing, how they're so good at it, you know, whatever the case may be, how they communicate, how they can talk through things, all of that stuff, stuff, all of that's really, really valuable. But if somebody is leading another person, arguably the biggest responsibility they have is the person on their team. Because that is the wavy area, that is the shaky area, that is the foundational area of them being able to do their job well. If their team is functioning at a high level, they will be functioning at a high level. But if we are always, if uh, they are always abdicating responsibility for the performance or functionality of their team because they don't have to be held accountable to these difficult conversations, then it is going to become your problem and you're constantly going to be trying to build a trickle down culture when instead we want to be able to empower everybody to understand their mission and their role down to the granular little tasks that are being done every single day and how that contributes to the bigger picture. The secondary effect of this is not something I'm going to talk about today, but creating a growth path within your company for people to move up is integral to making sure that you always have a talent pipeline that's coming through the ranks and that you can be adaptable and create opportunities for individuals that have been on your team for a long time. Longevity amongst team is one of the highest predictors of success within small business and returnover and low employee retention is one of the highest costs. So creating a growth pathway forward is also going to help contribute to your overall retention. Now being able to have difficult conversations and steer the ship is not really what we're talking about today, but in a future episode we'll talk a little bit more about how you can maybe see the link between a solid understanding of an assistant to their manager and their manager to you to make sure that they can kind of see exactly how the little things that they're doing on a day to day basis are contributing to the higher level overall goal of the company, which helps create a really solid understanding of uh, how the company works. And is actually a form of training for them to move up. And it happens naturally as long as our managers are fully, fully showing up as managers and not just individual contributors. Years. So basically, difficult conversations are tough to have. They're always, always, always going to be something that's running in the background. There's always somebody that we have to talk to, there's always somebody that we have to deal with, et cetera, et cetera. But your goal as a founder is to not only equip yourself to make sure that you can have agile discussions at the drop of a hat, because you're clear and you're direct, you're straightforward and you completely understand how you are playing a role in the functionality of your company, the goals that you're trying to hit, the vision that you're trying to shoot for, and the projects that you're working on to get there. But we also want to make sure that you are prioritizing time within your leadership to ensure that that same strategy is trickling in through your leadership team so that you can create a pathway for, from the bottom up, ownership. And that is only going to happen through friction and redirection. So everybody's going to always keep going down the same path that they're on every single day unless you redirect them. And that usually means a tough con. You want your managers to be able to approach those with confidence and simplicity and be able to really explain the why behind the what during every single opportunity. It's not just about documentation, it's not just about execution. It's about the understanding of, at the highest level of what the business is producing and how each individual contributes toward that. And the first step is literally just being able to clearly articulate what your goals are. So that's all I have for you today. Um, I did want to just remind you in our show notes to make sure that you are on our newsletter list so that you get alerted of new episodes that are coming out. Um, we have a bunch of really good ones coming up in the next few weeks, but I'm also really open if anybody has any suggestions or any questions or any follow ups. Um, you can send those to me on Instagram at any time. Um, and just as a reminder, we always have a kind of open line of communication in regards to what you might want to hear on the podcast. But the best way to help support and make sure that people on purpose gets into the AirPods of other founders and other leaders is to give me a five star review and maybe even leave me a little note. Um, outside of that, Instagram and LinkedIn are a great way to reach me, and I hope to get some more ideas for episodes from you based on what you enjoy about these podcast episodes so far. In the interim, I'll see you in our newsletter, and I hope you have a great week.