Leading with Kindness with Matt Cunningham

Matt Cunningham joins me on the podcast to chat about what leading with kindness looks like and how we can do it through conversations that actually produce value.
Matt Cunningham joins me on the podcast to chat about what leading with kindness looks like and how we can do it through conversations that actually produce value. Not only are conversations the key aspect of being a great leader, they also produce understanding for one another. Kindness is the key to these conversations though. Without kindness, we as humans lack empathy for our employees, valueable communication, and relationships that produce far greater results.

Find Matt on:
  • His website: https://epickindness.com/
  • Email him at: matt@epickindness.com
Full transcription below (may contain typos...):
[00:00:00] Matt: [00:00:00] start with kindness, ask great questions through managing the conversational model. So have that skill based, have that soft skills skillset homed to, to the best that you can.
And finally use a product like Waypoint. So make sure that you are set time and goal and space for these people that you're managing and these team members that you're working with to genuinely find out how they're doing. 
Keerstyn: [00:00:24] This week on the podcast, we have Matt Cunningham. He is a business coach. who owns Epic kindness, but she, he is also joining forces with our team here at Waypoint. just start selling way point too. really being an influential person within our team. We're really excited that he's joining us. and so to get to know him better, we decided to do a podcast. 
not only does he talk about the benefits of simply just having conversations with your team? He also talks about leading with kindness. And talks about why it's so important as a leader, as a manager, as an [00:01:00] employee. And it was simply just a person. In general, we go through some of those ideas that you might have about leading with kindness and if it's genuinely valuable and if it's the way to go. And I believe it is after I hearing Matt talk a little bit more about it. so yeah, we'll jump right in and. get ready to learn about leading with kindness 
welcome to the podcast, Matt. I'm really excited that you're here with us today. some background for all of our listeners, Matt Cunningham. Has just joined us, and is working with us, as a Salway point. he is a business coach, who has been in the industry for about 20 years.
So has a lot of knowledge and background. and, yeah. Do you want to tell us a little bit more about yourself and how you got involved in your work and what you do now? 
Matt: [00:01:45] Sure. Sounds good. really for the past 20 years, I have spent time helping people be better communicators. I focused on management, management practices and how people generally just don't oftentimes don't know how to manage [00:02:00] people.
They get promoted and they have not had experience managing others. And there's some challenges that come with that and managing people in general has some challenges. So for the past 20 years, I've been a manager, I've been a leader, I've been a business owner and, I've taken a coaching approach as often as I could.
Which is basically seek to listen, find out what someone's trying to say before you try to understand and help them solve. A lot of managers do that really well. And a lot of people don't. So I, I started, gosh, I started about five years ago. I started a coaching business and I am a professional, executive coach and I help managers kind of work through some of those challenges with their people to help them retain them.
Not only that, but. Also too, to just help them in general, as they communicate and have more conversations and better conversations with their team. 
Keerstyn: [00:02:51] Interesting. So what were some of those pains that you saw in the workplace as a manager and as an employee? what were [00:03:00] some of those struggles that managers were going through and, yeah.
why do they need this? The 
Matt: [00:03:06] biggest pains I saw in general were. Managers, struggling to connect, right? You have a team you're working hard, everybody's doing their day to day, and there's a struggle to engage. There's a struggle to connect to. There's a struggle to help people feel connected to the team or to the company.
So what I, that's the biggest thing. And then inevitably managers are trying their best. They're working hard. They're going through all these experiences. they're getting promoted. They're in meetings and their team members are leaving. 
Keerstyn: [00:03:37] Yeah. And why are they leaving? 
Matt: [00:03:41] The number one challenge in the U S right now is employees feeling engaged.
They just don't feel engaged. They don't feel connected to the company. They don't feel connected to their leader or their direct hire their direct manager. And they struggled too. Everything is, looks better somewhere else. And oftentimes I think people don't realize [00:04:00] until they've laughed at the grass really was never greener.
Just looked a little bit better. And, yeah, they. They take off and they run into the same challenges because those connections are happening everywhere or those disconnections as it might be. Yeah, 
Keerstyn: [00:04:13] absolutely. What are some specific things that managers can do to start upping this engagement rate, start retaining their people more, making the grass actually greener versus having it look a certain way, but it not actually being true.
Matt: [00:04:30] I, the number one thing that managers can do is connect, get regularly scheduled, conversations with their team and keep those conversations. It is truly, a struggle for managers to do that because of the schedules because of the day-to-day work. And I know that people get sent to different events or conferences or trainings, and they learn how to communicate better and they learn some great [00:05:00] skills and that is extremely helpful, but they come back to work and the schedule takes back over and they may not be able to use those.
So the number one thing that people can do is just schedule regular touch basis, regular one-on-ones with their team. And find out how they're really doing. And I'd say the second thing that they can do is make sure that they're understanding what a, a great effective conversation looks like.
Managers oftentimes get so busy trying to solve that. They forget that it's just the person sitting next to them, just like them. And there's, you're dealing with the same challenges. And so understanding what good conversation and communication looks like is key. 
Keerstyn: [00:05:41] Yeah. And how do you actually have the effective communication?
I know that some people are like, Oh, I'll schedule the one-on-one, but then they go to, and they're like, what do we actually talk about? what are some good questions or good, scenarios that would, play out in these conversations? 
Matt: [00:05:58] That's great. That's a great question. [00:06:00] I, the biggest thing that you can possibly do is get yourself some questions lined up that are open-ended questions.
Start your questions with what or how. Make sure that you're really trying to engage and listen to the answers. but really to answer the question, just get a list half, have some things written down and prepare yourself for what that might look like and there's tools out there. It's one of the reasons I, I joined Waypoint.
Wait points tool on helping people connect and really keep their one-on-ones and setting goals and having a slotted time that you're going to meet with them. All those things are extremely valuable to making sure that one-on-one goes well. 
Keerstyn: [00:06:41] Yeah, absolutely. And I think the other thing that you mentioned too, that I really do want to hit on is listening.
I think oftentimes our conversations are, we think that we're listening and then we realize, Oh, I have been talking for the past 20 minutes. And I actually haven't heard a single thing that my employee has said, or I [00:07:00] haven't dug deeper because they said their day is good. And that works for me. What. I guess are some tactics that you would, encourage people to do to actually start listening.
and not just saying that they're listening, but genuinely, making sure it happens. 
Matt: [00:07:18] I like to call that reflective listening. It's it's you know, a lot of people talk about repeat back exactly what you heard. And while that might be good to start, there is a point where. You need to ref reflect back on emotion, right?
Reflect back on what was actually said. A lot of people use the word I understand in communication and sometimes it just isn't. People don't feel it's genuine because really how can you truly understand someone else, even if you've had some of the same challenges and gone through some of these same experiences, do you really understand?
So I try to use keywords. Like it makes sense, [00:08:00] that you feel a certain way, or it makes sense that you're frustrated and you tap into the emotion, you tap into the things that you heard. And while you may not understand, it can make sense. So that would be something that I would really start to do.
It's a great starting point, to hear the emotion, to hear the connection and then, and to really listen well, so you have to listen well to hear sometimes those emotions between the 
Keerstyn: [00:08:25] lines. Yeah, absolutely. Are there some tools that you can use? So for example, would you encourage people to take notes during meetings or, to.
Make that list and then go back and go through it after the fact or what are some good ways to make sure that you're actually listening? but then proving that you're actually listening to yourself into that individual as well.
Matt: [00:08:53] No, Kiersten it's really interesting because the taking notes or not taking notes truly comes [00:09:00] down to the person's ability to, to recount the story. So I oftentimes don't take notes and I try to just really engage into what's taking place and listen, and go through the process with the person in front of me.
and hopefully recall those things as I hear them, or as they were said and talk about what someone might feel or the experience or the frustrations or the challenge, or even the joy and success. So those are great things there, but if you are the type of person that needs to take notes, then certainly take notes.
just have that conversation first. I have a very good friend who lets me know every time we chat, Hey Matt, I'm going to take notes. if you see my, if you see the top of my head, just remember I'm writing and it's, it clears up conversation that I, that I know.
They're not on their phone or something along those lines. So in, especially in the world, we're in today, it's really easy to get [00:10:00] distracted on a zoom call or on a chat, when you're chatting with someone online. So just communicate those things, share those things. That's, it's a really great, effective way to bring back.
And maybe you're just writing down the key words. So I always try to tag in keywords that you heard. The other tool that I try to use when listening really is try not to be thinking of your answer before the person's finished talking. So the next best thing to say out of your mind, oftentimes can be the worst thing to say.
So try to listen right through it, continue to go into what you're hearing and that will oftentimes give you clarity that you didn't even have. If you'd taken notes. 
Keerstyn: [00:10:42] I'm taking notes right now, Matt, don't worry. I'm not on my phone. I'm glad you said that because I think it clears up some of the, those weird things.
 Do you have a story about how a manager has, listened or not listened and like the, really the true reason why you wanted to get into this work? [00:11:00] Was it a bad manager? Was it you managing and really struggling with what you were doing?
what was it. 
Matt: [00:11:08] my best story I've got two stories. My best story is I worked for a very large company and, had a manager who just never, it just didn't get understanding people. They didn't get that people have challenges in life and events. So everything was targeted and managed from a perspective of a list.
This is the things that you have to do and nothing should affect that list. And there was very little empathy or kindness, and the relationships. there's a point where it begins to wear on you so much that you sit back and say, if you just asked me one or two more questions or just found out a little bit more about what was going on, that maybe you would begin to understand me.
And so I began to look for other work [00:12:00] just because of one person. So in the research I've done over the last number of years. That's and I think, you look at a book, out there called the manager. It was written for a reason. It was written because Gallup did research and found out that people don't typically leave jobs.
They leave people and they typically leave direct their direct hire manager, the direct report. Whether, where they're reporting to. So it's something you sit back and go, okay. So how does that happen? And so for me, I watched somebody get promoted that didn't know how to manage people. And then the work becomes so overwhelming.
they've been hired to manage, and now they're doing the work. It's not really, even their fault. they just get really busy and they continue to not manage people well, because nobody showed them. So that's primarily it. Do I have, some relationships with, have I had some great relationships with really great managers.
I have some really amazing, great relationships with good managers and [00:13:00] you sit back and you realize, they listened. they cared about you. They practice kindness as often as they could. they spent time. Genuinely wanting to know how you're doing. And the more I got that experience, the more I watched that happen, the more you see the people that work for them want to continue to work for them.
So those are the two big keys, I've I left jobs specifically because of bad managers. 
Keerstyn: [00:13:29] Yeah, absolutely. That's really interesting. I, so I actually remember my question now. So if, for example, say your employee is coming in and you're trying to be a great leader and have one-on-ones often with them, but it's just like a never ending negative circle.
What do you do? 
Matt: [00:13:50] so clarification, is it a negative circle from the employee's standpoint? 
Keerstyn: [00:13:54] Okay. 
Matt: [00:13:57] I start, I try to be kind and empathize [00:14:00] and see if I can find out the root of the negativity. And I know that sounds really easy. Genuinely, if you started asking some legitimately great questions, you can find some of those things out, tell me a little bit more about what's frustrating. You how's things going in life, just in general. How are things going in life? Just in general? what's your biggest challenge. What's your biggest frustration with the business? Just start asking some great questions, but here's the key to those great questions.
Don't look to solve their problem. It's not a manager's job to make an employee happy to manager's job, to make sure that the employee has the tools and the skills to be happy. At their job. So oftentimes managers will ask some great questions and I'll give you an example. So tell me, what's frustrating you, is it a, is it B, is it C if you can name one [00:15:00] thing and so they'll make the question of, tell me what's frustrating.
You, answerable by opinion. In other words, here's my opinion of what I think it is, as opposed to what I want to hear from you. And the reality is you just want to know what's frustrating them. A lot of managers don't just ask the question and then stop and wait and listen. so that's probably the first thing that I see that happens a lot.
You try to solve it for them. These are the things that I think you should be frustrated about, or that I see that you should be pressured about. So which one of those is it? And it might not be any of those, but once you've planted those things into their mind, You've lost the ability to listen to what they might have on their mind.
So ask the question, let the question, sit and wait for an answer. And so that's one of the first things that I would do. And oftentimes what people will do is they'll begin to actually feel like you, you generally want to know, I want to know what it is. It's frustrating. I want to get to the root cause of your [00:16:00] negative.
Conversations that we continually have. And then also be the person that changes that negative opinion into where that negative, energy into some positive energy, how can it help? What is it that we can do to support you better? What are the things that you think that would help move this into a positive, a more positive direction?
So plant those things in the conversation that'll allow for positivity to come out 
Keerstyn: [00:16:29] of it. Yeah, absolutely. I think those are really important things. So like you said before, managers often are just, they aren't equipped with the tools and resources and knowledge. once they're put in that managerial position, which often makes people leave, what are some of the things that you help people with as a business coach?
and how could you help those managers that are just simply not equipped? 
Matt: [00:16:56] great question. my biggest thing Pearson is talking to managers [00:17:00] about perspective. First, do you have a perspective of your people? Do you, are you practicing kindness? The greatest managers out there start with kindness and then they manage from that perspective, they manage from a coaching quality conversation.
Great. Open-ended questions perspective, but. They generally are trying to be kind to the people that are working for them. And that goes a long way. So that would be the first thing, which is the reason I have a company called Epic kindness. it's practicing something that we all need more of. And inevitably the people that work for you need more of, it's just the way it is.
And so start there. The second thing I do is. I've gone through courses and trainings and all kinds of different things and have a number of different certifications in communication, but knowing how to manage communication well, conversational management, it's a tool that I use. It's a great product.
And it's a course. That's taught by an amazing [00:18:00] company here in town called real retention. They have a tool that basically helps you really understand how to have a better conversation. And they teach you how to do it. It's a soft skill learning thing. A lot of people that come through the course and have gone through the course, even myself, I had a lot of tools and I thought I asked really good questions.
And I thought, I knew how to walk into a conversation with a team member. And I learned a lot of wonderful skills to teach me that maybe I didn't know as much as I thought and can I do it better? So it's a second thing I do. And then finally, Waypoint is a product that. really shows up in follow through it shows up and you being able to take the kindness and the conversation and the great questions and do it.
There's a lot of people that just there's a lot of managers that are comfortable, more comfortable canceling a conversation or a one-on-one with their employee because something else came up. But that [00:19:00] seems more valuable. But in the longterm, in the long run, it costs them more when an employee leaves than they ever know.
So how do you just continue to be consistent? So that's, those are my three, those are my three points, really, start with kindness, ask great questions through managing the conversational model. So have that skill based, have that soft skills skillset homed to, to the best that you can.
And finally use a product like Waypoint. So make sure that you are set time and goal and space for these people that you're managing and these team members that you're working with to genuinely find out how they're doing. 
Keerstyn: [00:19:38] Yeah, I really liked that idea. So one question I had that I don't know, it was a good question or a bad question, but I'm gonna, 
Matt: [00:19:46] they're all good questions.
Keerstyn: [00:19:49] Sometimes people have this preconceived notion that, leaders that are kind are just like too soft or, they're just trying to have the need to please, or they're. [00:20:00] They're just trying to be a one man shop and do it all because they're just so kind and so caring. What would you say to that? because obviously we want to get over those humps and the, those preconceived notions, because I agree with you that we all need to lead in kindness.
but oftentimes, the managers that are hardcore and really don't have a lot of emotion behind them will get promoted simply because of their work ethic. What would you say to that? 
Matt: [00:20:26] The first thing I'd say, and I don't know who the quotes from, but something along the lines of don't mistake, kindness for weakness.
it's not weakness to be kind it's the right thing, the thing to do, and we all need more of it. And if you just look at the society, the model's proven daily, through anger, if more people were    we'd have less anger and hate in the world, and that's just a fact. so the first thing that I would say is, being kind is not being soft on follow through, right?
So set your goals, hold your [00:21:00] team accountable. Do all of those things that, good managers do and good leaders do. And yes, there are plenty of great leaders in the world who aren't kind to, people who get promoted because at the end of the day, you need to be successful. But you can do both and you can have both.
And I would challenge those that think that you can't to try it. I bet they haven't tried it or they haven't tried it maybe from an appropriate standpoint, from understanding tools, having the tools to do it well now, with that being said, I have a philosophy that I came up with a number of years back that's, it's basically this, you need to understand very clearly where kindness intersects kindness and compassion really intersect.
business loss. And once you begin to have, someone on your team, that's truly effecting your business to a loss perspective, then you need to manage that through accountability. And sometimes that doesn't feel kind, which is fine, manage it well, but at least start with the other and see if you [00:22:00] can work through those challenges before you hit that intersection.
Keerstyn: [00:22:04] I really liked how you said that you can do both. I think that's appropriate and really needed. And, people don't realize that you can do both 
Matt: [00:22:13] and you can do with it. 
Keerstyn: [00:22:15] You can do both and you can try to do both and you can hire Matt Cunningham to help you do both. 
Matt: [00:22:22] I'd love to help in any way. But I think to remember remembering that, all along through this conversation, my key point is start with kindness.
If you, if other things happen after that, if you need to get into a more direct conversations and more detailed management, that's a different story, but you can start someplace and start with kindness. Yeah, 
Keerstyn: [00:22:45] absolutely. I love that. Cool. Matt, if there is a, are there any links that people can go to either get in touch with you, find out what you're about, any resources that you may have available to 
Matt: [00:22:57] anyone.
Sure. I've got a couple things right now. I'm [00:23:00] still working on some cleanup on some website changes, but, my website is Epic kindness.com. So you can go check that out there that actually started, That earlier this year, I opened this organization to really spread a little bit more kindness through the world.
sell some shirts on there and do some things. we're doing some drives coming up to, to help the homeless. So that's cool, to hand out shirts downtown, in grand Rapids and. So that's one thing they can do, and they can just reach out to me@mattatepickindness.com and ask for a consultation, got a number of people that I've worked with in town, a number of large organizations and small organizations as well.
Typically try to just help people grow their business, grow their team and help them become more encouraging. So I would love to chat with you and feel free to reach out at any time. And, we'll go from there. 
Keerstyn: [00:23:50] Awesome. Thanks. do you have any parting words before we leave today? 
Matt: [00:23:57] I don't think I do. I think I gave it to you at the end and start with [00:24:00] kindness.
Be a great manager, be a great leader and, get your people to want to follow you. You can make them follow you, but get them to want to follow you. And that starts with kindness. 
Keerstyn: [00:24:12] Cool. thanks so much, Matt, for joining me today. I'm glad that we were able to record and, hear a little bit more about kindness and why we need to lead first with it.
Matt: [00:24:20] Thank you. Yeah, 
Keerstyn: [00:24:22] appreciate it. 

Join our newsletter

checkmark Got it. You're on the list!