2480 - Leading Change Through Clarity, Compassion, and Communication with Connie Rawson Coaching's Connie Rawson

Leading Change Through Clarity, Compassion, and Communication with Connie Rawson Coaching's Connie RawsonIn a recent episode of The Thoughtful Entrepreneur Podcast, host Josh Elledge sat down with Connie Rawson, Executive Coach and Founder of Connie Rawson Coaching https://connierawsoncoaching.com/, to discuss how corporate leaders and business owners can navigate organizational change through high-impact communication. Connie, a seasoned executive coach who has advised leaders across tech and enterprise giants like Salesforce, Zendesk, and Workday, shares her battle-tested framework for executing difficult workplace discussions with clarity, courage, and empathy. This conversation delivers an actionable roadmap for executives looking to eliminate communication friction, handle performance reviews, navigate corporate restructurings, and lead through organizational transitions without damaging company culture or trust. The Executive Communication Blueprint: Mastering Candid Discussions and Driving Alignment During ChangeThe primary bottleneck stalling organizational growth during times of restructuring, acquisitions, or leadership pivots is executive communication avoidance. Connie Rawson explains that while uncomfortable conversations around underperformance or strategic shifts naturally trigger anxiety, avoiding these discussions creates severe organizational misalignment, low morale, and operational drag. To lead effectively, executives must approach every candid conversation with a defined purpose, establishing the desired productive outcome before initiating the dialogue. Giving team members a clear context advance notice—rather than sending vague meeting requests—lowers psychological defensiveness and prepares both parties for a constructive, solutions-oriented discussion. Balancing extreme messaging clarity with genuine empathy is essential for maintaining leadership credibility during high-stakes organizational transitions. Leaders often make the mistake of softening critical feedback so extensively that the core message becomes diluted, leaving the employee confused about expectations and next steps. Direct, succinct feedback must be paired with compassionate delivery, ensuring the recipient clearly understands performance gaps while feeling supported in their professional growth. Incorporating immediate alignment checks—such as asking open-ended questions and having the team member reflect back their understanding of key points—eliminates miscommunication and ensures mutual commitment to execution. Ultimately, sustaining long-term executive influence requires building a corporate culture grounded in radical transparency, dignity, and active listening. Treating employees with respect during challenging conversations—including lay-offs or role changes—preserves the internal brand, protects talent retention, and reinforces psychological safety across all management tiers. Executive leaders who invest in mastering candid communication frameworks build resilient organizations capable of adapting seamlessly to market volatility. When clear intentionality, contextual framing, radical feedback clarity, and compassionate delivery are synthesized into a single leadership architecture, executives remove friction, accelerate decision-making, and predictably expand enterprise valuation. About Connie RawsonConnie Rawson is an Executive Coach, leadership advisor, and the Founder of Connie Rawson Coaching. Drawing from extensive experience coaching high-level executives at major corporations like Salesforce, Workday, Mozilla, DraftKings, and Zendesk, Connie specializes in helping C-suite leaders and business owners navigate complex organizational change. She is a recognized expert in executive communication, team alignment, and change management, dedicated to empowering leaders to execute candid conversations with clarity and empathy. About Connie Rawson CoachingConnie Rawson Coaching https://connierawsoncoaching.com/ is an elite executive coaching practice and leadership consultancy engineered to help corporate executives, business owners, and management teams master high-stakes communication and organizational change. The practice specializes in delivering one-on-one executive coaching, team alignment facilitation, change management strategies, and communication frameworks. Through tailored coaching programs and practical leadership resources, Connie Rawson Coaching enables leaders to eliminate communication debt, build high-trust workplace cultures, and drive sustainable growth. Links Mentioned in This EpisodeConnie Rawson Coaching Official Website: connierawsoncoaching.com https://connierawsoncoaching.com/Connie Rawson on LinkedIn: linkedin.com/in/connierawsoncoaching https://www.linkedin.com/in/connierawsoncoaching/ Key Episode HighlightsThe Purpose-First Discussion Framework: Setting clear objectives and outcomes before initiating difficult conversations to keep discussions focused and productive. Contextual Framing to Reduce Defensiveness: Providing advance notice on meeting topics to eliminate anxiety and foster open, constructive communication. Balancing Directness with Compassion: Delivering clear, unvarnished feedback without sacrificing empathy or causing confusion regarding performance expectations. Systematic Alignment Checks: Utilizing open-ended questions and active reflection to confirm mutual understanding and prevent operational miscommunication. Dignity-Driven Change Management: Preserving organizational trust and culture by handling tough transitions, lay-offs, and restructurings with radical transparency and respect. ConclusionThe conversation with Connie Rawson underscores that mastering candid conversations is an essential operational discipline for any leader navigating organizational change. By setting clear intent, balancing direct messaging with empathy, and prioritizing mutual alignment, business leaders can transform challenging workplace discussions into powerful catalysts for trust, clarity, and sustainable growth. More from The Thoughtful Entrepreneur🎙️ Want to be featured on The Thoughtful Entrepreneur? Get your voice in front of 50K+ listeners. 👉 Schedule your guest spot here » https://go.upmyinfluence.com/podcast-guest 🤝 Consultant doing 6+ figures? 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• 0:03Speaker 00

  Welcome to The Thoughtful Entrepreneur. If you're committed to growing your business by serving audiences with generosity and real expertise, you're in the right place. This is a daily 15 minute show featuring leaders who believe real impact comes from generosity, not hype, which means as a listener, you're going to get the good stuff. In fact, we created podverified.com to give thoughtful leaders like you free tools to show up better on podcast stages like this one. That includes your free Pod Verified Score, free Pod Verified Guest Training, a free media kit builder, and so much more. It's the first ecosystem of its kind built by podcasters who genuinely want to help guests

• 0:44Speaker 00

  thrive and grow in podcasting. Visit podverified.com if you'd like to be featured as a future guest. I'm Josh Elledge. Let's get into it.

• 0:55Speaker 00

  With us right now, Connie Rossin. Connie, you are the founder of Connie Rossin Coaching. That's your website, connierossincouaching.com, which we have all linked up. Connie, it's so great to have you.

• 1:07Speaker 01

  Yeah, thanks for having me. Great to see you.

• 1:09Speaker 00

  You know, we're going to talk about your superpowers. I'm really excited to talk about this because one thing for our friends that are listening, I know one thing that you help with are candid conversations, which we're going to get into in just a second. Before we do, I always love talking to high level leaders, what they're doing for fun, or kind of geeking out on outside of work. And you and I just chatted briefly about this. Really impressive. What have you been doing for fun?

• 1:37Speaker 01

  Yeah, well, you know, ever since the pandemic, I've been saying I'm going to reteach myself the piano and I finally started. So I took a 20 year hiatus and I've been replaying again and it's been really fun.

• 1:52Speaker 00

  Wow. You know, I talk about this frequently and I just think it is such a great hobby for those of us, you know, kind of get into our 40s and beyond. And, you know, maybe parenting gets a little easier, maybe life gets a little, you know, we have a little bit more time for ourselves, maybe. And so I picked up the bass a couple of years ago and it is, it's one of those hobbies, I'm sure that's what you're experiencing. It's like, it's an endless amount that you can do and the fulfillment that you get, right? From, tell me about your experience, especially after a 20 year hiatus. Did you?

• 2:25Speaker 01

  Yeah, I mean, I was intimidated. I'm rusty. I'm still really rusty, but it was, you know, it's just, it's nostalgic. I started out saying, just do it for 15 minutes and then 15 became 45. I mean, we're on technology all day. And so it's really nice to step away from that and be creative and make my brain work in different ways. And, you know, it's fun to play songs you know, you know, popular songs or whatever. So yeah, it's great. It's been a lot of fun.

• 2:53Speaker 00

  How, so what do you use to play piano with? Are you using like an iPad with an app on it or?

• 3:00Speaker 01

  No, I'm old fashioned. I'm using books. I can, I mean, I can read music. That's how I learned as a kid. So I like having, I like having books and that's how I'm playing.

• 3:10Speaker 00

  And what is a song that, do you play contemporary songs as well?

• 3:15Speaker 01

  I mean, I'll play some classical stuff. The contemporary honestly is more fun, I think. So, yeah.

• 3:21Speaker 00

  Anything, anything I might know?

• 3:24Speaker 01

  I mean, Somewhere Over The Rainbow, you know?

• 3:26Speaker 00

  Oh, yeah, sure.

• 3:27Speaker 01

  Everybody kind of knows that song. So.

• 3:30Speaker 00

  Oh, that's great. Well, Connie, thank you so much. And to our friend that's listening, seriously, like some of these instruments are actually pretty easy to kind of get going, like even if it's like a, you know, ukulele or something, you're sorry, that was Hawaiian, ukulele or something. Those are really easy, but it's just, it really is, especially for those of us who work from home and we just need to be able to step into the next room and just like not think about work for a good, you know, five, 10, 15 minutes or something like that. Perfect, perfect hobby. Thank you so much, Connie. So let's, yeah, let's talk about your, the work you've done. You've worked with some, some really big names, Salesforce, Nationwide Insurance, Intuit, DraftKings, a bunch of others, Mozilla, Workday, Zendesk. So Connie, what are you doing with these clients?

• 4:16Speaker 01

  Yeah, I am helping leaders and their teams through transitions and change. And so, you know, we're going to talk about candid conversations and, you know, that's critical. Communication in general is tied to everything we do and it's really critical for leaders to be able to communicate effectively, especially, you know, in today's world of transition and the workforce and AI and all of the things. So I help leaders with their leadership goals and how to drive productive, effective teams.

• 4:52Speaker 00

  Okay. Well, I would have to imagine that, you know, there's regular change, which is just a constant. And then there's big change. Where, where are we talking?

• 5:06Speaker 01

  I mean, I would say all, you know, I think, I think change, whether it's regular change or big change, just depends on the person. You know, most people are change averse in some way, but I would say big change, you know, I, I live here in San Francisco. I'm kind of in this tech bubble. There's lots of restructuring, AI is coming into the picture. There's layoffs. I've done a lot of work in mergers and acquisitions. So to me, these are big, it's big change, but it can be as simple as a new leader coming on board and people have a new boss and that might seem small, but it's really important and that's change too.

• 5:46Speaker 00

  Yeah. Well, you know, I've, I think as leaders, Connie, you know, we all have the opportunity to have a conversation that we might be pretty uncomfortable with. Before we actually talk about the mechanics of how we might pre-communicate that or actually communicate that, how do we maybe get ourselves ready? Like, and not freak out and not imagine, oh no, it's going to be a big blow up. It's going to go bad, which sometimes, you know, again, our fear, our brains trying to protect us are thinking all about these worst case scenarios of how this might go. And, you know, then it's going to, you know, people are going

• 6:27Speaker 00

  to get hurt. I'm going to look like a fool. Like again, I'm sure, I'm sure other people don't have this problem. But, you know, if they did, you know, what would it, what could we do?

• 6:39Speaker 01

  Yeah. I like to think about it is, what's the end goal? Right? I think that when you're thinking about having to communicate something hard, you know, get, people can get in their own heads of like, how is the other person going to react? How am I going to feel? How can I make this less uncomfortable? Do I have to do this? And I think that the emotions come in really quickly and you lose sight of why you have to communicate it in the first place. So I think starting with the end in mind is really helpful.

• 7:11Speaker 00

  Yeah. And so let's say that this is some feedback that you need to share. This is a really, really common one. So managing a team, you know, we just have some issues that keep coming up. Well, Connie, is there a way to preface a conversation? I'll tell you this, you know, if we also want to be very mindful of the wellbeing of our team members, I was just, someone was just talking about this, like, don't say on a Friday, by the way, I want to talk to you on Monday. Like, don't do that, right? Yeah. What's, what's wrong with that picture, Connie?

• 7:49Speaker 01

  Oh gosh. I mean, that's happened to me before when I was an employee, you know, and then your manager says, do you have a sec? I mean, it could be, do you have a sec? I need you to do something. You're getting promoted or you're in trouble. I mean, you know, but I think just human nature, our minds go to like, oh no, what's wrong? Yeah. And so, yeah, absolutely. Kind of that, that heads up without context just leads people to play a guessing game and fill in the blanks. And that tends to be probably a little more on the worry or, or negative side.

• 8:23Speaker 00

  Yeah, that's, that's an easy one. Give them context. We're going to talk about.

• 8:27Speaker 01

  Yeah.

• 8:27Speaker 00

  And, and what about when there's, you know, you know, let's say there is a restructuring and we're like, it's going to be messy over the next six months. Give, because I know this is something you've done quite a bit. Mergers, acquisitions, change in leadership, restructuring, that sort of thing. How do we even begin to wrap our brains around how we're going to handle change man, is it's change management, right?

• 8:54Speaker 01

  Yeah, yeah. Change management is a huge part of communication. And so I think, you know, when you think about change management, you're thinking about who are your, who's your audience or audiences, right? You know, it could be a group of people and how might they respond? Not all change is bad. Some is good. For some people, it's neutral. And then I think just the acknowledgement, it's going to be hard and, and delivering hard messages takes courage. And, you know, I think that just really sitting in that acknowledgement and a willingness, it's part of the job. I mean, it is part of the job is to be able to be courageous for the sake of the people that need to get that message.

• 9:39Speaker 00

  Wow. So I know you've got a, and I don't know if we've been going through, I think we were just talking about courage here. You want to talk about clarity? So by the way, what we're referring to, if, if our friend is listening, go to connierossincouaching.com and then there's a tab that says resources. When you click on that, Connie, you've got a bunch of really good things here that I think are, I mean, well thought out. You've, you've got some different guides that folks can just click and start reading. You don't have to give you, thank you for not asking for the email address and all that other stuff. But they're just right here. So, and the one we're referring to, the folks can just grab and kind of follow along. It's called, are your candid conversations working?

• 10:23Speaker 00

  Which this is really great. In fact, this is, I mean, right now, as I'm looking at it like this, I mean, this would be such a helpful guide if I know, okay, I've got a contractor and we're having issues and, and it's causing problems. So for me to just kind of get clear on my own stuff first and trying to see it from another person's perspective, like if I do all of that ahead of time, I feel like it's just going to be so much more productive. But would you mind maybe talking about section two and three, clarity and compassion?

• 10:56Speaker 01

  Yeah, absolutely. So yeah, to your point, you know, no one likes having these conversations. And I think that, um, you know, when you're the person that has to deliver the conversation, you know, because most folks don't want to do it, sometimes the actual message gets lost. Right? There, there, there's almost so much empathy or they're trying to soften the message for the sake of their own discomfort and the discomfort potentially of the other person. When it's a hard message, the message that is not always clear. And so it's really important, A, to make sure that those points come across. But to also ask the, the person, you know, what's going on for you? What, you know, what are you taking away

• 11:39Speaker 01

  from this conversation? Um, do you have any questions for me? Uh, you know, making sure that the easiest way to know if your message is coming across and you're clear. Um, and there isn't an intent and a perception gap is to, to make sure you're hearing from the other person.

• 12:01Speaker 00

  You know, I just had a conversation that potentially could have because there, there was some, with a partner, there was some stuff that was, we were really upset about internally.

• 12:11Speaker 01

  Yeah.

• 12:12Speaker 00

  But you know, when I got into that conversation, he's good, really great guy, you know, so, um, but you know, the first, and it was really just kind of spontaneous. It kind of came out and I was like, oh, that was actually pretty good. But just, you know, beginning the conversation, just like, can I just ask, you know, what are your goals for, for our engagement here together? And then I just let him kind of go, you know, through that. And I'm like, well, shoot. I, I don't feel like we've, we're that misaligned now, you know, when I, again, just be the one to ask the questions first. And, and that's like, all that other stuff I was worried about, I don't know, even to get to that. Like, whatever, man, we can, we can move on. We're adults here.

• 12:50Speaker 01

  I love that. You know, it's so true. I think so much of, of this is almost just, it's a miscommunication or maybe a lack of alignment than it may, rather than an actual problem, you know, that may, that may be the key. You know, if you have to, if you have a performance issue with an employee, they may say, you know what, I just, I've had too much on my plate and I've been working, you know, this happened with one of my clients. They had to deliver a tough message and the, you know, the employees said, I've, I've been working late at night. I'm distracted. I've got too much on my plate. And you know, that's fixable, right? Like, uh, instead of assuming what is going on with the other person, just bringing it up and letting them explain what they think is going on. Um, can get to resolution much faster.

• 13:35Speaker 00

  Connie, um, you know, under compassion here, section three, you talk about, um, you know, having people being able to walk away feeling respected and valued as a person. That's not always easy. But I think it's also really helpful. A lot of these things is, you know, if we have a culture of that. And, um, any, any, I would imagine you're a fan of that. It's like, you know, then it's like, when you have to do it, it's not weird. It's like, yeah, that's just how we roll here, right?

• 14:03Speaker 01

  Yeah.

• 14:04Speaker 00

  But yeah, you know, particularly on the topic of, you know, making sure that folks feel respected and valued. Even if you have an underperformer, um, how, how do we do that?

• 14:14Speaker 01

  Yeah. Hey, you know, it's still, this is so important. The person that you're communicating, they're still a human being, right? And I often tell people, if you were in their shoes, what would you want? Would you want the truth? If you want performing, would you want to know? So that you could fix it? Or do you want this to just drag out and have your manager, you know, frustrated? Um, if you're getting, if you have to lay somebody off, right? Like I've seen this, it's really unfortunate happen where people are just getting an email saying, hey, you've been laid off. Just pick up the phone and make a phone call, you know? Um, just out of respect for the person that has to get that tough message.

• 14:55Speaker 01

  You know, lead with compassion. Um, let them have a voice, ask them, you know,

• 15:04Speaker 01

  if they have anything to say, really listen and, you know, and explain why, deliver the message, but do it kindly.

• 15:12Speaker 00

  Hmm. Connie, your website, connierossandcoaching.com. I assume coaching is what you do. So when folks go to your website, um, you know, obviously, you know, click on resources because that's what we've been talking about. And just honestly, you made my job real easy too. So I appreciate that.

• 15:28Speaker 01

  I use the guide myself. So, uh, yeah.

• 15:31Speaker 00

  Um, so, so, uh, your services, um, do you mind when, when, you know, when folks go there, what, what would you have them do? If they maybe want to grab a call or, you know, how you can help them?

• 15:42Speaker 01

  Yeah, absolutely. So, um, I've mapped out my services. I do one-on-one coaching. Um, I'll do some teamwork as well. And, uh, you know, I have a background working in mergers and acquisitions. So coaching, you know, that's kind of huge change. So coaching leaders through that change, you can see my services there. And then, you know, we've been referencing this, um, uh, candid conversation guide. I've got a number of other guides related to other leadership topics around communication and other things. And then they can get in touch with me directly, um, there. And I would love to, love to hear from folks.

• 16:18Speaker 00

  Connie Ross, and you're a good person to know, uh, for our leader friends who are listening. If you know, you've got some tough stuff coming up, or maybe you've had tough things going on, uh, with the organization, particularly think big change type things, uh, big evolutions, um, don't do that alone.

• 16:37Speaker 00

  I mean, even if you think you're really good at it, I know myself, it is always far better to at least, you work with someone as a sounding board, because I'm sure you've seen what, what otherwise might be very well intended. Uh, like on how to convey something or make a decision around something. And you're like, oh, no, no, no, no, no. If you do this, I know in your heart, you're trying to do the right thing. Do not do that. Right? Like, I'm sure you've had those kinds of conversations.

• 17:06Speaker 01

  It's always well intended. And even the best leaders stumble through these hard conversations. You know, we all, it, it happens to the best of us. So.

• 17:16Speaker 00

  Connie Ross, and you're on the web at connierossandcoaching.com. Connie, it's been a great conversation. Thank you.

• 17:21Speaker 01

  Yeah, thank you. Thanks for having me.

• 17:27Speaker 00

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