In short
How leaders can handle “candid conversations” during change using clarity, compassion, and effective communication—especially in restructuring, layoffs, mergers/acquisitions, and new leadership transitions.
Key claims
Don’t start hard talks with vague “I need to talk” heads-ups; provide context to prevent guessing and worst-case thinking. Start with the end goal to manage fear and emotion. For clarity, ensure the message lands by asking what the other person thinks/needs and what they’re taking away. For compassion, treat the recipient as a human: lead with kindness, explain why, listen, and respect them even when delivering performance issues or layoffs.
Notable examples
a partner conversation improved alignment by asking goals first; an employee performance issue resolved faster when the manager asked what was going on; layoffs handled via phone call rather than only an email.
Guest
Connie Rawson, founder of Connie Rawson Coaching; has worked with leaders/companies including Salesforce, Nationwide Insurance, Intuit, DraftKings, Mozilla, Workday, and Zendesk; background in mergers and acquisitions; coaches leaders and teams through transitions and change.
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Chapters
Tap a time to open that second in VOIntroducing Connie Rawson
0:51 to 1:11
Host introduces Connie Rawson and her coaching background.
Connie's Personal Hobbies
1:11 to 3:59
Discussion about Connie's return to playing piano and its benefits.
“your superpowers i i'm really uh excited to talk about this because um one thing for our friends that are listening.”
Connie's Coaching Focus
3:59 to 5:48
Exploring Connie's work with clients around change management.
“So let's, yeah, let's talk about the work you've done.”
Communicating Change Effectively
5:48 to 8:15
Strategies for effectively communicating during times of change.
“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?”
Handling Difficult Conversations
8:15 to 11:28
Tips on preparing for and engaging in tough conversations.
“And that tends to be probably a little more on the worry or, or negative side.”
Importance of Clarity and Compassion
11:28 to 12:53
Discussing clarity and compassion in communication during challenging times.
“come across but to also ask the the person you know what's going on for you what you know can What are you taking away from this conversation?”
Respecting Individuals in Hard Situations
12:53 to 14:01
How to maintain respect and value for individuals in tough situations.
“Then it may rather than an actual problem.”
Leading with Compassion in Tough Conversations
14:01 to 15:10
Learn how to communicate tough messages with respect and empathy.
“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, how do we do that?”
The Importance of Support During Change
16:15 to 17:22
Understand the value of having a sounding board during organizational changes.
“And I would love to love to hear from folks.”
Transcript
Automatic transcript. May contain errors.0:03Welcome 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 PodVerified score, free PodVerified 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 thrive and grow in podcasting.
0:46Visit podverify.com if you'd like to be featured as a future guest. I'm Josh Elledge. Let's get into it. with us right now connie rossin connie you are the founder of connie rossin coaching that's your website connie rossin coaching.com which we have all linked up connie it's so great to have you yeah thanks for having me great to see you you know uh i we're gonna talk about your superpowers i i'm really uh excited to talk about this because um 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.
1:26Before 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? 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. 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 forties and beyond and, you know, maybe parenting gets a little easier.
2:04Maybe life gets, you know, we have a little bit more time for ourselves maybe. And so I picked up the base 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? Tell me about your experience, especially after a 20 year hiatus. 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.
2:45And, 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. So what do you use to play piano with? Are you using like an iPad with an app on it? No, I'm old fashioned. I'm using books. I mean, I can read music. That's how I learned as a kid. So I like having books and that's how I'm playing. And what is a song that, do you play contemporary songs as well? I mean, I'll play some classical stuff. The contemporary, honestly, is more fun, I think. So, yeah. Anything I might know? Oh, I mean, Somewhere Over the Rainbow. Oh, yeah, sure.
3:27Everybody kind of knows that song. So, yeah. 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. Sorry, that was a Hawaiian. Ukulele or something. Those are really easy. But it 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, 5, 10, 15 minutes or something like that. Perfect, perfect hobby.
3:59Thank you so much, Connie. Yeah, absolutely. So let's, yeah, let's talk about the work you've done. You've worked with 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? 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 in the workforce and AI and all of the things.
4:43So I help leaders with their leadership goals and how to drive productive, effective teams. Okay. Well, I would have to imagine that, there's regular change, which is just a constant, and then there's big change. Where are we talking? I mean, I would say all, I think change, whether it's regular change or big change, just depends on the person. Most people are change-averse in some way, but I would say big change. 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.
5:31So to me, 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 changed too. 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? 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, again, our fear or our brains trying to protect us or thinking all about these worst case scenarios of how this might go.
6:25And then it's going to, people are going to get hurt. I'm going to look like a fool. Like again, I'm sure other people don't have this problem, but if they did, what could we do? 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.
7:06So I think starting with the end in mind is really helpful. 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 well-being 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 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?
7:55I 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. Um, 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. Yeah, that's an easy one. Give them context of what we're going to talk about. Yeah. And what about when there's, you know, let's say there is a restructuring and we're like, it's going to be messy over the next six months.
8:39Because 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 change management right 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 um it could be a group of people and how might they respond um not all change is bad. Some is good for some people it's neutral. Um, and then I think just the acknowledgement, it's going to be hard and, and, and delivering hard messages takes courage.
9:23And, 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. Wow. So I know you've got a, and I don't know if we've been going through it. I think we were just talking about courage here. Yeah. Talk about clarity. So by the way, what we're referring to, if our friend is listening, go to ConnieRawsonCoaching.com and then there's a tab that says resources. When you click on that, But, Connie, you've got a bunch of really good things here that I think are, I mean, well thought out.
10:06You've got some different guides that folks can just click and start reading. You don't have to give you a 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, 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 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.
10:50But would you mind maybe talking about section two and three, clarity and compassion? Yeah, absolutely. So, yeah, to your point, you know, no one likes having these conversations. And I think that, 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'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 that 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 can What are you taking away from this conversation?
11:42Do you have any questions for me? You know, making sure that the easiest way to know if your message is coming across and you're clear and there isn't an intent and a perception gap is to make sure you're hearing from the other person. You know, I just had a conversation that potentially could have because there was some with a partner, There was some stuff that was, we were really upset about internally. Yeah. But, you know, when I got into that conversation, he's good, really great guy, you know, so, 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.
12:22But 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 don't feel like we were that misaligned now. You know, when I just be the one asking questions first and all that other stuff I was worried about. We're not even going to get to that. Like, whatever, man, we can we can move on. We're adults here. 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.
12:58Then it may rather than an actual problem. You know, that may that may be the case. 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 employee said, 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 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 can get to resolution much faster.
13:35Connie, you know, under compassion, your section three, you talk about, 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 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. 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, how do we do that?
14:13Yeah. 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 weren't 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? 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 you know lead with compassion um at let them have a voice ask them you know if they have anything to say really listen and you know and explain why deliver the message but do it kindly Connie your website ConnieRawsonCoaching.com I assume coaching is what you do so when folks go to your website 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 I appreciate that.
15:28I use the guide myself. So, yeah. So your services, do you mind when, you know, when folks go there, what would you have them do if they maybe want to grab a call or, you know, how you can help them? Yeah, absolutely. So I've mapped out my services. I do one-on-one coaching. I'll do some teamwork as well. And, you know, I have a background working in mergers and acquisitions. So coaching, you know, that's kind of a huge change. So coaching leaders through that change, you can see my services there. And then, you know, we've been referencing this candid conversation guide. I've got a number of other guides related to other leadership topics around communication and other things.
16:11And then they can get in touch with me directly there. And I would love to love to hear from folks. Connie Rossin, you're a good person to know for our leader friends who are listening. If you know you got some tough stuff coming up or maybe you've had tough things going on with the organization, particularly think big change type things, big evolutions. Don't do that alone. I mean, even if you think you're really good at it, I know myself, it is always far better to at least work with someone as a sounding board. because I'm sure you've seen what otherwise might be very well intended, like on how to convey something or make a decision around something.
16:56And 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 kind of conversations. It's always well intended. And even the best leaders stumble through these hard conversations. You know, it happens to the best of us. So Connie Rawson, you're on the web at Connie Rawson coaching.com. Connie, it's been a great conversation. Thank you. Yeah, thank you. Thanks for having me.
17:26Thanks for listening to the thoughtful entrepreneur. If your goal is to grow your business, increase revenue and build authority without gimmicks. This show is designed for you. Each episode gives you practical insight from leaders who have turned trust and credibility into real business results. If you value short, thoughtful conversations that respect your time, make sure you're subscribed. We publish daily 15-minute episodes focused on growth that actually compounds. And if you're interested in being a guest or you want to turn podcast appearances into measurable business growth, visit podverified.com.
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From the publisher
In a recent episode of The Thoughtful Entrepreneur Podcast, host Josh Elledge sat down with Connie Rawson, Executive Coach and Founder of Connie Rawson Coaching, 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 Change
The 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 Rawson
Connie 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 Coaching
Connie Rawson Coaching 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 Episode
- Connie Rawson Coaching Official Website: connierawsoncoaching.com
- Connie Rawson on LinkedIn: linkedin.com/in/connierawsoncoaching
Key Episode Highlights
- The 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.
Conclusion
The 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.
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