Women in Sales: How Empathy and Active Listening Build Client Trust

Summary

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Women in Sales: How Empathy and Active Listening Build Client Trust

Podcast: Alliant Insurance Services
Host: Jenny Lee Crocker
Guest: Kristen Searcy, Workforce Strategy Advisor
Date: July 29, 2026
Episode Length: ~13 Minutes

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Episode Overview

This episode of Women in Sales focuses on the role of empathy and active listening in building lasting client trust, particularly in the insurance and sales industry. Host Jenny Lee Crocker sits down with Kristen Searcy, a seasoned workforce strategy advisor widely recognized for her skills in people-connection, client advisory, and empathetic leadership. Together, they explore practical strategies and real scenarios demonstrating how women in sales can leverage empathy as a business tool—and why this “soft skill” is, in fact, a competitive advantage in forging strong client relationships.

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Key Discussion Points & Insights

1. Empathy as a Sharpened Sales Tool

• Redefining Empathy:

  • Empathy and intuition go beyond just listening—they require “using all your senses” to read visual cues, body language, and tone of voice (02:03).
  • Empathy allows sales professionals to get to the “root cause” of client needs, beyond surface-level problems.

• Women’s Unique Advantage:

  • Jenny Lee emphasizes, “Women have this in a very distinct and unique way that we can deploy actively” (01:36).
  • Kristen notes the balance between masculine and feminine energy in a male-dominated field, explaining how women can use empathy to connect deeper with clients.

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2. Translating Empathy into Sales Meetings

• Personalized Approaches:

  • Kristen describes how she always tries to discern the real needs of individuals (e.g., CFOs busy with different pressures than HR or industry-wide stakeholders) rather than just focusing on generic business problems (03:18).

• Team Debriefs:

  • She often “unpacks” meetings with her team, challenging surface-level interpretations and diving deep into what truly matters for each decision-maker (04:10).

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3. The Art of Pausing & Active Listening

• Power of the Pause:

  • Kristen underscores that effective listening and intuition stem from being able to pause before and during meetings, allowing space for real understanding (05:11, 06:22).
  • “If we have talked more than they have talked, then we have not done our job” (04:59).

• Pre-Meeting Centering:

  • Tips include taking deep breaths, practicing mindfulness, and intentionally creating “white space” between appointments to mentally prepare and be present for clients (05:11, 06:49).
  • Kristen puts her phone on airplane mode before meetings: “I put my phone on airplane mode purposely, intentionally, to give myself that time” (06:49).

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4. Moving Past the PowerPoint

• From Presentation to Conversation:
  • Best meetings often happen when the discussion leaves the rigid PowerPoint structure and turns into a two-way conversation, allowing unspoken needs and opportunities to surface (08:15–09:22).
  • Asking clarifying questions and pausing to check for true understanding is seen as a sign of respect and partnership.

Notable Example:

• Kristen shares a story of meeting with a CFO backed by private equity. By pausing and asking for expanded insight, she uncovered key information about the client’s strategic autonomy that would have otherwise been missed (10:35).

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5. Empathy as Differentiator & Sign of Respect

• Respect Through Listening:

  • Jenny Lee comments, “I want to hear you and what a basic human need. Right. Like, thank you for pausing to confirm and clarify and also hear more of what I had to say” (10:03).

• Trust Building:

  • Allowing conversations to shift and being a genuine, curious listener helps build deeper trust and positions you as a true advisor, not just another vendor (09:24).

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Notable Quotes & Memorable Moments

• Kristen Searcy on reading the room:

  • “It’s not only listening, but it’s using all your senses. …reading the room from what you see visually, watching people’s body language, listening, hearing their voice—not their words, but how they speak.” (02:03)

• Jenny Lee Crocker on empathy’s edge:

  • “Great producers have empathy and it is a tool that you can refine and deploy. …Women have this in a very distinct and unique way…” (01:36)

• Kristen Searcy on client understanding:

  • “We have to win the mind of the CEO and the CFO, but the hearts of the HR team.” (03:18)

• On the value of pausing:

  • “If we have talked more than they have talked, then we have not done our job.” (04:59, C)

• On pre-meeting routines:

  • “Taking a couple deep breaths, making sure you’re centered to be a good listener and coming in to be of service.” (05:11, C)
  • “I put my phone on airplane mode purposely, intentionally, to give myself that time.” (06:49, C)

• On breaking out of presentation mode:

  • “The best meetings I have had is where we come off of that PowerPoint presentation deck and it turns into a conversation.” (08:15, C)

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Timestamps for Important Segments

• 00:29 – 02:03: Guest Introduction and setting the theme of empathy in sales
• 02:03 – 03:18: Defining empathy and its practical application in meetings
• 04:10 – 05:01: Debriefing meetings and true decision criteria
• 05:11 – 06:49: Pausing, mindfulness, and pre-meeting mental preparation
• 07:34 – 09:22: Moving from presentation to conversation; using curiosity to guide meetings
• 10:03 – 10:35: Respect through pausing and clarification; real-world application example
• 11:31 – 12:12: Key takeaways and practical tips for honing empathy and listening
• 12:12 – End: Final thoughts and episode wrap-up

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Practical Takeaways & Tips

• Pause before every meeting: Take a moment to center yourself and be ready to listen actively.
• Prioritize open-ended questions: Prepare engaging questions but allow room for the client to lead the conversation.
• Use all your senses: Actively read body language, tone, and non-verbal cues, not just spoken words.
• Respect client time & thoughts: Pause to clarify and invite further explanation—show genuine respect.
• Make "white space" on your calendar: Create intentional breaks between meetings to reset and be present.
• Build a mindset of curiosity: Approach every interaction as an opportunity to learn and serve, not just to sell.

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Episode Tone

The conversation is warm, insightful, and practical—full of real-life anecdotes and actionable strategies. Both Jenny Lee and Kristen speak with authenticity, encouragement, and mutual respect, modeling the empathetic principles at the heart of the episode.

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For listeners looking to become more effective and trusted advisors, this episode is an essential listen for practical, human-centric sales strategies that can be woven into any client-facing role.

Transcript

[A]

Welcome to Women in Sales, a podcast hosted by Jenny Lee Crocker, where we spotlight the voices, stories and strategies shaping the future of sales. In each episode, Jenny sits down with inspiring women across industries to share real experiences, practical insights and lessons from their journeys to success. Now let's get started.

[B]

Hi, I'm Jenny Lee Crocker. I'm with Alliant Insurance Services, and I'm also the host of the Women in Sales podcast. And today I get the great pleasure of having Kristen Searcy with me. Let me tell you about Kristen. Kristen is a workforce strategy advisor, but more than that, she's a great connector of people. She also, she and I share a lot in common in terms of our commitment to our health. She also, she shares. She's one of those people that isn't just keeping the things that she's learned about her health journey to herself. She's going to share it with you. She is an amazing mom who is a giant in terms of how she parents and cares about her daughter. And I am just grateful to have her here today for our topic, which is Empathy as a tool. Kristin, welcome.

[C]

Thank you. Thank you for having me. And thank you for the introduction.

[B]

Yeah, well, you, you are all those things. Connector, a great mom, and also truly a business advisor to your clients.

[C]

I appreciate that. Excited to be here today.

[B]

So.

[C]

And excited to talk about empathy.

[B]

So, okay, let me start with my premise. I believe that great producers have empathy and it is a tool that you can refine and deploy. And in my, in my mind, women have this in a very distinct and unique way that we can deploy actively. Tell me how you might use your personal empathy as an advantage in meeting with a client. Yeah.

[C]

So I think empathy is one of those things. Even as a woman, I think in a male dominated industry, we're pivoting as moms and we're working and masculine and feminine energy. But really, when I think of empathy and intuition, it's that pause, Right. And it's not only listening, but it's using all your senses. Right. So reading the room from what you see visually, watching people's body language, listening, hearing their voice, not their words, but how they speak. And I think that really, that allows me to understand the root cause. Of what, of how I could potentially help them.

[B]

Right. How often, Kristen, when you're either preparing for a meeting or you walk out of a meeting and the team will say, well, these are the reasons why they would choose us as their broker. And you pause and go, well, hold on. I think that that CFO Might be really busy and that might be important to the industry, but I don't know if that's important to that person. I feel like that's something that happens to me pretty often where I'm using my empathy to dig into what I believe is important to the human and not just the industry or the company. What about you?

[C]

I mean, I feel like it happens every single time. I always say when you look at all the decision makers at the table or the team you're working with to maybe provide a solution or service. Right. I always say we have to win the mind of the CEO and the cfo, but the hearts of the HR team. And so there's lots of personality. So yeah, when we kind of unpack a meeting, it's always interesting to me what they think the decision criteria is and what I heard. And so when we start unpacking it, they're focused on their lane of expertise and maybe they brought value for that specific situation or solution or gap or whatever we're discussing, but they're kind of missing like the overall of how they're going to make the decision and the timeline and whether they're really ready to move forward and what that process looks like. So I would say probably all the time, maybe not 90% of the time.

[B]

So I like that when you said you unpack it. So when you unpack it, is that your debrief with the team and you go, I know what they said the criteria is, but let's talk about the real criteria.

[C]

Yeah, that's basically it. Especially when you look at situations like RFPs or you've been presented with an email or an outline or an agenda, I think that's where empathy comes in. Like, yeah, they've given you areas of what they want to discuss. But if you're really asking good questions and using your intuition and that means you're pausing, right? And there's a lot of pausing to tap into that empathy and intuition and not just run through the presentation. And that's why I feel like if we have talked more than they have talked, then we have not done our job because it's really about them doing all the talking and us asking and pausing and asking and pausing. So that's what I find.

[B]

So let's talk about that intuition. Do you think that people can help hone their empathy meter? Do you think that that's a skill that you can either improve or grow?

[C]

Absolutely. Once again, it, you know, when we talk about our self care, like we're both into walking and drinking our Lemon water. I think it's like a. I wouldn't say every. I'm into meditation. I'm not saying everyone has to medit, but I think it's a mindfulness. Right. Like, so before you go into an appointment, taking a couple deep breaths, making sure that you're centered to be a good listener and coming in to be of service and how can you solve a problem? And so when you kind of like set that mindset to come in and with that kind of intention, then you know, you can pause and say, hold on one second, I think we might be getting off track. I'm looking at your face and you look a little confused. Did we answer the question correctly? And so that's kind of what I do before meetings. Just making sure, like I've taken a few deep breaths, I'm coming in to be of service. And that way I know I can pause throughout the presentation or even kick my teammate under the table or nudge someone or give them a look like, hey, we're going down a rabbit hole, they don't care about this, we're losing weight.

[B]

Right.

[C]

Kind of thing. Like, just someone's gotta be kind of reading the room. And so I think that's really what empathy and intuition is like, are you reading the room?

[B]

So I like that you said that you pause and you get centered before you have a meeting because you want to listen. I love that. Because two things you don't want to see when somebody comes in your office. I don't want to see somebody who's either coming in frantic or coming in hot. Because those two things mean that you're not even in a place where you can listen. Right. And that seems very critical to what you just described.

[C]

Yeah. And I think this day and age, when we're inundated with emails and texts and LinkedIn and people calling us, you know, it's hard to run from one appointment to the other, especially if you've had back to back zooms. So I've actually started putting white space on my calendar, making sure I give myself appropriate time to have that five minutes, whether it's getting on a zoom or driving. So I can, like, I don't take a phone call. I put my phone on airplane mode purposely, intentionally, to give myself that time. Because I know I've got to get into that space to be a good listener and be curious. Right. If I'm not curious, then I'm not going to do my potential new client. I'm going to do them a disservice if I'M not really listening and being present in that moment.

[B]

So this makes me really happy because this isn't a direction I didn't think we'd go today. But that concept of being mentally ready to receive what that person has to say. And it does matter because you've seen people who are going in to present. I'm here to present.

[C]

Yep, I'm ready. I'm not my agen.

[B]

Yeah, let's go to the PowerPoint. Let's present. Let's present. But the more effective producer would probably have two things going on for them and I want to make sure I'm hearing you right. They would have great questions prepared, which we've talked about before, the open ended questions and then the ability to pause and take it, like hear what that person actually has to say to your question. Yeah.

[C]

And I think it brings that like human component too to like, you know, we're all the same, we're not robots. And so when you're natural in a presentation and you say, you know what, hold up one second, I'm taking notes right now and I think I heard what you said, but can you say that again or did I hear this correctly? And you give yourself permission to pause in the presentation. I think they appreciate that because they know that you're listening. And I think it's great to come in with good questions and a great PowerPoint and feel like you're about to say, solve all their problems. But the best meetings I have had is where we come off of that PowerPoint presentation deck and then it turns into a conversation and, and that's. There's just there as a tool to make sure we are respectful of their time and we've covered everything. But I think some producers or people in a sales position just go in and they blaze through the presentation and they miss all the opportunities for questions or for sales, something else, another gap or an unspoken need to come up that really could be what they, you know, is the, I can't say the word differentiator.

[B]

I got you.

[A]

Thank you.

[C]

Yes. The human, the humanness there, there you go. But I mean, it allows you to like uncover something that every other person came in with their PowerPoint, they ran the same presentation, and when you pause and you let something else rise from the surface that you didn't even know was on their table to address then. Now like, you're like, wow, we didn't even realize we had this other gap or issue. And now talk about being different and really being a true partner and advisor and consultant and Someone they can trust. I mean, you've now brought something up that they weren't aware of.

[B]

You changed the dialogue. And what a sign of respect.

[C]

Right?

[B]

So what I. What I glean from that, Kristen, is that I just heard you say, oh, thank you, Ms. CFO. I'm over here taking notes. I heard something or I saw something, and I want to pause. I don't think I've ever had a producer who was selling me something do that. But I would consider that a genuine sign of respect. I want to hear you and what a basic human need. Right. Like, thank you for pausing to confirm and clarify and also hear more of what I had to say.

[C]

Yeah, absolutely. I mean, it happened to me today. We know private equity is a big deal in our space, and I met with some. A CFO today that they're backed by private equity. They are the decision maker around all vendor partnerships. And so some people would just kind of. Okay, well, thank you for your time. I'm out. But I paused, and I was like, can you elaborate? And what does that mean? Like, today versus six months from now? Like, can you tell me more of how that relationship goes? Could have. And when I paused, then all of a sudden she was like, well, actually, we just got the option to now be in control of our own merger, acquisition, growth. And we think, you know, and then the conversation changed.

[B]

So, Kristin, I think you've helped me prove that empathy is a secret weapon for producers. I think that women are very uniquely qualified to hear and listen. You've given us some great tips and tricks.

[C]

Right.

[B]

You talked to us about get that phone on airplane mode. My favorite tip and trick that you've given me today is pause before you walk in. Take a second, and make yourself get into the place where I'm actively a listener at this moment. I love that. Anything else before we sign off that you think, I would love to share this as one of your, like, do these things, and your empathy and your listening skills will always be up?

[C]

No, I just think taking the deep breaths and coming in with that mindset of curiosity. I'm here to be a listener and be of service, and I think it's just something you practice like anything else you want to build. Right. You just, you know, you may not nail it the first time I'm a fan like that.

[B]

We'll take that as our takeaway mindset of curiosity with your clients. That's wonderful. Okay, so this was episode four. I've thoroughly enjoyed having you. I've learned. I learned so much today, and it went in a direction I didn't expect, and that's brilliant. That is the best day. So, Kristen, you are a great guest. I'm sure we'll have you on in the future. Thank you again. Very grateful. Thanks, Kristen.

[C]

Thank you for having me.

[A]

Thank you for listening to Women in Sales with Jenny Lee Crocker. If you enjoyed this episode, be sure to subscribe, share it with a colleague, and leave a review to help more women discover these conversations. We'll see you next time for more stories, insights, and inspiration from women leading the way in sales.