Building Confidence, Navigating Setbacks and Leading With Preparation

Summary

Podcast Summary: Alliant Insurance Services – Women in Sales: “Building Confidence, Navigating Setbacks and Leading With Preparation” (June 5, 2026)

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Episode Overview

This episode of the "Women in Sales" segment—hosted by Jenny Lee Crocker—dives into the vital roles of preparation, confidence, and navigating setbacks for women in sales leadership. The discussion brings together two prominent industry leaders: Kristin Handel (Executive Vice President at Alliant) and Mariah Probus (President of Retail at RT). Together, they share actionable insights, practical career advice, and candid stories about the realities women face climbing the sales ladder, all with the aim to empower listeners to build confidence and drive success by embracing preparation, resilience, and continuous learning.

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Key Discussion Points & Insights

1. The Link Between Preparation and Confidence

• Host’s Theory: Jenny proposes that preparation can compensate for lapses in confidence, inviting Kristin and Mariah to react.
  • Kristin Handel (01:55): “Preparation just calms you down...just being prepared in what you want to say will relax you so you’ll come off naturally more confident.”
  • Mariah Probus (02:18): “Preparation is what helped me move my entire career forward. I rely on it to this day...you can actually control [confidence] through preparation.”

2. What Holds Women Back in Sales?

• Mariah points out that lack of confidence isn’t the only barrier; career pathing and lack of early recognition are systemic hurdles.
  • (03:26): “A lot of women have been groomed to be the second in command...not always the leader out front that organizations need.”
  • Calls for early identification, training, and providing a clear path for women to step into producer roles.

3. Reverse Engineering Success

• Visualization & Planning:
  • Kristin describes beginning with a clear vision of the desired outcome and mapping out the steps required.
    • (05:08): “Figure out what you want the end result to look like. Then dig into the details to get yourself there.”
  • Both guests emphasize planning for contingency scenarios.
    • Mariah (06:29): “Start with what do I want to leave that meeting with? ...And then I back the preparation into that...You also need a fallback position.”
• Metaphor for Resilience:
  • Mariah shares a memorable analogy for handling setbacks:
    • (07:41): “When they talk about climbing Mount Everest, you know what the most important part is? Getting back down...make sure you get to a safe place so you can try again.”

4. The Art of Open-Ended Questions in Sales

• Jenny’s best practice: prepare thoughtful, open-ended questions, not just notes.
• Kristin (09:14): “Making sure that you have a way to connect with who you’re speaking with...then digging into questions that will get them talking...that’s how you’re going to learn what’s important to them.”
• Mariah (09:51): “Talk less, listen more...open ended questions that give you time and space to actually sit back and listen to what the prospect is telling you is the most important content that you can glean in the meeting.”
  • Cautions about over-prepping questions—don’t lose track of the real conversation by clinging to a script.

5. Flexibility, Failures & Continuous Self-Optimization

• Staying relaxed and human:
  • Kristin (11:43): “It’s not life or death...even if I totally blow this, it’s still going to be okay...if you’re real and connect with them, you can overcome that and that will calm you down.”
• Failure as a Growth Engine:
  • Mariah (12:29): “Failure is what leads to greater success...What’s more important is how you regroup, Monday morning quarterback, do the right post mortem...you learn more and you gain more confidence when you fail and resolve to do things differently.”
  • Kristin (13:39): “I remember my losses more than my wins sometimes.”

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Notable Quotes & Memorable Moments

• Kristin Handel on Confidence (01:55):

  "Preparation just calms you down...just being prepared in what you want to say will relax you so you’ll come off naturally more confident."

• Mariah Probus on Career Pathing (03:26):

  "A lot of women have been groomed to be the second in command...not always the leader out front that organizations need."

• Mariah’s Everest Metaphor (07:41):

  "When they talk about climbing Mount Everest, you know what the most important part is? Getting back down...make sure you get to a safe place so you can try again."

• Mariah Probus on Listening vs. Scripting (09:51):

  “Talk less, listen more...open ended questions that give you time and space to actually sit back and listen to what the prospect is telling you is the most important content that you can glean in the meeting.”

• Kristin Handel on Handling Pressure (11:43):

  “It’s not life or death...if you’re real and connect with them, you can overcome that and that will calm you down.”

• Mariah on Learning from Losses (12:29):

  “You learn more and you gain more confidence when you fail and resolve to do things differently the next time...self optimization is a great way to think when you have a lifelong sales career.”

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Timestamps for Important Segments

| Time | Segment & Content | |----------|---------------------------------------------------------------------| | 01:15 | Introduction of guests and episode focus | | 01:55 | Discussion of preparation as the root of confidence | | 03:26 | Systemic barriers for women & the importance of career pathing | | 05:08 | Reverse engineering success and preparing for contingencies | | 07:41 | Everest analogy and the importance of fallback positions | | 09:14 | The power of prepared, open-ended questions | | 11:43 | Advice on keeping perspective and authentic connection | | 12:29 | Embracing failure and self-coaching as part of the sales journey |

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Key Takeaways

• Preparation leads to natural confidence, calming nerves and instilling poise in high-stakes moments.
• Women in sales may face structural and cultural obstacles; organizations must intentionally identify and groom female leaders for front-line sales roles.
• Reverse engineer meetings: start with the desired outcome, plan the path, and always be prepared to pivot.
• Ask open-ended, thoughtful questions and, most importantly, listen authentically. Don’t let over-preparation stifle genuine engagement.
• Humanize the sales process—mistakes are opportunities for growth, not career-defining disasters. Self-optimization and resilience set top performers apart.

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This episode is an inspiring, deeply practical look into the realities of building confidence, leading with preparation, and turning setbacks into career milestones—especially for women eager to take the lead in sales.

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]

Good afternoon and welcome to our third podcast for women in sales. Topic today is preparation and confidence. And I picked the best people for this particular topic today. So we have some all stars in the industry that we're surrounded by. First, Kristin Handel, executive vice president at Alliant, top producer leader, heads the producer council. She is a bombshell, an absolute delight to have here today. And Mariah Probus, who is also really well known in our industry and the recent promoted president of Retail at rt. So I'm thrilled to have you two ladies here today.

[C]

Excited to be here. Thank you.

[D]

Great to be with both of you.

[B]

I've got the right people here today. So if this is a topic that you're thinking about and you're considering either getting into sales or you're currently in sales and every now and then you're. Your confidence fails you. I like to throw out my theory and then test it against the experts. I've always felt that if confidence were ever something that that was lacking in your arsenal, the way to to prepare and fight it was preparation. If you could over prepare yourself into success and confidence, you can actually control it. I'd love for the two of you all to maybe kick this off for us. Right. How can preparation change the sales process?

[C]

I think that's a very good starting point for the podcast because I think that preparation just calms you down. So when you're ready to present or you're ready to speak to a new client or a colleague or a peer or your superior, I mean, just being prepared in what you want to say will relax you so you'll come off naturally more confident.

[D]

Yeah, I get a lot of questions on on confidence and I would say two things. I'm not sure it's always confidence. That's the attribute that holds women back in sales. Love to talk about that, but I do think that that is the predominant reason why women aren't as successful as they can be in a sales career or leaning into a sales career when we see someone ready to take a lead producer role in our respective firms. I agree completely with Kristin. Preparation is what helped me move my entire career forward. I rely on it to this day. It's what gives me confidence not just in the sales process, but for any big Meeting or any big forum when you need to show up. It calms me down, too, Kristen. It's a process I use and it has me feeling very prepared for what's going to come. I don't wing it. I don't like to talk extemporaneously at anything, and I certainly don't want to waste a sales opportunity. So preparation is key to building your confidence that you can win that sales opportunity and you can close that deal.

[B]

So wait, now I need to know what else do you think is holding women back? I'm curious. I mean, there's multiple things, but you brought it up. So let's do it.

[D]

Yeah, we talk about this at our firm. I mean, we've got a number of top women that run our t specialty teams at our firm, and that's great. We'd love to have more because those teams are multifunctional and very, very successful. I think it's a number of factors. One, I think, I think a lot of women grow up in the insurance industry not naturally being groomed for a sales role. Traditionally, a lot of women have been groomed to be the second in command or the account manager or the client executive, but not always the leader out front that our organizations need so much, particularly in a sales environment. So I think one, it's career pathing for women. I think we have to identify far early on women that are high potential to be very, very successful producers and create the right training and career. Pat. And secondarily, I think if you grow up as a part of a support team, being recognized and again, push to take that lead chair is something I think our organizations need to constantly be on our front foot around. And I'm not sure that we're necessarily on the lookout for that versus just let's find the next big producer. Sometimes for us, the next big producer is the person who's sitting on someone else's team that just needs a chance to run the show for themselves and bravo when it's a woman.

[B]

So I love this lead chair concept. Right, Kristen. But what I often hear when I start to push somebody, I think you have the skillset. I think you've got the chops. I think you should do this is that confidence thing is it's. It's like, okay, I'm here. So, Kristen, maybe talk to me about how preparation as a tool to gain confidence could be the game changer. How do you over engineer it?

[C]

I think it's all aspects of figuring out what you want the end result to look like. So. And Then digging into the details to get yourself there. So you're almost visualizing it. So you're trying to figure out what is that perfect outcome for me. And making sure you're doing the research as to how do I present this, how do I explain this, how do I talk to my peer, my boss, my client, my prospect about it? And then how do I make sure that I'm prepared to answer? Because in any of those conversations, you're speaking with another person that can ask you a question that's going to take you off your path, that you prepared for. So making sure you understand your concept. So that's either what you want out of the end game or how to get across to that person, I think is the best way to feel confident because you really understand what you're speaking to.

[B]

Right? Reverse engineering. Start with the end and what's the

[C]

plan to get there and go through all paths.

[B]

Right, go through all paths.

[C]

Because it may not go how you planned it to go.

[B]

So you scripted that for me because I call that my fallback. So if option A didn't work, what is the fallback? And being prepared for the fallback, Mariah, is that something you go through as well? Like the end game, the option A, the fallback, you.

[D]

I play out all the scenarios 100%. I think what I used to do early on in my career is I was like creating the path to get somewhere. So I was like mapping out the steps. Women naturally are very organized and process oriented. The second half of my career. Now if it's a big meeting, a big negotiation, I start with what do I want to leave that meeting with? What's the number one goal that I have? And then I back the preparation into that. So it's kind of like turning around the process I used to use early on in my career. But you do also need a fallback position. I mean, all of us have been in a sales situation where the sale is not going in the direction you want it to, the meeting time is getting cut short, the client, the prospect, they don't like what you're saying, they're not leaning into what your pitch is. You always have to have the fallback position as well. The worst thing in a sales situation is when you're not prepared. You've got this map, this path that you've created with this end goal. The situation swings, you're not prepared and you get defensive. I've seen it happen a thousand times. That's the natural human instinct. It's not going your way and you're starting to make excuses. I almost think that fallback position is more important in your prep so that you can graciously close that opportunity and get back to the table if you didn't win it at that time. I'll give you one quick analogy. You know, when they talk about climbing Mount Everest, you know what the most important part of climbing Mount Everest is? Getting back down. And I think that's a great metaphor for this in a sales setting. You're not getting to the top of the mountain on this climb. Make sure you get to a safe place so that you can try again or that you can get back all the way down and start all over again. So the fallback position is equally as important. What will you pivot to if it's not going the way you imagined?

[B]

So I have the two of you all here and you've been giving some excellent advice, right, Kristen, I love that you start with your end, start with the end and then figure it out. I love the idea of fallback. But when we, when we get into that concept of presentation, negotiation and the things that each one of you as experts do, I love hearing it. You know, it's almost like your tips and tricks. Like if I really think about my one thing that I think I do really well for these moments, I prepare my questions. I love to prepare my questions. Not just my notes and what I know about the company or the person. But I think the art of the open ended question is often overlooked. How do I ask this question in a way that's going to glean the information I want? I'd love to hear from you all if you have something like that in your again, it's sort of like in your backpack that you go, this is how I get myself extra prepared.

[C]

I think it starts too with making sure that you have a way to connect with who you're speaking with, regardless of again, is it the team or is it the client or is it a prospect? But making sure that you're going to make that connection first and then digging into questions that will get them talking. Because getting them talking is how you're going to learn what's important to them. Use the knowledge you have because you have the confidence now, right? Because you've got them talking, you know what they want out of the conversation and that will get you to the end goal for both parties much easier.

[D]

Yeah, I love the prepping questions in advance with a caveat. They need to be open ended questions that are designed to make the prospect or client talk. So I Think that's very important. Versus again, earlier on in my career I was like scripting all. I was going to ask 30 questions that would show the prospect I had done all my homework on them.

[C]

Right.

[D]

But the reality is talk less, listen more. So the open ended questions that give you time and space to actually sit back and listen to what the prospect is telling you is the most important content that you can glean in the meeting. And I would go one more on that. If you over prep your questions in advance, you are naturally going to be poised to continue asking your questions and following your agenda. Okay. Versus really listening to the conversation. I'll admit this and I would imagine both of you have had this happen. I'm so ready to ask my next smart question in the meeting. I lose track of the conversation. Right. I am prepping myself mentally so much for this blockbuster question I'm going to ask. You've suddenly lost the conversation. So I, I think the prepping is super important. But at the same time, you've got to be able to practice and coach yourself. Reeling off your list of questions can't take over the content that the prospect's giving you. And you've got to be spacing the time to listen and give a little bit of margin there if you need a pivot moment. Besides, and you're not going to get it if you're just ready to fire away at your next question.

[B]

Right. Flexibility. I love that. Well, look, anything else you want to talk about in terms of confidence in for women in sales or anyone entering sales is there when you look at like these, the words of wisdom, which you guys have been great today. Let me know what else you're thinking about how someone can be change that confidence gain.

[C]

I think a couple things, I mean a, it's not life or death. So that will relax you if you can just take a deep breath and be like, okay, even if I totally below this, it's still going to be okay. And I could pivot. People are people, right? So everyone has a bad day or they have a brain freeze and they lose track. But you can, if you're real and connect with them, you can overcome that and that will calm you down. And I think that's the biggest thing people can see. If you are panicked or if you are confident and you feel like, okay, I have this, I know my subject matter, I know what I want to do for you and I can do it. That will come across, you know, there's

[D]

a lot written on this now that actually failure is what leads to greater success in life. And I think, Kristen, exactly to your point, I was having a conversation yesterday with a younger, less experienced broker at my own firm who actually lost a pretty sizable renewal. And I mean, he was pretty heartbroken over it. And I said to him, listen, one deal is not going to make or break your career. You're going to have 10 more deals like this over the next couple of years. What's more important is how you regroup Monday morning quarterback, do the right post mortem. Where could you have done better? Now you're looking through it in a diagnostic way, in a safe space. You're learning from it. You're going to do better the next time and you're going to take some of your own observations, coach yourself and and be better prepared. So you learn a lot when you win and man does it feel good. But you learn more and you gain more confidence when you fail and resolve to do things differently the next time and how you're going to take and incorporate that to propel yourself forward. You know, self optimization is a great way to think when you have a lifelong sales career. And to be able to do that, you've got to synthesize the losses as well as the wins.

[C]

So absolutely, I remember my losses more than my wins sometimes.

[B]

Well, look, I want to thank you both. I feel like I had the insurance superstars today. I feel like I, I got, I'm like Jimmy Fallon and I got the two biggest stars in Hollywood. And so thank you. I'm very grateful. I hope this is helpful to folks who are entering sales or looking to fine tune their skills. Thank you both.

[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.