Medicare Sales Playbook

Tough conversations are part of the job — whether you're setting appointments, handling objections, talking commissions with an upline, or walking a client through less-than-ideal plan options.

In this episode of the Medicare Sales Playbook, Dallas and Matt break down how to tackle hard talks without being "the conflict guy"… and without being the apologetic agent who disappears until the "32nd of never."

You'll learn:

• How to set appointments with respect (start with "Is this a good time to talk?")

• Why you should stop opening calls with apologies and start leading with confidence

• How to handle objections with the "3 A's": Agree • Answer • Ask

• Why prepping for the "potholes" in the conversation makes you look prepared and in control

• How to explain "bad options" honestly without making the tone negative

• 5 keys for hard conversations (from Fierce Conversations):

1. Set the tone

2. Understand the risk

3. Savor the silence

4. Look for clarity, not conflict

5. Walk away with an answer (set a follow-up time)

Dallas and Matt also share practical lines you can use when a prospect says "I need to think about it," plus a reminder that time kills deals — and the hard conversation usually isn't as hard as you've built it up to be.

Want to catch the team on the road for MSP Training Days + updated tour dates? Check the website + follow along on social media (they'll post where they are — and might even do lunch or coffee). https://medicaresalesplaybook.com/

📩 Questions or want to connect? Email us: [email protected] 👇 Drop a comment with: • A topic you want covered • A guest you want us to interview • What stood out most from today's episode

👍 Like • Subscribe • Turn on notifications so you don't miss the next episode.

What does it take to go from struggle… to 365 apps in a single AEP?

In this powerful episode of the Medicare Sales Playbook, host Dallas Keithley sits down with Keith Laferriere of Care Connect Insurance Advisors in Bradford, New Hampshire — and this one goes way beyond production numbers.

Keith breaks down:

• How he generated 365 apps during AEP

• His exact Medicare seminar system (4,000 mailers → ~80 attendees → 35–40% appointments)

• Why simplifying Medicare is the key to standing out

• How to thrive when carriers decommission plans

• The mindset shift that turns setbacks into opportunity

• His personal journey from addiction and adversity to leadership and impact

This isn't just about Medicare sales.

It's about: ✔ Systems ✔ Consistency ✔ Faith ✔ Accountability ✔ And refusing to let your past define your future

Keith shares his "FOCUS" framework: Faith. Opportunity. Consistency. Utilization. Service.

If you're a Medicare agent looking to build predictable production… If you're struggling with mindset… If you need proof that transformation is possible…

This episode is for you.

👉 Want a copy of our Long-Term Care webinar mentioned in this episode? Email: [email protected]

👉 Interested in Medicare Sales Playbook Training Days? Check the website for upcoming cities starting in Charlotte, NC this March.

If this episode encouraged you, comment below and let us know what stood out most.

👍 Like. 🔔 Subscribe. 📩 Share with an agent who needs this message.

Dallas Keithley is back on the mic with an episode built for agents who want to level up in the middle of chaos.

In this conversation, Dallas sits down with Casey Peterson and Lee Wilson from Teton Medicare (Idaho Falls and Pocatello, ID) — two former competitors who merged agencies and turned that partnership into massive momentum. They break down what happened during a wild AEP (including major plan disruption in their market), how they stayed calm, how they pivoted fast, and what it actually takes to build a real Medicare business that lasts.

You'll hear:

• Why adaptability is the difference between agents who survive and agents who win

• What it looked like to handle major market shifts while protecting clients and team culture

• The mindset behind betting on yourself, reinvesting, and "doubling down" on what works

• Marketing moves that produced growth (and a few that absolutely didn't)

• Why hiring help before you feel ready can change everything

• How they think about culture, recruiting, and hiring the right people

• The importance of knowing your why and building a business that still protects your family time

If you've ever felt stuck at a comfortable level — or overwhelmed by changes you can't control — this episode will help you reset your mindset, get strategic, and move forward.

📩 Questions or want to connect? Email us: [email protected] 👇 Drop a comment with: • A topic you want covered • A guest you want us to interview • What stood out most from Gabe's story

👍 Like • Subscribe • Turn on notifications so you don't miss the next episode

Two years in, and we're still blown away by what this business can do—both for agents and the clients we serve. In this episode of the Medicare Sales Playbook, Matt Smith sits down with Gabe Cordova, owner of LifeMark Advisors in Mount Vernon, Missouri.

Gabe shares his unexpected path from full-time ministry into Medicare, including the first client who showed him exactly why this work matters. We talk about what it really takes to succeed early on (spoiler: it starts with getting in front of people), why diversifying your product focus is non-negotiable, and when it actually makes sense to start recruiting agents.

We also dig into something every agent feels at some point: this can be a lonely industry—and why building a real community (where people know you care) is often the difference between burnout and long-term success. Plus: Gabe's weekly cadence for team culture, bringing family into the business, and what's next for LifeMark as they expand into a new facility.

If you're new, stuck, or building a team—this one will hit home.

📩 Questions or want to connect? Email us: [email protected]

We made it — 100 episodes of the Medicare Sales Playbook 🎉

In this milestone episode, Dallas and "Mr. Medicare" Matt Smith look back on what the last 2+ years have taught them — and the one word that keeps coming up: gratitude.

You'll hear:

• Why gratitude can change your perspective (and your business)

• A simple leadership principle: find people who are great at what you're not

• Favorite episode highlights and the lessons behind them (TikTok lead gen, activity, leadership, serving others, reinvesting, cross-selling, and more)

• A reminder that most people know what to do… but few commit to action

PLUS: Training Days are coming to cities around the country (including Phoenix, Denver, Seattle, Charlotte and more).

📩 Seen all 100 episodes? Message us your favorite moment:Email: [email protected]

In this episode of the Medicare Sales Playbook, Dallas Keithley and "Medicare Matt" get real about what separates the agents who last from the agents who flame out: a servant mindset + the ability to find (and verify) answers fast.

Dallas shares his mantra for the year—"How can I serve you?"—and they break down the "Can I?" part: What can I do to put myself in a better position to serve people today? The conversation turns practical quickly: how to use tools like ChatGPT the right way (great for brainstorming, dangerous as your final authority), why you should verify everything with trustworthy sources like Medicare.gov and CMS.gov, and how saving screenshots of official guidance can protect you (and your clients) later.

They also hit a huge leadership lesson: if you're the person everyone calls for answers, you may be building dependency—not a scalable agency. The solution? Train your people to find the resources and lean into community, mentorship, and your organization's support channels.

If you want to be more self-reliant, more confident in the field, and better equipped to handle the weird Medicare scenarios that pop up mid-appointment—this one's for you.

Key takeaways:

• How to think like a "resource finder" (not a walking encyclopedia)

• Using AI as a brainstorming tool—then verifying with official sources

• Why Medicare.gov + CMS.gov should be your go-to references

• How to avoid costly mistakes (like Part B penalty misunderstandings)

• Community > isolation: success happens with the right people around you

👉 Subscribe for weekly Medicare training, Tuesday Tips, and Last Wednesday Webinars

👉 Watch for upcoming in-person training events across the country 👉 Join the January 28 webinar on transitioning Medicare conversations into Long-Term Care

📩 Questions or want to get on the training list? Email: [email protected]

In this episode of the Medicare Sales Playbook, Dallas and Matt unpack a simple phrase that has the power to completely transform your sales results:

"How may I serve you?"

In a world where every agent has access to the same Medicare contracts—Humana, UnitedHealthcare, Aetna—the real differentiator isn't the plan.

It's you.

This conversation dives deep into:

• Why clients are really "buying the agent," not the policy

• How observation, listening, and preparation separate average agents from elite ones

• What service actually looks like before, during, and after the appointment

• Real-world stories from airlines, restaurants, Chewy, and everyday client interactions

• Practical ways to stand out without breaking compliance—or your budget

You'll learn why being a student of the game matters, how noticing small details builds lifelong loyalty, and why the greatest return in sales often comes from giving first.

💡 Challenge of the episode: This week, pick three people and give them something meaningful (under $5) that shows you truly listened. The return may surprise you.

If you're serious about building trust, retention, and long-term referrals in Medicare sales, this episode is for you.

👉 Subscribe for weekly Medicare training, Tuesday Tips, and Last Wednesday Webinars 👉 Watch for upcoming in-person training events across the country 👉 Join the January 28 webinar on transitioning Medicare conversations into Long-Term Care

📩 Questions or want to get on the training list? Email: [email protected]

Want to add Long-Term Care to your Medicare conversations—without getting overwhelmed or "starting from scratch"?

In this episode of the Medicare Sales Playbook, Dallas Keithley sits down with Jay Curatti (Director of Retirement Planning, Lasting Mark Retirement Group) to break down:

• What long-term care actually means (it's not just nursing homes)

• How LTC qualifies (the 2-of-6 ADLs rule) and why that matters

• Simple, natural conversation starters to transition from Medicare → LTC

• How to overcome the two biggest objections: "I'll never need it" and "I can't afford it"

• Why LTC is about options, choice, and peace of mind—not fear

• A smart way to help clients without becoming an LTC expert: the Elevate / Empower support model (including how agents can stay on the call, learn the process, and earn 50% of the commission)

📅 Don't miss Jay live on the Last Wednesday Webinar: January 28 @ 4:00 PM CST Learn the full strategy, product options, and get your questions answered.

🔗 Learn more about Jay + the Elevate team: lastingmarkretirement.com

📩 Want to get added to Tuesday Tips + the Last Wednesday Webinar invite list? Email: [email protected]

✅ If this episode helped you, subscribe and drop a comment: "What's the hardest part about bringing up long-term care with your Medicare clients?"

It's officially 2026… and this episode is the definition of "Don't Give Up. Don't Ever Give Up."

Dallas sits down with Brian & Patti Askins to unpack the real story behind how Lasting Mark was built—starting with a moment in February 2014 that rocked their world. What happens when corporate America turns the lights off overnight… while your family is depending on you… and your spouse is battling chemo?

You'll hear the behind-the-scenes leadership lessons most people never talk about:

• How Brian went from being terminated to building again from zero

• Why culture + community + value are non-negotiables if you want to grow

• Why leadership is getting in the trenches (even when it's not glamorous)

• The role Patti played from day one—and why partnership at home matters

• A reminder that tomorrow isn't promised… so build a life you don't regret

If you've been "punched in the face" by life or business, this one's for you.

✅ Connect with Lasting Mark: lastingmark.com ✅ Interested in Training Days / Bootcamps? Visit the website for upcoming cities & dates.

Subscribe for weekly Medicare sales training + real conversations with real builders. Drop a comment: What's one thing you needed to hear heading into 2026?

#MedicareSales #InsuranceAgent #Leadership #Entrepreneurship #SalesTraining #MedicareSalesPlaybook #LastingMark

Welcome to a special New Year's Day "Keep It 100" episode of the Medicare Sales Playbook.

Dallas Keithley sits down with Cody and Lauren Askins for a real conversation about what changes you, what strengthens you, and what actually matters when you're trying to build a business (and a life) you're proud of.

In this episode, we talk about:

• Why your circle matters more than you think (and how to "check your circle" for 2026)

• How to reflect + reset without beating yourself up over the past year

• The truth about effort (and why "I'll do it later" is costing you)

• Why community beats isolation every time

• The power of speaking life into yourself: stop thinking, start saying out loud what you want and who you're becoming

If 2025 was rough… this is your reminder: the chapter is closed. 2026 is a reset. Get back up and keep going.

✅ CHECK OUT CODY ASKINS EVENTS: Find your community by attending an 8% Roadshow, or the world renowned 8% Conference! Tickets and information can be found at: https://8percentnation.com/ or https://codyaskins.com/

✅ NEXT STEP: Subscribe for weekly Medicare sales training + mindset that helps you win. ✅ STAY CONNECTED: Want updates on training days / bootcamps + future episodes? Email: [email protected]

#MedicareSales #MedicareAgents #InsuranceSales #SalesMindset #Leadership #PersonalGrowth