Two Quarters Down: A Sales Coaching Roleplay for Insurance Teams

1. 1

   Before you open your mouth: pull the tape

   Do not walk into this with a feeling. Walk in with six things printed: 1. **New opportunities created per week, last 90 days.** If they created 7 in month one and 2 in month three, that chart is the entire conversation and you barely have to talk. 2. **Coverage against next quarter, split by carrier type.** Mutual, regional stock, national. A pipeline that's 3x on paper but 80% mutuals in a closed planning cycle is not 3x. 3. **Stage conversion vs. team median.** Specifically: first call to second call. In claims tech, that's where the floor drops out, because the first call is where you either got the Chief Claims Officer to say their days-from-FNOL-to-final-payment number out loud or you didn't. 4. **Closed-lost reasons.** Count how many say "price" or "no budget." Then count how many of those had a documented loss ratio impact or a quantified leakage number in the CRM. It'll be close to zero. 5. **Who they actually met with.** Meetings with a Director of Claims Transformation are not meetings with an SVP Claims. Innovation-team meetings should be logged separately, because that's where claims vendors go to die. 6. **Two recordings, timestamped.** One won, one lost. If "my territory is all mutuals" is real, you'll see it in their meeting-to-second-call rate matching a peer's on the same segment. If it isn't, you'll see their meeting rate is fine and everything after the first call is where it collapses. Know which is true before you sit down.

2. 2

   Open: name the stakes in two sentences

   "Two quarters is a pattern, not bad luck, and I'm not going to sit here and pretend it's variance. But I didn't book this to read you your attainment — you know your attainment. I want to work out what's actually going wrong, because I think it's one thing and not five, and I genuinely don't know yet which one it is. Fair?" That's it. No "how was your weekend." They know why they're here. The false warmth reads as a setup and they lock down before you've asked a real question. Do not say the words "performance plan" in the first ten minutes — the second a rep hears it, they stop diagnosing and start building a defence, and you've lost the only honest thirty minutes you were going to get.

3. 3

   Drain the tank — every excuse, before you touch any of them

   "Before I say anything at all, give me the full picture. What's making this hard? Everything — I don't want the diplomatic version." Then after each one, only two words: **"What else?"** Ask it three times minimum. Write them down where they can see the pen moving. In this territory the list usually runs: my accounts are all mid-migration and IT has nothing until 2027; cat season wiped out April and May because half my claims contacts were on storm duty; every mutual in my patch says surplus is policyholder money; the challenger is 20% under us; every SIU Director I talk to got burned by a fraud analytics vendor two years ago and turned it off. Then read it back flat, no editorial: *"So — core migrations, cat season, mutual budgets, price against the challenger, and the SIU fraud-vendor hangover. That's the list? Nothing else?"* Getting explicit agreement that the list is complete is what closes the escape hatches later. If a sixth thing appears in minute twenty-five, you get to name it.

4. 4

   Sort the list: real, partly real, story

   Work each one *with* them, and take it completely seriously before you test it. Start with the one you can settle with data: "Let's take mid-migration first, because if every account in your patch is frozen until 2027 I need to go argue about territory design and I'd rather know now. You had 38 target accounts. Priya had 34 in the same segment mix. She booked 16 first calls, you booked 15 — so at the top you're identical. Where it splits is after: she moved 9 of 16 to a second call, you moved 3 of 15. Help me understand that gap." Then stop talking. Ten seconds of silence here is worth more than anything you could add. On price: "Five of your eight losses say price. Of those five, how many had a number attached — like, this carrier is running 4% leakage on $180 million of paid losses and here's what one point back is worth? Walk me through Keystone Mutual. What did the VP of Claims Operations say their average cycle time was, and what did they say a day was worth?" When they can't answer, do not say "exactly, that's the problem." Say: **"Okay. What do you make of that?"** And concede the true one out loud, by name: *"Cat season is real. The April hail event pulled three of your live accounts into storm response and you lost six weeks of calendar. I'm not going to pretend that didn't happen."* Conceding the real grievance is what buys you the right to press on the invented ones. A rep who feels heard on one thing stops defending all of them.

5. 5

   Make it safe to say the real thing

   "Let me say the thing that's probably sitting between us. I am not building a file right now. If the answer is 'I got spooked after the Cardinal Casualty loss and I stopped picking up the phone in week three' — that is a fixable thing, I've fixed it with reps before, and it stays in this room. What I can't fix is a version where nothing is in your control, because then neither of us has anything to do on Monday." Then the two questions that usually crack it: "If I handed you fifteen warm Chief Claims Officer intros tomorrow, do you hit the number?" The hesitation is the admission. Let it sit. Then: "What's the part of this you'd fix if nobody was watching and there were no consequences?" Or the direct route into activity: *"Walk me through the last three weeks of the quarter. What did Tuesday morning look like?"* A rep who's stopped prospecting cannot describe a Tuesday morning. They'll describe deals instead of activity, and they'll do it fast. One warning: if you get a flat "yeah, you're right, I need to prospect more" at minute six, before a single number has been on the table — that's not an admission, that's a rep managing you out of the room. Slow it down and go to the tape.

6. 6

   Go to the tape — a moment, not a theme

   "Your discovery needs to be deeper" is a horoscope. Play ninety seconds. "This is minute nine of the Keystone Mutual first call. Their VP of Claims Operations says — and I'm quoting — 'we're supposed to close auto at twelve days and we're sitting at twenty-six, and the board asked about it in November.' Listen to what you do next." [play it] "You went straight into the fraud scoring screen. Give me three questions you didn't ask." Let *them* name the misses. The good ones are sitting right there: what does a day cost you in DOI complaints; what's your ALAE per claim on those files; is the twenty-six days an adjuster capacity problem or a queue problem; what did the board actually ask for; who else in the building owns that number — is it you or is it the COO. If they can name the misses, this is execution. They know the move and aren't making it, usually because they're rushing to prove value before the buyer has admitted a cost. If they genuinely cannot name them, it's a skill gap and your plan is training, not accountability. That distinction decides everything you do next — don't skip it.

7. 7

   Land on one root cause and say it plainly

   "Here's where I've landed. Cat season cost you six weeks and that's real. But the thing actually killing you is that you're demoing at minute nine instead of getting them to say what the cycle time is costing them — so every deal turns into a feature comparison against the challenger and you lose on price. And because you only created eleven new opps in ninety days, you can't afford to disqualify the Meridian deal that was never going to clear actuarial, so you spent October on it. The thin discovery and the thin pipeline are the same problem feeding itself. Does that match what you see?" Ask for agreement. If they push back with a real argument, listen properly — you might be wrong. If they push back with a new excuse, name it: *"That's a sixth thing. We agreed the list was five. I think you're hunting for a reason this isn't about the calls."*

8. 8

   Let them write the plan, then make it checkable

   "Given all that — what do you want to change first?" Manager-authored plans get complied with for eleven days. Rep-authored plans get done. Whatever they say, convert it into something you can both look at on Friday: - "Prospect more" → "Tuesday and Thursday, 8 to 10, blocked in the calendar, five new opps a week, and mutuals count the same as stock carriers." - "Better discovery" → "No product on a first call for three weeks. If they push, you say: 'I'd rather show you the two screens that matter to your cycle time than all forty — give me ten more minutes of questions first.'" - "Quantify it" → "Nothing advances past stage two without their paid losses, their leakage estimate, and their current days-from-FNOL-to-close written in the pain field. In their words, with a name next to it." Then your half, out loud: *"I'll sit on your first two discovery calls this week and debrief within ten minutes of hanging up. And I'll go pull the list of regionals in the Southeast that aren't mid-migration so you've got something to backfill the accounts that are frozen."* Coaching that only assigns work to the rep reads as a warning, not a partnership.

9. 9

   Close with the standard, not a pep talk

   "So: Tuesday and Thursday mornings blocked, no product on a first call for three weeks, and a dollar figure on every stage two. I'm on your Harborline call Wednesday. We meet Friday at four and we look at opps created — opps, not deals. And to be straight with you: a third quarter like the last two changes the nature of this conversation. I don't think that's where we're going, but I'd be doing you a disservice not to say it." Then: **"What did you hear me commit to?"** Their summary tells you whether any of it landed. Do not finish with "you've got this" — that tells the rep the last thirty minutes were theatre and nothing has to change by Monday.

10. 10

    If they never admit anything

    Some versions of this end with the rep still holding the line: it's the migrations, it's the mutuals, it's price. Don't force a confession — you'll get a fake one and it'll cost you the next three months. "Alright. We disagree on cause. Let's test it instead of arguing about it. Run no-product first calls for three weeks and hit five new opps a week. If it's genuinely the territory, that will change nothing, and I'll take the segment-design fight upstairs myself with your data in my hand. If it does change something, we've learned what we're actually dealing with. Either way we know more in three weeks than we know right now." That turns a stalemate into an experiment, keeps the relationship intact, and gives you a clean decision point with a date on it.

1. Rep

   Two quarters is a pattern, not bad luck, and I'm not going to pretend otherwise. But I didn't book this to read you your attainment — you know it better than I do. I want to work out what's actually going wrong, because I think it's one thing and not five. Fair?

2. Buyer

   Fair. But I'll be honest, I think you already know what it is. My patch is eleven regional mutuals and four stock carriers, and three of the four are eighteen months into a core replacement. Every conversation ends the same way — 'we've got no IT bandwidth until 2027, come back after go-live.' That's not a me problem.

3. Rep

   Understood. What else?

4. Buyer

   Cat season. The hail event in April pulled Keystone's whole claims leadership onto storm response. My VP of Claims Ops there stopped answering for six weeks. Same with Harborline. You can't run a sales cycle when the buyer is deploying independent adjusters at three times internal cost.

5. Rep

   What else?

6. Buyer

   The mutuals. Every one of them tells me surplus is policyholder money and there's no technology line the way a stock carrier has one. And then there's price — we're twenty percent over the challenger. Oh, and every SIU Director I talk to got burned by a fraud analytics vendor two years ago, drowned in false positives, shut it off. I'm selling into a room that's already decided.

7. Rep

   So the list is: mid-migration accounts, cat season, mutual budgets, price against the challenger, and the SIU fraud-vendor hangover. That's the whole list? Nothing sixth?

8. Buyer

   That's the list.

9. Rep

   Then let me give you the one that's real before I push on any of it. Cat season cost you six weeks of calendar and it's not arguable — I watched two of your accounts go dark in April. That's a legitimate headwind. Now let's take the migration one, because if your whole patch is frozen until 2027 I need to go fight about territory design, and I'd rather know today. Priya's segment mix is almost identical to yours. She booked sixteen first calls last quarter, you booked fifteen — you're identical at the top. She moved nine of sixteen to a second call. You moved three of fifteen. Help me understand that.

10. Buyer

    Her accounts are bigger. She's got two nationals with a real Director of Claims Transformation who has a budget and a mandate. I'm talking to a Chief Claims Officer at a mutual who's also effectively the COO and has four other jobs.

11. Rep

    I pulled that too. Of her nine second calls, six were mutuals under $400 million in written premium. Same buyer profile as yours. So what do you make of that?

12. Buyer

    …I don't know. Maybe she's getting luckier on timing.

13. Rep

    Maybe. Let me play you ninety seconds and you tell me. This is minute nine of your Keystone Mutual first call. Their VP of Claims Operations says, quote, 'we're supposed to close auto in twelve days, we're sitting at twenty-six, and the board asked about it in November.' Listen to what happens next. [plays] You opened the SIU scoring screen. Give me three questions you didn't ask.

14. Buyer

    …What the fourteen extra days are costing them. Whether it's showing up in DOI complaints or non-renewals. And what their ALAE per claim looks like on the files that sit longest. I know. I know those are the questions. I had the deck open and I wanted to show him the thing I thought would land.

15. Rep

    Okay — that's useful, because you can name them. That means this is execution, not a skill gap, and it's a much shorter fix. Let me say the other thing that's sitting between us. I am not building a file right now. If part of this is that after the Cardinal Casualty loss you stopped picking up the phone for a few weeks, that's fixable and I've fixed it before. So — walk me through the last three weeks of Q3. What did Tuesday morning look like?

16. Buyer

    Tuesday I'd be… working Meridian, mostly. Building the leakage model for their chief actuary, then reworking it because he wanted it back-tested against closed claims. That ate most of September.

17. Rep

    That's a deal, not a Tuesday. You created eleven new opps in ninety days — seven of them in month one. Here's where I've landed. Cat season is real and it cost you six weeks. But the thing killing you is that you're going to product at minute nine instead of making the Chief Claims Officer say what twenty-six days costs them — so every deal becomes a feature comparison and you lose to the challenger on price. And because you only built eleven opps, you couldn't afford to walk away from Meridian in week two, which is what you should have done. Does that match what you see?

18. Buyer

    Partly. I still think the migration thing is bigger than you're giving it credit for.

19. Rep

    Then let's test it rather than argue about it. What do you want to change first — you pick.

20. Buyer

    No product on a first call. For three weeks. And I'll block Tuesday and Thursday mornings for pipeline, eight to ten, five new opps a week. If the migration story is real, that won't move anything and you'll owe me a territory conversation.

21. Rep

    Deal, and I'll take that fight upstairs myself if the data says so. My half: I'm on your Harborline discovery Wednesday and I'll debrief within ten minutes of the hang-up, and I'll pull you a list of Southeast regionals that aren't mid-migration to backfill. One more rule — nothing moves past stage two without their paid losses, their leakage estimate and their current FNOL-to-close in the pain field, in their words. Friday at four we look at opps created, not deals. And straight with you: a third quarter like the last two changes this conversation. I don't think that's where we're going. What did you hear me commit to?

What makes a sales coaching roleplay for insurance teams different from a generic one?

The excuses are different and so is the coaching. A rep selling claims technology has genuinely hard headwinds — core migrations that freeze accounts for two years, cat season pulling claims leadership onto storm duty, mutuals with no discretionary technology line, and SIU Directors who turned off the last fraud analytics tool. A generic coaching roleplay lets the rep say 'bad territory' and the manager say 'work harder.' An insurance-specific one forces the manager to test each claim against segment data and forces the rep to defend it in the industry's own language: paid losses, leakage percentage, ALAE per claim, days from FNOL to final payment.

Who plays which role in this scenario on DrillCall?

You practise as the manager. The AI plays the rep who has missed two quarters selling into carriers — cooperative on the surface, defensive underneath, with four or five pre-loaded and partly true grievances. The AI is instructed not to volunteer the real problem (thin discovery, and prospecting that stopped in week three) and to give a fast, hollow 'you're right, I need to prospect more' if you press too early. You only get the real root cause if you drain every excuse, concede the true one, and put a number in front of them.

How do I stop the roleplay turning into an argument about territory?

Bring data into the scenario before you start. The drill works best when you've decided in advance what the peer comparison looks like — same segment mix, near-identical first-call rate, second-call conversion a third as good. That single comparison ends the territory debate without you having to say 'that's not the real issue.' The rule inside the roleplay is that you never rebut an excuse with an opinion, only with a number or a recording, and you concede the one that's genuinely true out loud and by name.

What does a good outcome look like at the end of the call?

One root cause named plainly, one behaviour the rep proposed themselves, and a check-in with a date on it. Not a nine-point plan. In this scenario a good landing usually looks like: no product on a first call for three weeks, two blocked prospecting mornings with a weekly opp target, and a stage-two rule that nothing advances without the carrier's paid losses, leakage estimate and current cycle time written in the rep's own notes. Plus something you committed to — sitting on two discovery calls, or pulling a backfill account list — because a plan that only assigns work to the rep reads as a warning.

What are the most common ways managers fail this roleplay?

Four, in order of frequency. Rebutting the first excuse the moment it lands, which buries the fourth one — usually the closest to the truth. Opening with small talk when both people know why the meeting exists. Coaching a theme ('your discovery needs work') instead of playing minute nine of a real call and asking which three questions were skipped. And accepting a flat admission at minute six, before any number has been discussed — that's the rep managing you out of the room, not a breakthrough.

How often should sales managers run this drill?

Before any 1:1 where you already suspect a pattern rather than a bad month, and once a quarter as maintenance. The specific muscle it builds — asking 'what else?' three times without flinching, then sitting in ten seconds of silence after handing over an uncomfortable number — decays fast under pressure. Most managers can describe the sequence perfectly and still cannot hold the silence in a live conversation, which is exactly what makes it worth rehearsing.

• All Insurance playbooksEvery call type for Insurance, in one place.

Other Insurance calls

• Cold CallThe Insurance Cold Call Script That Keeps a Claims Leader on the Phone
• Demo CallInsurance Product Demo Script: Running a Claims Demo for Carrier Buyers Who Are Looking for Where It Breaks
• Discovery CallDiscovery Call Questions for Insurance: A 25-Minute Playbook for Selling Into Claims
• Pricing Negotiation CallInsurance Pricing Negotiation Script: Holding Your Number With a Claims Buyer After the Technical Win
• Renewal CallInsurance Renewal Call Script: Saving a Claims Platform Account at a Carrier That's Already Halfway Out
• Upsell CallUpsell Script for Insurance Customers: From Claims Account Review to a Recovery Module Expansion
• Warm CallWarm Call Script for Insurance: Cashing a Peer Referral with a Claims Leader in 90 Seconds

The same call in a neighbouring market

• Manager Coaching Call for SaaSSales Coaching Roleplay for SaaS Teams: The 1:1 After Two Missed Quarters
• Manager Coaching Call for Financial ServicesSales Coaching Roleplay for Financial Services Teams: The Two-Quarter-Miss 1:1
• Manager Coaching Call for HealthcareSales Coaching Roleplay for Healthcare Teams: The 1:1 After Two Missed Quarters

Related reading

• You Got Put on a PIP. Here's the 30-Day Plan.A PIP is a countdown, not a conversation. Here is the practical thirty-day version: get the number in writing, convert it to daily activity, and fix the stage that is actually broken.
• Roleplay vs Call Reviews vs Live Coaching: Which One Actually Fixes a RepCall reviews build awareness, live listening catches habits, and roleplay is the only mode that rehearses the moment under pressure — here's how to run all three.