Sales Coaching Roleplay for Legal Teams: Running the 1:1 After Two Missed Quarters

1. 1

   Before you open your mouth: pull the tape

   You cannot coach a story about partner politics. You can coach a number and a recording. Walk in with six things, printed: - **New opportunities created, last 90 days, by week.** If Devon opened 8 new firms in month one and 2 in month three, that graph is the entire meeting. - **Stalled-stage census.** How many open deals are sitting in "with the technology committee" or "awaiting security review" with no activity in 21 days? Count them. That's not pipeline, that's a filing cabinet. - **Sponsor coverage.** Of their open deals, how many have a named Practice Group Leader, Litigation Chair or Director of Legal Operations who has described a specific live matter that is hurting? Not "we met the CIO." A sponsor with a matter. - **Security questionnaire cycle time.** Days from first meeting to the questionnaire landing with the firm's CIO / Director of Legal Technology. Compare to the team median. This is the single most diagnostic number in legal sales — reps who avoid the security conversation until month three lose to it in month four. - **Closed-lost reasons.** Count how many say "price" or "ALSP." Then count how many of those had a documented cost figure — write-downs on first-level review, cost per document including the associate QC pass, realization on that practice group. Usually zero. - **Two recordings.** One won, one lost, with timestamps. You will play 90 seconds of one of them. If "the firms won't move" is real, you'll see it in slow cycles across every rep on the team. If it isn't, you'll see Devon's first meetings happen at a normal rate and the floor drop out immediately after.

2. 2

   Open: name the stakes in two sentences

   No warm-up. They know why they're here. > "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 numbers — you know your numbers. I want to find out what's actually going wrong, because I think it's one thing and not five, and I don't know yet which one. Fair?" Do not say "how's your week going." False warmth in this meeting reads as a setup, and they'll be locked down before you've asked anything real.

3. 3

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

   > "Before I say a word, give me the whole picture. What's making this hard right now? Everything — I don't want the diplomatic version." Then after each one, three times: **"What else?"** Write them down where they can see you writing. In legal the list usually comes out in this order: risk committees veto anything hosted; partners bill 2,200 hours and won't take a pilot meeting; OCGs stop firms passing technology costs through so there's no budget line; ALSPs undercut us; marketing keeps sending Directors of Knowledge Management at firms with no litigation volume; the last three deals died because one senior partner said "I'd want to look at that more closely." The fourth or fifth one is usually closest to the truth. You only hear it if you don't argue with the first.

4. 4

   Say the list back and close the escape hatches

   > "So: risk committee vetoes, partner governance is slow, no budget line under OCGs, ALSP pricing, and the lead mix is wrong for litigation. Five things. Is that the list, or is there a sixth?" Get explicit agreement that the list is complete. You'll need that in twenty minutes when a sixth one appears.

5. 5

   Concede the true one out loud, first

   Give them the real grievance before you press on the invented ones. A rep who feels heard on one stops defending all five. > "Cycle length is real. Firms don't have a buyer, they have a technology committee, a risk committee, an executive committee and a practice group chair with no interest in a pilot. Six weeks at a corporate account is two quarters at a firm. I'm not going to pretend that isn't a headwind, and I'm not going to score you as if it isn't." Then the pivot: "Which is why the only thing that ever moves these is a sponsor who's personally bleeding on a live matter. So let's look at how many of your deals have one."

6. 6

   Test each excuse against the number you brought

   Take the excuse completely seriously, then hand them a number they can't argue with and ask them to explain it. > "Risk committee first, because if firms are just refusing hosted vendors I need to know that and go rebuild the security packet. You've had fourteen first meetings this quarter. On how many did the questionnaire get in front of their CIO or Director of Legal Technology inside two weeks?" > "Two. Team median is seven of ten. Meanwhile every one of those firms already runs a hosted e-discovery platform and most run a cloud DMS. Help me understand the gap." Then silence. Ten seconds. Do not fill it. Same treatment on price: > "Five of your nine losses say ALSP pricing. Of those five, how many had a total cost per document written down — the $28 an hour plus your associates' QC pass plus the privilege log? Walk me through Halloran Wick. What did their COO say their realization was on first-level review?" When they can't answer, don't say *exactly, that's the problem.* Say: **"Okay. What do you make of that?"**

7. 7

   Make it safe to say the real thing

   > "Let me say the thing that's sitting between us. I'm not building a file right now. If the answer is 'I got quiet in week three and stopped calling into new firms' — that's fixable, and I've fixed it with reps before. 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 crack it: > "If I handed you twenty firms tomorrow, all mid-market commercial litigation, all with a Managing Partner who takes the meeting — do you hit the number?" The hesitation is the admission. Follow with: > "What's the part of this you'd change if nobody was watching?" Or the direct route: *"Walk me through the last three weeks of Q3. What did Tuesday morning look like?"* A rep who stopped prospecting cannot describe a Tuesday. They'll describe two deals.

8. 8

   Go to the tape — a moment, not a theme

   "Your discovery needs to be deeper" is a horoscope. Play 90 seconds. > "Minute nine of the Marchetti call. He's the Litigation Chair. He says: 'we lost two second-years in March and the privilege log on the Delacroix production is going to blow the cap.' Listen to what you do next." [play it] "You went to the review dashboard. What were the three questions you didn't ask?" Let **them** name the misses. What you're listening for: *what did you write down on that matter last quarter; what's your standard realization in that practice group — 83, 88, 90; what was the fee cap and how far over did you go; who besides you has to say yes and who gets origination credit on Delacroix.* 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 a partner loses patience. If they genuinely can't name them, it's a skill gap and your plan is training, not accountability. That distinction determines everything you do next. Don't skip it.

9. 9

   Land on one root cause and say it plainly

   > "Here's where I've landed. Firm governance is slow and that's real, it cost you at least one deal this quarter. But what's actually killing you is that you're presenting at minute nine instead of getting a Litigation Chair or a COO to put a number on the damage — what a 30% write-down on first-level review costs them, what lockup at 110 days does to their distributions, what losing four second-years to attrition costs to replace. So every deal becomes a features-and-security comparison, and you lose to a $28 hourly rate. And because you only created two new opportunities in the last six weeks, you can't afford to disqualify a firm that's obviously never going to clear its risk committee — which makes the discovery problem worse, not better. Does that match what you see?" If they push back with an argument, listen — you might be wrong. If they push back with a new excuse: *"That's a sixth thing. We agreed the list was five. I think you're looking for a reason this isn't about the calls."*

10. 10

    Let them write the plan — then make it checkable

    > "Given that — what do you want to change first?" Manager-authored plans get complied with for eleven days. Convert whatever they say into something you can both look at on Friday: - "Prospect more" → "Tuesday and Thursday, 8 to 10, blocked. Five new firms opened a week, and 'opened' means a first meeting with a Managing Partner, COO, Litigation Chair or Director of Legal Operations — not a Director of Knowledge Management who took the call to be polite." - "Better discovery" → "No product walkthrough on a first call for three weeks. If they ask, you say: 'I'd rather show you the two screens that matter on your production than all forty — give me ten more minutes on the Delacroix matter first.'" - "Quantify" → "No deal advances past stage two without a dollar figure in the pain field and a named live matter. Write-down amount, cost per document, or replacement cost of the associates they lost." - "Security" → "Questionnaire in front of the CIO or Director of Legal Technology inside fourteen days of the first meeting, every deal, no exceptions." Then your side: *"I'll sit on your first two discovery calls this week and debrief straight after. And I'll get the single-tenant deployment one-pager and the Rule 1.6 language rewritten so you're not improvising it with a Loss Prevention Partner."* A plan that only assigns work to the rep reads as a warning, not a partnership.

11. 11

    Close with the standard, not a pep talk

    > "So: Tuesday and Thursday blocked, five new firms a week, no walkthrough on a first call, dollar figure and a named matter on everything in stage two, questionnaire out inside fourteen days. I'm on your Sattler Reyes call Wednesday. We meet Friday at four and look at opportunities created — not deals, opportunities. And to be straight with you: a third quarter like the last two changes this conversation. I don't think that's where we're going, but I'd be doing you a disservice not saying it." Then: **"What did you hear me commit to?"** Their answer tells you whether any of it landed.

12. 12

    If they never admit anything: turn the stalemate into an experiment

    Don't force a confession. You'll get a fake one, and fake ones cost you the next three months. > "Alright — we disagree on cause. Let's test it. Three weeks: no first-call walkthrough, five new firms a week, questionnaire out inside fourteen days. If firm governance is genuinely the wall, none of that moves and I'll take the segment fight upstairs myself and stop pointing at your calls. If it does move, we know what we're dealing with. Either way we know more in three weeks than we know right now." That keeps the relationship intact and gives you a clean decision point with a date on it.

13. 13

    What to drill before the real calls

    Between now and Friday, put the rep through three reps of the two conversations they're avoiding, out loud: 1. **The Loss Prevention Partner on Rule 1.6.** They must be able to ask, without flinching: *"What do your top clients' outside counsel guidelines actually say — notice and consent for third-party processing, or prohibition? And who's already hosting your e-discovery?"* 2. **The COO on realization.** They must be able to ask for the number: *"What's your standard realization in commercial litigation right now, and how much of the gap is first-level review getting knocked back?"* — and then say nothing. Both are better drilled against a roleplay partner who pushes back than practised on a Managing Partner you only get one shot at.

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 numbers — you know them. I want to figure out what's actually going wrong. Before I say anything: what's making this hard? Everything, not the diplomatic version.

2. Buyer

   Honestly? The segment. Firms don't buy, they deliberate. Halloran Wick had a Litigation Chair who loved it, and it still died because their risk committee won't approve any vendor that touches client data. Rule 1.6, malpractice exposure, done. That's not a selling problem, that's a profession.

3. Rep

   Okay. What else?

4. Buyer

   Pricing. Sattler Reyes has an ALSP doing first-level review at twenty-eight dollars an hour. I'm not going to out-price that. And their COO told me straight — their clients' outside counsel guidelines won't let them pass technology costs through to the client, so there's no line item for us at all.

5. Rep

   What else?

6. Buyer

   Lead mix. Half of what I get routed is Directors of Knowledge Management at 40-lawyer firms with no real document volume. And even when it's a good firm, everything ends the same way — 'send me something and I'll circulate it to the technology committee.' Which meets quarterly.

7. Rep

   So: risk committees, ALSP pricing and no pass-through under OCGs, lead mix, and the technology committee black hole. Four things. Is that the list, or is there a fifth?

8. Buyer

   That's the list. And I'd add that nobody else on the team is selling into commercial litigation the way I am, so the comparison isn't fair either.

9. Rep

   Cycle length is real, and I'm going to say that out loud so it's not in dispute — a firm with a technology committee, a risk committee and an executive committee takes two quarters to do what a corporate buyer does in six weeks. That's a genuine headwind. Now let me test the risk committee one, because if firms are flatly refusing hosted vendors I need to go rebuild the security packet. You've had fourteen first meetings this quarter. On how many did the questionnaire reach their CIO or Director of Legal Technology inside two weeks?

10. Buyer

    …I'd have to look. A couple. It's not something you lead with — you bring up security in week one and the whole thing turns into a compliance review before anyone's seen the value.

11. Rep

    Two. Team median is seven out of ten. And every one of those firms is already running a hosted e-discovery platform. So the question isn't whether they'll accept a cloud vendor — they did that years ago. What do you make of that?

12. Buyer

    I mean — maybe I'm arriving at the security conversation late. But that's not why Halloran Wick died. Their Litigation Chair had no budget and no appetite.

13. Rep

    Let's listen to him. Minute nine of the Marchetti call. He says: 'we lost two second-years in March and the privilege log on the Delacroix production is going to blow the cap.' Here's what you do next. [plays] You went to the review dashboard. What were the three questions you didn't ask?

14. Buyer

    …What the cap was. How far over they went. What that write-down actually did to their realization. Probably who else has to sign off — and who has origination credit on Delacroix, because that's who kills it.

15. Rep

    That's four, and you named them cold, which tells me this isn't a knowledge problem. Here's where I've landed. Governance is slow, that's real. But you're presenting at minute nine instead of making a Litigation Chair or a COO put a number on the damage — the blown cap, the realization sitting in the low eighties, the replacement cost of the second-years who walked. With no number, you're a feature comparison against twenty-eight dollars an hour. And with two new opportunities created in six weeks, you can't afford to walk away from a firm that's obviously never clearing its risk committee. Does that match what you see?

16. Buyer

    Partly. I still think the leads are thin. But yeah — I stopped calling into new firms around week three. I had Halloran and Sattler and I told myself they were both live.

17. Rep

    Thank you for saying that. That's the most useful sentence in the last thirty minutes, and it's fixable. So — what do you want to change first?

18. Buyer

    Two things. Block Tuesday and Thursday mornings for new firms — five first meetings a week, and only with a Managing Partner, COO, Litigation Chair or Legal Ops Director. And get the security questionnaire moving in the first fortnight instead of hiding from it.

19. Rep

    Done, and I'll add one: no product walkthrough on a first call for three weeks, and nothing advances past stage two without a named live matter and a dollar figure. My side — I'm on your Sattler call Wednesday, and I'll get the single-tenant deployment and Rule 1.6 language rewritten so you're not improvising it in front of a Loss Prevention Partner. Friday at four we look at opportunities created, not deals. And straight with you: a third quarter like these two changes this conversation. What did you hear me commit to?

What does a sales coaching roleplay for Legal teams actually rehearse — isn't the rep's problem the law firm's buying process?

Partly, and you should concede that out loud on the call. But the behaviours that decide legal deals are all rehearsable: asking a COO for their standard realization rate and then staying silent; asking a Loss Prevention Partner what their clients' OCGs require rather than assuming prohibition; asking a Litigation Chair what the blown cap on the last production actually cost. Reps skip those questions because they're uncomfortable in front of a partner who bills 2,200 hours. Roleplay is where you get comfortable, instead of burning your one meeting with a Managing Partner learning it live.

How do I tell whether my rep has a skill problem or an effort problem?

Play 90 seconds of a real first call and ask them to name the three questions they didn't ask. If they can name them cold, it's execution — they know the move and aren't making it, usually because they rush to show product before a partner loses patience. That's coaching and roleplay. If they genuinely can't name them, it's a skill gap and you're training. Then check activity separately: new firms opened per week, by week, over 90 days. A rep who created eight in month one and two in month three has an effort problem sitting on top of whatever else is true.

Which numbers should I bring to the 1:1 for a rep selling into law firms?

Six. New opportunities created per week for 90 days; how many open deals are parked in a committee stage with no activity in 21 days; how many deals have a named sponsor (Litigation Chair, Practice Group Leader, COO, Director of Legal Operations) tied to a live matter; days from first meeting to the security questionnaire reaching the CIO or Director of Legal Technology; closed-lost reasons with a count of how many tagged price had a documented cost figure; and two recordings, one won, one lost.

My rep insists the risk committee kills every deal. How do I test that without starting a fight?

Take it completely seriously and then hand them the number. "If firms are refusing hosted vendors outright, that's my problem to fix — so on how many of your fourteen first meetings did the questionnaire reach their CIO inside two weeks?" If it's two against a team median of seven, the rep is avoiding the security conversation, not losing it. Also worth asking: does that firm already run a hosted e-discovery platform or a cloud DMS? Most do, and that reframes the deal from 'first cloud vendor' to 'another vendor under an existing standard.'

What if the rep never admits anything?

Don't force a confession — a fake one costs you the next quarter. Convert the disagreement into a three-week experiment neither of you can argue with: five new firms a week, no product walkthrough on a first call, security questionnaire out inside fourteen days, a dollar figure and a named matter on everything past stage two. If nothing moves, you take the segment fight upstairs yourself. If it moves, you both know what you're dealing with. Either way you have a clean decision point with a date on it.

How do I use DrillCall between this 1:1 and Friday?

Assign two scenarios, three reps each, before the rep's next live call. First: a firm GC / Loss Prevention Partner who opens with Rule 1.6 and client OCGs prohibiting third-party processing — the rep has to get to what the guidelines actually say and what the firm already hosts. Second: a COO who won't hand over a realization number and keeps redirecting to the ALSP's $28 hourly rate — the rep has to get to total cost per document including the QC pass and privilege log. Then debrief the recordings on Friday alongside opportunities created, not deals.

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