Lesson 52 - Hold a Deal Retrospective

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Reflecting on past deals can reveal valuable lessons. In this lesson, you’ll learn how to conduct a deal retrospective to analyze what went well and what could improve for one of your recently closed opportunities. Your assignment will involve planning, holding, and documenting a retrospective for a closed-won or closed-lost deal.

Transcript

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Nicholas, welcome back to the daily quota. I'm your host, Nicholas Hill, and in today's lesson, you'll hold a retrospective to review a recently closed opportunity. Now, what the heck is a retrospective? A retrospective, which you might also call a retro, is a meeting where you bring together all of the individuals that were involved with an opportunity from beginning to end, and you review all of the steps that you took in that opportunity, and you review what went well, and you review what could have gone better. The goal of a retro is essentially for you to learn, just like we talked about in our lesson on preparing for your QBR, right? You want to understand when you win an opportunity, why did you win? When you lose an opportunity, why did you lose? So a retrospective is a formalized way of doing that, and these are incredibly valuable and not enough sales. People are doing retrospectives to understand why an opportunity was won or lost. So let's walk you through how to do this step by step. Step one, I want you to pick a recently closed opportunity. It doesn't matter if it was won or lost. Any recently closed opportunity will do. Step two, map out the opportunity from beginning to end, this is a really important step. You need to map this opportunity visually from the very first contact, the first time you talk to somebody about it, through the discovery calls, through the demos, the technical calls, the security reviews, the business case, any other stakeholder it calls all the way through legal contract closure, you need to map out every step, and then I want you to write down all of the individuals from your team and theirs that were involved in every step, who were on these calls. And it's especially important that you think internally. Was it you, your se, your SDR, your CSM, your renewals manager, your manager, your product lead, everyone involved, write them all down then and Oh also, make note and screenshot all of the communications that went back and forth. Did you send an email? Did you make a call? Did you record that call? Put the link. You really want this to be a full archival record of the entire opportunity. Then I want you to set up a 45 minute call. Typically, it's about 45 minutes, and invite everyone internally. Don't invite the prospect. Invite everyone internally that was involved from beginning to end. Your se, SDR, you know, manager, CSM, etc. Then I want you to hold the retrospective. Oh, and by the way, in this study, in your study guide, I've given you an invite template that you can use to invite people to to a deal retro. So then you're actually going to hold the retrospective. You're going to open the call by reviewing the opportunity. So set the stage, give the context, walk through the deal chronologically from the initial contact to the final result, review whether the deal was won or lost, discuss any key touch points, Discovery calls, demos, presentation, business case, communication, introduce who all was involved internally, hopefully they're on the call. And then if time allows, have each person on the call explain their role and what they did very briefly, very succinctly, then you're going to actually start the retrospective exercise right up until now, you've just been reviewing everything that happened that's that's just reporting the news, right? But you're setting the context. Now you're going to actually hold the retrospective exercise. You should designate a note taker, someone to write down any ideas that come up, or you can use, you know, something like, something like an online whiteboard or visual collaboration space to kind of collect all of these ideas, give the team some dedicated time to brainstorm, make sure that they are you know, that they know this is a safe space to write down anything that they're feeling about the opportunity, and the first thing you're going to do is review what went well. So give some time to review what went well, so that they can write all these down and answer questions like, what was the key factor that led to the win? How did you differentiate yourself from your competition? Was there specific messaging or demo tactic that resonated with the prospect? How did you engage with the decision makers and at what stage, what steps led to the most momentum in the deal? What were the things that you did to effectively build your champion you want to be answering? Questions like that, and this will be in your study guide, so that you can understand like, What specifically can we learn from this once you've had time to put down ideas, organize them into groups or trends, and then discuss them as a group, and then review any action strategies or decisions that are repeatable, that you can leverage in future opportunities. Next, you're going to talk about what could have gone better again. Give the time the team dedicated time to brainstorm this, to ideate, to collect ideas for this one, it might actually be valuable to collect ideas anonymously, if you can, if you have a mechanism for doing so because some people might be afraid to speak up about things that didn't go so hot, right? They don't want to look like they're pointing fingers or blaming. And by the way, don't point fingers or blame, right? A retrospective is not about you or me. There's no such thing as you should have done this better. I should have done this better. A retrospective is all about we, collectively, we as a team. What should we have done differently to make this work? And that's why I like to call it a retrospective and not a post mortem. You'll hear these called post mortems. I hate that term. I think that's a really stupid term to use for something because it's like you're automatically going in with something went wrong, and we need to figure out whose fault it was absolutely not. These are meant to be constructive meetings that help you learn for the future. When you are talking about what went wrong and what could be done better. You need to be thinking about a few questions. One, did you engage the right stakeholders at the right time? Did you tailor your messaging to the prospects decision criteria? Did you lose to a competitor, and if so, which competitor and why was there a misalignment between your solution and their pain points, and then, were there any red flags or objections that they raised that you felt you weren't able to address properly once you've had time to put down ideas, discuss them as a group, identify any Internal obstacles, missed opportunities, challenges that impacted the customer or the outcome, and make sure, again, that you're learning from these losses. You're using them to glean insights to improve your future deals. It's not about beating yourself up over past mistakes after you've discussed what went well and what could have gone better. Make sure that you're discussing actionable next steps. So as a group, you should be summarizing the key lessons learned. You should be outlining how they'll be applied to future opportunities, any practices or tactics that should be scaled. And the most important thing here is to make sure that everybody leaves with a clear action next step on how to enhance future sales efforts. Remember, a successful retrospective is honest. It's constructive. It focuses on actionable, actionable improvements. Once the retrospective is over, you want to share all of the insights that you gleaned with the wider team. So even for people that were not in that retrospective, you should be sharing with the wider team what you discussed as a group, what actions you landed on to improve future deals. Cool. The other thing that I really haven't touched on here, but should be included in a retro, and this might even be like a third exercise that you do is, how did you work together as an internal group? So we talked about like, what went well with the deal, what didn't go well with the deal. Make sure that you're also including what went well with us. How well did we work together? How what were the friction points that we raised? Were we struggling to communicate? Were we struggling to identify who was responsible, accountable, consulted, informed on different areas of the deal? Were we late to things? Were we prepared for things? Make sure that you know how you can better work together as a group moving forward as well. All right, now it's your turn for today's assignment. You are going to conduct retrospective calls on two of your recent deals, a deal that you won and a deal that you lost. So analyze both deals using the framework that we covered, what went well, what can be improved, what you should keep doing, what you should stop doing, how your team worked together, and afterwards, share your finding with your manager, your larger team. It can be good to work with a peer who's done one of these retrospectives before. Maybe that's your mentor, manager, new hire buddy, but someone on your team that's done that, and of course, your study guide is going to walk you through this. And. Detail, and that is it for today's lesson on the daily quota. Thank you for listening, and we'll see you next time you.