Sharing Sales Fails: How to Hold an Effective Postmortem

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Claire Murdough
Claire Murdough



Ever get a terrible feeling in the pit of your stomach when you remember a deal you just lost? It’s only a matter of time before the “If only…” thoughts start bubbling up.


If only I’d just called sooner. If only we’d had this feature at the time. If only I’d been less pushy. If only [insert detail] -- then we would have won.

These feelings are enough to drive anyone mad. But what if you could funnel those frustrations and worries into something proactive? Something that actually helps you fear losses less and become a better seller for it?

Enter the sales postmortem.

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What is a postmortem?

A postmortem is a meeting held at the end of a project, launch, or activity. The goal of these meetings is to reflect and talk candidly about what went well and what didn’t go well during a given project. Postmortems offer the unique opportunity to gather perspective and information that can be used to avoid making the same missteps down the road.

4 Benefits of Holding Postmortems

Postmortems have several benefits. Beyond giving your projects a natural and thoughtful end, they also:

  1. Encourage learning based on exploration rather than blame.
  2. Equip teams with valuable knowledge and experience that they can use to avoid future losses.
  3. Cultivate cross-team communication between teams in and outside of sales.
  4. Act as a reminder that there are many important pieces on a chessboard. When a sales team loses a deal, lots of teams are involved in different ways and problem-solving should be tackled by many minds, not few.

And though it might sound scary to discuss a failure or a loss, postmortems keep teams honest, hungry for improvement, and open to sharing mistakes as a way to collectively learn.

Postmortems have been incredibly helpful in creating a strong, honest selling culture at HelloSign. Here’s how you can hold your first effective sales postmortem.

The 5 Steps to Holding a Successful Sales Postmortem

1) Commit to a date

At HelloSign, planning for a postmortem starts as soon as we map out a project. During activity planning, we’ll earmark a line item for a postmortem to be held at the end of any important activity or project. For less structured things -- like unexpected lost deals -- we have impromptu postmortems, though these have become built into our system and are pretty expected by now.

A natural point to talk about when to have a postmortem on a sales team might be when you’re creating your strategy -- both big-picture strategy and strategy for a specific deal. Then, commit to holding the postmortem a certain amount of time after a deal closes -- for example, holding postmortems no later than a week after a lost or won deal ensures the details are still fresh in everyone’s minds.

2) Determine the structure and share the rules

Next you’ll want to plan out the structure of the postmortem. This includes figuring out how to frame the meeting and what questions or concerns you’ll go over. A few popular questions to cover in a postmortem are:

  • What went well?
  • What didn’t go well?
  • Based on this experience, is there anything we should stop doing?
  • Based on this experience, is there anything we should start doing?
  • Is there anything we underestimated?
  • Is there anything we overestimated?

Or you can simply section the meeting out into “The Good,” “The Bad,” and “The Ugly.”

The structuring step is also a great time to determine who will run the meeting and what their role will be. Assign a person to run the meeting -- the “keeper of the postmortem.” This person will be responsible for keeping the meeting on track and adhering to the rules set forth. It should be someone who is intimately familiar with the details of the project or the deal, but it doesn’t necessarily need to be the star player in the project. Everyone involved should be aware of the leader and their role and agree to respect the rules in advance.

Pro tip: Planning is all for nothing if you don’t share transparently with involved members early on. If it seems like over-preparation, it shouldn’t. Most people need to be introduced to an idea early on in order to warm up to it. People won’t be honest if they don’t feel they can be. Make sure to share the purpose, the rules, and the expectations with everyone involved prior to inviting everyone into the meeting room.

3) Align on the facts

Consider the next step the “homework” portion of a postmortem. Before you kick off the meeting, ask everyone to think about and come prepared to share the facts about their involvement in the deal or project.

Fact-based alignment helps guide a conversation based on reality rather than bias. Without it, you’re pulling in all sorts of varied perspectives that may or may not be accurate. You don’t have to agree on everything (in fact, you likely won’t), but you do need to agree on the bare-bones facts.

4) Convene and dig deep

The discussion portion of the postmortem has arrived! After preparing, sharing, and aligning, you’re finally ready to meet with all involved individuals to talk candidly about the project. Remember that you already planned out the structure earlier, so you can simply follow those guidelines during the meeting.

A few extra tips here:

  • Encourage follow-up questions. These tend to get to the meat of an issue more than a single or exploratory question.
  • Silence isn’t always bad. If people aren’t contributing, don’t get nervous and assume the meeting is a failure. Try offering up a specific example, phrasing the question differently, or asking if people would rather write down answers anonymously to start out with.
  • Remember the goal. The easiest postmortem in the world is one where only vanity errors are addressed. It’s a bit like circling all the micro copy-edits on an essay without critically assessing the framework or structure of the content. While it might be easier, it’s also less effective in testing the integrity of the piece. Avoid nitpicking in favor of surfacing things that are less obvious, focusing on the strategic health of a team, etc.

5) Digest and disseminate your findings

At HelloSign, once we hold a postmortem with those directly involved, we often share our learnings to a wider audience. This can happen at our weekly company meeting or during meetings with relevant departments.

This transparency encourages a blameless environment from the top down and also doubles postmortems’ value by presenting an opportunity to update a wider audience with important information. It’s also a way to strengthen your culture -- if an employee can stand at the head of a room filled with co-workers and talk about a “failure” without fear of judgment, you know you’ve reached a special place of psychological safety.

4 Bonus Tips For a Successful Postmortem

1) Time box the meeting.

There’s only so long you can talk about something before the conversation becomes stale or circuitous. Save yourself (and your team) the headache by allotting a certain amount of time for your postmortem. An hour might be the magic number. An hour and a half might do you better. You’ll begin to understand the right length as you hold more postmortems.

2) Name it.

There’s a reason history’s most memorable events have powerful names. It’s in the name that events of great importance can be quickly recalled without needing a huge long summary. So try naming a big sales loss after something. Beyond making it easier to remember, it has the added benefit of minimizing the importance of one loss and building a coherent picture of evolving sales practices at your company.

3) Don’t expect perfection.

Defensiveness. Resistance. Offensiveness. These are emotions that will most certainly show up in most postmortems. Why? Because we’re all human and it can hurt to remember something that brings up feelings of frustration, shame, or embarrassment. Self-identifying weaknesses and mistakes is an excellent way to grow, but it’s not always easy. Don’t expect robot-level perfection during these meetings.

4) Wins deserve postmortems, too.

You can learn just as much from a win as you can from a loss. It’s worth encouraging the postmortem culture for most deals, not just losses.

It’s important to note that postmortems are what you make them. When you put real effort into the planning and execution and make it a priority to encourage honesty and candor, you’ll get all sorts of insights that would have otherwise stayed buried. Give yourself -- and your team -- the benefit of retrospection and consider hosting your first one for your next lost deal.

HubSpot CRM

Topics: Win-Loss Review
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