Learning from the Past: A Sales Team's Guide to Post-Mortem Analysis

Today, I want to share a personal story.

Stefano, a former Engineering Manager at Boom, is a great manager and he was one of my peers during those years. Stefano taught me something that improved my sales leadership without even realising it.

Stefano was known to be the master of retrospective and post-mortem analysis.

His team would sit down at the end of each major release and look back at what they had accomplished.

He would deep dive into each part of the release, including the sprints, the bugs, the implementation, and everything in between.

These sessions were incredible. Everybody was engaged, asking questions, challenging each other and being so meticulous about what happened during the previous release.

They were analysing each detail with an incredible curiosity.

I had the pleasure of shadowing one of them, and I learned the power of post-mortem analysis.

It was an excellent coaching moment and an opportunity to build and strengthen their already great team culture.

A few days later, I realised that even if I was conducting a retrospective with my team, I wasn't doing it systematically with a post-mortem structure.

I would have 10-15 minute look-back sessions here and there, during sales meetings or quarterly business reviews.

However, I wasn't focusing on the past and diving deep into what happened. I was more inclined to forget the past and focus on the future.

As human beings, we often think that if something bad happened, we can leave it in the past. While this might be true for personal situations, in business, if something didn't go according to plan, it's important to revisit it and make necessary changes.

Therefore, inspired by Stefano and his team, I began implementing post-mortem analysis for my sales team.

It’s been a game-changer.

How do you run a post-mortem with your team?

I have implemented 12 moments throughout the year for my team and me to get together and conduct a post-mortem. Since we are on a monthly goal, each month is a learning opportunity for us.

We start by sitting together on the following Monday after the end of the month and hold a live session.

I would open a Miro Board with a template I built (grab it here) and start moderating the session, asking each team member to share their thoughts during an open-floor session.

We would then do a deep dive into the past month, trying to bucket the key facts into four quadrants.

  1. What did we do well?

  2. What should we do differently?

  3. What have we learned?

  4. What we do not understand?

Each quadrant is self-explanatory, but let me explain the things we usually place in them.

We analyse quantitative and qualitative KPIs, including conversion rates, win and loss rates, deal size, and deal cycle.

Additionally, we look at the number of activities, emails, calls, and meetings booked over time. For each team.

Next, we list all of these points on a board and track them month over month.

Finally, we place them into one of the four quadrants. Looking specifically at the results of the previous month.

Two quadrants deserve particular mention: “Things We Have Learned” and “What We Do Not Understand.”

Listing what we have learned is crucial for challenging ourselves and determining if the lessons are valuable.

Additionally, what we do not understand is essential to track. Sometimes, we cannot explain why a deal fell through or why our deal size has been reduced. Although we may find the reasons after some time, putting these issues in the fourth quadrant will make us think and work together to solve them.

The session is incredible.

We laugh while thinking back about some of the weirdest moments, but we also challenge ourselves by examining bad results.

We celebrate our wins and pat ourselves on the back if we have tried our best.

There is also a little recap at the end where we look at the board and write down the most important steps we are going to take forward. But post-mortem is not about the future, it is about the past.

Summary

Engineering teams after each release sit down and do a post-mortem. I found this not to be a common sales practice until I started doing it with my teams.

From a cognitive aspect, people tend to learn quicker and more effectively from past experiences therefore implementing a monthly, quarterly, and post-mortem has a massive benefit for your sales team.

In fact, as human beings, we tend to disqualify past experiences and move on. If the past wasn’t great, we don’t want to go back.

However, if you keep doing this you won’t learn, you will change and will potentially get some traction but the real learning comes from deep dive, analysis, questions and moments like the Post-Mortem analysis.

This Week's Action Step

If you haven't implemented anything like this, try to understand if it makes sense for you and your team to do so.

You can use this template to start scheduling your post-mortem moments, whether you choose to call them QBR, MBR, or something else.

Hopefully, it will have a positive and effective impact on your team.

Thanks for reading this far. See you next week!

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