How to always win, even from deals you lost

Three steps to implement a tight and structured win/loss analysis program that generates usable sales, product, marketing, and strategy insights.

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Your sales team has been working hard on two particular opportunities. The first one comes back with a signed contract. There’s a sigh of relief, and after the celebratory gong it’s on to the next. 

For the second, instead of a signed contract, you get a rejection email . You lost to a competitor. There’s a sigh of annoyance, and after sending a hail mary to see if the deal can be saved, you move on.

Sound familiar? Of course it does. 53% of opportunities are lost1.

But if you’re just moving onto the next opportunity without having a framework to review and learn, you’re always going to be a step behind.

In this post, I’m going to walk through three steps to learn and improve with a simple win/loss analysis program. With this process, you’ll:

  • win more deals

  • drive higher average contract values

  • shorten your sales cycle 

  • improve your positioning and marketing

  • improve your forecasting ability

  • better understand and react to the market


What is a win/loss analysis program? 

The goal of win/loss analysis is to understand why an opportunity was closed and passing those insights back into the business. These insights can feed into product development, improve the sales and marketing process, and reshape business strategy.

From both won and lost opportunities, you’ll want to understand:

  • Why they chose you, or chose an alternative solution

  • What they liked / didn’t like about the sales process

  • How they think about the market, your competitors, and your product

  • What their buying process was like

  • How they think about the value your product is delivering

  • What’s going on in their business

It’s key that someone other than sales - preferably a product marketer - manages the win/loss program. A product marketer should be skilled at spotting patterns at different levels and thinking through to first- and second-order impacts.

How do I set up a process?

I’ve detailed three stages to think through when building a useful win/loss process, focusing on high-volume data, objective research, and utilizing insights.

1: Capture information in your CRM

You’ll want to ensure every opportunity has completed, mandatory fields at time of close that ask the rep to enter their understanding of why the deal did or didn’t progress.

These don’t have to be difficult, clunky, or overbearing - but they do need to be communicated with the common goal in mind: to increase the number of deals that we win as a business. You might feel some pushback from sales reps who think you’re evaluating them, or from CSMs who want to protect their relationship with the customer - so make sure to build understanding and trust in the process.

Hopefully over time, your throughput of opportunities will begin to provide some insight at a statistically-significant scale, helping you be more confident in the actions you’ll take with that data.

Win/Loss reason code fields

  • Close reason - dropdown.

    • Win reasons. Try to distill the key point of influence that motivated a buyer to make the purchase decision. Your reasons should represent the above-and-beyond reasons, and should be worded as such. Avoid using single word reasons like ‘feature’ or ‘price’, and try to capture the specific sentiments that led to the win.

      • High feature fit

      • Bargain price

      • Beat competitor propositions

      • Highly motivated buyer

      • Excellent sales skill

      • Confident social proof

      • Positive brand affinity

      • No single reason

      • Other

    • Loss reasons. Depersonalize loss reasons from the rep and place emphasis on the points of failure in the sales process and the prospect’s evaluation. These will encourage reps to be more specific and less defensive.

      • Sales process miss

      • Lack of urgency

      • Lack of authority

      • Lack of expertise - i.e. prospect lacks knowledge

      • Deprioritized - lack of internal bandwidth

      • Predetermined decision - not a real opportunity

      • Poor product understanding

      • Poor brand perception

      • High switching costs

      • Poor qualification

      • Wrong target

      • No budget

      • Insufficient budget

  • Close reason note - free text field. Encourage reps to leave full sentences that explain their thoughts on why the win/loss reason was selected.

  • Closed next steps - checkboxes. Ask the rep to select what should happen to the rep next. Evaluate this to see whether you’re able to reignite opps later on, burning opps completely, or ending conversations in good standing.

    • Handover to CSM - set a task for CSM

    • AE to revisit - set a task for an AE to reconnect, as there may be another sales opportunity soon

    • BDR to recycle - set a task for a BDR to reconnect, as the contact should be nurtured

    Within this section, ask reps to check whether prospects are:

    • Friendly, good to engage - okay for CSMs / product marketers / etc to follow up with

    • Hostile, do not engage - remove from sales queues and mark as do not contact

  • Lost opp, prospect next step - dropdown. Try to capture what the next step for the prospect in their journey is. Use this to rethink objection handling, the discovery process, and positioning against alternative solutions.

    • No change

    • Renew/re-engage current provider

    • Switch to competitor

    • Search still underway

    • Other

These four fields will help you understand why an opportunity closed, what should happen next, and what the prospect is doing next.

Evaluating these regularly, and asking follow-up questions to reps, can give you some really powerful insights to adjust your processes and get ahead to ensure other deals don’t slip too.

Having an ‘other’ field for the win/loss reasons allows you to regularly review other reasons and see if they need to be included in your main list, or if they are just anomalies.

2: Create a win/loss research interview program

Whatever objections sales or success have, it’s really imperative that prospects are engaged for objective research by an impartial, non-sales team member.

This is where you can get really juicy details, hear how customers think about the world, and better understand their mindset.

You’ll capture key snippets to help improve marketing conversion rates, elements to dial down in the sales process, and small product wins that could have a huge impact on conversion.

Automate and streamline it as much as possible to remove resource, but don’t let this valuable source of insight get deprioritized. Your hit rate of calls booked is likely to be around 30%.

Choose your audience

If you’re capturing CRM data as above, exclude hostile prospects - and you may want to skip prospects where the AE will re-engage within a certain timeframe.

Hopefully you're tagging stakeholders in your CRM against a persona, so you can focus automated outreach on champions to provide a continual stream of general insights. You can also do manual outreach to learn from other stakeholders as and when needed.

Set up your outreach

Using your CRM or email marketing platform, set up a low-touch sequence of personal, friendly outreach emails set over roughly six weeks from the close date.

Positioning win/loss calls as strict research activities can work well. In those emails, explain that you’re:

  • Working with the product research team

  • Not looking to sell

  • Looking to learn from their expertise

  • Able to speak at a time that suits them

You may want to incentivize the conversation to catch those that need some motivation - I’ve found offering the choice between a personal gift-card or a donation to charity works well.

Schedule meetings using Calendly or just good ol’ calendar back-and-forth. Ask for both a phone number (in case they don’t show up), as well as confirm the meeting will be via Zoom/Google Hangouts/etc.

Don’t forget to plug in some reminder emails 24hrs and 1hr before the call, providing any links again.

Have the call

Ask if they’re comfortable for you to record the call so you can take notes later - most will agree.

Have a set list of interview questions arranged by topic, but don’t stick to them rigidly. Ensure the call is fluid, and that it feels like a conversation. Offer pauses and allow the interviewee to fill in the gaps. Use open-ended questions. Ask them to walkthrough from end-to-end, to provide rough timings, to add color and personal details to help bring their full experience to life.

You’ll want to understand key areas like:

  • Their perception of the product and company

  • Their experience in the sales/marketing process

  • Their interpretation of your products value and pricing

  • Their thoughts on the competitor landscape

  • Their general experiences in their role and what matters to them

During the call, make quick notes on key things that stood out, so you have a list of areas to dig into using the recording after.

Create a summary for each call

These summaries will be useful for either CSMs or for AEs/BDRs in the future when they re-engage. Make key notes on:

  • Their profile - their persona, segmentation, jobs to be done

  • Their behavior - process details, actions they took

  • Their fit - their thoughts on the product and experience, competitors, etc.

  • Their pain - their business challenges they were looking to solve, other problems they experience, etc

You’ll want to tag the summaries with key points from the journey, so you can pull them up later when reviewing personas, buyer journey, product plans, etc.

Interpret each research call as objectively as you can. You’re not looking to prove or disprove things at this stage, for fear of biasing your interpretation.

3: Collate, share, discuss, utilise

The value of both win/loss tactics is not achieved by docs just sitting somewhere in a CRM or in a folder, never to be read again.

Make sure these insights are fuelling action and satisfying curiosity across the business.

Democratize access

  • Have a CRM dashboard that summarises key win/loss CRM fields

  • Create a single source-of-knowledge in your intranet for all win/loss interview notes

  • Post every win/loss CRM update and published summary to a Slack channel, and promote it every month.

Proactively share

  • Share interesting tidbits and new learnings in your team updates

  • Run a regular lunch-and-learn session that highlights interesting stories - especially if you can involve the sales rep to give their side of the story

Package up your insights

  • Create monthly/quarterly reports using CRM data and analyze to help support sales, product, and marketing tactics and strategy

  • Include win/loss updates in your Voice of Customer reports, sharing them widely to help teams feel closer to the customer

  • When you have significant enough insight into a particular themes, create a focused pack of evidence and start to build buy-in to overcome challenges or innovate further

Utilize

  • Work with product teams to use win/loss insights in product strategy

  • Use your insights in quarterly planning for sales and marketing to improve processes, tweak messaging, or try something different

  • Gain exec buy-in as a sponsor for your win/loss efforts and encourage them to bring win/loss summaries into leadership meetings

  • Create win/loss review segments in your regular sales meetings and work with a rep to explain how the deal went, what the outcome was, and invite feedback and suggestions on how to replicate or avoid certain aspects

  • Pull up summaries and reports when working on regular updates to personas, buyer journey docs, positioning and messaging, product roadmaps - they are artifacts and evidence that fuel your iteration in those processes

Every opportunity is a learning opportunity

You’re going to lose ~50% of your deals anyway, so make sure you take something positive away from them.

The win/loss streams of work detailed in this post give you the best of both worlds: CRM data at scale to support sales enablement and further investigation, objective research interviews to step back and look at the bigger picture, and ensuring insights are used across the business.

The sales and marketing process is - at its heart - an assumption-testing exercise. Where better to learn what’s needed to iterate, than from your wins and losses?


Thanks for reading! Let me know what you thought - find me on Twitter and LinkedIn.

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