WHY ARE Retrospectives IMPORTANT?

There are three primary reasons for conducting Retrospectives:

  • allowing your customers to be heard
  • taking steps toward cultivating long-term loyal customers
  • agreeing upon the “sprint plan” that outlines what both sides are tasked with accomplishing ahead of the next scheduled retrospective

Routine Retrospectives provide the framework for you to check in on your customer in a scheduled way to understand what’s working and what’s not. Simple agendas for Retrospectives allow you to use the time to nurture the relationship and foster stronger relationships, which, in turn, foster greater loyalty. Incorporating simple agendas that focus on emotionally rewarding topics, rather than reviewing numbers (usage rates, ROI, etc.) can reap greater loyalty points in the long run. (Check out our friend Ed Power’s video on the science behind this approach.) And, finally, Retrospectives should result in agreement about the next set of  priorities and tasks for the subsequent sprint.


Retrospectives are typically conducted by Customer Success Managers; however, the methodology for conducting Retrospectives which affect your customers’ emotional connection to you and your product is an approach all customer-facing teams should know.


Retrospectives begin happening about a month after you have officially Launched your customer. They should then happen in regular intervals as your team deems appropriate. The frequency with which you conduct a Retrospective depends upon how customizable your solution is. However, Retrospectives should be conducted in regularly scheduled intervals, such as monthly or bi-monthly, and to coincide with the projected duration of your designed sprint cycle.

GUIDELINES FOR Retrospectives

In the agile world of Customer Success, Retrospectives are the preferred, iterative way of remaining close to your customer. SaaS customers find Retrospectives less intimidating than QBRs and, when conducted properly, the Retrospectives are more manageable, provide strong data points for business reviews (which should be conducted semi-annually), and are simply more effective in cultivating loyalty than just having traditional QBRs.

Here are some basic guidelines for incorporating Retrospectives into your Customer Success model:

  1. Schedule Retrospectives routinely. We recommend scheduling Retrospectives monthly as ½ hour meetings with simple agendas. Adjust the length and frequency according to your customers’ needs, and your designed sprint cycle.
  2. Use a simple 3-question format to each meeting:
    1. What should we continue or start doing?
    2. What should we stop doing?
    3. What are some ideas for the future?

This simple open-ended format allows for easy and honest conversation. It takes the focus off of the technology and opens up the discussion to look at process and culture as they impact value attainment and goal progress.

  1. Include as large a group of users and stakeholders as can collaborate and establish a consensus. Unlike a QBR, you want as much input about priorities and next steps as you can get. A large group is good, but make sure the group that convenes has the ability to build and establish a consensus within the account.
  2. Focus on process, rather than technology. By focusing on processes, you provide an opportunity for your customer to look more holistically at how they are doing reaching their desired goals. They will look at internal challenges, as well as your technology, in assessing their progress.
  3. Allow teams to vent. Usually what they will vent about isn’t a feature of your technology, but rather a challenge they are having with a process that may have more to do with internal processes, culture, or communication. By being a listener, and having a team of users present, your Retrospective provides them with an opportunity to understand the root causes for their inability to progress toward their desired goals. When customers vent during Retrospectives you have an opportunity to help them overcome a challenge, and that positions you as an advocate and trusted advisor. These opportunities are what build loyal customers.
  4. Appeal to your customer’s business and social needs. When your customers know, like and trust you and your solution, they are more likely to make an affective commitment and grow in their loyalty. (see and hear more about this at Ed Powers’ video, Optimizing Customer Success Through Neuroscience)
  5. Keep your promises. Whatever you and your customer decide to do moving forward from the Retrospective, make sure you follow through.
    Being a trustworthy resource is a key factor in customer loyalty.
  6. Set (or confirm) date and time for next Having a standing date and time, or calendaring the next meeting, affirms the value you place in these meetings and sets the expectation that you are accountable for all that was decided in the Retrospective.


Consider Retrospectives exercises in building customer loyalty, rather than analyzing Return on Investments. (There’s a place and time for that business agenda, but monthly Retrospectives should not get mired in the numbers.) Make it your goal to find concrete steps to take from each Retrospective that will help grow your customer’s trust, and therefore loyalty. Additionally, if we are not learning more about what works and doesn’t work within our customers’ unique environment at each Retrospective, then we need to revisit how we are conducting them. While all the steps that precede these regular meetings are vital to setting a customer up for success, these routine meetings are what build the long-time loyalty we want from our customers.

About the Author:

Haresh is the Chief Executive Officer and Co-Founder of Bolstra. Haresh is a veteran B2B SaaS industry executive having served in key roles with emphasis in product strategy, sales and marketing.


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