Effective Legacy Product Management

At a Glance

How to gather customer feedback in legacy environments, including:

• Building feedback loops: How to create connections to users through site visits, proxies, and advisory boards

• Shortening feedback cycles: Strategies to make these feedback mechanisms happen more frequently

• Embracing imperfect information: Why sub-optimal feedback is still better than flying blind

Hey folks,

In the product management world, we're constantly told to get quick customer feedback. But what about those of us working with legacy systems, regulated industries, or on-premises deployments? The standard advice often falls flat when your software updates happen annually rather than daily.

This newsletter tackles the often-overlooked challenge of gathering meaningful customer feedback when traditional methods simply aren't available. I've spent years working with government agencies, healthcare organizations, and enterprise clients with legacy systems, and I've learned that getting customer insight is still possible; it just requires more creativity and persistence.

Let's explore some practical approaches that have worked for me and might help you bridge that feedback gap in environments where "ship fast, learn fast" isn't always an option. 

– Jeff

P.S. Mark your calendars for two upcoming events: Our free webinar "OKRs and Performance Management Metrics" on May 27, where I'll team up with Josh Seiden and Mastercard's Lynda McDonald to discuss measuring performance in customer-centric organizations. Also, for Spanish speakers, check out our "Certificado en Lean Product Discovery" program, which starts on June 4 (early bird pricing available until May 5).

Article: Effective Legacy Product Management

By now you've likely heard the various digital product development mantras of “move fast and break things” and “build, measure, learn,” and “ship, sense and respond.” These are, generally speaking, good, directional approaches to modern product development. They work well in environments where access to customers is robust, feedback is relatively easy to get, and deployment cycles can be shortened. But what if you work in a highly secure environment? Or, perhaps your products are installed on-premises rather than in the cloud? Or you simply work for an organization that is hesitant to make regular updates to their software infrastructure in short cycles? How do we build modern product management work into these environments?

Building feedback loops

As with any problem, let's start by figuring out the most important thing first. In the case of highly secure and on-premises software installations (think government, military, infrastructure construction, air traffic control, healthcare, etc.) continuous software updates delivered automatically as new code is released don't happen on their own. These deployments pass through lengthy vetting processes and are deployed in cycles that are measured in years more often than in months, weeks, or days. Our first challenge is just to build in feedback loops. Without a regular connection to the users and the usage of the systems we're building, it's hard to know if we're delivering value to our customers.

Site Visits

Perhaps the most obvious way to begin overcoming this lack of insight is to schedule site visits. As a vendor to these institutions, you should be able to, in theory, schedule site visits that allow you to meet with your users and watch them use your products in real time. These contextual visits should be a top priority for teams working in these situations. Observing your systems in use and asking clarifying questions in real time is a powerful way to understand consumption patterns and needs and the way in which your product is meeting those needs.

Proxies

Another option in these situations is to find proxies for the users you work with. Proxies are folks who have had these jobs in the past and no longer do that work anymore or don't do it with your clients. In these situations, you're working with subject matter experts (SME). These SMEs can give you a general sense of how these products are used and how what you're designing may meet current users' needs. You can find these folks on LinkedIn, in professional user groups, and at conferences at the very least.

Advisory Boards

A third option for getting feedback in these situations is to build an advisory board. We did this with our enterprise clients at a startup I worked at in the late 2010s. Every quarter, we'd recruit representatives from our biggest clients and meet with them on a monthly basis. These advisory board members agreed to provide us with candid feedback on our work and roadmap, among other things. In return they received discounts on our products, as well as previews of and influence over upcoming features.

Shortening feedback loops

Once we have these feedback loops in place, our next task is to make them happen more frequently. Shortening the time between feedback cycles ensures that, when our customers do upgrade to the new product, they are familiar with the coming changes and that the new features meet their expectations and needs in easy-to-use ways.

In my experience, if you can get quarterly site visits with a few of your customers that is often the best you can hope for. It will likely require some travel for you and members of your team, but the value you bring back makes any cost more than worth it. Start with annual or bi-annual visits, then increase frequency as customer trust grows.

Finding and speaking to proxies should be an ongoing process. Your teams should be continuously searching and recruiting proxies for short, live conversations either in person or online. This is likely your easiest source of information. Plus, the more frequently you can get feedback from folks who have done this work in the past, the better the options you show to your customer during your site visits become.

Finally, advisory boards can be expected to meet at least quarterly. However, depending on your relationship with these folks, getting them to meet monthly ensures your feedback loops are never longer than four weeks. In addition, ask them to be available for the occasional email-based question as part of your advisory board agreements.

Sub-optimal is better than nothing

These legacy and secure settings make building your sense-and-respond feedback loop difficult. They don't, however, mean that you can't get any feedback at all. Pushing for on-site visits and insight from proxies and advisory boards means that you're getting some information. That information may not be perfect and it may not always be from direct product users, but even sub-optimal information is better than no information.

What techniques have you used to get information about your work from customers in these situations?

What I’ve been up to

I went on holiday to Sardinia. It’s lovely and the people, food, and history continually surprised us (even if it did rain a bit). Honestly, old European alleys in the rain mean you run into some of the most surprising little stores, food shops, and bars you otherwise would’ve missed. 

On the work front, we have a free webinar coming up on May 27, 2025 about OKRs and Performance Management Metrics. This topic is so important because most organizations will set up their OKRs and then ignore how they measure, reward and promote their people. We’ll tackle this hard question with a special guest. Sign up for free here. 

I'm also excited to share our upcoming Spanish-language certification program: Certificado en Lean Product Discovery. This comprehensive workshop runs from June 4–25, 2025, with four live two-hour masterclass sessions (5–7pm CEST each Wednesday). 

Developed by Josh Seiden and myself, this course will be taught in Spanish by our certified training partners Carlos Iglesias (CEO of Runroom) and Laura Polls (Head of Experience Research at Runroom). The program provides practical frameworks for customer-centered product discovery, hypothesis validation, and evidence-based product creation. Early bird pricing of €750 is available until May 5th, with team discounts of 15–20% for groups. Learn more and register here.

We just completed another Train the Trainer session for our newest cohort of Certified Training Partners at Sense & Respond Learning (see pic below). We’re continuing to grow and would love to talk to you and your company becoming a training partner with us. Just hit reply to this email or head over to www.senseandrespond.co and fill out the interest form.

Watch, Listen, Read

Watch: The Last of Us Season 2 / Handmaids Tale Season 6 – Man, these shows are stressful, like “red wedding at Game of Thrones” stressful but it’s nice to have them both back.

Listen: Skeleta by Ghost – Love ‘em or hate ‘em, Ghost is fun and even better live. A new record likely means a new tour and it also likely means I’ll be there :-) 

Read: Greenlights by Matthew McConaughey – A funny, interesting, and occasionally enlightening autobiography that I’m listening to since it’s read by the author. Alright alright alright.

What’s new on the blog

How to create an OKR-based roadmap [VIDEO] - In this short video demonstration, I walk through how to build an effective OKR-based roadmap, starting with the Lean Strategy Canvas as a foundation. I cover the basics of Objectives and Key Results before diving into the roadmap section, providing a complete visual example that many of you have been requesting.

The Sardinia story: lessons in storytelling for product & business - My recent trip to Sardinia revealed how even knowledgeable experts can miss opportunities to connect with their audience when they only focus on facts and figures. I explore how using connective storytelling techniques ("therefore," "so," and "but," instead of just "then") transforms simple information into compelling narratives that engage audiences and bring meaning to your product presentations.