Gold as an investment

Why your enterprise product strategy might not be working

Oct 1, 2022

You’ve got the strategy, you’ve got the buy-in and you’ve even got the resources. On paper, everything should be working. I’ve worked in Enterprise Product Design for almost 5 years and worked with hundreds of people as part of Design Education Programs. Here are four reasons your approach might not be working:

Chances are if you work on an enterprise product team you have a meeting on your calendar with the word alignment in the subject. It is one of the biggest obstacles to overcome in any corporate environment. Organizational design is its own specialty and I’m not going to pretend I’m a specialist but ultimately — the more dots that need connecting, the more problems that arise. In an aligned organization, those dots are connected, or at the very least the dots have visibility of each other.

Many black ink dots on a white page

Photo by Nagy Arnold on Unsplash

What is lazy alignment? To no one’s surprise; Emails, Instant Messages Meetings are the Modus Operandi of many organizations. They are very easy to send or schedule. We all know that they can become productivity suckers. Lazy Alignment, however, is the idea that just because you have sent a message or had a meeting about a topic then there is cross-functional alignment or visibility. This could be true in organizations that have focused priorities or fewer dots that need connecting. From my experience, In large organizations with a magnitude of priorities, cross-functional teams, and business units — misalignment is often more common than not. True alignment requires transparency, intention, and action.

“Make your intentions clear. The universe does not respond well to uncertainty” Joe Duncan, Before 5am

Without transparency, intention and action — ambiguity and a “throw it over the fence” mentality can fill the void, resulting in circular meetings, finger-pointing, and that well-oiled product machine will trundle to deliver on any product strategy.

How To Avoid Lazy Alignment? I won’t pretend that I have all answers. I do have some themes and frameworks that have worked for me in organizations that I’ve worked in.

  • OKRs (Objectives and Key Results) — When used correctly, these can help ensure efforts are focused on the same issues across the organization. The ability to recalibrate cross-functionally (to course correct) and be aspirational are core tenets of OKRS that I don’t believe should be compromised. However, like any framework — it’s not a one size fits all solution.
  • Problems Over Solutions — Spend time talking about the problem you are solving. As someone that has facilitated many alignment workshops in complex enterprise product teams — I guarantee you there is typically misalignment on what the overarching goal is.
  • Share Early Often — As a self-proclaimed perfectionist, early in my design career, I realized that for me to be successful I had to be ok with sharing “unpolished” work. The earlier you can share an idea, design, drafted document (whatever it might be)— the more likely you can catch misalignment. This is critically important for those in leadership roles and a muscle that requires flexing.

INNOVATION. Part of the lexicon for many tech companies and product teams. Earlier in my career, I worked as part of a design team that was part of a 0–1 team that‘s purpose was to look at tech innovations and define product opportunities for the fintech space. One particular project I worked on was exploring AR/VR and how it might be used to improve a particular aspect of a workflow in the credit card space. During a research session with a User, I was talking to them about some of their problems. A memorable takeaway from this conversation and a theme we encountered in many projects was that many people didn’t want a radically overhauled “innovative” product, in many cases, they wanted better workflows, simpler product experiences, and reliability. Or in one memorable case — “forget that headset, give me a better spreadsheet”.

Innovation often means something different to your Users. I believe there is an important balancing act in defining your product strategy between new product “innovations” and iterations based upon insights from actual Users. (Later in this article I’ll talk about how top-down product strategy is failing you). I believe this is particularly pertinent to companies or organizations that are in Feature Factory mode. If you’re not sure if that’s you, I highly recommend checking out John Cutler’s article 12 Signs You’re Working In A Feature Factory. I’ve observed three common behaviors that you can encourage to help create a culture of iteration over innovation.

  1. Measuring User Success — Take the time to understand what you’re building and the impact that it’s having on a User. This can be particularly hard to implement in any product landscape for a plethora of reasons, however, I believe if User outcomes are at the heart of your product strategy then success should shift away from pure delivery and investment in your User’s Experience.
  2. Sweat The Small Stuff — I don’t believe there’s been a more detrimental term to the quality of product experience than Minimal Viable Product (MVP). While I could write a whole article on MVPs (maybe I will?). I believe it’s particularly dangerous in an enterprise product environment. Why? From my experience, there’s an engrained misunderstanding that enterprise Users don’t care about experience. I believe this stems from the early days of many enterprise products being Command-Line based, workflows/ Users being technically-natured, and often the lack of competition. As someone that has interviewed many enterprise customers in my career, I can tell you that they very much care about the small stuff. I speculate that because the purchasing/renewal process is different than the consumer space it can mean there is a lag between User dissatisfaction and that dissatisfaction showing up as an impact on the bottom line. No matter how much “innovation” you ship, if you don’t have a culture of sweating the small stuff your product and underlying strategy will eventually fail.
  3. Reflection Retrospectives — The most successful teams that I’ve worked with have a strong culture of reflection. This often showed up commonly in the form of retrospectives but reflecting on the process, strategy, and product quality was a strong part of the everyday culture.

Photo by Riho Kitagawa on Unsplash

When I think of Iteration, I can’t help but think about Kintsugi, also known as “Golden repair” — a centuries-old Japanese art form. I can’t help but think of this in the context of product development organizations and what many products would be like if we chased iteration over innovation. I will leave you with the definition from Wikipedia for you to infer your own opinion:

“the Japanese art of repairing broken pottery by mending the areas of breakage with lacquer dusted or mixed with powdered gold, silver, or platinum; [..] As a philosophy, it treats breakage and repair as part of the history of an object, rather than something to disguise

(Source: Wikipedia)

Unlike many consumer products, enterprise products often have a larger spectrum of viewpoints to talk to during the discovery phase of product development. With Consumer products, usually, the person buying your product is the same person that would be using it. With Enterprise products, this can get tricky as there are often many other people involved at different stages of the product journey. Everybody from buyers, end-users, admins, executives and departments— often these are all different types of people who can have entirely different needs. Your ability to decipher between the different stages of a product journey and recruit the necessary representation to evaluate the experience at a particular phase of that journey can not only be an extremely difficult skill to build but often requires broader organizational education and investment to be done successfully.

Photo by Volodymyr Hryshchenko on Unsplash

Some pitfalls to watch out for:

Seek Users not Buyers — Often the person buying the product is the easiest touchpoint because their contact details sit in your sales platform and/or they have an existing relationship with your company. However, more often than not, that Buyer may be far removed from the product and day-to-day tasks that you want to dig into. The example I use with my team is:

Think about a tool that you use at work every day, an example might be your email client. Like any product we use regularly, I bet there are frustrations, workarounds, or insights that would be valuable to the people that make that product. However, often the only relationship that the company building the product has is with a person/team in your company that is likely far removed from you.

We’ve helped enable our teams to get easier access to Users by Investing in tools that allow you to recruit within the product, building out databases of users that are interested in talking with us, and building deeper relationships with companies.

Build Common Definitions — Coming from a predominately B2C background, one of my biggest observations around this subject was that when someone would ask a simple question like “Who is our User?” there would often be 10 minutes of confusion. Not because we didn’t have an answer but often we’d all have slightly nuanced names or start to have a conversation with terms like “the end-end User is and the end-User is”. As a, designer I used to have an adverse reaction to artifacts such as Personas but I’ve come to terms with the fact that they can be incredibly useful for enabling teams to have a common definition of a User that can help increase efficiency and understanding when collaborating in highly distributed product teams. If you would like a much more eloquently written stance on the benefits of personas — I highly recommend checking out my colleague Lindsey M. West Wallace’s article: Personas — training wheels.

In my previous article (Don’t Ship Features, Solve Problems), I wrote about the dangers of feature-based solutioning and why companies should use customer insights research to help guide decision-making. In addition to these dangers, I’ve been reflecting on three other reasons your enterprise product strategy might feel disconnected.

Photo by Michael Dziedzic on Unsplash

Analysts are not your Users— For many enterprise-focused product teams, there is a coveted position and that is the top right of an analyst’s market position. Analyst sentiment is often used to dictate an approach to a product roadmap. While Analyst insight and understanding of market-positioning are important, I often see Analyst sentiment being misconstrued as actual needs from Users. It’s important to understand that there is an inherent bias in Analyst reports in that their business model is completely centered around the self-interests of large vendors than towards the actual consumers or Users of your product.

Sales Support are not your Users — It’s likely if you’re selling in the B2B space that you have a sales and support team. These teams are often integral interaction points for customers to get demos, and support; to ultimately be successful with the product that they have purchased. They can often be an incredibly valuable source of insights from customers. However, it’s important to recognize that these insights have been filtered through layers of bias.

Executives are not your Users — In many organizations — objectives, priorities, and strategy are defined at the top layers of the organization. There is nothing inherently wrong with this. However in this model, what can happen is that teams switch from a user outcome mindset to an output model because they have locked themselves into delivering a very specific roadmap based upon those trickled-down feature-based priorities. This is particularly dangerous territory if those feature-based priorities have not been built upon strong User Research. Melissa Perri puts it best in the article What Is Good Product Strategy :

Product Strategy is a system of achievable goals and visions that work together to align the team around desirable outcomes for both the business and your customers. Product Strategy emerges from experimentation towards a goal.

Ultimately top-down strategy that is not communicated in the right way can restrict customer feedback, serendipitous insights from research, and experimentation from every being executed. How your strategy is defined, and the way you work, should be a combination of top-down and bottom-up collaboration.

I’ve talked about four areas for why your Enterprise product strategy might not be working. Talking to peers this seems like it’s a problem across not just enterprise organizations but product delivery in many companies. When I think about the four areas outlined in this article:

  1. Lazy Alignment

2. Innovation Over Iteration

3. Building For The Wrong Person

4. Disconnected Strategy

When you dig beneath the surface, the problems and solutions for these are not on the surface very complex. Many of these in fact can be solved by talking to the right people at the right time. When this is in the context of product delivery organizations many factors can make these trivial items become multilayered challenges. Factors such as company culture, org structure, incentives, leadership, and process all play a huge part in the delivery of your product strategy. I do believe a lot of these problems can be solved by having strong UX Design Research capabilities embedded at all layers of your organization but what do you think?

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