Lessons Learned on Leading Technical Product Organizations

Amit Kumar Gupta
4 min readMay 16, 2020

I’ve had the privilege to work with some wonderful people. Here are a few lessons I’ve learned, specifically from working with and observing the impact of senior leaders and executives of technical product organizations. In truth, many of the challenges associated with leading a large group of people towards a shared set of goals are universal, and hopefully resonate with people outside of the software industry or even the business world.

Use Your Product

If you want to build a customer-centric product and engineering organization, use your product like a customer would. Hold your product to a high bar for user experience and give your team direct feedback when it doesn’t meet your bar. You can tell your organization to care about customer experience, but actions speak louder than words. When people see senior leaders and executives use the things they built, they respond.

Time or Scope, Pick One

If you want to release a product on a fixed date, you have to be okay with cutting scope. If you want to release a product with a fixed scope, you have to be okay with pushing timelines.

You will make plans, and have targets, that’s all good. As you approach a release date, you will inevitably discover some intended scope that’s at risk of delivery. If you think you can rush to get all the scope in on time, you’re picking time over scope — you just might not realize it because you’re not stopping to think about what scope you’re cutting. It will likely be some unarticulated requirement, like quality, cohesion, documentation, or some other blind spot.

There’s no inherent right answer when trading off time vs. scope, but you’re better off when you intuitively understand that there’s always a trade-off. Leaders especially need to understand the global calculus of incrementally adding the N+1ᵗʰ feature to a release at the cost of delaying the N features that are already ready to ship, when the N+1 feature team sees only the incremental value.

Quality is Everyone’s Responsibility

Quality is not something you bolt on afterwards. Quality is not a task a manager can assign. If you want a quality product, hold everyone responsible for quality.

Get Outside the Building

It’s easy to become deeply engaged with your product and your organization. This is good, but too much leads to tunnel vision and living in a bubble. Leaders especially must understand the much bigger picture: how you fit into the wider world and how the wider world sees you. Chances are, most of the world has no idea who you are; it’s healthy to remind yourself of this from time to time.

You especially need to get outside the building to build partnerships. It’s very hard work. Progress is very non-linear. Internal influence is hard to build, external influence is even harder. If you’re a leader, this hard job is yours.

The Power of Storytelling

Narrative and storytelling are deeply powerful. If you’re an executive leader, hone this skill. This one is worth stepping back and thinking about for a bit. A brief sidebar…

Think about how much time we spend reading and watching stories.

Think about how much more we understand about history through literature than through an enumeration of historical factoids.

Think about how much mythology and parables have shaped every society.

We aren’t machines; stories are able to convey more truth to people than facts. If you’re a leader of a group, the stories you tell define the shared history and identity of the group you lead, and they define the future that doesn’t exist yet that you’re all working together to build…

So tell stories. Spend the time to make them compelling. (Whatever you do, don’t substitute vision and storytelling with an enumeration of features — no one really cares about that, and if they do, they can SELECT * FROM Jira.)

Embrace Change

If you work in tech, especially software, change is going to happen especially fast. This industry is driven as much by fashion and tribalism as it is by true technological and scientific progress. Change in tech might not be so fast as to be seasonal, but it’s probably faster than you’d like if you’re not prepared to embrace it. The thing you’re working on will probably become obsolete. Your long-term mission should endure, but expect your tools and technology to change. If they don’t, fine; if they do, embrace it.

Be Kind

Working in tech can be stressful. There’s competition. There’s politics. There’s burnout. At the end of the day, tech is just tech. People matter more. Always be kind.