A few reflections on my first month leading a Product org

(Or the advice I wish someone had shared with me ahead of time)

July 21, 2017

I joined a startup, User Interviews, as the VP of Product in June of 2017. Coincidentally, I had also been reading Product Leadership by Martin Eriksson, Richard Banfield, and Nate Walkingshaw at the time. This fortuitous combination led to a lot of insightful self reflection as I was getting up to speed as the first dedicated Product hire at the company. In the spirit of Austin Kleon’s urge to “Show Your Work!” (which I also found inspiring) I wanted to document and share the lessons I’ve taken away from the experience thus far.

Immerse yourself in everything… but don’t try to do everything

To be effective in a Product role, you need to be able to consume a fire hose of information. You need to be able to take inputs from all possible areas — customers, prospects, design, engineering, sales, marketing, competitors, adjacent industries, consumer trends, etc. — and somehow connect the right dots to find the opportunities worth pursuing.

To be effective in a Product role, you need to be able to focus. You need to be deliberate about what the team is tackling at any given point in time and ruthlessly ignore distractions. You know your team is most effective when you’re all pulling in the same direction towards a specific, measurable goal.

This is why onboarding can be difficult for Product hires. I deliberately tried to expose myself to all parts of the business as quickly as possible. I wanted to know the fabric of the organization and how all the various threads connected. And don’t be mistaken, this was an effective approach. The challenge with this approach, however, is that you’re seeing a multitude of things for the first time with fresh eyes. For Product thinkers this inevitably means that you’re seeing opportunities everywhere you look and starting to be overwhelmed by your own ideation.

In order to avoid being paralyzed with ideas (and perhaps by how much work lays ahead), let me refer you to the next point.

Be opinionated… but flexible

Once you’re able to form relatively cohesive thoughts on the product — start sharing them. During my career, I’ve found that sharing your thoughts before they are “ready” is a great way to build a collaborative, trusting environment. Plus, c’mon, if you’re reading this then you’re familiar with the latest in design thinking, lean methodologies, and all of that. Rapid iteration is your friend, especially when it comes to your own emerging perspective on a product.

My approach to this was to start a document where I could store all my emerging opinions and ideas as I had them. The initial goal was to have a reference for myself. Pretty quickly, I was able to refine this into a somewhat coherent set of ideas that I could easily share with others, which I did.

This was uncomfortable. At that point, I had been at the company for less than two weeks in a role where I was being tasked with leading and building the Product function. I felt pressure to come across as impressive and make a good early impression. Despite that, I knew the benefits of establishing the right working style were more important than my ego. So I shared the document in all its rough draft glory with the co-founders with the following preface.

Disclaimer — I’m deliberately sharing an early and rough draft on my emerging product thoughts because it should accelerate our thinking and alignment here. There are undoubtedly bad ideas included below. That’s okay — just explain to me what I’m overlooking. The more debates we can have and items we can align on before any of these ideas go any further, the better.

My rationale for doing this was simple. I knew that the people who had dedicated themselves to building this company for the past 2 years were going to be the thought partners I needed. It was hugely helpful. They quickly pointed out dynamics I was overlooking, suggested alternatives that might be easier to pursue, shared customer feedback I hadn’t heard, and started adding their own thoughts to the document to give me a richer perspective on their thinking.

The alternative of arrogantly working in a silo to polish my nascent thoughts might have felt productive but would have ultimately backfired.

Me: “Here is a slick presentation of an idea I’ve overworked and I’m now presenting with unfounded confidence.”

Them: “Yea, we tried that 6 months ago. It was a complete flop.”

Don’t fall into that trap. Remember, you’re new. A learning curve is expected. Just be humble about it and do everything within your power to accelerate it.

And despite being new, you can still do the following.

Find ways to add value immediately… but not at the expense of longer term thinking

At an early stage company, simply being another pair of hands to do work is materially valuable. Leverage that. Identify ways to be helpful from the start. Maybe you take over testing the new feature that was already being developed. Or facilitate the logistics of an upcoming sales call. Or organize the customer feedback they’ve been collecting. Trust me — there is plenty you can do to be helpful that will be directly relevant to your role.

In my case, I took over some analytics that needed to be run, made introductions to people in my network who might be target customers, and made a pull request to add Google Tag Manager to the site. Nothing earth shattering but important tasks nonetheless.

That said, don’t lose sight of the fact you’re ultimate ability to add value hinges on big picture thinking. The roadmap you create and priorities you set are the levers that will move the organization forward in a significant way. Be deliberate about finding a balance and setting boundaries. You were brought in to establish for the vision for the product, not to be an intern.

Without an established vision, you’ll be making reactive decisions instead of strategic decisions. Be conscious to regularly pull your head up to avoid only dealing with urgent day to day issues.

I found there are plenty of things you can do to help yourself manage that balance.

Add process / structure… but only where it is valuable

Look, I get it, nobody wants to be the person to come into a small organization and immediately start scheduling meetings and adding a ton of process. So don’t be that person.

But there is no reason to be process-phobic either. One of the most valuable things I did was setting up a weekly roadmap review with the co-founders. This forces me to synthesize and refine my big picture thinking every single week. It also ensures they’re engaging with me in the most valuable way possible— “what customer problem should we be solving next?”

We’ve already iterated on the format for these discussions a few times and started to land on a template for tracking new ideas in a consistent way. And it is letting us get ahead on the solutions which will require more research. We’re still in the early days here but we can already feel our sprints becoming more focused as a result of this process.

Just don’t get carried away. Remember, you were likely compelled to join the company because they’ve been successful without you around. You don’t need to mess with things that are already working effectively. Things will evolve anyways as the company continues to grow and you’ll have an outsized impact on that evolution so don’t make the mistake of thinking things will be set in stone if you don’t change them right away.

This type of stuff can rock the boat a bit because you’re starting to assert how you engage with the rest of the organization, which means this last point is perhaps the most important.

Be proactive about establishing your role… by having candid conversations

If you’re the first product hire in an organization then it means there isn’t an established product playbook.

Rememberthat’s why it is exciting.

But that’s also why it requires work. You need to actively manage the situation and make sure everyone in the organization is comfortable discussing your role and providing constructive feedback on how it’s evolving. Your ability to succeed is positively correlated to the frequency and honesty of these conversations. It is no different than the success of the product itself and the dependence on regular customer feedback.

I actively looked for interactions that, at the least, warranted a “hey, is that how we want this to work long term?” type of exchange. I found a simple question along those lines naturally prompted a productive conversation about roles and responsibilities while there was a recent example for everyone to consider. Sometimes we aligned over a few quick emails and other times we agreed to keep monitoring things and discussing it.

We’re starting to align ahead of time on the design expectations of a given feature so I have autonomy to make the day to day decisions while it is being implemented. A small tweak, but one that has increased clarity and made us a bit more effective.

Anyways, that’s all I got… I’m sure I’ll learn a bunch more as more time passes!