4 Reminders for startup product leaders (and my future self)

A set of reminders for starting a new role in a new start up.

During my 15-year career in product leadership roles in start ups I’ve often had the chance to reflect on what I’d do differently or better next time. Sometimes this reflection has come a few years after a startup was acquired, with the benefit of distance. Sometimes it comes when I am working with a startup team and advising them in their journey. I remember being in their shoes and seeing things that they don’t see when they are in the thick of it. I can’t help but notice mistakes they are making and knowing I have made the same mistakes as well. So I’ve made a set of reminders to myself, to coach myself when starting out in a new role at a new start up.

There’s a lot of content about how to hire, motivate, align and empower teams; how to organize for speed; and how to manage business processes within and across the product organization. Blitz Scaling, The Making of a Manager, High Output Management and others have been phenomenal. I concur with all of that good work on mastering the essentials of startups. These are tips that are the advice I share over coffee with friends.

The 1-pager

For every start up you consider joining, evaluate the start up and write a 1-pager of your impressions. Write this as if the CEO is someone you care deeply about and you’re in a position to give unfiltered advice for the success of the company. Do this for every start up you consider. Most start ups you won’t join, but eventually you’ll find the one that makes you want to jump in.

Here are some things from 1-pagers I wrote about various start ups:

• “The economics of enterprise sales are not going to work for them”
• “Lots of machine learning people and explanations, but doesn’t yet make the product value concrete for users, e.g. the product changes x by y”
• “The product actually doesn’t work”
• “The sales people make no sense for the sales model or industry; they seem to be friends of friends”

I use the 1-pager to test whether the CEO is someone I could work with. You can learn a great deal from how the interaction goes when you’re talking about deep issues. Do you feel nervous talking to this person? Can you be open and direct? Does it get defensive? Is the conversation a productive dialog?

After joining I refer to “the 1-pager” often. It is easy to see things from the outside that you don’t see once you’re inside. And routinely ask “Now that I am here, am I making an impact on these things?”. You join a startup so that you can significantly move the needle. But it’s so easy to get into a situation when things stay on the list far too long. You put off addressing an issue because you’re busy, or because you have other priorities.

Have the crazy meeting, regularly.

This one came to me as an insight when I was an advisor at NfX. I’d meet frequently with founding teams — the main 2–4 people in the company — and have incredible white boarding sessions, producing clarity of thinking and prioritizing the most important paths to go down. We did 20–30 of these every week, week after week, and it was always very successful. The team itself did much of the thinking and did their best thinking when they were meeting with us, in these short white boarding sessions.

I wondered why this worked so well. Part of it was the knowledge and frameworks that NfX was providing. A big part was, I realized, the element of mental freedom. When meeting with us at NfX everything was on the table. We could ask any question. We could think broadly. We could admit what was not working. We could be creative. We could pontificate about what worked elsewhere and agree to copy an idea from another industry.

A big part was, I realized, the element of freedom. When meeting with us at NfX everything was on the table. We could ask any question. We could think broadly. We could admit what was not working. We could be more creative.

In my last start up I wanted to recreate that experience from the outset. We didn’t have the benefit of sitting around the table every week with an external advisor like NfX, but I tried to create the same dynamic amongst the core team. I intentionally started “The Crazy Meeting”. This was completely outside and orthogonal to all the usual types of interactions and led us to break throughs. Some tips on doing this:

• Say “This is the crazy meeting”
• Meet somewhere completely new and be able to white board or have lots of blank paper
• Avoid anything from the day to day (people will want to ask you about something related to the latest features— but kill that thread)
• Keep it crazy. Depending on the personality of your team, figure out how to keep everyone in the crazy zone. At the time Uber was doing some amazing things that were in the news, so I asked engineers, “What would Uber do?”. It was a way of making it clear that nothing was off the table.
• Don’t have an agenda. Don’t structure it. This was a big one for me — I tend to be the person who wants an agenda for every meeting, along with pre-reading and structured conversation. But for the Crazy Meeting there was only one sentence.
• We found 90 minutes was a good amount of time. It was enough to explore, think and whiteboard, and was feasible.

Build to solve distribution and user needs together.

I started my career focusing on user needs, and it became a natural instinct, but now I work on solving the existential question very early: distribution. It’s harder to get products into the hands of the intended users than it is to build products that meet user needs.

Here’s a few things on my cheat sheet that I try to run through at the early stages of the company.

• Get funded by the channel. If there is a mega player who happens to already be entrenched in all of the target customers, don’t just partner with them but take money and make sure they’re going to get your product into the hands of their customers. Recently, Vlocity did this, starting the company with strategic funding from Salesforce.
• Imagine collaborative features, where each user is going to use your product to work with multiple other users — at least for some aspects — and in doing so is going to invite more users to your product. Intentionally design for organic spreading of your product, increasing its viral co-efficient.
  I remember explaining this to my 8 year old, during a ride to school, in the context of how germs spread and hearing him doing the math in the back seat of the car: if each kid that gets sick goes to school instead of staying home, and now each kid infects 6 people, in 10 days, how many people will be sick?
• Which mega-trend in the media supports us? If there is a mega-trend already in the market, that can help greatly. Headspace and Calm had this advantage when mindfulness and meditation topics reached mainstream popularity, even though virtue products are notoriously hard.

Build Products that Use Network Effects

Your job is to make the product better and more valuable to users. It is also to build a defensible company. In commercial companies this drives corporate value, while in non-profits this drives sustainability. In both cases it drives the ability to attract top tier talent to further the mission. Building product doesn’t mean shipping more features, or building for the sake of building, no matter how established or dominant your company is.

• Build user network effects: product/experience gets better as each user joins.
• Build data network effects: product/experience gets better as more usage leads to more data, which leads to better product/experience, which leads to more usage. This is very true if your product uses machine learning in ways that drive the user experience. The PMs and engineers who work on this problem are a different breed than those that work on other software problems, so you might need to use external help if you don’t already have this skillset internally.

There’s really good examples and explanations of all the network effects from NfX here.

I’ve found it is worth holding working sessions where the preparation is to first review/re-read this content, and then come up with ways to apply this to the business at hand. I’ve found that if you can access direct user feedback, you can take that feedback and connect it with an element of network effects and have that amazing “Aha!” moment when you find something that is going to work really, really well for your market.

4 things to remind my future self

1. Brutally direct 1-pager
2. Crazy thinking
3. Distribution
4. Network effects

My advice to my future start-up self is to avoid focusing on just one of these. Early on, even when the company is tiny, try to pick one thing in each bucket.

Tags: startups, software, product, network effects