#non-obvious | Photo by Lisa H on Unsplash

10 Non-Obvious Tips For Startup Product Leaders

After 10 years working in product management, these are my top 10 non-obvious tips for succeeding in a product leadership role.

As we start a new decade, I took a lot of time to reflect on my nearly 10 years working in product. I took a lot of notes on the lessons I’ve learned along the way, and this essay shortlists the top 10 – prioritized by practicality and non-obviousness so I could feature things we don’t see spoken about all that often.

TL;DR

  1. Talk to your users more!
  2. Take a balanced portfolio approach
  3. Develop a single source of truth for your product initiatives
  4. Cultivate a template & checklist culture
  5. Get the paper cut problems onto your roadmap
  6. Slow down to speed up
  7. Get serious about meeting etiquette – it pays off
  8. Fight for fixed-time and variable scope
  9. Turn solutions into problems
  10. Invest in continuous value delivery

P.S. I’m writing a book on product management, learn more.


Prefer your tips in bite-sized chunks?

There’s a lot of content in this post, so if you’d prefer to get these 10 tips in bite-sized chunks, delivered straight to your inbox over the next 10 days… I’ve got you covered.

Plus I’ll send you a PDF & ePub version instantly so you’re not torn between diving in and knowing what number 10 is!


1. Talk to your users more!

I know, I know. I promised you in the title that this would be non-obvious tips. This is the one exception because it really can’t be overstated.

I know how easy it is to procrastinate speaking to your users. For most product managers, it’s nowhere near the top of the favorite things to do.

Speaking to users is one of the single highest leverage activities a product leader can do. In essence, our job is to advocate for users and build product that meets their needs. Ideally, we do that in a way that generates profit. To do that job well, you have to know our customers intimately, and there’s no substitute for talking to them directly (ideally, one-on-one).

If you’re already talking to your customers regularly, would it hurt to do it more often? Are you involving your team? Are you sharing your notes and recordings? Are you focusing too much on problems or solutions?

618 million search results for "talk to your users more"
That’s a lot of content about talking to your users…

If you search google for advice about talking to your users more, you get 618 million results! What’s even more impressive is that searching for “bacon” only has around 8% more results.

It’s clearly been said a LOT that you should talk to your users more, but we’re all guilty of putting it off and doing it less often than we think we should.

671 million search results for "bacon"
Only 8.5% more pages about bacon on the entire internet than pages about talking to your users!

Set yourself a goal for this year. How many users do you want to talk to each month? Now go and block out time in your calendar for customer interviews and time to plan/schedule those interviews.

2. Take a balanced portfolio approach

You wouldn’t have to look very hard to find 100 articles on roadmap prioritization. It’s a popular topic – I suspect at least part of why is it being as much art as science. One standard approach to roadmap prioritization is to take all the things you want to work on for the quarter/year and rank them 1-to-n.

How do you rank them? Another vast topic, but the most popular and practical methods, uses a set of criteria with associated scores and an ‘algorithm’ for rolling the scores up to a single number. Then you just rank the list from highest to lowest score. What kind of criteria do they use? Most systems incorporate some form of business impact, risk, and effort. Another popular method is to give each person in the group a fixed number of votes to apply against the full list of options (sometimes allowing multiple votes on each item) and then ranking the options based on total votes given across the group.

Across the teams I’ve worked in, advised, and consulted to – this approach of taking a giant punch list of ideas and force-ranking them is probably the most-used approach I’ve seen in my career. But I see some significant flaws in this approach and prefer a different approach – one that’s only marginally more effort.

Generally, taking a long list of ideas and ranking them leaves you to figure out your strategy after you’ve figured out your tactics. It’s backward!

Poorly planned sign on the "college of planning" building (ran out of space)
Alignment matters… so does planning.

And even if you lay out your strategy first, there’s not a lot guiding the prioritization process towards aligning with the strategy.

The single-list approach tends to leave you very focused on a certain kind of work – essentially putting all your eggs in one basket. At the end of the process, you’ll probably end up with a highly-concentrated focus that amplifies any blind spots or weaknesses you’ve already got.

Before you write off this approach, it’s not always a terrible idea! If you’ve got a smaller engineering and product team – this approach is probably your best bet. Save your energy for moving fast, learning quickly and focusing your energy. Plus, if you’ve essentially got a single team in your product & engineering organization, the portfolio method won’t work out-of-the-box. Feel free to read on, but I’d suggest applying this abstractly rather than literally.

Once you have multiple product teams, I think there’s a better way.

The approach I actively recommend using for roadmap prioritization is centered on thinking about your product & engineering efforts like an investment portfolio.

Let’s say you’ve already got your list of projects. Before you start ranking them, let’s “cluster” them into groups or categories.

Ideally, these categories link to the customer impact, value mechanism, or business metrics they’re expected to impact. If you’re feeling stuck, try to group them before you think about what you’re grouping them by.

It’s easiest if you can do it with post-its on a wall (last time I did this, it was via video call across New York, Toronto, and Los Angeles).

If you’d rather stay digital, choose something that’s super flexible and won’t slow you down. A simple excel sheet or virtual whiteboard like Miro would be my first choice.

Ideally, you’ll land on enough groups to average 1-2 product teams per category. As you’re planning, keep in mind how flexible your current team structure is – nobody wants to be in the habit of a quarterly restructure.