Excellence Under Uncertainty by Slack’s Head of Core Product — An Event Sponsored by Women in Product

So how do you make good decisions when you’re uncertain about the outcomes and under pressure? Paul Rosania, Slack’s head of core product, gave a great talk the other night, telling us how to do exactly that.

He started with the Mars Climate Orbiter, NASA’s super expensive mission which resulted in a failed mission, where the orbiter disintegrated into the atmosphere. Not great. He used this as an example of something to avoid when making products, but also to caution us, that as PMs, we can make mistakes, and it won’t be as costly or as dangerous as building a rocket.

He defined several challenges and things to watch out for, starting with…


  1. Define what the problem is, so you solve the right problem from the get-go.

2. Make sure you use a solution that users will understand. Be careful of scope creep, though there are good reasons to creep scope. For example, you may need to spend more time and resources to make it easier for users to understand, but you do have to balance that with the roadmap.

3. Complexity risk — big projects have a lot of edge cases and you can’t catch them all! (The opposite of Pokemon, so don’t even try, because you’ll be wasting your time for such a small segment of users.)

4. Market risk — customers are using other products, and those products affect their needs, which can change. So make sure you’re watching what they are doing, as what they do is going to change what your users want and expect from your feature!


  1. Over-precision — you need to understand the customer… and not assume you know their problems.

2. Priority risk — understand you work with a lot of people and there are competing needs and yours might be lower than theirs!

3. Staffing needs — vacation, people who are working on two projects and need to split their time. Things are always going to come up, so make sure you’re aware!

4. Technical risk — implicit assumptions are made by engineers all the time, so be prepared. An engineer could build a feature that may not work with what you plan to build in the future, and that’s always going to be an issue that is hard to prepare for.

5. Dependency risk — sometimes, in order to build something, you’ll need to modify systems that are owned by other people, and that can be tricky and slow you down.


  1. Empathy risk. Sometimes people don’t always give you honest feedback because they care about you. Always ask for it, because it’s better to get it now, than after your product launches.

2. Stubbornness. Don’t stick to your idea, because it’s yours. It may not be the best idea and the best solution.

3. Working with people. Sometimes you’re going to have to ask someone to do things (such as a mockup) multiple times. Be okay pushing them to get to the best version, even if it means going back to the drawing board… again.

4. Reputation risk — There are going to be times when your reputation feels like it’s at stake. Trust your gut and your team, and realize that you will make mistakes.

5. Focus — when everything is important, nothing is important, make sure you focus on #1 priority

For example, threads in Slack was one of the first features that Paul worked on, which so many complexity risks. He and his team were so confident in the first design that they launched it internally and it failed. It touched all of the core product and code, while simultaneously, competitors were bringing similar products to market and based on that, users now wanted and expected different things. So the team had to go back to the drawing board!
humans are bad at assessing risks, and we over-mitigate, given our many biases
“people sometimes make errors”

Know that, and move on. As PMs, we like to measure, but sometimes, the things we measure are not operating in a closed system. Instead, there are a multitude to different factors that are affecting the variables you’re trying to measure.

So don’t take a long time to make a decision, because factors are rapidly changing. Sometimes you can’t prove everything, and you’re going to get mixed results, no matter what you test.

“the best ideas aren’t measurable”
So, Paul advises, it’s best to let go and act so you can make forward progress.

How can we do that as PMs?

  1. Focus

Pick the one, two, and absolute maximum three things that actually matter and make them super clear to the team, so they can challenge you and each other to make sure you are sticking to the biggest and most important problems.

2. Agility

Be agile and adaptable, because this allows to you react to new info. You’re never going to be perfect. But you can adapt and change to better face new challenges.

3. Ambition

Always chase big opportunities! You need to make sure that you’re solving the problems that are most important to the business, customer, and the market.

Remember, you’re smart and know your customer, the cost of making a mistake is cheap, and if you move quickly, you can build great things and delight customers.

Some last tips:

  • Measure your changes, but be able to make recommendations for when you fail.
  • Being really focused on the problem means not agonizing on the small decision.
  • PMs ideally, should think 12–18 months ahead of team. Know the problem you’re trying to solve and why you’re trying to solve it. This should be done before you begin to work on the problem!
  • Talk to your customers and use your own product, because informal research can give you really great ideas.

Speaker Bios

Paul Rosania, Head of Core Product, Slack

Paul Rosania leads the Core Product team at Slack, where he and his team build the interfaces millions of people use to get their work done each day. Previously, he led the Timelines Team at Twitter, where he spearheaded the transition to an algorithmically ranked feed. Paul graduated Dartmouth College with a BA in Computer Science and has spent the last decade building software he hopes brings people closer together.

Jessica Fain, Product Manager, Slack

Jessica is a Product Manager on Slack’s Enterprise team leading Security, Compliance, and Identity initiatives. She was previously at Box where she worked in both Product Management and Customer Success, working on scale programs for small and medium businesses. Jessica is a Miami native and graduate of Northwestern University. She is also mom to two-year-old Judah and is expecting #2 this upcoming tax day.

Ayesha Bose, Associate Product Manager, Slack

Ayesha Bose is an Associate Product Manager on the Core Product Messaging team at Slack, where she is responsible for helping you get work done through threads, files, and notifications. Prior to Slack, she completed her Masters and Bachelors at MIT where she studied Electrical Engineering and Computer Science, focusing on Human-Computer Interaction at the MIT Media Lab.

This event was sponsored by Women in Product and Slack. Women in Product is a highly-engaged community of women builders and leaders. You can join our community or sign up for our newsletter for monthly events, networking opportunities, and much more!

Slack is an enterprise software platform that allows teams and businesses of all sizes to communicate effectively. Slack works seamlessly with other software tools within a single integrated environment, providing an accessible archive of an organization’s communications, information and projects.