I really like Vrushali Paunikar’s approach to onboarding new product managers in an organization. In particular, the focus on three different time horizons with distinct goals is very important:

The first 30 days are about breadth. Put together a 30-day checklist broken up by people, product, and process to help your PM gain context and develop peace-time relationships.

The first 3 months are about perfecting execution. Give your PM projects she can actually launch within the 3-month window to help her establish early wins as well as learn your product development process.

At the end of the first 6 months, your PM should have a point of view on the direction of her product. Set this expectation early and empower her to own product strategy and vision.

One crucial point that is implied but not explicitly stated in Vrushali’s post is that PMs should avoid coming in with guns blazing in the first month and try to change/introduce a bunch of stuff. The first month is about really, truly, honestly listening and understanding. You’ll have plenty of time to have an opinion. Make sure you understand the context of the company and the product before you start having and communicating them.

For further reading on this, a while back I also wrote about What a Product Manager should focus on in the first 90 days.

In Egoless Innovation Sari Harrison reminds us that ideas are not personal. As product managers our goal should always be to get the best outcome, not to win or be right or for everyone to “just get along”:

When the idea you are advocating for gets challenged, an egoless innovation mindset means choosing to see the challenge as a gift to the innovative outcome which the idea hopes to someday become. It means looking objectively at the input, responding to it authentically, saying “wow, good point, I’m going to take that back to the team” if it was a point you hadn’t considered and saying “yes, we thought of that and…” if you have. It means you don’t get flustered by questions or negative comments because you are focused on achieving the best outcomes, not your own status. If you can embody this, you will be helping move the culture towards more and more innovation occurring with less and less friction. And you will be more successful.

Herb Caudill’s Lessons from 6 software rewrite stories is an extensive analysis of the rewrite projects of companies like Basecamp and Trello, why they succeeded or failed, and what we can learn from them:

Once you’ve learned enough that there’s a certain distance between the current version of your product and the best version of that product you can imagine, then the right approach is not to replace your software with a new version, but to build something new next to it — without throwing away what you have.

Eventually all product managers face a decision like this, so I found these case studies invaluable.

I agree with Chris LoSacco that “Why Not?” is a dangerous questions to ask for any product team:

Often stakeholders assume that if their ideas aren’t bad, they should be on the roadmap. “This isn’t hard; let’s get it in front of the engineers.” But the burden of proof is the other way around — ideas should get turned down unless they clear a high hurdle.

Just because a feature is easy or obvious doesn’t mean you should build it. This is why I prefer the question “Why Now?”:

What is the danger of not doing this project right now? If we don’t solve this problem or add this feature right now, what do we lose? Are sign-ups going to drop? Are we going to lose customers? Are we going to miss a major shift in the market? If so, then, yes, now is a good time to work on it. But if the room suddenly falls silent and everyone comes up short on the downside of skipping over the idea, that’s a pretty good indication that it can wait for later.

This is an incredibly brave and insightful post by Erin Chan that I think every product manager should read. In The Hard Thing About Complex Products & How I’ve Grown as a PM she describes a long, failed project at Shopify in detail, and what she learned. The section on creating “tripwires” for complex projects is something I’m going to start using immediately:

A tripwire is a mechanism or an indicator that you define, and when it gets triggered, flags are raised.

For example, you should set the tripwire of ‘time’ when a milestone isn’t completed after a defined period (for me, this should have been two months). When that happens, my recommendation is to have a serious discussion with the team and make your Leadership and stakeholders aware of what is happening. Communicate the changes that you will make to the team or process to get the project back on track. Next, outline what happens if the milestone isn’t completed in three months, then four. These are your tripwires as determined by time, but you can define tripwires in whatever form you see fit for your initiative.

Related to the podcast discussion I shared the other day, Andy J. Ko wrote a really good essay called The problem with “learnability” in human-computer interaction. He argues that most software is learned socially, not independently:

We just have to think about our own personal experiences to see that nearly everyone learns how to use all but the simplest software socially, not in isolation. Our friends and family introduce us to new software and teach us how to use it. Our parents call us and ask for help troubleshooting software behavior they don’t understand. Our children teach us about new apps.

He then goes on to ask what it would look like if we designed software for this kind of social learning:

What would it mean to design for teachability rather than learnability? It might mean supporting the creation of not just one tutorial, but a myriad of tutorials, each supporting learners with different prior knowledge and interests. It might mean software companies having their app’s splash screens start with the question, “How do you want to learn this app?” rather than dropping users to a home screen and giving them a few tooltips. It might mean designing software to have teacher modes, where someone could go through and annotate key parts of the interface for someone they are teaching how to use an application (e.g., “Dad, remember to always click this box this before you submit!”).

These are good questions to think about as we work on product onboarding strategies.

I found this discussion on the Product Love podcast really interesting. Eric Boduch talks to Adam Avramescu (Head of Education at Checkr) about the importance of educating customers on how to use your product. They cover a bunch of topics, including the myth that you don’t need education if your UX is good enough, the right way to approach documentation, and how onboarding is an important part of customer education but not the only thing you need.

Listen on Soundcloud or Overcast.

Ryan Bigge makes some very good points in his post about better personalized recommendations through transparency and content design:

Data-driven companies know something that the user doesn’t. Yet the language used to convince people to act on recommendations lacks variety and explanatory power.

Algorithms aren’t neutral — or as Ryan puts it:

Every facet of machine learning is fueled by human judgement, so it must be multi-disciplinary.

Users are getting more skeptical about where these magical recommendations for what to watch, listen to, and buy come from. To establish and build trust, companies have to get better at explaining exactly why they’re recommending a specific product or action.