How to Survive the Hardest Part of Product Management by Janna Bastow "Product people - Product managers, product designers, UX designers, UX researchers, Business analysts, developers, makers & entrepreneurs July 07 2020 True #Mtpcon2, Janna Bastow, Mind the Product San Francisco, Prodpad, Mind the Product Mind the Product Ltd 1284 Janna Bastow at #mtpcon SF Product Management 5.136

How to Survive the Hardest Part of Product Management by Janna Bastow


There is probably one part of the product management job we can all agree is the hardest – people. People are unpredictable, they have strong opinions and unconscious biases. Many people in your organisation have more power than you, yet they are wrong just as often. In this illuminating talk from Mind the Product San Francisco 2017 Janna Bastow, Co-Founder of Mind the Product and Co-Founder and CEO of ProdPad, shares her own stories of dealing with people, and how she handles the toughest part of the job.

We all come to product management from different backgrounds, but one thing that has long been true and is only just starting to change, is that when we start this job our training generally consists of Googling. And while blogs, talks, and books can help us to pick up hard skills, it’s not a great way to learn soft skills – which are often, ironically, harder to learn.

It’s interesting then to contrast our approach to training with other job roles. Janna had a sales job in college and recounts how intense the training was – with role-playing exercises, secret shoppers, and scripts  – and how focused it was on dealing with people.

Frankly, selling pet food to adoring pet owners isn’t exactly a hard sell. But the training was intense!Janna Bastow

This sales training laid the foundation for the survival tactics Janna still uses today to manage people.

Janna Bastow at #mtpcon

Ask questions

One of the hardest challenges in product management is getting people aligned – especially if they have different reporting lines and objectives. Here it helps to remember that our job is not to have all the answers – but to ask the best questions. Ask open questions and use prompts like “yes, and?” to get people to continue their train of thought so you can truly uncover their motivations and objectives and start to bring them all into alignment.

Roadmaps are stories

“I’ve spotted a trend: a bad roadmap is a symptom of underlying issues in the company. And a frustrated product manager is a symptom of people and alignment issues in their team.”

A lot of roadmaps are simply incomprehensible. Go take a look at your roadmap right now. How many acronyms and feature names are there that require you or a scrum master to translate? If your took your roadmap to your mom, could she understand it?

Your roadmap needs to tell a story of how you’re going to reach your product vision. “And that strikes at the essence of being a product manager – you should be a storyteller. Stories have massive power to translate difficult concepts and to get people on your side. It’s why we write user stories and jobs to be done; why we craft buyer and user personas. It’s not our job to be the best coder, copywriter, or closer. It IS our job to be the best communicator, and stories, in our roadmaps, our specs, and everyday work, are one of our best tools.”

Janna Bastow at #mtpcon

Building a roadmap from scratch

Often product managers make the cardinal mistake of simply presenting their roadmap as a fait accompli, but nothing is more certain to cause pushback. Instead, Janna emphasises the need to involve your team in the process throughout to ensure that all the little trade-off decisions and architecture challenges that inevitably come up when developing a roadmap are surfaced and clear to everyone on the team.

A great way to do this is to turn process into a game, and use an exercise like the Product Tree. The Product Tree game helps you visualize the growth of your product in a non-linear way while taking into account the architecture required to get there. Playing this game helps you discuss what you want to build without tying anyone down to release dates and detailed deliverables.

Rebooting teams

When you’re facing rifts of misalignment and distrust within or between teams, you may need to reboot the team. That doesn’t mean firing everyone, rather you should rally everyone around a project, even if it’s just a hackday, with the goal of giving them something they can own and execute together without the usual constraints and pressures. This teaches everyone to be a team again, and can start to set build the psychological safety that all great teams need to be able to speak up and disagree productively.

A great way to start this is to simply phrase questions so they begin with: “How might we…”. This turns the issue into a collective problem and supposes a point a view instead of asserting it. It’s also really powerful to start talking about your assumptions as bets. Simply by saying “I bet that…” you give yourself permission to be wrong – and we know we’re all going to be wrong a lot of the time. These semantics may seem really subtle, but they’re key to setting the stage for psychological safety.

Janna Bastow Audience at #mtpcon

Managing up

When you and your boss can’t agree on a direction, it’s useful to think about exercises that can help to bring your viewpoints to the table. Product Box is a storytelling game, which is perfect for when you need a lean validation tool for a new pivot or feature. The product box is like something you’d find at a trade show or in the cereal aisle, and by the time you’re done, it will be covered in what your team thinks are the biggest selling points. By taking these boxes and practising selling to other groups, you quickly get a feel for what benefits and ideas stick. This will help build a much more cohesive roadmap that the whole team can get behind.

And if all else fails, show them the money. Executives hate wasting time and money, so whenever you can do use data and show the cost of delay or the potential cost of getting an expensive decision (like a five-year roadmap) wrong. Bringing in the bottom line is a great way to change the conversation.

Just as your first prototypes and MVPs are likely to get trashed by early customers, your roadmap is meant to change and adapt as you learn more. Having a massive, fixed roadmap doesn’t give you the chance to be agile in the long run.

Don’t forget about you

We all landed in this role by happy chance and accident, and we’re all making it up as we go along! It’s normal to feel a touch of imposter syndrome, it only means you’re self aware and you know what you don’t know. Great products are built with learning and iteration but so are great product managers and great product culture.

The most important product you’ll ever work on is your product culture, and it’s defined by how your team interact with your product and with each other.

Janna Bastow at #mtpcon SF

You’re a multi-skilled miracle, spinning plates and managing products like the bad-ass you are.Janna Bastow

Get in the building

You’ve all heard Steve Blank’s age-old advice of “Get out of the building”. Let’s add to that: Get in the building. Go sit with your team. Go meet your stakeholders. Go up a floor to where your execs live.

Great products are always more than the sum of their parts. They’re the direct result of teams who work well together, who aren’t letting miscommunication and misalignment tear them apart. Watch this engaging talk and think about how you can communicate more and better with the people involved in your product – from your customers to your team – and if some of these survival tips can help you out of a challenging situation.