Staying curious in crucial conversations 😡

As Product Managers, we have to stay curious, and it is a big positive trait that can help us in many situations. But that doesn’t mean it is easy to remain curious in all situations. In this article I’d like to reflect a bit on tactics which can help to stay curious in crucial conversations.

“Crucial conversation is one where opinions vary, the stakes are high, and emotions run strong.” from LEADERSHIPNOW

So, let’s talk about crucial conversations. Those are the ones where the outcome has significant impact, and maybe isn’t reversible quickly or cheaply. So when the above things are true, plus the consequence is impactful, then you find yourself in a crucial conversation. As Product Leads, we sometimes just end up in these, but often we also need to facilitate them. For example, a critical piece for a project requires buy-in from a team which has very different priorities. So not getting alignment could derail a lot of work that has already been invested, but doing it might derail the other teams priorities. Creativity is a good weapon, but also knowing what type of conversation we are in at the moment.

Knowing when you are in a crucial conversation is as important as knowing how to react

Making ad-hoc adjustments is tough. I like the approach Chris Hadfield promoted in his book ‘An Astronaut’s Guide to Life on Earth’. Besides having one of the cooles book titles ever, Chris describes how the intense focus on preparing for every possible outcome has helped him cope with the intense situations that might happen during a journey into orbit. In some ways this is blueprint I found accessible most times (but not always): to take time to prepare, be curious (before the meeting or conversation) how things could play out, and build up some thoughts around what to do in each potential outcome. This has not been possible when the situation was urgent (lack of time), or if this was a true ‘out of the left field’ type situation. Sometimes you just get hit by the truck coming from a side you didn’t know trucks could come from. $hit happens.

If you do have time to evaluate, use the indicators to spot a potential critical conversation:

• Opinions vary: Does the engineering lead express a totally different angle? Is a marketing expert coming at your plan from a very different POV? What has an important stakeholder group done before?
• Stakes are high: What is the consequence of this going wrong? Will the team be derailed, the product suffer irrecoverably?
• Emotions run strong: Are stakeholders deeply invested? Is this something the VP cares about?

Sometimes all you can do is prepare and hope; but prepare well

I just relocated to the Bay Area from the UK, and started as a PM at Google. My task was to gain approval for a project which previously was rejected by Ads leadership. This was a daunting task. I worked in Analytics at the time, which was technically part of Ads, but somewhat separate. I felt that Analytics had to work extra hard, and be extra diligent with their proposals for Ads to be open to them.

My goal was simple: get Ads to accept your team investing in this new measurement technique, or pack up. The consequence (in my head, mind you) was crazy. So the stakes were super high for me. My good friend and mentor then helped me to get a pre-meeting call with a senior Ads engineering lead. This chat helped me tremendously. He helped me understand the stakes of the other side on the table, the Ads team. He said: “Look, these folks get tons of proposals all day every day. Some of those proposals are good, but a lot of them have unknown risks to our ads business. The folks you are about to present to are asked to manage this risk.” What he told me was key. I knew now how to position my proposal to have a chance.

Smart by birth, grumpy by choice

When the meeting started my heart fell lower and lower. More and more senior Ads engineering people came in. These are the folks I only heard of from others. Engineers who build whole components of Googles famous ad stack. I was getting more and more nervous. One individual had a t-shirt which said ‘smart by birth, grumpy by choice’. This put the icing on top. On top of it we were at a meeting room somewhere back in the building (finding large enough meeting rooms was difficult), and my engineers didn’t find it on time. I was all along when we started.

I decided to go all it. I started by addressing the elephant in the room: “What I am about to present has been rejected by this group before. I am here to tell you how this proposal has changed and why we are now in a better position to move forward.” I also acknowledge the role of the individuals: “Your role is to preserve the integrity of our ads systems for our advertisers and Google, and I can show how our proposal meets these high standards.” These words opened the audience to me. Now I had to deliver. I told them how we were able to make our analytics technique work for advertisers, who early tests have been successful, and how we’d like to expand from there, with caution.

The meeting ended up being the second more favorite meeting of my career (so far), and I think back on it often. 10 minutes in my tech lead and senior engineer burst into the room, totally out of breath, the underestimated how long it takes to get to the meeting room, but when they saw the list if invitees knew how important this meeting had become, and decided to run.

My curiosity led me to the main factor overcoming obstacles: understanding the groups incentives

The main thing that I am grateful for is that my curiosity got me to talk to my coworker, who in turn suggested to talk to someone with more information, and it helped me understand the incentives of the group I ultimately needed approval from. This was a key ingredient. Before, I made assumptions (the wrong ones) and built a ‘head to head’ strategy for the meeting which would have spectacularly backfired. So, the value of staying curious is key, and ideally time allows to front-load this curiosity.

Take Action 🎬

📅 Book a private coaching session with me to grow your PM career. I will share my 15+ years of experience as a Product Manager, all my learning and pitfalls, with actionable tips and concrete lessons to model after.

📚 To learn the foundations of Product Management, I recommend reading INSPIRED by Marty Cagan. Marty has been leading the Silicon Valley Product Group for over two decades. His work is foundational for Tech Product Managers – a must read.

📝 This article gives a primer on the topic of the book Crucial Conversations, by Joseph Grenny at. al. An amazing work helping teams understand the power of knowing that crucial conversations are, how they occur, and how to navigate them to your advantage.

📚 The book An Astronauts Guide to Life on Earth helps prepare for all eventualities. Preparing is the main job of an astronaut, since they are on earth most of their careers, preparing for short periods of time (if at all) in space. When not busy, prepare for a ranked list of eventualities. So critical for Product Managers.