Crucial Conversations for PMs and Product Leaders: Advanced Techniques

The key concepts + advanced extensions to engage in more important conversations that change your product's direction and enhance your impact as a leader

• Giving a negative performance review.

• Sharing feedback on a teammate’s work.

• Talking to a team member who is failing to keep their commitments.

These are crucial conversations.

And the best PMs don’t just write great PRDs and Roadmaps, they have crucial conversations.

Along with saying no and politics, crucial conversations are amongst the most important soft skills for PMs.

I’ve had to coach my fair share of PMs on these skills, as well as improve my own.

I’ve been shaping - and re-shaping - my views over time.

My favorite text

I’ve now read a bunch of books and articles on the topic.

Before writing this today’s deep dive, I returned to my favorite - this book:

(And hence the name of this piece)

I actually heard from two people in the last month that it was recommended to them.

This post is an extension of the book for PMs, edited by my experience in the field. It’s meant to relive the concepts in a product context.

Because crucial conversations are one of the most important soft skills for PMs, it also goes a step further.

The book is without replacement. It’s more of an ‘experiential read’ anyways. So buy it.

As humans, we erroneously deprioritize these “soft skills.” But, as the book says:

Twenty years of research involving more than 100,000 people reveals that key skill of effective leaders, teammates, parents, and love ones is the capacity to skillfully address emotionally and politically risky issues.

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Today’s Roadmap

1. 10 of the top lessons from Crucial Conversations, applied to PMs and Product Leaders

2. Advanced Crucial Conversations - 7 extensions of the book for product folks

3. Most common mistakes PMs and Product Leaders make

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1. Top lessons from Crucial Conversations for PMs and Product Leaders

Let’s cover the lessons that make the book my favorite before we go into the extensions.

These are fundamental axioms for crucial conversations.

We’ll apply them to product contexts.

Lesson 1: It’s your job to have crucial conversations

Crucial conversations are those with opposing opinions, strong emotions, and high stakes.

The fact is: your job as a PM is, in part, to initiate the crucial conversations.

Individuals who are the most influential—who can get things done and at the same time build on relationships—are those who master their crucial conversations.

— Crucial Conversations Book

As the role on the product team that is most looked at to lead by influence instead of direct outputs, PMs have to often be the initiators of these conversations.

The fact is: engineers and designers have other outputs they can point to for their success. The PM is most often left with the outcomes.

If there’s some person or personality in the way of those outcomes, it’s up to the PM to tackle them:

• An engineering manager who has engineers who want to quit their team

• A designer who is putting business issues second to user issues

• An executive who believes the wrong features will win

These aren’t optional for a PM to achieve outcomes, they’re required.

(And by the end of this piece, we’ll have covered each.)

Lesson 2: The Fool’s Choice

You’ve probably been in a situation like this yourself.

Product Team Meeting

CPO (Skip-Level): We should spend all our time focused on retention.

Director (Your Boss): I think that could be a good north-star, but we don’t want to abandon our acquisition efforts entirely.

CPO: Those efforts haven’t been paying off for us.

Another Director (Your Boss’ Peer): We also have several cost reduction efforts that seem high ROI.

CPO: Let’s just focus on one thing for this quarter.

Another PPM (Your Peer): The problem with a retention north-star is the high ROI SaaS optimization efforts won’t make it above the line.

CPO: (A little louder this time) Let’s just not do them.

(Room gives up.)

The room clearly disagrees with the leader, but the leader is not getting the message.

At this point, most people give up.

Because they all feel they are in The Fool’s Choice:

We believe that we could make an enemy of ourself with the CPO. So, we suffer in silence. But - in fact - there’s another way.

It’s the way of dialogue.

Lesson 3: Dialogue

The core of successful crucial conversations is the free flow of meaning.

This is the definition of dialogue:

In this case of the product team meeting, it’s up to you share your view, even though it might be unpopular to the CPO.

It sounds like this:

PPM: It definitely can make sense to focus. Can we spell out our reasoning?

I know more than a few engineers and designers who will have questions.

I’ve heard a couple concerns people have about the retention north-star: acquisition, cost reduction, and SaaS optimization.

Why do we want to prioritize retention instead?

This is adding to the free flow of meaning.

The relevant information and reasoning for why to go over the prioritization reasoning has been stated - to propagate it to the broader org (and the meeting attendees).

And it’s structured with an agreement to move the pace of the conversation forward.

In many cases, at this point, the CPO may respond with realization:

CPO: Okay. We can make time for that. Let’s go one by one…

How do I know this? I’ve been that PPM.

Lesson 4: We need to start with heart first

The key in dialogue is, we need to start with heart.

Let’s play out a different scenario.

1:1 with your manager

SPM (You): I think I’m ready to go up to promotion for Lead Product Manager. Last cycle, the growth areas we discussed of teaming with design and adding innovative features have both been addressed.

Manager: I hear you. I think there’s two things. We need to see more time for some of your impact. And there is room to go with innovative features.

At this point you have several options. You might respond with silence:

SPM: Ok. Got it.

Or, worse, you might begin to respond with violence:

SPM: You said that 3 months ago. I’ve been a Senior PM for 2 years and deserve this promotion.

Either of these ways of responding are not to conductive to your case.

It’s time to catch yourself and focus on what you really want:

Recognizing what you’re doing - silence or violence - is the first step.

I’ve had direct reports respond with silence or violence.

But I’ve also had some focus on what they really want - maybe even recover from silence or violence.

For example:

SPM: That makes sense. We’ve also talked about those two areas.

Here’s how I think I’ve progressed:

Time for Impact: The new app redesign has now been live for 4 months, and, with cross-sell up 10%, I think it’s safe to say we achieved the A/B test lift. Our Data Scientist tells me that’s an annualized impact of $426M.

Innovative Features: Our latest app pop-up architecture looks at user state to customize the sequence and frequency capping. A/B tests are showing +4% in Purchases per user.

Manager: Got it. That’s progress that I can point to in hiring committee.

We’ve made progress in the 4 major areas. Let me socialize this with my boss and get back to you.

SPM: Great.

The stating of facts focuses on the progress - and brings the manager (in that case, me) along.

The quicker you can snap away from your bad conversational patterns, the better - which is our next lesson.

Lesson 5: Play the game, don’t be played

You have to act on emotions, not let them act on you:

• The worst at dialogue keep a professional silence and make subtle jabs

• The good at dialogue try to choke down dialogue but their emotions come spilling out in a crucial conversation

• The best at dialogue act on their emotions, think them out, and have crucial conversations in a calm, collected way

Let’s take another example, this time as a product leader.

Senior Leadership Team Meeting

CEO (Your Boss): We’ve missed our projections for revenue in the enterprise segment. What happened?

VP of Sales (Your Peer): We’re just losing in enterprise. We don’t have the enterprise product we need. Our team is losing big deals everyday. We should give up enterprise.

VP of Product (You): We’ve made significant progress on user access controls, security, and privacy. I met with a few prospects in Enterprise who love the latest dashboards last week.

VP of Sales: I doubt those will pan out. All the prospects I’ve talked to believe our Enterprise product is hopeless. Those features have taken too long.

VP of Product: That’s the sales team’s fault. They’re not selling them well. We need to performance manage there.

I’ve seen this happen.

The product person falls of the rails at the end there, resorting to high-level attacks on another leader’s organization — something highly unlikely to be received well.

What’s happened?

You felt hurt, worried.

This meeting was with the CEO. Then, at the end, the VP of Sales said something about the features taking a long time - and it set you off.

This happens all too often to us. Feelings led us to act in silence or violence:

We need to regain control.

Lesson 6: Retrace your path to regain emotional control

We tend to lose control because we’ve told an entire story about a person or situation.

In the case of the VP of Sales, you start to think something like:

You (The Voice in your Head): He’s out to make me look bad in front of the CEO. He never supports our product org.

It’s the storytelling that’s really at the center of the problem, not what the VP of Sales has said.

There are three damaging stories we tell ourselves

1. Victim stories: these are where the other person has made us the victim of their actions, and it absolves our responsibility.

2. Villain stories: these are where they have bad intentions and succeeded in ruining something for you.

3. Helpless stories: these are where we have no ability to succeed or do more given the situation, giving us an out to not act.

The key is to be able to identify them. The steps involved are:

1. Act

2. Feel

3. Tell Story

4. See/ Hear.

It looks like this:

So - with our VP of Sales and CEO, let’s go through the steps.

1. Act: I am in a form of violence. I may have crossed the line with some of those statements about the performance management of the sales org.

2. Feel: I am feeling this way because I felt threatened about the product org’s performance in front of the CEO.

3. Tell Story: The story I am telling myself is that the VP of Sales is attacking the product org.

4. See/hear: He was bringing up a strategic idea to not focus on enterprise. And he said our features took a while to deliver. He didn’t explicitly ask for performance management of my org. It was me who did that to him.

It’s after catching ourselves, and then asking ourselves these questions, that we can return to the conversation and make it safe.

Lesson 7: Make it safe

Now that you’ve gone ahead and said negative things about the VP of Sales’ org, it’s time to make it safe again.

The best in dialogue apologize when appropriate.

Let’s say the conversation continues like this:

CEO (Your Boss): Our enterprise features did take a while, making it harder to performance manage.

VP of Sales (Your Peer): Performance management of my org doesn’t seem warranted. We are crushing. We passed all our numbers this past quarter. We hardly have a problem selling. It’s the product org that’s behind.

The CEO was responding and the VP of Sales even fell into violence after your violence.

It’s not atypical.

The solution is to: step out, decide which condition of safety is at risk, and apologize when appropriate.

VP of Product (You): I apologize. It’s not a problem with the sales org. I think we’ve turned a corner in our enterprise product offerings over the last two quarters. Our access controls are now on par with our competitors and our security is 10x.

CEO: That’s true. We’re now competitive in enterprise.

VP of Sales: I see the point. I’ll check in with the team and how we’re doing selling the latest features.

Of course, apologies aren’t always the answer.

The trick is to decide whether mutual purpose or mutual respect is at risk.

• If others don’t believe you respect them, then it can make sense to apologize.

• If others don’t believe you care about their goals, then a better response can be to re-establish that.

Here’s how…

Lesson 8: CRIB to create mutual purpose

Let’s shift gears to another scenario.

You’re working with an underperforming engineering manager.

1:1 with Engineering Manager

You (LPM): I want to talk about some issues I’ve heard from engineers on the team. George mentioned he’s considering moving to another team. I’m worried that losing him will slow down our progress.

Engineering Manager (Your Peer): I talked to George. He wanted to learn a new tool stack.

You (LPM): I did hear that reason. I grabbed a beer with him and he also mentioned several concerns with on-call rotations, sprint planning, and career progression. I also heard from Laura and Cristal recently about the on-call rotations.

Engineering Manager (Your Peer): Everything is fine! These are just normal complaints.

You (LPM): I don’t want you to think anything is wrong with our relationships. I am concerned about some of the complaints though.

Engineering Manager (Your Peer): Why aren’t you on my side? Aren’t we on the same team? I thought we were good.

At this point, the engineering manager is beginning to lose the conversation. They may be descending. It’s time to create mutual purpose.

This skill of managing others is critical in crucial conversations.

And the antidote is to create a mutual purpose with CRIB:

Here’s what the thought process is like.

• Commit to mutual purpose: We’re trying to make the whole product team perform at its best and hit our commitments for this quarter.

• Recognize the purpose behind the strategy: The goal is to make sure my engineering manager is helping me along the way and keeping our best talent.

• Invent a mutual purpose: He also wants to get great reviews and do well.

• Brainstorm new strategies: We can go issue by issue and talk about how he wants to do things.

After the thought process, you’re ready to return to the conversation:

You (LPM): I am on your side. I am on your team. In fact, I am bringing this up because I want the team to function best. I want to help you succeed, and I’m concerned about this feedback from engineers. Let’s go one by one, starting with on-call rotations. Sound okay?

Engineering Manager (Your Peer): Okay. With On-Call Rotations, I did make a mistake. I over-assigned some to George because he’s so good.

You (LPM): Got it. So can we create a plan to make sure they are evenly distributed?

CRIB helps you bring others back to flow of meaning - by creating mutual purpose.

Lesson 9: STATE your path

One of the hardest part of these conversations is knowing what framework to use for them.

The framework is STATE:

Let’s take the example of a product leader who wants to work with a VP of engineering on the culture.

Here’s the STATE method in action:

1:1 with VP of Engineering

VP of Product (You): I’d like to chat about our product engineering culture.

VP of Engineering: Okay. Let’s.

VP of Product: What I’ve observed is that many of our engineers have waterfall expectations in product development. I’ve seen this manifest in relatively little engineers talking to customers. They tend to go through PMs. I’ve also seen them want fully detailed PRDs, versus figuring out some edge cases themselves. These observations have led me to think a push for more product engineering skills would help us. What have you seen?

VP of Engineering: I’ve also seen that engineers always revert back to the PMs on product questions actually. But I don’t think that’s about product engineering. That’s about PM’s sharing their learnings.

VP of Product: What worked well for me at Google was for us to have an expectation that PMs facilitate but don’t make decisions. That engineers actively talk to customers and shape products after PRDs are written. What do you think about testing something like that with the 10% of our engineers that are former Googlers?

VP of Engineering: We can chat with them.

The VP of Product shared their facts, told their story, asked for the VP of Eng’s path, talked tentatively, and encouraged testing.

When you go through STATE, it makes influence much more approachable as a product person.

Instead of complaining about the engineering culture at your company, you go change it.

That’s why the skill is so highly valued in PMs.

Lesson 10: Be patient

The final lesson is to not always expect the resolution to go as fast as some of these examples.

Let’s pretend we’re sharing feedback with a researcher on the timelines of their work.

PM (You): I was under the impression that the pricing page research was going to be ready Friday. That’s putting our feature timeline at risk.

Researcher (Your Peer): A couple of our conversations got canceled so it will take to the end of this week.

PM: Got it. Our feature gate and terms research also ended up taking longer. I think that’s fine, but it would be helpful if we make commitments we can stick to.

Researcher: Yeah, I know. I’ve been struggling here.

PM: I appreciate your research. This is not a reflection on you.

Researcher: Yeah.

PM: People often cancel calls. If we just update our estimated dates, we can plan around it. The work is always helpful.

Researcher: I appreciate that.

PM: I’ll try to help! We can then focus on the right stuff.

You don’t want to expect them to just have moved on.

It takes some massaging after delivering feedback if someone really is vulnerable and shares they are struggling.

You need patience in these conversations before moving on to the next thing.

Patience is like the magic pill for these conversations. Space allows time to pass, emotions to subside, and stories to lose their pull.

It all works together.

Summarizing All 10 Lessons

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2. Advanced Crucial Conversations for Product People - 10 Extensions of the Book

Those are the axioms of crucial conversations, the things you know but are useful to turn into principles.

Now let’s get into my meditations applying this stuff in a product career.