10 Keys to Unlocking a Winning Product Team: Part 2

Welcome & Introductions

Roger Snyder | 00:00:00–00:02:41
Good morning, good afternoon, and welcome everyone to the second session in our two-part series: 10 Keys to Unlocking a Winning Product Management Team. I am joined once again by Jen Cano, who is based in Philadelphia — or at least based in Philadelphia today, because she is literally moving houses. So first, a huge thank-you to Jen for being here even though her home is nearly empty.

For those who don’t know Jen, she began her career navigating between marketing and product management back in 2003 and has since built a career on leading by influence. Today she is Vice President of Product at Elsevier, where she drives product strategy and vision for healthcare solutions.

And I’m Roger Snyder, Vice President of Marketing and Principal Consultant at Productside. Thank you for joining us.

Before diving into today’s material, I want to share a few housekeeping items. First, I encourage you to join our LinkedIn group. It’s an active, helpful space for product leaders to share challenges, ideas, and articles. I’ll paste the link shortly.

Next, throughout today’s webinar, please use the Questions panel in GoToWebinar. We’ll gather questions as we go and answer as many as possible at the end.

Finally, the most common question we get is: Can I watch this later?
Yes — all attendees will receive an email with the recording and an additional resource that we’ll introduce near the end.

Why Team Culture Matters More Than You Think

Roger Snyder | 00:02:41–00:06:10
Team culture is not an abstract concept. It’s the emotional and psychological environment your team shows up to every day — and right now, with so many product teams working remotely, culture matters even more.

Culture includes shared values, expectations, assumptions, communication styles, and the unwritten rules of “how things get done around here.” What’s important is that culture dramatically affects velocity. It influences innovation. It determines whether product managers feel confident making decisions or whether they get stuck waiting for approval.

INC magazine said it well:
“Company culture is an essential component in any business’s ultimate success or failure.”

Gartner went even further:
“Culture, more than strategy, determines how businesses grow and transform.”

In this series, we’re encouraging you — the product leader — to stop letting culture form accidentally. Shape it deliberately.

Understanding the Four Attributes of Team Culture

Roger Snyder | 00:06:10–00:12:24
Last month, we introduced Gartner’s framework describing four attributes that define business culture. Whether or not you were with us, I’ll recap briefly because these four areas will anchor everything we cover today.

1. How We Make Decisions
Are decisions fast or slow? Data-driven or opinion-driven? Transparent or opaque?
Your team needs explicit clarity. Decision philosophy is part of culture.

2. How We Engage
What is our communication style? Do we favor formal documents or informal Slack messages? When do we escalate? When do we collaborate?
Without clarity, misalignment grows quickly.

3. How We Measure Success
What KPIs matter? Do we evaluate product managers based purely on product outcomes, or on their leadership behaviors, too?
People follow whatever you measure.

4. How We Work
What processes do we follow? How do we problem-solve? How do we allocate budget?
These day-to-day operating norms become the backbone of culture.

Throughout today’s session, we’ll link each of the remaining five keys back to these four attributes so you can translate concepts into practical culture-shaping actions.

Supporting the Leap from Imagining to Doing

Jen Cano | 00:12:24–00:19:40
This next concept is one I see across entire companies, not just product teams: the difficulty of moving from imagining something to actually doing it.

Barbara Sher has a quote that I absolutely love, and I want to read the full thing because it captures the reality perfectly:

“Thinking about swimming isn’t much like actually getting in the water. Actually getting in the water can take your breath away. Your defense mechanisms want you to stay away from anything this intense. But anything worth doing is worth doing too soon.”

That’s the leap we’re talking about — the leap from imagining a perfect future to taking imperfect action right now.

Product teams often create an inspiring three-year vision or a North Star. That’s important. But at some point, strategy has to become execution. And when that moment comes, we need to shift our thinking from “big and beautiful” to “small and learnable.”

A helpful analogy is the evolution from skateboard → scooter → bicycle → car. If the true goal is transportation, then even a skateboard is a valid starting point. It’s valuable because users can react to it.

When I joined an innovation initiative a few years ago, we had a bold multi-year vision. The team’s instinct was to jump straight into building something sizable. But we pivoted. Our goal became: What is the smallest slice of value that users can respond to?
Not something commercially perfect — something testable.

We’re not trying to deliver the Ferrari on day one.
We are trying to deliver something real enough for users to react to, so the next move is smarter than the last.

Roger Snyder | 00:19:40–00:21:15
And that’s the heart of this. You need that big North Star, yes, but you also need the humility to walk toward it in increments. Those incremental steps are what make the strategy real — and make it survivable.

When you empower product managers to think this way, they stop treating the product roadmap like a list of promises and start treating it like a sequence of validated bets.

Don’t Be Afraid to Fail

Roger Snyder | 00:21:15–00:27:55
There’s a quote I love from Tom Watson Jr., former CEO of IBM:

“If you want to increase your success rate, double your failure rate.”

Product managers are often raised in organizations where the mantra is “failure is not an option.” But in reality, failure is the mechanism of learning. It’s how teams evolve from opinion-driven decisions to evidence-driven decisions.

Here’s the shift we all need:
Stop treating things as failures.
Start treating them as experiments with results.

If an A/B test underperforms, you didn’t fail — you gained information that protects you from a more expensive mistake later.

To build this culture, product leaders must:

1. Change the language

Stop praising perfect execution and start praising discovery.
Say things like:

• “What did we learn?”
• “What surprised you?”
• “What experiment should we run next?”

This rewires the team’s emotional relationship with risk.

2. Fund learning

Teams don’t experiment because no one gives them the time or budget.
As a product leader, you must allocate resources — or experiments simply won’t happen.

3. Require data for decisions

Don’t approve roadmap items without evidence.
The moment you make data a prerequisite, behavior changes overnight.

4. Reward experimentation publicly

If a product manager ran five experiments last quarter, showcase that in leadership meetings. Normalize learning. Normalize trying. Normalize adjusting.

Jen Cano | 00:27:55–00:30:12
One of the ways I evaluate a product manager in interviews is this:
“Tell me about a time you failed.”

And I don’t ask it as a trap.
I ask it because great PMs embrace failure as responsibility and as raw material for growth.
If someone can articulate what they learned — and how it shaped the next thing they did — that’s the sign of a PM who will thrive.

Becoming a Trusted Partner

Roger Snyder | 00:30:12–00:37:50
Trust is currency inside an organization. It determines whether you get included in strategic conversations or get informed after the fact.

Stephen Covey said it well:

“When the trust account is high, communication is easy, instant, and effective.”

But trust isn’t just personal. It exists in two layers:

1. Trust in each individual product manager

Are they reliable?
Do they follow through?
Do they communicate openly?

2. Trust in the entire product management function

When PM as a discipline is trusted:

• roadmaps are easier to negotiate
• engineering partners collaborate more naturally
• executives feel confident making bold investments

To build trust, PM leaders must ensure:

Be true to your word

Do what you say.
Say what you do.
And only promise what you can realistically deliver.

One of the fastest ways to destroy trust is overpromising under pressure.

Be transparent

PMs should proactively explain:

• how decisions get made
• what evidence is being used
• which risks are still unknown

Opacity breeds suspicion.
Clarity builds trust.

Model a partnering mindset

There was a moment earlier in my career when a peer director made a mistake that caused a schedule slip. I could have thrown him under the bus in front of the leadership team. Instead, I said, “We’ll resolve this as a team.” Five minutes after the meeting, he called to thank me.

That moment bought us years of collaboration.

Be expert — but not arrogant

Expertise should bring confidence, not rigidity.
Being a trusted partner means you’re willing to listen, adapt, and incorporate input when the situation calls for it.

Jen Cano | 00:37:50–00:39:15
And I’ll emphasize that last point. If you set expectations that decisions are data-driven, then people will rise to that standard. Eventually, you’ll find yourself in an organization where everyone brings evidence — not just opinions.

That is how trust compounds.

Enabling Ownership

Jen Cano | 00:39:15–00:47:52
Let’s talk about ownership — and not the superficial kind where someone updates a Jira ticket. I mean true ownership, where a PM feels the weight and pride of being responsible for the outcome.

I learned this from one of the most influential managers I ever had early in my career — his name was Keith Newman. He taught me that product leaders should empower their teams to solve problems, not just surface them.

He used to tell me:

“Never bring me a problem without bringing at least one proposed solution.”

Not because he expected me to have the perfect answer, but because thinking through a solution is the moment you begin taking ownership. It shifts your mindset from “This is happening to me” to “I am accountable for what happens next.”

As product leaders, we need to reinforce this by:

1. Encouraging solutions — always

When your team brings you a problem, ask:

• “What have you tried?”
• “What do you think the right path is?”
• “Which option produces the best trade-off?”

This is how you transfer authority instead of bottlenecking it.

2. Giving them space to finish the thought

Too many leaders interrupt with the “real” solution before the PM articulates theirs. Don’t do that.
Let them get through their full recommendation before you weigh in.

It reinforces confidence and competence.

3. Asking your team to put YOU to work

This is one of my favorite leadership patterns:

“Tell me where I can remove obstacles for you.”

It flips the dynamic. You’re signaling:
I trust you. I support you. I believe you can lead this.

And they rise to that belief.

4. Cultivating a volunteer culture

If someone repeatedly complains about something, assign them to help solve it.

Not as punishment — as empowerment.

You’re saying:
“You clearly see this problem. I trust your instincts. Take the lead on making it better.”

That’s ownership.

5. Providing tools and support

Empowerment without support is abandonment.
So give your PMs:

• templates
• playbooks
• stakeholder maps
• decision frameworks
• leadership time
• coaching

Ownership grows when people feel equipped to succeed.

Roger Snyder | 00:47:52–00:48:55
I completely agree. The moment a PM truly owns their product — really carries it — everything becomes easier. They become sharper, faster, more influential. Great PMs aren’t task managers; they’re owners.

And our job as leaders is to create the environment that lets that ownership emerge.

Instilling Servant Leadership

Jen Cano | 00:48:55–00:56:40
Servant leadership is often misunderstood. It isn’t being soft. It isn’t being passive. And it definitely isn’t being a doormat.

Servant leadership is about lifting your team so they can excel without you in the room.

And again, I go back to Keith Newman — the same leader who taught me about ownership. Keith was the embodiment of servant leadership.

Here’s what he did:

He took all the blame and none of the credit.

If something went wrong, he stepped in front of it:
“Put it on me. I’m the leader.”

If something went right, he stepped behind his team:
“They made it happen.”

That simple posture earned him extraordinary loyalty. His team would walk through fire for him — not out of fear, but out of respect.

He invested time — every day

He didn’t lead from a distance. He sat with us.
He asked questions.
He clarified obstacles.
He listened without rushing the conversation.

Time is the currency of leadership, and he spent it generously.

He shielded us from noise

When executives were frustrated or pressure was rising, he absorbed it first.
He filtered the chaos so the team could stay focused and effective.

He wasn’t a doormat — he gave honest feedback

Servant leadership requires backbone. It requires truth-telling.

He would pull me aside when I was off track and say things like:
“Jen, you’re better than this. Let’s fix it.”

That level of honesty is a gift — and it’s one of the most servant-oriented things a leader can offer.

He led proactively, not reactively

This one is huge.

Being proactive prevents burnout.
It prevents fire drills.
It prevents teams from being in a constant state of reactivity.

Servant leaders think ahead. They anticipate needs. They remove future obstacles before the team even sees them.

That is service.

Roger Snyder | 00:56:40–00:58:10
Yes. Servant leadership is about creating conditions where people can succeed at a higher level. And part of that is seeing beyond the day-to-day — looking not just one step ahead, but five steps ahead.

The more foresight you have, the more stability you give your team.

Closing Reflections & Practical Tools

Roger Snyder | 00:58:10–01:03:52
So let’s step back and summarize where we’ve been across this two-part series.

We started with five foundational keys last month — staying curious, focusing on outcomes, leading with influence, becoming an expert, and starting with the customer.

And today we added the remaining five:

1. Supporting the leap from imagining to doing
2. Embracing experimentation instead of fearing failure
3. Becoming a trusted partner across the organization
4. Enabling true ownership
5. Instilling servant leadership

If you build a team around these ten touchstones, you will not just have a functional team — you will have a powerful one.

One more thing: We created a worksheet for you. It includes all ten keys, reflection questions, and a planning template so you can choose which areas to focus on first with your own team.

It’s a practical way to translate today’s ideas into the daily rhythm of your leadership.

Jen Cano | 01:03:52–01:05:05
And I encourage you to treat this as an iterative process. Pick three of the ten keys you want to strengthen. Write down the behaviors you’ll commit to. Share them with someone you trust for accountability.

Great leadership is built brick by brick.

Roger Snyder | 01:05:05–01:07:15
We’ll wrap here, but thank you all for joining us. And Jen — especially with you literally moving houses today — thank you again for being here.

These are the kinds of conversations that elevate our profession. And we hope you’ll join us for next month’s webinar as well.

Thanks everyone, and have a great rest of your day.