Client Story - Reframing Risk and Decision Making
Dave Masters - Former Sr. Director of Product at Realtor.com
How Dave Masters Reframed Risk and Decision-Making at Realtor.com
When Dave Masters was Senior Director of Product at Realtor.com, his team found itself at a crossroads.
They had a promising product idea.
They had smart people in the room.
They had options.
What they didn’t have was clarity.
“It was sort of old think meets some new think,” Dave recalls. “We didn’t really know which way to go.”
Debates were happening. Perspectives differed. The path forward wasn’t obvious.
So instead of pushing ahead and hoping for the best, Dave made a different choice.
He brought in an external lens to help the team map the uncertainty before committing to a direction.
The First Session: Turning Debate into Structure
In that initial workshop in the Bay Area, the room was full:
Engineers
Product managers
Designers
Senior leaders
Rather than arguing opinions, the team began mapping assumptions.
They explored multiple paths.
They identified risks.
They surfaced what was unknown.
They shaped a proposal for how to test before committing.
“We literally started mapping stuff out. We talked about all the different options. We identified the risks. We identified the path forward.”
The outcome wasn’t a decision made on instinct.
It was a plan to test which path deserved investment.
And as Dave put it:
“It saved us a hell of a lot of time discussing.”
Instead of circular debates, the team had a structured way to reduce risk and move forward with evidence.
Coaching Beyond the Workshop
The workshop was just the beginning.
Over the following year, Dave and I met regularly. He brought real, live product challenges:
A team struggling with alignment
A feature under debate
A bet that felt too big to commit to
An idea that needed pressure testing
Each conversation centered on one question:
How do we reduce risk before we build?
Dave describes that period as pivotal in his career.
“It was one of the most pivotal moments in my career. I felt like I always had a fresh lens to think about things in a different way.”
He had already been exposed to Lean principles earlier in his career, making things smaller, tighter, more iterative.
But this was different.
This was about building a deliberate testing toolkit.
Testing Is Not Just A/B Testing
One of the biggest shifts Dave describes is this:
Testing isn’t just running experiments inside a shipped product.
It’s not always an A/B test.
It’s asking a more fundamental question:
“What do we need to know before we even run an A/B test?”
That means:
Clarifying assumptions before writing code
Designing concierge experiments
Running smoke tests
Validating demand before committing roadmap capacity
Creating evidence before governance reviews
Dave had run scrappy experiments in the past.
“I didn’t even know what they were called,” he says.
What changed was not just the behavior, but the structure.
“You helped me shape a toolkit that said, hey look, there’s many different ways to go about this.”
That toolkit became embedded in how he led teams.
And it didn’t stay with him.
“I’ve encouraged my teams to run with it. I give Testing Business Ideas as a recommendation to every product manager.”
A Fundamental Shift in How Work Gets Done
The most important takeaway for Dave wasn’t a single workshop or a set of templates.
It was a mindset shift.
“Hiring somebody like David is going to fundamentally change how you approach work.”
And that’s the point.
Because most teams don’t fail from lack of effort.
They fail because they:
Debate too long
Build too much
Validate too late
Discover risk after committing resources
Dave saw an alternative:
“We spend a lot of time wasting, debating, building stuff that isn’t useful. When we could actually get in there and de-risk this thing in a much cheaper way, much faster.”
But doing that requires:
A system
A shared language
A robust toolkit
Leadership discipline
It’s not about being “leaner.”
It’s about making risk visible early.
From Certainty to De-Risking
Dave described his earlier training as one that valued certainty.
The shift was moving toward structured de-risking.
Not guessing.
Not debating.
Not hoping.
Designing tests before commitment.
Building clarity before scale.
Making evidence visible before governance.
That shift shaped his leadership philosophy, and how he approaches product decisions today.
The Long-Term Impact
Some consulting engagements deliver a slide deck.
Others deliver a momentary boost.
The best ones change how leaders think.
As Dave puts it:
“It requires work. But it’s work that pays off dividends in the end.”
Because once a team has a structured way to extract assumptions, map risk, and test before committing, the debates get shorter.
The roadmap gets sharper.
And capital gets allocated with more confidence.
Transcript
Dave Masters Testimonial – Former Senior Director of Product at Realtor.com
00:00:03 Speaker 1 (David J Bland)
Can you explain why you brought me in to help you out?
00:00:18 Speaker 2 (Dave Masters)
Yeah, so we were at a crossroads for a product idea that we were trying to work through and we didn't really know which way to go. And so it was sort of old think, title some new think, and we said, let's get everyone together to do a coaching session to sort of map this out and figure out what could or couldn't work.
And I remember that first session you came in, our office in the Bay Area, and we worked through that as a team.
We literally started mapping stuff out.
We talked about all of the different options.
We identified the risks.
We identified the path forward.
And ultimately, I think it saved us a hell of a lot of time with discussing, because now we had a proposal about how we might go out after the fact and actually kind of test which path was the right one.
00:01:07 Speaker 1 (David J Bland)
How did we work together?
00:01:13 Speaker 2 (Dave Masters)
Yeah, I mean, so I would say for the first session, we worked together a few different times, but the first session was you coming in and coaching our whole team.
So we had, in that meeting, we had a group of engineers, product managers, designers, senior leaders, and we all got together in a room and you sort of helped guide us through the process, which was thorough, robust, and you helped us kind of shape the thinking into a way that we could actually extract our assumptions, create a plan for how we might think to test some of these ideas and reduce risk as we went through that was one path.
The second path is, you did some coaching with me where I, for, I don't know, it must have been a year or so, it felt like, where we were meeting regularly.
And I was talking about all of the things that I had ongoing with me and my team.
Hey, I need some coaching through this particular problem that I'm facing or I need help with.
Can we talk through this particular challenge and how I might think to test this?
And I would say for me personally,
It was one of the most pivotal moments in my career where I felt like I always had a fresh lens to kind of think about things in a different way than how I was maybe trained to in the previous days of certainty was key.
This was no, no, no, let's de-risk and get onto a path of a little bit more clear as where we're going.
00:02:38 Speaker 1 (David J Bland)
Did working with me change how you approach risk or how you approach making decisions?
00:03:04 Speaker 2 (Dave Masters)
There's been a couple moments in my career that I would say absolutely shaped how I think about product.
One of them was probably like at the start of Lean where I thought, oh, like just make everything a little smaller, a little tighter, to then basically going, oh, well, there's actually a whole toolkit for how to actually test and de-risk these ideas.
And I would say that this was one of those moments where it's like,
Testing isn't an A/B test always.
It's a, hey, no, what do we do to even know that we should run an A/B test?
We got to get to a different level of certainty.
And so I'd say that like, you know, I had run concierge experiments in the past.
I didn't know what they were called, but we had done that because we were limited in resourcing.
I think that like one of the things you really helped me do was shape a toolkit that said, hey, look, there's many different ways to go about this.
And I would say that I have taken that and run with it big time.
And I've encouraged my teams to run with it.
And I would say that I use the testing, I give the Testing Business Ideas book as a recommendation for every single product manager out there.
Because I think it's such important material for them to have a robust toolkit about how they might want to test these ideas early on.
00:04:20 Speaker 1 (David J Bland)
Anything else you want to share?
00:04:34 Speaker 2 (Dave Masters)
I think the most important factor as part of hiring somebody like David would be, it is going to actually fundamentally change about how you approach work.
And I think that is a good thing, because frankly, we spend a lot of time wasting, debating, building stuff that isn't useful.
when we could actually get in there and really de-risk this thing in a much cheaper way, much faster.
And so it requires a whole way to think about it and a whole system of tools and a whole approach to actually do that for real.
And it's going to require work, but it's work that is going to pay off dividends in the end with the whole suite of tools that actually help you make sure that you're on the right path.
So that's how I would, you know, think about it.
And yeah, you should just hire David.
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