Product Management Interview With Cyndy Bates Finnie

Product Management Interview With Cyndy Bates Finnie

Welcome to our continuing series of candid, one-on-one interviews with product management professionals!

In the spotlight today is Cyndy Bates Finnie, known in some circles as the Technology EMT.

What process has he found to be most successful for working with sales? And how does she apply her Scrum Master skills to her personal life? Read on…

Cyndy, how would you describe your journey as a product person so far?

My father is an engineer and my mother is a liberal arts major, so I was born being able to translate between geeks and non-geeks.

One of my early jobs was reviewing products for PC Computing magazine. To keep myself motivated, I imagined different people reading the review and made sure to address their concerns in the review. I was creating personas and use cases before I even knew what they were. It also gave me impetus to understand the technology and, more importantly, how to apply it.

After that, I went into product management, creating content destinations for a search engine (, developing a search engine for a healthcare publisher (UBM Medica), and developing connected digital platforms for a B2B expo & conference business (UBM).

Every step along the way I applied product management skills: discovery, analysis, recommendation, then build-analyze-iterate. The introduction of Agile was wonderful! Instead of the product manager being the one-stop shop for all solutions, it allows us to define the problem and business value of a solution while turning over the solution architecture to the experts in UI/UX and development.

Sounds like you’re a fan of Agile methodologies?

I approach almost everything in my life now with an Agile mentality. For example, when we had the opportunity to combine two instances of JIRA into one, the team was at a bit of a loss, since this wasn’t a stakeholder request. How do we prioritize? What is the business value?

I proposed we treat it like any other project: We identified the Product Owner and the other Scrum roles; we wrote user stories and included them in Sprint Planning just like any other project. Because the stakeholders were us, we had more flexibility with the project.

I also use Scrum Master skills with my family. Teachable moments become retrospectives (what went well for you, what could you improve upon next time). I remove impediments for them, to empower them to do it themselves. Which is something my daughter has been asking for since she learned how to talk!

Can you describe a challenge you’ve faced with Sales, and how you overcame that?

Sales is a deeply personal. They put themselves on the line to represent our products to customers. They need to have confidence and faith in those products to do their job. Because of that sometimes the communication style comes from a place of influence or even emotion.

When a Salesperson or Sales Manager asks for a detailed roadmap or present a “difficult” request, they aren’t trying to make your life harder; they’re asking to make their job just a little bit easier. Sometimes they really do need a date to get a customer to say ‘yes’ or to get their manager off their back. Sometimes they need a confidence booster or a renewal of faith in the product, business line or themselves.

My approach is to first listen and diagnose what they’re really asking for. What is this person trying to accomplish? What problem are they trying to solve? And then think about what you can do to help.

It’s exhausting sometimes because they often out number us in the organization, so think about what you need in return. Want to hear from some customers directly? Or get more visibility into the sales cycle? Now’s the time to ask.

What’s most challenging about product roadmaps?

I once inherited a product development team that had a full-time person whose only job was to manage the product roadmap. She spent all of her time gathering requests from stakeholders, prioritizing them, getting resource commitments from engineering, and updating the PowerPoint for the next quarterly review.

She was trying to give stakeholders visibility into what was getting done and what wasn’t, and trying to give Engineering clarity of direction. The problem was that the volume of projects in the roadmap would have required about ten times the number of resources as the business was funding.

That’s a gap that can’t be bridged no matter how fine the presentation, nor how many extra hours the Scrum team put in. As my Scrum trainer used to say, “There’s reality and there’s expectations. Reality always wins.”

The problem with roadmaps is that they are at best estimates of what can get done given what we know now. It’s hard to put yourself and your team on the hook for delivering something that hasn’t been defined yet. Remember you are not alone: Sales, Marketing, Finance all commit to annual projections amid unknowns.

Stakeholder-facing roadmaps are narratives telling the story of what can be accomplished. Like any real life story they are going to change and evolve. One of the things the roadmap manager did well was showing each quarter what new requests came in and were accommodated and which things were paused as a result.

What’s your process for prioritizing features?

Whichever process the organization will accept! I mean that in all earnestness. Prioritization must be done. And each organization has its own values and its own way that it makes decisions. Ultimately, you want the results of prioritization to be accepted and understood.

Is the organization built around influencers? Then you’ll not only want to keep department heads aware and informed, but let them influence the process on a monthly or so basis.

Is it a command-and-control organization? Then you’ll want to identify the commander and review your prioritized list with them on a regular basis.

Is the organization conscientious or data driven? It’s fun with numbers time. I’ve used this prioritization scheme but instead of 1-5 ranking, use Fibonacci (1,2,3,5,8,13) which sets apart the truly important from the merely important.

One company I did this with was global and placed a strategic value on technology solutions that could scale across business units or divisions, so I added a score multiplier for those.

The formula was: (Business Value x (Strategic Importance x Scale Multiplier) x Dissatisfaction with Current Solution) ÷ Level of Effort to Deliver

It’s also possible to combine styles. So in an Influencing organization, let the stakeholders score the Business Value, Strategic Importance and Dissatisfaction.

What’s the biggest professional mistake you’ve ever made?

Early in my career as a Product Manager, I had a tough time working with Sales. I didn’t know anyone in Sales, so it was a job function and communication style I didn’t understand.

One day a rep I was friendly with invited me to sit in on a call with a customer. The rep, the customer and I brainstormed a bit and we got off the call very excited about the progress. The rep had several questions about what we had just brainstormed and I happily told her that we could deliver everything we’d just talked about in six months or so.

Her face fell.

She then patiently explained to me that that it would have been better to not promise something to the customer that didn’t exist yet.

I felt awful!

I thought getting onto the call that I knew what success looked like, but it was very different than how the rep defined it. So, when Sales asks me to be on a client call, I do some discovery beforehand, describing my role and defining what success for the call looks like.

If the Sales mantra is “Always be closing”, the Product mantra is, “Always be discovering”.

What’s your favorite product or service? (One you haven’t personally worked on.)

Overdrive, which allows me to borrow ebooks from my local library to read on my Kindle. It’s a multi-step process — too many steps, really — but it’s free books.

I’m also a huge fan of I started researching my family tree before the Internet was in common use so every time I find a digitized record or newspaper account, I’m like a kid in a candy store. Their data store is ginormous and yet queries complete in microseconds.

They also cultivate crowd-sourced data. Subscribers upload their own family trees — names, dates, places — and are allowed to do so in largely free form ways. Ancestry allows multiple variants of New York (NY, NYC, Kings County, etc.). They suggest correct forms, but allow users to enter whatever they want. I can see a couple of Engineers I know cringing at this very idea.

Are you a genealogist?

Genealogy is personal passion of mine. Identifying and getting to people who lived in various areas around the United States and in other countries, who are unknown to me, but who have this deeply personal connection through me is really fun and satisfying.

It’s a hobby that’s been completely disrupted — in a good way — by digital transformation. It used to be that one had to travel to the locals where your ancestors lived to look up records. So many of them have been digitized now that they come to you via the Internet.

Each piece of information is a kind of micro profile of their life at a particular time and place. The micro profiles need to be assembled into a narrative that gives meaning to their lives, to their motivations and challenges, to how they fit into their family, their town, state, and country.

Looking at history through this lens of personal connection is truly fascinating.

Follow Up

To connect with Cyndy, contact her via LinkedIn or @cyfinnie on Twitter.

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2 thoughts on “Product Management Interview With Cyndy Bates Finnie

  1. One of the biggest takeaways for me on this was the story about committing to product features before the customer had signed. Product people and executives often make the assumption that they are pinch hitting for Sales when they get on Sales calls with customers, and it’s not always that simple.

  2. For sure! It’s sometimes hard to initiate a conversation about expectations *before* you get on the phone with a customer – and yet do! It’s better to ask for the obvious than make a bad assumption. Every customer relationship is different.

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