Hi, fellow future and current Data Leaders; Ben here 👋
Before diving into today’s newsletter, I want to take a moment to thank this issue’s sponsor, BMC. Many data teams still spend too much time babysitting pipelines and stitching together scripts. Control-M helps automate that work, coordinating data workflows, triggering ML jobs, and syncing across cloud platforms, so teams can focus on analysis instead of maintenance.
Check out their latest case study to see how it can simplify complex workflows.
Now let’s jump into the article!
A common challenge for data teams is figuring out what to work on that will drive the most value.
In some cases, the business has projects they believe should be taken on that you might disagree with, but you don’t have a solid list of suggestions, so you’re stuck with what they’ve asked you to work on.
In other cases, the business team might not know exactly how they’d like to use data, other than perhaps a dashboard or two. That means you can’t just ask, “What data projects do you need?” and expect a helpful answer.
Instead, you need to ask questions that uncover pain points, opportunities, and processes where data could make a meaningful difference.
At Facebook, we conducted this exercise every six months to realign priorities and identify new, high-impact projects. We’d go and talk to our business partners to understand their current and future needs. From there, we’d work to come up with projects we believed aligned.
If you are looking for questions to help you better align with the business, here are seven questions you can ask to surface valuable data. (Also, I’d love to hear if you have any questions you’d recommend.)
1) What’s keeping your team from hitting its targets right now?
Not everything is about data. Many leaders recognize that there may be areas where they are struggling to meet targets.
Perhaps they aren’t converting enough on ads, or their team has consistently missed the mark when it comes to delivering products on time. There are real-life situations where data may or may not be helpful.
But instead of asking, Where can data help, your focus should be on understanding the bigger picture.
Department Specific Versions Of This Question
Finance - Are there recurring surprises in expenses or revenue that you wish you could predict earlier?
Marketing - Are there channels where you feel you’re spending too much but not seeing results?
Operations - Where do delays or inefficiencies tend to pop up in your daily workflow?
2) If I could give you insight to metric A and it went up or down 20% what would you do?
This is a question I ask as a follow-up to the question: What key metrics are your team responsible for over the next half, and which ones do you not have access to that you wish you did? Once they answer, my next question is posed as a way of taking the leader through a thought experiment.
Let’s say you do have insight into this metric, and it does change.
So what?
Can you do anything about it? Have you even thought that far? Some business leaders seriously haven’t.
Department Specific Versions Of This Question
Finance -If your cash flow projection changed by 20%, what levers would you pull?
Marketing - If organic conversions dropped 20%, how would that change your strategy?
Product - If churn went down 20%, what would you double down on?
3)When was the last time a data insight changed your plan or decision?
This question is somewhat of an “are you a believer question. Everyone likes to say they are data-driven, but if you ask someone this question and they don’t have an answer, this should cause you to pause.
My follow-up question would be something along the lines of “Why not?”
This could lead them to say something along the lines of “I don’t trust the data,” or perhaps they simply rely on their intuition.
On one hand, you might need to address the data quality issue if it is a legitimate concern. On the other hand, this stakeholder might not be the right one for you to take a project from.
Department Specific Versions Of This Question
Finance - When did a forecast or variance analysis cause you to change your spending plan?
Marketing - Did any A/B test results surprise you recently?
Product - Did data ever contradict what user feedback suggested?
4)Where are we spending a lot of effort without seeing results?
Many business teams have established workflows that they must follow. Finance and accounting teams must close the books every month, while other teams may need to make partner payments and utilize a CSV-heavy process to calculate them. Additionally, there are numerous board reports and other tasks to attend to.
An alternative question could be - What’s something that feels “manual” or time-consuming in your process?
Department Specific Versions Of This Question
Finance - Which recurring reports take time to create but don’t seem to influence decisions?
Marketing - Which campaigns require heavy effort but don’t convert well?
5) Who are the key stakeholders you report to, and what metrics do they care about most?
I really enjoyed my conversation with Celina Wong a few months back. One of the points she brought up is that often, we deliver metrics, reports, and analyses that don’t stop with our stakeholders.
They are heading to the next stakeholder(often in a more condensed manner). I’ve had multiple conversations where the leader on the other side said something along the lines of, “I can sell that to the CEO” or “I just need a clear narrative to tell the board.”
Our work as data teams is going somewhere, so we might as well know where.
Department Specific Versions Of This Question
Finance - What metrics does the CFO or board scrutinize every quarter?
Marketing - What story do you have to tell in your quarterly review?
Product - How do you summarize product impact for leadership?
6) What win in the last 3-6 months are you looking to double down on?
I enjoy giving my business partners space to share with me the wins they are most proud of. One, I like knowing what drives other partners, but it could also show where there might be an opportunity for the data team to amplify a recent win.
Department Specific Versions Of This Question
Marketing - Which campaign or audience segment performed better than expected?
Product: - Which recent feature exceeded expectations, what might be driving that?
7) When was the last time you made a bad (or late) decision because you lacked the right data?
This question provides several benefits. First, it allows you insight into how a business leader thinks about data. Have they thought through where data might have been helpful in making a decision in the past?
In some cases, this question might get you a very empty answer, where the business leader might not really say anything because they have never really used data anyway.
In other cases, there might be very clear pain points that you elicit by asking this question. Where the business leader will be like “Why yes, in fact, two weeks ago I was trying to decide on how to spend marketing dollars…”
If they do say “Two weeks ago,” I’d push back on that and see if that was merely recency bias. But overall, it’s a great question to start digging even deeper.
Department Specific Versions Of This Question
Finance: - When did missing or delayed data make it hard to forecast or budget accurately?
Marketing - When did you launch or pause a campaign without knowing how it was performing?
Product - When did a lack of user or performance data delay a product launch or decision?
Final Thoughts
When you ask, “What do you need from data?” you’re really asking them to think like you. And that limits what they’ll say, because they can only imagine the solutions they already know exist.
If you flip it, and start from their perspective , their pain points, their decisions, their blind spots, you’ll uncover work that actually changes how the business runs.
As always, thanks for reading.
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“The default state of data teams is failure.”
This was in the early 2020s, when many data teams felt like they had ballooned in size. Everyone wanted to be data-driven and cheap money made it easy.
Fast-forward to 2025 and the landscape looks very different. Companies are running leaner. Many have intentionally shrunk their data teams and, in some cases, lean more on external partners instead of adding headcount.
As a consultant, I’m often brought in when a previous team has disbanded or when leadership wants to turn around a struggling data environment. Across these engagements, I’ve seen recurring patterns, root causes that explain why some data stacks and teams fail to deliver, and what it really takes to bring them back on track.
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End Of Day 197
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Ben, this is a fantastic list. I especially appreciate the framing around not just asking the business what they need from data directly, but rather, focusing on their pain points and decisions. It's so easy to fall into the trap of providing data for data's sake, but these questions really help to uncover opportunities where data can drive tangible value.
I'm a big believer that data teams should be deeply embedded within the business, acting as strategic partners rather than just service providers. These questions are a great starting point for building those relationships and ensuring that data efforts are aligned with business priorities.
One question I'd add to the mix, particularly relevant in today's fast-paced environment, is: "What are the biggest assumptions you're making right now, and how could data help validate or invalidate them?" This can be a powerful way to identify areas where data can mitigate risk and inform strategic decision-making.
When you have answers to these questions, Where do you exactly go from there? Is there a specific framework to apply?