The Questions Executives Should Be Asking Marketing

Pipeline is just the beginning. These 9 questions help uncover how marketing drives strategy, efficiency, and growth.

In too many companies, marketing is either misunderstood or misused.

Executive teams often focus on what’s easy to measure: pipeline generated, campaign activity, maybe some website stats, and awards. And while pipeline generated is a valuable metric, it’s not the only one, and if your lead-to-close (LTC) process is shaky, it can be deeply misleading.

After 20+ years leading GTM for B2B companies, VC-backed, PE-owned, and publicly traded, I’ve seen a clear pattern. The most effective executive teams don’t just measure marketing. They engage with it. They ask better questions. They dig beneath the surface-level metrics to understand what’s working, what’s not, and where strategic adjustments are needed beyond pipeline generation.

Here are the 9 questions I wish more executives teams (and boards) would ask their marketing leaders because when they do, alignment strengthens, results improve, and strategy stops operating in a silo.

Strategy & Positioning

1. How are we differentiated in a way that matters to buyers?

   Differentiation isn’t useful unless it’s relevant. Most positioning is written for internal consensus, not market clarity, and that’s a problem. If you haven’t pressure tested or focus-grouped your differentiation, you are guessing, and it may be completely wrong.

2. Where are we winning and losing deals from a positioning perspective? And why?

   You can’t fix what you can’t see. So many companies don’t invest in win/loss analysis to understand their true strengths and weaknesses in the buying cycle. Understanding how your story lands in competitive deals should be non-negotiable.

3. Is our messaging aligned with what the market already believes? Not just what we hope they’ll believe?

   Aspirational messaging might win applause internally, but buyers act on urgency. They care about what you’re solving today, not what you promise tomorrow.

Pipeline, Revenue & Efficiency

4. What part of the pipeline is marketing accountable for, and how are we tracking against it?

   As we all know, pipeline is a strong signal and should be reported on weekly (or available via live dashboards). As I shared above, if your LTC process is broken, even great pipeline metrics can give you a false sense of security. For example, if AEs create an opportunity and enter pipeline before true discovery, you’re pipeline is likely over-inflated and the projected close date is considerably off.

5. Where are we seeing diminishing returns in our GTM efforts?

   This is one of my favorite questions, and it is rarely asked. And worse, when it is asked, I’ve seen too many marketing leaders not have an answer. More budget doesn’t guarantee better results. Especially in this market, efficiency and signal detection matter more than spend.

6. If we had to cut 20% of marketing spend tomorrow, what would we keep and why? And if you were given an increase of 20%, what would you do, and what impact would it have?

   This is a pressure test. It forces clarity on what’s truly driving business value. I will never forget being asked this question when I was at Salesforce, and it completely changed how I prioritized. On the flip side, I was routinely handed $1M at the end of the quarter and expected to drive results. The takeaway? You should always know what you’d cut and where you’d double down.

Customer & Market Insight

7. What are we learning from customers that sales and product may not have surfaced yet?

   Marketing sits closest to the top of the funnel. What’s the BDR team hearing? What’s resonating in campaigns, or not? When paired with feedback loops from win/loss analysis and customer success, marketing insights become an early warning system.

8. What signals are we seeing that the market is changing?

   Good marketers watch trends. Great marketers spot inflection points. Talk to your G2 rep and ask them what they are seeing. Partner with market analysts and schedule regular calls to understand their perspective. And look at your own data (win/loss, customer success, AE call transcripts) to get a read on what is happening in the market.

Innovation & Adaption

9. How are we adapting to changes in buyer behavior, such as AI, privacy laws, and content fatigue? What have we learned from our experiments?

   How buyers discover, trust, and evaluate vendors is quickly evolving. Does your team understand how buyers are searching for answers and how generative engines come up with responses (from where they learn)? Are you testing new channels and formats? If not, that’s a blind spot.

If you’re on the executive team, these are the conversations you should be having regularly with your marketing leader. Not just in board prep. Not just in QBRs. But as part of an ongoing bi-directional conversation about how your go-to-market strategy is performing, evolving, and adapting to what the market demands.

And if you are the marketing leader, don’t wait to move the conversation beyond pipeline. You own the GTM strategy. It’s your job to connect the dots between insight, execution, and growth, and to bring strategic questions and insights to the table, not just metrics. Because high-performing companies don’t just generate pipeline. They build GTM strategies that convert, scale, and withstand change. That kind of performance? It starts with better questions and stronger alignment.

---

If you’re new here, welcome. Growth, Accelerated is a weekly newsletter on go-to-market strategy, leadership, and the real work behind high-performing teams. If you found this useful, subscribe or forward it to someone who needs this reminder today.

Related Articles