The 54 Questions to Ask for a Brilliant B2B Buyer Enablement Content Strategy

TLDR: My whole life I’ve been told that I’m too curious and ask too many questions. I figured it was high time to call it a strength and double-down :D. Here’s the short version of the 54 Questions You Should Ask.

Your B2B buyer is on a journey to solve a challenge in their business.

They’re doing research, meeting with colleagues, picking the brains of their peers, meeting with vendors. And sifting through mounds of marketing content. Ideally, some of yours.

The problem is, even with most B2B companies using content marketing— we’re still failing at simplifying the purchase process for our buyers.

Ideally, we want our B2B buyer enablement content to begin building trust with our buyers. And so, our content should:

Resonate with buyer needs
Anticipate their obstacles
Answer the questions that will come up within the buying group
Help them build consensus
Validate the buying decision with their peers
Be written using buyer language

But according to Uberflip’s 2021 B2B Marketing Report: The Experience Disconnect, many buyers are frustrated with the lack of relevant, useful content in the purchasing process, and in fact, 33% of buyers see “too much irrelevant content” as a top pain point.

This is a serious problem. When we're building content based on buzzy topics without any backbone, we miss opportunities to build trust with our prospects by providing valuable insights that will help them navigate the buying process. Instead, we risk inundating them with semi-conscious blather that is more of a frustration than a help.

Not surprisingly, when asked about the top drivers for taking action, 61% of buyers reported that they need content relevant to their needs. Duh, right? But interestingly, marketers underestimated the value of content relevancy for buyer engagement, ranking it near the bottom of the list, at #6 out of eight methods of getting a buyer to take action (Uberflip, 2021).

After tackling content strategy for +40 B2B big and small businesses over the last 8 years, here’s what I think is the single reason why so much content marketing is irrelevant to buyers (and thus fails to generate the pipeline impact we wish it would):

To be clear, this is not the pastel colour-coded buy-from-us awareness-consideration-purchase journey, tidily mapped against the funnel. Most of us have that sorted.

I'm talking about the vendor-agnostic, blood-sweat-and-tears QUEST of a complex B2B purchase decision.

Too much content marketing has become about checking off boxes on an editorial calendar than meeting actual buyer needs.

Your marketing VP might be happy that the resource centre is full and that you're meeting your lead targets.

But when busy, frustrated prospects are on the hunt for high-quality, credible information, vendor-brag fluff content is not going to pass the relevance test or incite action. Avoid this stuff at all costs.

Look at the Buyer Journey Through the Lens of Your Buyers

Rather. The best groundwork you can do to develop an effective B2B buyer enablement content strategy is this: Immerse yourself in the world of your buyers. Understand how your product or service fits into the overall context of what they’re trying to achieve. Find out whatever failure is keeping them up at night and help them steer clear of it.

That said, it can be hard to capture a clear buyer perspective of your B2B product/service when you and your in-house marketing colleagues are all drinking the brand Kool-Aid.

But practicing empathy is a good start to help flip your perspective and see things through their eyes. You can ask your buyers questions like:

What are you trying to accomplish with our product/service?
What have you been struggling with that led you to us?
What hurdles have come up through this purchase decision?
Whom else do you need to sell on this purchase?
What would help you build a business case?
How will you measure the success of this investment?
What sources of information did you consult through the purchase decision? Which sources were the most useful?

There is no substitute for having conversations with closed-lost and closed-won buyers. If you haven’t tried it yet, it’s literally golden time spent. You can also listen in on prospect calls and you’ll get good stuff as well.

If you aren’t doing this already, let me be clear: Start tomorrow. But…

Uncovering Buyer Journey Intelligence From Within Your Organization

…in addition to regularly interacting with buyers, there are other sneaky ways of collecting "buyer intelligence" and filling in the gaps in your understanding. See, there are little pockets of insight hidden all-around your organization if you take the time to poke around (and you know where to look).

Here are some examples:

Taking time to connect with your Product team can reveal not only what's coming up on the product roadmap but why it's been prioritized. Often, this relates to buyer needs that have come up in user feedback.

A quick chat with your Sales team can shed light on new types of buyers who have appeared on the scene recently and different questions they may be asking.

Touching base with Customer Success can reveal implementation challenges that keep coming up over and over again.

And the odd chat with your (fingers-crossed) visionary CEO can open your eyes to market shifts that they foresee around the corner.

Sometimes you’ll uncover buying process insights you can immediately apply to your content strategy.

For example, now that you know that buyers are struggling with X implementation challenge, you realize that you should add a new implementation guide to this quarter’s content plan.

Other times, you’ll log the information away to guide your strategy in the future.

For example, getting insight from the CIO to understand how changing regulations may affect your business 6-months from now can help you understand how the messaging may need to shift.

Content marketing can't operate on a little island of its own and expect to be successful.

As a content marketing manager, I checked in every month with a few colleagues on the Sales, Product, Customer Success and Executive teams to sniff around for insight, context, and other clues to help me better understand our buyers' world. I'm a sucker for structured processes, so I'd schedule a running 30-mins meeting once/ month to cover the following questions.

The Questions You Should Ask Sales

What does the sales cycle look like these days?
What are the most common objections and questions coming up?
Where are prospects/influencers getting stuck/ slowing down/halting? Why do you think it’s happening?
Which types of buyers quickly understand the value of our product (and buy without too much friction)? Can you describe these buyers?
Who struggles to understand the value of our product? Can you describe these buyers?
Anything new going on in our buyers’ businesses? Any shifts they are dealing with that we should be aware of?
Any new types of buyers or stakeholders involved in the purchase decision?
What percentage of MQLs converted to closed-won in the last month?
Why do you think buyers are buying from us versus competitors? Who do we tend to lose to? Why?
Any new competitors on the scene?
How is retention? Who tends to stick around?
Any churn issues? Who tends to churn?

The Questions You Should Ask The Execs

Do you foresee any significant shifts happening in our industry?
What's the vision for our product in the short term? In the long term?
Do you foresee any government regulations or industry-wide changes that may affect the way we do business in the next 3-12 months?
Do you see any buyer groups for whom our product may be more or less relevant?
What's our "Why" and how has it evolved?
From the perspective of our buyers, how do you think we are different/better than competitors? Are we?
What data points/benchmarks do you feel would help build out our story and value proposition?

The Questions You Should Ask Product

Any new insights about our users?
What's new with our product/solution? What's coming down the pipeline in the next 3-12 months?
Are you generating any valuable insights from usage analytics? Care to share?
What's the vision for the product/solution?
Any new competitors on the scene?
From the perspective of our buyers, how do you think we are different/better than competitors? Are we?
What are the strengths/weaknesses of our product, and how are they evolving?

The Questions You Should Ask Customer Success

What are the most common questions you hear from buyers?
Where do they encounter friction when implementing our solution?
How do buyers measure the results of our product?
How much support do you offer buyers to help them track/measure their results?
Where do they run into issues when trying to get results out of our solution?
Are you tracking customer benchmarks?
What do you do to help coach them on improving results? Do you currently use content to do so?
Which types of engagements tend to be the most successful? What is our sweet spot?
Any new potential case study candidates?

I recommend meeting with someone at least your level of seniority and higher if possible since they'll ideally have the ability to crystallize insights into more of an overview. If you're a content manager, at least speak with a sales manager and even better if you can sync up with the VP of Sales.

Once You’ve Asked These Questions, What Do You Do With These New Insights?

When you start landing on a few golden buyer insights, I’m confident that you have good instincts and can figure out what to do with them. But some examples could include:

With insights into which buyers are buying with the least friction...Develop a case study strategy that focuses on these priority buyers.
With insight into competitor products and messaging...Take a pass at your product/feature messaging is differentiated and doesn’t sound like everyone else.
With insight into the implementation challenges that buyers are experiencing...devise a new implementation guide and project management template that helps them navigate these obstacles.
With insight into the consensus creation challenges that buyers are having...work with sales to create a resource explaining the top 5 internal meetings that must happen to build a business case for this purchase and what questions need to be asked.

...And the list goes on. Now, go forth and question everything!