• 05
  • January

20 Questions Every B2B Marketer Should Ask, Heading into 2020

With 2020 upon us, let’s give ourselves (as marketers) the best chance to succeed in “the year of perfect vision.” To inform our activities—to make sure we’re doing the right things—here are 20 marketing (and related) questions we should ask before we get going on anything else.

It is not the answer that enlightens, but the question.

Eugene Ionesco

Setting the Stage

Let’s start by ensuring we understand the broad context of objectives and strategies—everything else is just tactics (and those should always come last).

It ain’t what you don’t know that gets you into trouble. It’s what you know for sure that just ain’t so.

Probably not Mark Twain

1. What are the company’s objectives for 2020?

What are your company’s handful of top-level objectives for 2020? Maybe there’s only one (e.g., “Grow”, “Grow by 30%”, “Survive”) or maybe there are a few—but there definitely shouldn’t be more than five, or you’re getting into Dilbert territory and you should maybe find a different employer.

2. What are the marketing organization’s objectives for 2020?

Knowing the company’s objectives lets you orient your marketing objectives to ensure the department’s efforts are directed toward the most important outcomes.

So, with the company objectives as the backdrop, make sure you understand what specific objectives the marketing department is working toward.

Since time and resources are finite, we can’t do everything; these objectives serve as our guiding beacons when things become messy and decisions need to be made.

3. What are the Marketing organization’s strategies for 2020?

With the objectives in mind, we should agree on a handful of strategies. Make sure the strategies are consciously chosen in pursuit of the objectives, and not out of convenience (e.g., easy tactics) or tradition (e.g., what you did in 2019).

Our Market

As marketers, we need to know our market (the clue was right there in the name all along!).

That might seem obvious, but this topic is one of those which can get overlooked—everyone just assumes that everyone else knows the market, and a quasi-mass-delusion sets in which is shaped entirely from internal assumptions and echo-chambers.

So let’s ask some questions about our market.

In all my affairs it’s a healthy thing now and then to hang a question mark on the things you have long taken for granted.

—Bertrand Russell

4. Who are our best customers?

Knowing who your best customers are lets you craft positioning and messaging which appeals to prospects who fit the same mould—making all our efforts more effective and more efficient.

What does “best” mean in this context? It could mean a few things: most profitable, happiest, most eager to adopt your newest solutions, and so on. Plus, “best” might change over time, depending upon your company goals.

Anyway, the point here is to agree on what “best” means for your company, at this time, then identify existing customers who exemplify that meaning, which ultimately lets you spot common characteristics which unite them.

5. What barriers, obstacles, or complications can prevent a prospect who likes us from buying our solution?

Let’s say someone loves your solution. They want to buy it. But something is getting in their way.

Your job is to identify all of those potential somethings—buying barriers—and then work to systematically eliminate them.

6. Why are other potential customers not choosing us?

Here’s something I’ve seen play out in many companies: they win some customers and then work to serve those customers really well.

What’s wrong with that? Nothing, provided the company’s also doing other things.

But here’s the risk: the company (especially Product Management) becomes so focused on serving those customers, that you forget to look at the rest of the market. You develop incremental features which don’t win you many more customers.

Here’s something to keep in mind: unless you’ve got dominant or majority market share, more prospects are choosing alternatives than are choosing you.

If you want to win these prospects as new customers, then you need to understand what alternative paths they’re following: maybe they’re just living with the pain (i.e., do nothing), maybe they’re developing a solution in house, maybe they went with Oracle, maybe they hired a few interns to manually manage the problem, maybe they’re using Excel, or maybe they chose one of your peer competitors.

This last option, by the way, is frequently top of mind for you, but often the least frequent in reality.

Knowing Ourselves

Like understanding the market, really—and honestly—knowing ourselves often gets overlooked or taken for granted.

And that’s risky, so let’s revisit it for 2020.

Knowing yourself is the beginning of all wisdom.


7. What’s our value proposition?

What value do we bring to the table?

Presumably, we want prospects to give us money, and in return we will provide something. Yes, I realize I’m spelling out some first principles here, but this exchange is often overlooked. Many a company leader scratches their head wondering what the problem is when the answer is that prospects don’t sufficiently value what you’re selling to justify forking over precious money.

So let’s look at the two most common ultimate ‘value’ options:

  • We help you make more money: give us X, and you have a good likelihood of generating X+Y
  • We help you save money: some problem is costing you X; our solution costs Y; our solution solve the problem, so you save X-Y

Of course, your solution might not be as directly connected to the ultimate value proposition as indicated above. Perhaps you help with regulatory compliance, and the prospect gives you money so that they comply with a regulation, so that they probably avoid a potential fine. You’re a few steps removed, but you’re still in the “save you money” value prop.

What if your solution improves customer satisfaction? Well now, maybe your pitch is that you reduce churn—you can tie into eliminating unnecessary support costs and the burden of customer cost of acquisition (save money), while also protecting revenue streams (make money).

Ugh, things are getting complicated! In general, the farther you are from the money saved or made, the harder it is for you to show a clear value proposition.

Anyway, the point here is to have an honest conversation about your value proposition, and not just an immediate agreement that your value is obvious and only an idiot wouldn’t see it. If you find the conversation falling into that trap, then here’s a doozy to ask: “If our value is so great and so clear, then why don’t we have more customers?”


8. What are our meaningful differentiators?

Here’s a fun fact, in the Waterloo Region Technology Marketing Spotlight, we asked participants to rate the significance of each of five common sales enablement challenges; respondents reported the most significant challenge to be “Creating differentiation versus alternatives (e.g., competitors, ‘do nothing’, an in-house project, etc.).”

So it’s worth taking some time to identify your meaningful differentiators.

Two things to keep in mind on this one:

  • To be a differentiator, a thing has to be different from (at last most of) the alternatives
  • To be useful for your customers (and for you), that different thing has to be meaningful

Many companies are so inside-out that they just can’t see the obvious: that things they think are differentiators aren’t, and that things that are legitimate differentiators just don’t matter to customers.

Again, you’re better off having a tough, honest conversation than in ignoring the truth.

9. Why should someone choose us?

I mean, when it comes right down to it, if you can’t answer this question—quickly and powerfully—then you’re in trouble.

Here’s a fun exercise: at your next meeting, hand out cue cards which ask the question, “Why should someone choose us?” and give each participant a few minutes to write down—secretly/anonymously—their response.

Then review. (Hilarity or tears may ensue)

Learning from the past

If we want different results, then we need to try new things. Far too many corporate plans for 2020 are the corporate plan for 2019 plus or minus a few budget percentages here and there.

Unless you’ve got some leading indicators which suggest you’re legitimately (!) on the cusp of a breakthrough, then incremental plans are a surefire way to achieve only incremental differences.

Want 2020 to be different? Then do different things.

If you do not know how to ask the right question, you discover nothing.

—W. Edwards Deming

10. What worked well in 2019?

Do more of it/them in 2020.

(unless you have real reason to believe that something worked well purely due to luck)

11. What didn’t work well in 2019?

Do less of it/them in 2020.

Now, one caveat here: maybe you had a good idea but executed it poorly. In this situation—and only if you have information which strongly suggests the idea was sound—then you can try doing the thing, but make darn sure to do it differently this time around.

Practical Matters of Scheduling

I always like to keep the schedule in mind, as it’s part of the overall context for your activities.

It is better to debate a question without settling it than to settling a question without debating it.

—Joseph Joubert

12. What fixed/unmovable commitments do we have?

Make sure you’re aware of commitments like tradeshows, conferences, and other events which are already scheduled (say, customer workshops). These form part of the backdrop against which all your activities will be conducted.

I’ll also use this opportunity to state that I’m very much opposed to contriving releases and initiatives around these shows and conferences—to me, that’s backwards thinking. Instead, I advocate for running your business based upon what’ll best serve your customers, then leveraging calendar events as is practical, rather than trying to cook up some big release or launch just because there’s a show happening.

13. When are things coming, and what are they?

This confusingly worded question is worth at least an entire post in and of itself, and I’ll oblige at some point. For now, though, let me just say that for marketing people to properly do their jobs, they need to know (in advance!):

  • When things (releases, products, etc.) are going to arrive (be ready to sell)
  • What those things are

In that counterintuitive order.

Sales Enablement

Very broadly, there are four main mechanisms by which marketing contributes to increased sales effectiveness. These questions get to the heart of those mechanisms.

It is not your customer’s job to buy from you. It is your job to find out what would make for an exceptional experience from their point of view, and invite them into it.

—David Nour, in Co-Create

14. How can we bring in more good leads?

Bringing in more good (!) leads lets you increase the absolute number of wins even while keeping the win rate constant.

15. How can we increase our win rate?

To increase the proportion of opportunities which you win, you should explore activities and content which shows compelling value and overcomes buying barriers.

16. How can we shorten the sales cycle?

Shortening the sales cycle lets you close more deals with the same number of salespeople.

While your prospect has ultimate control over the buying process, you might be able to accelerate their decision-making by actively directing them through the learning and evaluation process (always suggest next steps) and by avoiding stalls (e.g., by rapidly addressing inquiries via self-service content or by having answers to common questions available at hand).

17. How can we increase our average deal size?

Here are two ways to increase the average deal size:

  • Sell more things (e.g., by showing solutions to more problems, by demonstrating positive ROI) in a single deal
  • Limit discounting (e.g., by proving meaningful differentiation)

The details are left to you, dear reader.


Content is the vehicle by which your messages get out into the market and in front of your target audiences, whether handed over by a salesperson, delivered in a presentation or webinar, downloaded from your website by an existing customer, or organically discovered by a new prospect searching for a solution to a problem.

A comprehensive content portfolio helps you get a prospect’s attention, anticipates and meets their needs through their buying process, and arms your champions:

  • Top-of-funnel content increases awareness and starts to build demand
  • Middle-of-funnel content enables prospects to understand and evaluate your solutions
  • Bottom-of-funnel content seals the deal and helps prospects justify their decisions

Ideally, your content anticipates and specifically addresses buying barriers at the precise stage in which they arise. Moreover, a great content library substantially improves your search relevance, raises the bar versus the competition, and is vital to scaling up your sales and marketing efforts efficiently.

Now is the winter of our discontent.

—Shakespeare’s Richard III

18. What knowledge gaps exist in the market?

Identifying knowledge gaps is a crucial step in super-charging your sales and marketing activities. Once you’ve identified gaps, you can take steps to address them—through content, through campaigns, through improved sales processes, and so on.

So start by asking what misconceptions exist in the market, what technical concepts are poorly understood, what symptoms are misdiagnosed…?

Additionally, ask yourself:

  • What concepts or general topics do we have to explain, over and over?
  • What questions do our prospects frequently ask?

19. Where are the gaps in our content coverage?

In the Waterloo Region Technology Marketing Spotlight, we asked survey participants to rate their company’s content library. Unfortunately, respondents indicated that there’s much to be desired:

  • Both Top-of-funnel content and Middle-of-funnel content landed between “Meh” and “Good enough” (which, frankly, isn’t good enough)
  • Even worse, Bottom-of-funnel content—the content which pushes deals over the finish line by demonstrating ROI, by proving differentiation, etc.—averaged much lower

Clearly, there’s much work to be done (I mean, opportunity!), and 2020 is the year you make your content shine. To find out where to invest your effort, ask yourself two questions

  1. What gaps do we have in terms of funnel stages? (for instance, maybe you’ve got good top-of-funnel content, but then you leave prospects hanging when they want details)
  2. What gaps do we have in terms of portfolio? (for instance, maybe some products have decent coverage, and others have little)

And Finally

A prudent question is one-half of wisdom.

—Francis Bacon

20. Why is 2020 going to be better than 2019?

If we can’t answer this one, then we’re in trouble.

What’d I miss? What do you think?

Please share your thoughts below!