How to get better answers to tough questions


When studying with a master teacher, one of  the most important things you can do is to arrive with your burning questions. Your burning questions are the questions you must get answers to. This is something that I learned from my teacher’s teacher, Stephen Hayes.

However, some questions are better than others. Some questions will get you an answer, but not an answer that you can use to make advancements in your own growth. Your task as a questioner is to devise questions that yield real, usable answers.

How? The way to devise a great question is to know what a great answer looks like. 

A great answer has in it not only the overall knowledge you need, but what immediate next steps you need to take in order to bridge the gap between the question and the big picture.

A good answer is efficient. It does not contain lots of information you already have.

Finally, a good answer cuts to the heart of the matter immediately. Some people ask questions just to talk, or to show off in front of others. You’ve likely been at marketing conferences where someone’s question during Q&A is a 30 second ad for their business before they finally get around to asking something. 

Based on all of this, what does a great question look like?

A great question has three parts:

  • Create a little bit of context by stating the specific problem you’re encountering
  • Concisely indicate what information you already have
  • Ask for the big picture and next steps

Here is a mundane example using email marketing. 

A mediocre question would be, “I am having some trouble with getting my emails delivered. How would you fix this?”

A great question would be, “My emails to consumer domains like Hotmail on not getting through. I have set up SPF, DKIM, and DMARC in monitor mode. I’ve checked my Sender Score and it is clean. What should I do next? Is there a trend in deliverability that I missed?”

The quality of answer you’ll get to the latter question should be significantly more helpful than the quality of answer you’ll get from the former question. Use this 3 part format when you’re asking speakers questions at conferences. Use it when asking questions of your teachers and mentors. Use it during sales and business development meetings to advance the sale.

Ask better questions to get better answers!

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What’s Your Best Day in Marketing?

DemandBase (a SHIFT client) asked the following question:


A fine question for a lighter Friday blog post.

What’s the best day for me as a marketer? It’s not a big win, though those are certainly nice. It’s not a hire, a promotion, or a bonus. Again, those are nice things to have, and I certainly would never spurn them.

No, the best day for me as a marketer is a day when I learn something new that I can use, or I create something new that I or others can use. In modern marketing, applied knowledge is power.

When you get a new customer, that’s a temporary increase in your revenue. Customers come and go. Money comes and goes, too.

When you learn something new? That’s a nearly permanent increase in your marketing power. There’s something you can do that you previously could not do. There’s some advantage you now have, even if it’s just leveling the playing field with your competitors. When you create something new, you have a distinct, tangible advantage that few others can match, at least for a while. This is why innovation is so important.


Innovation is about making something new, about creating something new. True innovation is hard to come by, but once you have new knowledge, you have new power.

Those rare days in marketing? Those are the best days of my career.

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How answering questions proves authenticity in marketing

One of the questions asked recently at Social Media Marketing World was how much authenticity matters. How much does it matter if you don’t personally write your own social media posts and content, especially at a brand where it’s assumed that a social team will be at work anyway? For example, when I write for the SHIFT Communications blog, does it actually matter if my name is on the post?

If your audience is only consuming content and not interacting with the brand, then it doesn’t matter whose name is on it. You could be reading Seth Godin’s intern or Chris Brogan’s robot army, and as long as the content was still genuinely helpful, great.

Here’s where non-authenticity bites you: the moment someone asks you a question. If you’re doing a webinar or speaking onstage and someone references a blog post you wrote, it’s awkward and telling when it reveals that you don’t even know what you’ve written. “Hey Chris, in your post on Bitly URLs for social media analytics, why didn’t you address the JSON array from the API instead of using Google Sheets?”

If I hadn’t written that post, I’d be at a loss. Imagine responding with, “Oh, yeah, um…” I’d have to make something up or guess. In that moment, any credibility I have with the questioner would evaporate, and if that questioner was a potential business lead, my lack of authenticity could cost me thousands or millions of dollars.

Instead, if I know what I’ve written, if I actually am who I say I am, then I could say, “Absolutely you could, and in fact, a good portion of Bitly’s API is accessible ONLY by JSON, but that’s outside the scope of the blog post. You’d have to build the custom ImportJSON function from Trevor Lohrbeer to do that.”

The answer to the question often tells you more about what level of knowledge you have than the posted content itself.

This is why authenticity – meaning that you are who you say you are – is so vital. Answering insightful questions are the absolute best way to demonstrate the depths of your personal expertise.


If you are who you say you are, you welcome questions rather than avoid them, and you ask for the hardest questions people have so that you can expand your own knowledge and growth.

To quote Oscar Wilde, be yourself. Everyone else is already taken. That includes what you post on social media. It’s fine to automate. It’s fine to schedule. But know what you’re sharing so that when someone asks you a question about it, you know the answer. In the words of friend and mentor Tom Webster, “Do your own work.”

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