I wrote this internal piece in 2023 reflecting on the approach of Automattic's customer support division, and suggesting a strategic approach our support agents could use. At the time, they were seeking to shift customer support towards customer success, by integrating sales into support conversations.

Something we’re moving towards [at Automattic] is improving conversational strategy. As I work to figure this out alongside you all, I’d like to insert an advocation of closed questions into our dialogue.

The purpose of this post is an exploration, suggestion and questioning of how we can communicate more effectively with customers in our work, and not an instruction or directive.

As an autistic person, I’m very used to thinking highly strategically about how I communicate. I’ve become mostly good at holding nuanced conversations (with occasional spectacular failures!), but the strategy behind interpreting what the other person means and what my next intervention in the conversation should be, always feels like a game of three-dimensional chess.

As Alis Rowe puts it rather well,

“[Autistic people] can become very good at mimicking common social skills. But while they may look like they’re socialising happily, it’s often actually incredibly hard work… it’s important not to automatically assume that an autistic person won’t understand a nuanced conversation – some [autistic people] can learn to spot [non-literal conversation] cues, but it’s not easy.”

— Alis Rowe, 10 things autistic people want others to know about talking to them

Because I do this really hard work every time I interact with anyone, at any time, I think being autistic sometimes helps me see the meta-conversation more readily than some people, and to approach conversation ‘naturally’ in a more conscious and strategic way than some. So, here… I think I’m recommending inserting some autistic skills! into your day to day conversations with customers.

Open questions

We’re talking a LOT about open questions, and that’s right. It’s common knowledge that asking open questions is good sales technique that encourages exploration and opens up depth and nuance in our conversations with customers, and helps us understand their needs. Here’s an article on this and here’s another. And internally, the resource which covers this in the clearest way that I’ve seen so far, is the series Let’s Practice Inquiry:

“By asking open-ended questions and actively listening to their responses, we can gain insights into their underlying assumptions, values, and beliefs. This information is critical to building rapport, establishing trust, and creating a shared understanding of the customer’s situation…. Why does this customer have a website, or why are they considering building one? How are they pursuing that goal? How comfortable are they with online tools? How much effort do they want to put into this aspect of their work? What is working well for them and what isn’t? ”

— 'Let’s Practice Inquiry' (internal Automattic post)

This is strong, and important, and we’re rightly emphasising this type of approach. However, sometimes in our enthusiasm to insert an open question, we end up asking users “what are your goals for your site?” or similar open questions, that are just too open:

“Some questions can be too open and not lead to the kind of answer desired. For example, if a sales professional wants to learn about their customer’s timing and budget, asking “What are you looking for in a solution?” is too broad. Without added structure and context, the customer could end up talking about any aspect of the project, quickly taking the conversation off track.”

— Richardson

Closed questions

Closed question can start with “do” or “is” and result usually in a shorter answer, or “yes” or “no”. While it’s definitely true that this can close things down in a sales conversation if that’s all we do, ClearVoice comments that closed questions can be really useful for fact-gathering.

“When used by salespeople, closed-ended questions can also be a tactic to assess how cold or warm a lead is, and to move the sales process along. For interviewers such as writers, closed-ended questions are often used to establish background facts about a topic or person… When the answer is provided, it will determine whether or not it makes sense to continue pursuing a lead (especially related to budget and timeline).”

— ClearVoice

So, closed ended questions may be just fine to use as part of your conversational strategy, if they help you a) gather specific information, b) prompt the conversation to its next stage and c) open the floor for an open ended question and deeper exploration.

“The key is to use close-ended questions alongside open-ended questions to yield as much information about your prospect as you work to get them across the finish line.”

— VanillaSoft

So, the key is to combine both approaches. This could mean that your actual conversation opener, is a closed rather than open question:

“Do you think [insert area] is a problem for you? If they say yes, you can explore. If they say no, same thing. You can push them with questions that get them to question their initial response. As the expert, you’ve seen what problems other companies in their space face. This question both establishes you as knowledgeable about their industry and exposes potential pitfalls. You can very quickly get a great deal of information by employing closedended questions. Of course, each answer can be followed with a “why?” or “tell me more about that” to dig deeper. The best sellers use a mix of open-ended and closed-ended questions to conduct a thorough needs discovery, touching on a number of different topics.”

— How to Use Closed-Ended Questions in Sales

Examples from real website support sales conversations

If we look at the site early in the interaction, we can use closed questions to actually actively coach the customer into identifying their own needs. Here are some examples that start with “do” or “are”:

• “It looks like you’re in the early stages of setting up an online shop. Do you have a plan yet for how your customers are going to make their purchases?” – eCommerce upsell opportunity
• “Your logo and branding are great – are you aiming to design the site to match those exact colours?” – design services/tools upsell opportunity
• “I see the site is advertising a local restaurant. Are there any other features you’re planning on adding (online ordering, for instance?)” – website functionality upsell

Technically, all these could be answered by yes or no, and if we leave it there, we’re shut down. But, here are a few possibilities for how these initial closed questions could then be flipped to open questions:

• Do you have a plan yet for how your customers are going to make their purchases?
• Yes, they’ll email me the product they’re interested in and their address, and I’ll send them my bank details.
• I see! What are your future plans to grow the site as you start to make more sales?

We could also have asked this customer open questions around their comfort level with website building, or their level of experience running an online store. We could also have asked a few more closed questions before going ‘open’, such as “Would you like customers to be able to pay online using their credit card?”

• Great! With the [eCommerce add-on], you’ll be able to set up a fully functional cart and checkout on your site, with online ordering and card payments included.

Another example:

• Are you aiming to design the site to match those exact colours?
• Yes
• Great! What sort of look are you going for?

We could also have asked the customer more closed questions around their level of satisfaction with their theme, before going ‘open’. The extra information we gather here helps us make a really targeted and personalised recommendation:

• Yes, the [upsell product] will let you specify that colour and font. It looks like X, Y or Z themes might be a good fit, based on the examples you’ve shown me: those are available with the [upsell product] as well.

Leading the user through the support-success-sales conversation funnel

The superpower of the closed-questions approach to getting a conversation started is doing it as part of the validation phase of a support interaction, before we start to troubleshoot. To take an example scenario:

• A user comes into chat wanting help adding captions to images in their gallery.
• We know (from the site context itself, which says so on the home page) that they want to use the site to sell their home made greetings cards.
• The user is a beginner, and has so far just an empty page with an image gallery of different greetings cards (in which they’re struggling to add captions to describe each greetings card).

How would it feel to turn this into a sales interaction? Key point: The user doesn’t really need a gallery with captions. The longer they spend on trying to achieve this, the more time is wasted.

We could guide them on the captions aspect, then ask them something open like “what are your next priorities to build your site?” It might work. But, they may just engage with that pretty briefly. They may consider the interaction finished. This may be particularly true of some customers who simply have a briefer or more abrupt conversation style – this type of customer may not respond very willingly to open questions. We can adapt our approach based on what they do. (Just like in chess!)

A few example possible closed questions, asked during the validation phase of a support interaction, can nudge the user gently into brainstorming with us. These are sales questions (some of which are really closed, and some of which are less so) but they feel like support. Users who have asked a specific question, are being led gently through an exploration with us, so that we thoroughly understand their broader goals before we start troubleshooting:

• When your customer clicks the image, what would you like them to see or do next?
• What would you like this image gallery to do, in your site?
• What action would you like your site visitors to take when they visit this page?
• How would you like the site visitors to actually buy the cards from you?
• Are you hoping to take customers’ payments for the cards through your site?
• How do people get in touch with you if they want to buy a card?

Why I think this is important, is that I think it touches on the core of where some support agents feel uncomfortable around “sales”. All of the above is a sales approach but it is also profoundly a support approach of diving into empathy, curiosity, and enabling the customer’s success.

Conclusion

I think getting strategic and leaning into being true communication professionals is the key to success for support agents. Stepping into that meta conversation space (backing away from social instincts and instead using social strategy) enables us to wield open and closed questions like a dance – using words and approaches consciously, playing the three dimensional conversational chess that sometimes involves moving one piece to see what the other party will do, then adjusting our original plan accordingly.