6 characteristics of great questions

It’s easy to get behind the idea that a Customer Success Manager should cultivate relationships with the executives inside their customer accounts.?

Most often, sponsors hold the budget for our products and services. As such they are typically contract signers, and are accountable for the success of the relationship. These can be C-level executives, business unit leaders, or even division or department heads depending on the size and nature of the company.

To maintain engagement with an executive sponsor, there are several approaches commonly used in customer success oriented companies:?

• Post-sales transition to customer success
• Exclusive executive forums and events
• Executive sponsor programs?
• Targeted content sharing
• Periodic business reviews

As CSMs work to cultivate relationships in these settings, there’s one skill that comes in more handy than any other. That is the ability to ask great questions.?

Asking powerful questions unlocks valuable discussions and insights while elevating the status of a CSM in the eyes of the executive sponsor.?

I believe that Customer Success is more akin to consulting than either sales or support. Consultants know how to use questions to create alignment, develop a spirit of partnership, and to get to the heart of a business matter.?

Consultants know how to use questions to create alignment, develop a spirit of partnership, and to get to the heart of a business matter.?

With this backdrop, I want to share six characteristics of powerful questions to consider as you prepare for upcoming meetings with customer executives.

Great questions are relevant

Most people are more interested in talking about themselves than hearing about us. It’s human nature. Knowing this, we can use questions to open the floor for executives to do just that.?

This is where a little prep goes a long way. Instead of asking generic questions about strategy, goals, and initiatives, we can use public information such as earnings calls, press releases, social media posts, and insights from other contacts to gain context.?

Use that information to formulate relevant questions, like this:?

“Listening to your most recent earnings call I noticed Mary [CEO] spent a lot of time discussing your EMEA expansion plans. How is that initiative impacting your plans for the coming year?”

Beginning with some context shows that we’ve done our homework; we took time to prepare and that we are genuinely curious about their business. Execs will be more likely to share specifics with you if they don’t feel like they are starting from scratch.?

Great questions are deep

Executive sponsors can help us understand the direction and strategy of their businesses so we can help figure out where and how we fit into it. Not only that, we need to find out what role they will play in supporting us.?

Questions like the following can help us get beyond surface-level talking points:

“What opportunities did you see that make now the ideal time for international expansion?”

Great questions are open-ended

This is like motherhood and apple pie, but I often find myself unintentionally asking questions that are “closed” in nature. Closed questions typically can be answered with a simple ‘yes’ or ‘no.’?

For example, “Have you adjusted forecasts in light of the current economic slowdown?”

Here’s a better version of the same question: “How has your forecast changed given the current economic slowdown?”

Open questions typically begin with “how” or “what.”

“How have things changed since…?”

“What are the impacts of X on Y?”

Open questions give the respondent an opportunity to elaborate fully on the topic at hand.?

Great questions are intimate

Companies are made up of people. And every person has unique hopes and dreams. These could be aspirations of a promotion, recognition, or even better work-life balance.

When we understand a person’s underlying motives, we can align our efforts toward helping them achieve their personal goals. When we do this we create customers for life.?

Questions like the following convey personal empathy:?

“What concerns do you have about the shift in company strategy?”

“What impacts will this shift in strategy have on you and your management team?”

“What does this mean for you in the short and long term?”

Great questions offer value

In the world of vertical SaaS solutions, we’re lucky to have broad visibility into common opportunities and challenges faced in the markets we serve. We should incorporate these insights into many customer interactions, however they are particularly relevant to executives.?

Executives often take an interest in how their peers are performing, what decisions they are making, and how they’re evolving processes.?

We can incorporate these elements by using these insights as the basis for questions. For example:?

“We have several customers who are utilizing 3rd party managed service providers to accelerate global expansion and offset risk. How are you thinking about risk, and are you considering any special mitigation techniques?”

Here we want to make sure that comparisons are relevant to industry or use case scenarios that will resonate with our contacts.

Great questions offer partnership

Finally, strong relationships should result in strong customer partnerships. Partnerships set us up for win / win value propositions. Our customers gain value, achieve goals and accrue return on investment. In return, we retain their business and gain advocates who will support us in the marketplace with positive references, reviews and referrals.?

Questions like the following help us harvest insights as to the state of our relationship and where we need to focus in the weeks and months ahead:?

“We are monitoring [XYZ industry trend]. How are you thinking about this?”

“Where can we [our company] to better align with you in the year ahead?”

“Are there other individuals within the company that we should be engaging with along the way?”

Engaging with confidence

The most common challenge I see when it comes to executive engagement is lack of confidence. While these types of questions are quite commonplace for value-based and consultative sales teams, they represent a shift for many customer success teams.

Stepping outside of the safety of product and process level topics can be intimidating, especially for CSMs coming from a support, implementation, or even a transactional sales background.?

In any case these conversations are important, and by engaging with great questions, you can build credibility as an advisor while gaining a deep understanding of the markets you serve.?

Like most things in life, repetition and consistency are key. The more you practice, the more confident and successful you will be.

So what great questions will you ask today?