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Challenger Sales Questions

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25 HIGH-IMPACT

CHALLENGER SALES
QUESTIONS
Master the Challenger sales methodology with this list of powerful
questions for every stage in the Challenger sales playbook.
THE WARMER

These questions are designed to understand the problem your


customer faces:

1. Can you walk me through [Operational area] process from [first


step] to [business outcome]?
2. How do you currently manage [Business problem] on your team?
3. How much do you currently spend on [Operational area]? What
results are you seeing?

Aim For 11-14 Targeted Questions In Discovery Calls


Top performers ask the “sweet spot” number of questions
on their discovery calls. Too many sales discovery questions
(15+), and you are running an interrogation. Too few, and
you’re unlikely to unearth what matters – pain points.

Source: gong.io/blog/best-discovery-call-tips

2
THE REFRAME

Using a question to introduce a provocative insight can soften


the challenge:

4. Did you know that [Reframe]?


5. Have you ever considered [Reframe]?
6. What would you do differently if you knew [Reframe]?
7. What sounds most intriguing to you about [Reframe]?

Ask Questions Only A Pro Would Ask

Have you ever heard the phrase “You get delegated to the
person you sound like”? Use your questions to demonstrate
expertise by using the right vernacular and getting buyers to
think. Here’s what that difference sounds like:

DON’T: What’s your sales process?

DO: Can you walk me through your sales process


from first contact to close?

3
RATIONAL DROWNING

Offer up your best proof to support your reframe. Use questions to


engage your buyer:

8. Our customers see a 15% increase in ROI in [Operational area].


How much are you currently spending on [Operational area]?
9. Before [Product/Service], [Customer Name] was struggling with
[Operational area]. With [Product/Service] they were able to
achieve [Strategic goal]. Is this a priority for your team?
10. Leading companies in your industry like [Name], [Name], [Name]
are switching to [Product/Service]. The #1 reason is [Benefit]. Is
[Benefit] valuable to you?

Beware Of ROI Claims

Presenting ROI at any point in your sales process


correlates with a 27% drop in close rates. To avoid ROI
backfiring, your customer story should tell both the
before and after. The beauty of this approach is that your
customer has no ROI assumptions to argue with, you’re
simply sharing a story.

4
EMOTIONAL IMPACT

Capitalize on the rational evidence you provided with these


questions to create emotional impact:

11. Is the organization committed to fixing the issue now?


12. What happens if you do nothing?
13. Who else is affected by this issue?

PRO TIP: By using emotional words like “frustrated”, you tap into pain
by surfacing the buyer’s reaction.

Avoid This Mistake When Selling To The C-Suite

Senior executives have “discovery fatigue.” By the time


they have a meeting with you, they’ve likely been through
2 or 3 discovery calls with other sellers. Answering
all those questions feels taxing. Be strategic with the
questions you ask when selling to C-level execs.

5
VALUE PROPOSITION

Here are some questions to introduce a necessary behavioral


change to help buyers reach their goal:

14. How much [Time/Money/Resources/Opportunity costs] is it


costing you to continue with your current process?
15. How are inefficiencies in [Operational area] preventing you from
reaching your goals?
16. Can you walk me through how [Strategic initiative] affected by
challenges in [Operational area]?
17. Tell me about a decision you had to make to mitigate the current
issues in [Operational area]?
18. Help me understand what happens if we don’t address this [Pain/
challenge] now?
19. How does solving [Problem] bring you closer to
[Strategic objective]?

Ask Questions That Trigger Long Responses


According to Gong Labs, there’s a strong link between
buyers’ response lengths and closed deals. Consider the
following question starters to draw out a longer, richer,
more in-depth response from your buyer:
• Can you help me understand …
• Can you walk me through …
• Can you tell me about …

Source: gong.io/blog/best-discovery-call-tips

6
SOLUTION
Now it’s time to introduce your solution with an “interest” CTA:

20. Does it make sense to explore how we can [Positive outcome]?


21. Interested in unpacking how we can help with [Pain]?
22. Are you open to learning more about solutions involving
[Product category]?
23. Would achieving [Outcome] help your team deliver on
its [Initiative]?
24. Have you tried [Type of solution] before?
25. Are you game to explore how [Company name] can help
with this?

WAIT!
THERE’S MORE...
Follow Gong on LinkedIn to get the latest
data-backed sales insights and learn why the
best salespeople always top the leaderboard.

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