Closing Time

5 Sales Discovery Questions to Double Deal Size & Shorten Sales Cycle

Quality sales discovery questions separate good reps from great ones.

In this episode of Closing Time, Chip House welcomes Krysten Conner, a sales coach with experience at, Salesforce, and Tableau.

Krysten shares 5 of her 9 ‘deal doubling’ discovery questions to help sellers understand the buyer’s perspective, establish credibility, maintain transparency, and align on urgency. This episode is for you if you want to refine your discovery process and build stronger relationships. 

Watch the video:
Key Moments:
Question 1: Establishing Credibility

Discovery questions are essential tools in sales conversations, designed to uncover the specific needs and pain points of potential buyers. Salespeople often ask the wrong questions, which can lead to missed opportunities and a lack of connection with the client.

The right discovery questions help salespeople better understand their clients, establish credibility, and foster open communication. Ultimately, they help transition reps from being seen as mere vendors to trusted advisors

In her career, Krysten has witnessed her fair share of poorly framed discovery questions, which led her to create a list of 9 Deal Doubling Discovery Questions. She kindly shares five of them on Closing Time. Let’s start with the first:

Discovery Question 1

Krysten explains that this question works universally, regardless of the product or service being offered. It was inspired by Charles Muhlibauer, a LinkedIn expert on Discovery.

This approach helps establish credibility early in the conversation. By identifying common industry problems, it signals to the potential buyer that the salesperson understands their challenges. This understanding puts the buyer at ease, allowing for more open communication.

Moreover, the question is designed to invite correction and input from the buyer. This engagement is crucial because it acknowledges that every organization has unique issues, encouraging the buyer to share specific concerns. This not only provides valuable insights but also leverages the human tendency to correct others, especially salespeople.

By incorporating the buyer’s corrections, the salesperson transitions from merely selling a product to becoming a trusted advisor. This shift is essential for building a strong, collaborative relationship with the potential buyer.

Question 2: Quantifying Problems

Asking pointed, quantifiable questions in sales conversations will help sellers understand the depth of a buyer’s needs. She introduces a powerful question designed to uncover specific metrics and the scale of the buyer’s goals:

Discovery Question 2

This question, a combination of insights Krystern gathered from Craig Henehan and Dave Rubinstein, is particularly effective because it prompts the buyer to quantify their goals. Krysten explains that asking, “Are we talking millions or tens of millions?” helps the salesperson grasp the magnitude of the problem.

This approach serves multiple purposes. It helps the salesperson determine if the problem is substantial enough to warrant a solution. Often, buyers haven’t fully articulated their needs, and this question encourages them to think more deeply about their challenges. For example, a buyer might realize they need to increase their pipeline by 10.2 million, which can be a significant revelation.

Effective discovery questions like this not only provide the salesperson with a clearer understanding of the buyer’s challenges but also help the buyer see their problems from a new perspective. This deeper understanding fosters a sense of empathy and connection, making the buyer feel understood. The more a salesperson can step into the buyer’s shoes, the better the entire sales process will feel for the buyer, ultimately strengthening the relationship.

Question 3: For Newly Hired Executives

Executives face unique challenges and goals when entering a new role. During their first 60 to 90 days, these leaders are immersed in assessing the company’s situation, understanding its messaging, and getting to know the target audience. This period is crucial for setting the foundation for their future success. Recognizing this, Krysten introduces a vital question for engaging with new executive hires:

Discovery Question 3

This question originates from an insightful comment by a VP of sales (at the big blue cloud company that we don’t mention), who pointed out that executives are never hired to maintain the status quo. They are brought in specifically to drive change and achieve new successes. This revelation inspired Krysten to adopt the question, “What did you get hired to change or start?”

Executives are often hired based on their track record of success, with the expectation that they will replicate these achievements in their new role. For instance, a CMO who has delivered impressive results in one organization is brought into a larger company to achieve similar outcomes. These executives typically have clear objectives for their initial months, focusing on key initiatives they plan to implement.

Asking this question resonates deeply with new executives because it aligns with their immediate priorities. It’s a straightforward question for them to answer since it reflects their current focus.

In the B2B space, many executives are hired specifically to act as change agents, tasked with driving significant transformations. When a salesperson asks about these changes, it demonstrates an understanding of the executive’s role and priorities, fostering a deeper connection.

Krysten notes that this approach taps into something very important to the executive, making them eager to share their plans. This not only provides valuable insights but also positions the salesperson as a thoughtful and engaged partner in the executive’s success.

By understanding the specific changes and initiatives that new executives are focused on, salespeople can tailor their approach to better support these goals, ultimately strengthening their relationship with the client.

Question 4: Understanding Strategic Priorities

If you want to increase deal size and urgency in the sales process, sellers first have to understand the scope and priority of the buyer’s problems–not just on the buyer’s team but across the entire organization. Krysten shares a question just for this purpose:

Krysten explains that this question is crucial, especially when meeting with someone who holds a manager or director title. Managers and directors often focus on the performance and challenges of their specific teams. Their concerns are typically centered around immediate, team-level issues. However, when dealing with VPs or CXOs, the focus shifts to broader organizational concerns such as risk, market share, and strategic priorities.

Krysten shares that she has learned from experience that sometimes managers and directors care deeply about issues that are only relevant to their teams. Unless these individuals have enough budget to purchase the solution independently, these concerns won’t gain the traction needed for a sale. This realization underscores the importance of understanding whether a problem is a strategic priority for the organization as a whole.

By asking this question, salespeople can help managers and directors think aloud about the ease or difficulty of pushing an evaluation through their organization. This approach saves time for both parties if the issue is not broadly recognized or strategically important. Conversely, if a problem is identified as a strategic priority, this insight can significantly boost the chances of closing the deal.

Krysten highlights that knowing if an issue is a top priority for the organization, such as being on the CEO’s top three list for the year, is invaluable. When a director or VP indicates that an issue is of high strategic importance, it signals a strong potential for the deal to proceed. This understanding helps salespeople align their efforts with the organization’s critical goals, making their proposals more relevant and increasing the likelihood of a successful outcome.

Question 5: Matching Urgency

Pushing a buyer into a rushed decision is the fast track to a negative experience and, ultimately, a lost deal. Instead, salespeople can build stronger, more respectful relationships by respecting their timelines and offering genuine support. To help both parties align on urgency, Krysten recommends asking:

Discovery Question 5

Krysten explains that this question, inspired by a successful seller at Tableau, is highly effective and mutually beneficial. She typically uses it at the end of a first or second call, framing it with the following context:

“Generally, there’s about three reasons why CMOs join a call like this. One, they’re just looking at new tools and are in education mode. Two, they have a big problem they need to solve and are hoping that something we do might help. And three, they have a problem that’s not yet a priority but will be in the next 12-18 months. I’m curious where you put yourself on that spectrum.”

This approach allows the buyer to clarify their current situation without feeling pressured. By giving the buyer an “out” to be in education mode, Krysten emphasizes that she respects their timeline and won’t push aggressively. This transparency often leads to buyers being more forthcoming about their priorities.

For instance, an executive might reveal that a particular issue is their top priority for the upcoming quarter, requiring immediate action. Conversely, if the problem is important but not urgent, the buyer can indicate a longer timeline. This honesty helps the salesperson align their efforts with the buyer’s actual needs, avoiding unnecessary pressure and fostering a collaborative relationship.

Krysten believes in the long game in sales. If a buyer indicates that a priority will arise in six to nine months, she commits to providing value and staying engaged without being pushy. This patience and respect for the buyer’s timeline turn the salesperson from a mere vendor into a trusted consultant.




If you liked these questions, be sure to download Krysten’s full Deal Doubling Discovery Guide and explore her other sales training materials. 


Welcome to Closing Time, the show for. Go to Market leaders.
My name is Chip House.
I am CMO of Insightly CRM, and I’m joined today
by Krysten Conner, who is a sales coach, a trainer,
and she specializes in helping companies increase their win rates and deal size.
Welcome to the show, Krysten.
Hey, Chip, it’s so great to be here.
So I love your background and I’d like to start there
because you’ve had so many impressive logos with Outreach and Tableau, but
it sounds like you started out as a teacher.
Is that right?
Yeah,. I started out teaching eighth grade U.S.
history and.
Wow. Yeah, it was, as it turns out, a great prep,
a great way to get introduced to sales because in teaching
you are literally standing in front of an audience
who for the most part doesn’t care what you want to say
and you need to hook their attention right, and be able to keep their attention
and then be able to help them discover something
that you know that they don’t
and be able to do that in a way that’s not condescending
but piques their interest and gets them to learn more.
And so like if you just sub out teacher
for salesperson like that, it’s very, the jobs are similar.
So Krysten, this is why I was excited to talk
because you’ve come up with nine discovery questions that you say
you wish you had learned earlier in your career.
What mistakes do you think reps, particularly
the new ones, make in terms of discovery?
early on in our careers we overindex on questions about features
and functions related to our product,
and that is really not the fault of the rep
because most of the training that reps get is around
the product, it’s around feature and function and they’re designed
and many of the questions that they’re taught to ask are leading questions.
They’re almost like gotcha questions.
How can I lead this person into a trap of saying they need this thing
versus, and to be honest, it’s much easier to train a rep
how to use a product or the features of a product than it is to teach them
business acumen and how to have and guide an open conversation.
So there’s a lot of mistakes, but they’re honest mistakes.
Sales reps, want they want to guide good discovery.
I think it probably starts a bit with curiosity and truly
being concerned and interested about the buyer and their business.
So I think the questions that you have definitely touch
on some of that curiosity and so let’s start with some of these
questions and I’m going to read these to make it easier on myself.
So your first question is, “in this role,
I talk to industry leaders all day long.
They tell me about the heartburn around problems such as A, B and C.
How much of that sounds like your world?
And what did I miss?”. Why is that a great question?
Yeah, the best discovery questions work
no matter what product or service we’re offering.
And this one works no matter where you are.
And this is why and I actually adopted this from a guy named Charles Muhlibauer.
He is on LinkedIn.
And all he talks about is Discovery.
He’s a great follow, because Discovery is one of those things
that you can work on forever and just keep getting better at.
But the reason this works is it immediately starts
to establish our credibility if we nail the problems, right.
Like if we know the top three things that are generally
on the mind of the persona that’s joining the call,
what that tells them is it puts them at ease
because they know, oh, well, Chip knows, he understands my problem.
Now, I don’t have to explain the basics to him,
like where it starts to put us more at a peer level.
And now that you know, you don’t have to, now that I know I don’t have to
educate you now, I can speak openly about what it is that I’m facing.
And you’ve established credibility
and you’ve also left it open because these are the typical problems.
But every organization is different.
And so that last question is so important.
You know, how does this sound like your world?
And what did I miss?
Because we want them to correct us.
We want them to tweak it and adjust it, because that’s
where the really important information comes in.
And we’re playing into that human tendency.
Humans love to correct other humans.
They especially love to correct salespeople.
So we want to give them that chance because it’s a win for everybody.
Yeah, it seems like it’s the first step of moving
from a salesperson to the trusted advisor role that you’re trying
to get into and be accepted as by the potential buyer.
Yes, I love this other question that we’re going to talk about.
So you might ask a buyer.
“So you’re looking to change or improve a specific metric
by how much?” What does that do for you?
I think I was just talking with a sales leader this morning
and we were talking about how the best sellers are always collecting
discovery questions.
This one I learned, this is a combination question I learned from Craig
Henehan and Dave Rubinstein when I was working with them at Outreach.
The second piece that goes along with that is, is quantifying by how much.
So I say, okay, Chip, you say that you’re the CMO.
CMOs usually care a lot about Pipeline, so you want to increase
the pipeline that you have.
But how much?
Are we talking millions or tens of millions?
Because then we start to wrap our arms around like,
how big is the size of this problem?
So we start to understand,
you know, is this a problem likely worth solving?
And then the buyer sometimes they haven’t even said that out loud to themselves.
And so sometimes they’re like, oh, gosh, Well, I actually think
we would need to increase it by probably about 10.2 million.
That’s our gap.
And then all of a sudden everybody’s like, Whoa, right?
Like, the best discovery helps the buyer think more deeply about the problem.
And it helps you get into their shoes a bit and see the problem
from their angle, which I think has to help as a salesperson.
Yeah, the more we put ourselves in the shoes of the buyer,
not only in discovery calls, but throughout the entire process,
the better that’s going to feel to the buyer.
Everyone wants to feel understood.
Make sense.
So I know what it’s like to be a new executive, you know,
especially the first 60 or 90 days.
You’re trying to assess the situation and learn as much as you can
about the company, the messaging, your target audience, etc..
And so you have a very specific question
for new hires, and it’s, “what kinds of things
did you get hired to change or start?”. I love that.
Yeah. This one,
a VP of sales
at Salesforce, was leading a team meeting and he said, Guys,
do you realize that no executive gets hired to keep things the same?
And we were like,. Yeah. Whoa, that’s right.
If they wanted things to stay the same, they wouldn’t have brought in this person.
So then that’s where I started
asking the question, “What did you get hired to change or start?”
The other thing is when executives change jobs, usually the reason they got
hired is to duplicate the past success that they demonstrated somewhere else.
So if you’ve been a CMO at one place and you’re how you get that next job
at the bigger company is you say,. I did this and this and this and how that.
And then the other company says,. That’s exactly what we’re looking to do.
And so you come into that role going, okay, this is, these are the results
I drove here.
That’s what I’m looking to recreate here.
So you usually come into that 30, 60, 90 days going,
These are the three things that I want to do or put in motion.
So when we ask about that, it’s not a hard question
for the executive because that’s what they’re thinking about all day long.
I mean, I think yeah, definitely in the executive role,
a lot of us in the B2B space were hired to be change agents.
And so when you ask about that change,
you’re asking about something that’s very important to me. Yes.
And I want to tell you all about it.. Exactly.
You’re exactly right.
Here’s another great question
that can be very powerful in terms of increasing deal size
since you get a broader look at the organization and the response,
The question is, “how widely
felt is this pain across your whole organization?
Is it just a few teams or is it a top three strategic priority?”
Yeah, this is really important to ask if we are having a first meeting
with someone who has a manager or director title
because managers and directors are thinking about like in sales, it’s
always about what’s in it for me and what’s in it for them is
they’re concerned about the performance of their own teams.
When you get to that VP and CXO level, that’s
where they’re more concerned with risk, market share, strategic priorities.
That’s what they’re thinking about.
But managers and directors, a lot of times still thinking about
how do I make life better or how do I reach the results of this team?
And so there can, I’ve learned from hard experience
of doing it the wrong way that sometimes managers and directors
care very deeply about something, but it only matters to their team.
And that’s not, unless they have enough budget
to buy your solution, that’s not going anywhere.
And so again, you’re helping them think out loud
about how easy or hard it is going to be to get
this evaluation pushed through their organization.
And so hopefully we’re saving everyone a bunch of time
if it’s something they love as a manager, but it’s not going to get traction.
We don’t want
them to waste their time on it and we don’t want to spend our time on it
because in the end it’s not going to go anywhere.
Yeah, but if it’s a strategic priority, you definitely need to know that, right?
Like if the CEO cares about this thing, you want to know.
Oh, exactly.
Exactly right.
That’s the best case scenario. Right?
And so if you have a director or VP level saying, hey, you know what, we did SKO
about six weeks ago and on the top three slide, you know,
in the top three things for the year, this was number two on the slide.
Now you’re golden. Yeah, that makes sense.
You know, sometimes as a buyer too, you may have a problem and you need to
solve it, but you’re not ready to or you don’t have the budget to.
And there’s sort of like this
tension with the salesperson maybe.
And that’s why I like this next question that you ask.
And I don’t think I’ve ever been asked this question, and that is, “how
can I best match your urgency?”. I love that.
That’s so cool.
This is one again that I this is one I’ve collected.
I heard this from a great seller at Tableau, but it really does help.
It’s very much a win win
because I usually use this at the end of a first or second call
where I would say, Hey, you know, Chip, it’s been great to talk with you today.
Generally, there’s about three reasons why people, why CMO’s
would join a call like this.
One, They’re just looking at new tools.
They want to understand what’s out there.
They’re in education mode.
Two is they have a big problem that they need to solve
and they were hoping that something we do might help solve that problem.
And the third thing is they’ve got something that
it’s a problem, it’s not yet a priority.
It’s they’re going to be looking at something in the next 12, 18 months.
I’m curious where you put yourself on that spectrum.
And I’m asking because I never want to be the one to chase anything.
I’m not going to try to blow up your inbox.
If you’re in education mode, that’s just fine.
When we give people an out to be like, I’m
just looking right, like, that’s hugely helpful.
And if we have truly an executive buyer and they need to get something done
and they have a feeling you can help,
they’re going to tell you this is my top priority for Q2,
we have to get this done because of X, Y, and Z.
But when we give them multiple choice, we allow them to opt in or out,
and then everyone like I just am the big fan of being transparent.
And if we’re transparent, the more likely the buyer will be as well.
Yeah, makes sense
and you can definitely feel disrespected as a buyer if it feels like you’re being
rushed into a decision.
And so I think that that sort of disarms the buyer.
That’s why I like it so much.
It’s interesting that you’ve never been asked.
I think that’s I think that’s sad.
But I also think reps get,. I think reps get happy ears, right?
Because if you like what I’m showing you, that’s
not the same as saying it’s the thing that’s the most important to me.
And I’m also never a huge fan of when I’ve heard people say,
timeline is an excuse or whatever, that’s I find that to be utter BS.
Like there are ten fires, 12 fires that executive is dealing with.
The top three are what they’re doing right now.
But that doesn’t mean that the other ones aren’t going to be dealt with.
And I think I’m always a fan of the long game in sales.
Like if you tell me it’s going to be a priority six, nine months from now,
I’m going to work to provide insight to you, to stay,
to add value, to stay on top of your radar until the time that you’re ready.
Because I believe, hopefully,
I’ve given you an out to tell me if it’s not important.
And so you say it is important, but just a few months from now,
I’m going to honor that and I’m going to work to show you
a good buying experience as we move along your timeline.
Yeah, I love that because,. I mean, if you’re working with me
on my timeline and, you know, okay, maybe it’s not the top priority,
but it’s number four or five or six
and you’ve now moved from salesperson
to consultant who is helping you solve a problem, which is great.
So Krysten, I love this discussion,
all the way from a teacher to a sales trainer extraordinaire.
And so where can our listeners get
a copy of your nine discovery questions?
Yeah, if they head over to my website, which is just
they can sign up right at the top and it’ll shoot that right over to them
and if they find me on LinkedIn there’s a link to my website from there too.
So lots of ways to find me.
Thank you so much for having me.
I’ve loved this discussion.
It was so great.
Krysten, thank you so much for joining us.
And thanks to all of you for tuning in to this episode of Closing Time.
And we’ll see you next time.

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