How to Earn the Right to Ask a CFO the Hard Questions

Introduction: Why Buyers Withhold Information

When engaging in enterprise sales, the most important information usually comes out in subsequent discussions.

Buyers won't share everything right away about the true situation going on in their business. Rather, they proceed carefully, keeping the discussion general in nature and leaving things unsaid. Issues are toned down. Challenges are downplayed.

Again, this isn't reluctance. This is a matter of prudence.

After all, CFOs and other executives work in positions where discussing internal weaknesses, financial constraints, and strategy gaps might put them at risk.

This explains why discovery meetings usually don't dig very deep. Not because of any issues with the questions being asked, but because of a lack of rapport that would warrant an honest answer.

And this is when the importance of trust in enterprise sales discovery emerges.

Great Account Executives realize that trust is not given, but earned.

Why Hard Questions Matter in Enterprise Sales

Tough questions lead to true discoveries. They delve beyond superficial obstacles and reveal the real drivers that influence decisions. They identify the underlying reasons for the problems faced by the company, the threats they pose, and the pressing need for change.

Without tough questions, the process of discovery will never be complete.

Tough questions also show the gap between the current situation and the desired future situation. They measure the magnitude of the problems encountered and the consequences of not taking action.

These considerations are crucial when building a compelling business case.

Moreover, tough questions open up strategic discussions. Rather than being centered on operational concerns, the conversation should be directed toward achieving greater business objectives like profitability, competitiveness, and sustainable growth.

This is where the value lies. It's imperative to know how to ask these tough questions during discovery in enterprise sales.

The Trust Barrier in Discovery

If asking tough questions is so critical, why is it so challenging to ask them?

Trust is the reason.

There is a Trust Barrier that exists within most enterprise sales engagements. The barrier does not exist because of any lack of access or seniority. The barrier exists due to credibility and intentions.

A conversation on the surface level feels like it is low stakes. The customer can participate without having to share anything sensitive.

Conversations on a deeper level are completely different.

They involve the customer disclosing information that can make them vulnerable or uncomfortable. This might include problems with their finances, organizational politics, and strategic considerations.

A conversation cannot take place without trust. That is why trust is non-negotiable within enterprise sales discovery processes.

How to Build Credibility with Executives

Building trust with the executive is a conscious effort. The trust must be established before even asking a question.

The first thing you need to do is prepare well.

Executives are expecting you to know about their business, industry, and challenges. These include market trends, competitive dynamics, and financial drivers of their business. Showing that you've prepared adequately demonstrates professional respect.

Secondly, speak the business language.

CFOs don't talk about features or user flows; they discuss numbers – revenue, cost, risks, and return on investments. Using their terminology shows understanding of their challenges.

Finally, offer an insight.

Don't ask questions straight away. Instead, begin by providing an insight into some aspect of their business, something you learned from doing research.

Such actions will earn your trust. And trust is the cornerstone of enterprise sales discovery.

How Deal Architects Ask Difficult Questions

After creating trust, asking difficult questions becomes very important.

Deal Architects don't ask difficult questions abruptly. Deal Architects create context before asking difficult questions.

Before jumping into any difficult questions, Deal Architects give the buyer an explanation for the importance of the question. This prepares the buyer.

For instance, in asking how a particular decision affects the business, they can start by giving reasons why it's important to understand the business implications.

Furthermore, they ask difficult questions confidently and calmly.

Asking a difficult question depends on the tone and content. Directness is important, and at the same time, it needs to be accompanied by confidence.

Equally important is making sure they're not aggressive.

It should be clear that it's not an interrogation but just a part of an engaging discussion.

Timing: Understanding When to Dig Deeper

The timing of your questions can make all the difference.

Timing is a fundamental element of trust in sales discovery for enterprises.

During the early stages of the process, you should concentrate on building rapport and gaining a basic understanding of the buyer's needs. Then, as credibility builds, you can start asking deeper questions.

Such a process allows the buyer to gain confidence when sharing information with you.

Being too eager to dig deep will erode trust. While being overly cautious about doing so could inhibit discovery.

This is what the Deal Architect understands and leverages when they manage the conversation.

It's what enables them to always dig deep into conversations.

The Effects of Trust on the Result of Deals

The amount of trust that exists in a sales process has a huge impact on the outcome of the deal itself.

If trust is minimal, then the amount of information that exists is very little. The discoveries are only surface-deep, and there's an understanding of the problem, but not an actual one, which creates bad positioning and risks.

If the level of trust is high, then the opposite takes place.

The customers offer lots of information; they give context, details, and a point of view, helping the salesperson achieve deeper insights into the problems.

Therefore, trust in discovery processes within enterprise sales has a tremendous effect on results.

Conclusion: How Deep You Go Is Determined by How Much Trust You Have Earned

In the context of enterprise sales, the most valuable insights do not come from any report or presentation.

These insights are uncovered during a conversation.

However, conversations can only be insightful when there is trust involved.

A CFO will not be willing to share confidential data. You cannot skip straight to credibility. And you cannot hope to uncover anything deep when your engagement has been superficial.

The best account executives know this.

They have done their homework. They use the business's terminology. They add value before extracting any. And they ask tough questions that make sense.

By doing so, they are able to establish trust in enterprise sales discovery.

And once that trust is established, all else falls into place.

For once, the buyer trusts you, and they tell you the truth.

And once you know the truth, you no longer have to guess.