Is Your Deal Stuck?

Welcome to Sales Skills For Founders, a weekly newsletter with one actionable skill for sellers who are tired of tips, tricks, and scripts. AI isn’t going to close deals for you so let’s master sales, one skill at a time.

Today’s Skill: Asking Yourself The Tough Questions

Every founder knows the frustration of a stalled deal. The silence, the unanswered emails, the endless "follow-ups."

There are a lot of skills that help us avoid this frustration but, inevitably, it will happen to all of us.

So, let’s self-exam today. Here are 9 key questions to ask yourself about your deals to help you gauge any of your sales opportunities’ health. The more definitive answers you have to these, the clearer you are on how tight the partnership fit might be.

Pair this with a Pipeline Audit and you start to get hyper-specific on where the gaps are.

1. What's Their #1 Problem?

Can you accurately name it? You can't sell a solution if you don't understand the problem. If the issue isn't urgent or costly, your solution may be a "nice-to-have." Nice-to-haves don't make the budget cut.

The better you know the pain, the more you can create solutions to fix it.

Pro Tip: A great question is, "What has been the cost of this problem over the last X period?" Getting them to quantify the issue (either in dollars or some other metric) can add urgency to their problem or identify if it is really that big.

2. Why Do They Need Your Product?

Why you? Why now? Avoid the trap of "happy ears," where enthusiasm clouds your judgment. Be honest: does your product solve their problem, or are you trying to fit a square peg into a round hole?

Deep probing helps you know how their problems align with your products and informs you on how tight the fit really is.

Pro Tip: Identify alternatives. Whether it's another vendor or an internal workaround, knowing what you're up against helps you guide the conversation with transparency and credibility. There are always competitors, they may not be as glaringly obvious as you might think.

3. Do They Have a Compelling Event?

Is there a deadline driving their decision? Compliance requirements, budget deadlines, or strategic initiatives can all create urgency. Without a compelling event, your deal may drift for an indefinite period.

If you lack a compelling event, ask, "When would you like to start [or finish] this project?" in order to gauge if they’ve even thought about this. Most buyers don’t realize the time it takes to solve this problem so you have to lead them in this conversation early to set the tone.

Pro Tip: Work backward from their timeline. If they want results by a specific date help them understand what's needed to hit that target, including purchase and implementation deadlines. This helps them know when they have to get started in order to hit a desired date.

4. Who Is the Actual Decision Maker?

Don't assume the person you're talking to can make the final decision. That could be the final decision on vendor and/or budget. They might be different. Deals often involve many stakeholders: champions, influencers, economic buyers, board approval, etc.

Pro Tip: Ask "Who makes the final call on this project?" Early clarity helps you navigate the internal dynamics and politics that often come up during the buying process, especially if you have a higher-priced product. It ensures you engage the right people at the right time and don’t leave any stone unturned.

5. Has This Project Been Budgeted?

A deal without funding isn't a deal. At some point, they must be willing to pay for it. Some people have a set budget before they evaluate while others evaluate and then work to make the business case for it. You need to know where they are at so you can meet them where they are.

Pro Tip: Ask directly, "What's the budget range for this project?" If they hesitate, explore why: Is it a lack of clarity, or are they holding back intentionally? The more you discuss money, the better you can strategize with them.

6. What Are Their Evaluation Criteria?

What's their decision-making process? How are they selecting between vendors? How will they know when they find the right one? Without this insight, you may focus on benefits that don't align with their priorities.

Transparent clients will appreciate that you are trying to understand them more. Hesitant ones may try to keep things "close to the vest."

Pro Tip: Ask early on, "Can you share how you're evaluating vendors for this project?" or "Do you have a list of the evaluation criteria for this project?". No answer is a big red flag.

7. What Other Vendors Are in the Mix?

You're not the only option on the table. And that's okay! Knowing your "competition" allows you to position yourself effectively without bad-mouthing others.

It also could be a "tell" when they go dark. Many people choose another vendor. They don't want to be confrontational by telling you. So they ghost.

Trying to find these details early on allows you to have more transparency in your sales process.

Two Outcomes:

1. They share who else they're considering, giving you a chance to differentiate yourself.

2. They refuse to share, signaling a potential trust gap or them not being fully engaged in the buying process.

Pro Tip: Most people do research outside your conversations. Don’t avoid these convos, embrace them. Make sure you are keeping track of what else they are seeing in the marketplace and coach them appropriately. Going back to #1, the more you understand their problem the better you can guide them.

8. Are You Their Vendor of Choice?

If you're not sure where you stand, you're guessing. Test their interest with respectful, direct questions when you get to the point where you feel there is a fit. A question like "Are you ready to partner with us on the project?" does wonders to let you know how they feel.

A verbal commitment, even a tentative one, can shift the dynamic of the conversation. If they hesitate, you've uncovered a chance to address unspoken doubts.

Pro Tip: Most sellers are scared to “ask” for the business. Instead, they set up more calls and answer more questions. This prolongs the sales process unnecessarily. When it feels like the solve to the problem is clear, ask if they are ready!

9. What Red Flags Do You See?

Your prospects likely have concerns; they might not have voiced them yet. Depending on your relationship, you might have to be the one to ask the question as many people don’t want to say the “bad stuff”.

This is where many deals fall off the rails. Sellers get “happy ears” thinking everything is gravy but the buyers have a couple concerns they haven’t voiced. If they go unanswered, the buyer will make up a story to satisfy their need.

Don’t let that happen! You must be in control of the narrative as much as possible.

Pro Tip: Follow my simple framework: Ask, Acknowledge, Address, Active Listening

First, Ask something like ““What concerns did you have about the partnership that we haven’t discussed yet?

Second, Acknowledge what they say. “If I am understanding correctly…”

Then, Address each individually. “Let me tackle X first…”

Finally, Actively listen for how they respond and make sure they’re concern was answered and satisfied.

When concerns are discussed in collaboration, it’s a win-win for everyone.

Final Thoughts

A stalled deal doesn't mean a lost deal, but it does mean there's work to be done. Stay curious, proactive, and empathetic. Then, you will be a trusted guide, not just a salesperson.

These questions aren't just for evaluating an opportunity's health. They're key to building stronger relationships and better decision-making.

Remember: You’re not going to “win” every deal. The goal should be to focus your energy on the right ones. And, to approach each opportunity with clarity and confidence. Asking these questions gets you closer to that outcome.

Your Action Item:

In your next Pipeline Audit (you're doing those, right?) uncover a "missing piece" with one of your deals that you can bring up on your next scheduled call with them.

If you don’t have a scheduled call (make sure you’re setting those!) send them an email to uncover that missing information, if relevant. Keep it simple and direct.

Don't miss the opportunity to build rapport and gain clarity.

It might be exactly what you need to keep this deal from stalling.

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