The Goldilocks Zone: When to Ask for the Business

Today’s Skill: Knowing When to Ask for the Business

Have you ever thought about when you should ask for the business?

Not just hope for the right moment but know when the time is right?

Most founders fall into one of two camps.

→ Some jump in too fast.

→ Others keep waiting… and waiting.

Like the classic Goldilocks tale, one approach is too hot, the other too cold.

Let’s find the one that’s just right.

The 4 Things You Need Before Asking

To confidently ask for the business, and get to a “Yes”, you need to consider you have…

1. Clear Problem with a Clear Solution

The problem behind the problem is often where the real value lies. Know exactly where they’re challenged and how your solution addresses it. We must pry and not take surface-level answers as gospel.

2. Acceptance of Pricing

They understand your offering, know the cost, and have signaled it’s within budget. It doesn’t mean they have budget yet or won’t negotiate, it means there’s been some discussion that you’re at least on the same planet.

3. Defined Timeline

You’ve discussed when the problem needs to be solved, how it will be solved, and by when. If they’ve mentioned a start date, that’s a cherry on top! If it’s ambiguous, that means the problem might not be big enough to solve or isn’t a priority.

4. Addressed Concerns

You’ve talked through concerns around deliverables, pricing, timelines, and more and they’re confident in your answers. If you only hear, “looks great!” every time but there hasn’t been any action to start, then something is on their mind that needs to be addressed.

A Note of Clarity

Asking for the business ≠ Signing the contract.

🤝 It’s a handshake.

It means:

“I’ve shown you the value. You trust I can help. Let’s move forward.”

→ Legal, procurement, or additional internal approvals may follow but those are good problems to have. You aren’t wondering if they want to go with you, you’re not walking side-by-side with them to make it happen.

Are You Asking Too Soon or Not at All?

You’re Asking Too Soon If:

You pitch 11 minutes into a discovery call after asking a few “qualifying” questions. Then, you jump right into your pricing and ask what they think.

Unfortunately, you haven’t earned the right, yet.

What happens next?

You hear polite brush-offs like, “I’ll think about it” or “Let me get back to you.”

Then… silence.

Why? You didn’t build enough value to justify the cost.

You’re Waiting Too Long If:

You book call after call, “exploring” the partnership.

You think more meetings mean progress. But many people overthink.

Without tension, they get overwhelmed. Or the problem wasn’t painful enough.

And the deal fades.

So, When Should You Ask?

There’s no perfect time but there is a sweet spot.

Once you’ve checked off the four boxes above asking becomes a wonderful temperature gauge:

→ If they push back, great. Now you know where they stand and can dig deeper into what is left to explore.

If that happens, you can ask:

“What questions do you need answered before you feel confident in partnering with us?”

However, if you are confident in those 4 “check boxes” you will likely get a YES! Remember, people don’t always know how to buy and there can be a lot of indecision and overthinking if it’s new for them. You might have to step out on the ledge first before they are willing to take that next step.

At this point, stop selling! It’s time to move on to finalizing the partnership.

Your Action Item:

Do an accountability check…

Are you the “Premature Asker” or the “Never Asker”?

If Premature: Slow down. Take an extra call. Build trust and credibility.

If Never: Run through the 4-checkpoint list. Once you’re confident, ask.

Either way, get comfortable with healthy tension.

It shows confidence. It positions you as a leader.

It’ll let you know if the time is just right.