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This week I ran an in-person sales workshop for a small room of Founders, consultants, and a couple of folks still pre-revenue.

I opened with one question.

"Do you have a set time each week where you audit every deal in your pipeline?"

The answers were all over the map. The general consensus…it’s not being done consistently.

This isn’t just necessary for the year end push but needs to be a healthy practice for you every week.

Otherwise, deals slip.

That one you thought was definitely coming in was missing key information about their buying cycle, budget, evaluation process, etc. Now, not only do you miss the timeline you thought, the deal might be in jeopardy altogether.

I’m publishing this issue on Oct. 4th.

That leaves roughly 52 business days before people pack up for the Christmas holiday on Friday Dec. 18th. Seems like a lot but that time flies fast, especially if there are still unknowns in your deal that you have to hammer out with your buyers.

To start to do that effectively, let me give you five questions you must get crystal clear on immediately. Because if you don’t know these, your deals are farther from closing than you think.

There are many nuanced questions that need to be asked to get deep understanding of the strength of your deal and the likelihood it will close.

Start with these five.

If you’re missing these, you’re behind and need to gather more details to get on the same page with your buyer.

The person on your call may make the decision. They may not control the money. Or they don’t make the decision or control the money.

You need to know their role and where they come in to the picture.

One might evaluate, while another makes the decision, while another has to approve the budget.

Ask early: "Who else needs to be involved in this decision?"

In Q4 this gets riskier. The person who approves the budget might be out for two weeks in December, and you'll only learn that the week you expected a signature unless you ask now.

Make sure you know all of the players so you can better navigate the conversations and bring the right people in at the right time.

Buyers usually lead with the surface problem.

I spoke with a founder recently who told me he had a lead problem. Once I pried deeper I found out he'd run 40 discovery calls in nine months and closed zero.

More leads won't fix that. His problem was that he wasn’t good at managing the sales process and building trust and value with the buyer.

When you only know the surface problem, your proposal ends up talking about your product. Once you know the real one, you can talk about their transformation.

That's what people buy.

If your notes on a deal say "wants to be more efficient," you don't know their problem yet.

Dig deeper. Gain an understanding of specifics and the impact this is having on their business.

Someone can have a real problem and still never buy if it sits at number 11 on their priority list.

When your alternator on your car craps out, you get it fixed that week.

That's the level of priority you're looking for.

Ask, “Where do this rank on your priority list given all the other things you deal with?” or ask, “What changed recently that made this worth a conversation today?”

One of my favorites: "If I hadn't reached out, what would you have done?"

Everyone is juggling year-end priorities right now. If yours isn't near the top of their list, you're looking at a January deal. Better to know that now than find out on December 14th.

Have they shared when they need to get started or when they need the solution operational? Get a date and work backwards with them.

If they need this up and running in January and budget approval takes six weeks, the decision has to happen in early November. Walk them through the specifics.

People open up fast when they see it laid out.

If they're replacing someone, ask when that contract renews. Nobody wants to pay for two solutions at once.

Use their timeline instead of the one you're hoping for and get their buy-in that they are committed to hitting that date.

It’s amazing how quick deals move when there is a clear plan of action in place.

A lot of founders hear "yes" and assume all that's left is a signature.

Is there procurement? Legal review? Is the budget available now or after a new fiscal year starts? How many people have to sign?

When I was selling to local government, I had a deal I was sure would come in that September. Then my contact called and said legal takes six months, no matter how big or small the deal. We signed in February.

I couldn't speed it up no matter how much I wanted to.

But, since I knew that in September, I could forecast it in my pipeline and not keep pestering my buyer. We were on the same page, it was just out of our hands.

Ask: "What needs to happen on your end to get this approved and signed?"

If they don't know, that's okay. The key is that they're willing to find out. If they aren’t, that could be a major red flag that they don’t have the authority or this isn’t priority enough to battle for now.

A high number of sales are lost purely because the seller didn’t get enough information.

When you lack intel, you lose out on what steps have to happen internally.

What people have to be involved.

How decisions get made.

How budgets get approved.

…and the list goes on.

Get ahead of that early. Start by doing your own pipeline audit. Ask the questions above and see if you start to notice patterns in your deals.

Are you missing out on the same information over and over again?

You might be the right partner to help this buyer solve the thing they are challenged with.

That’s half the battle.

The other part is helping them to the finish line to actually buy it.

Pull every deal you expect to close before December 18th.

Next to each one, write your answer to who, what, why, when, and how.

Anything you guessed on becomes the agenda for your next call with that prospect.

And if you don’t have a next call, reach out and set one!

Hit reply and tell me what deal is definitely going to close and why. I read every one!

Need to get a quick W?

I offer one-time sessions to go deep into the specifics of whats happening today.

→ Set up a deal review audit: It’s deep-dive into active deals and how to get them over the finish line.

→ Get a sales call roasted: I review a real sales call and provide an in-depth, tactical overview for immediate improvement.

Want to build a repeatable sales foundation?

These help you build the skills and systems for the long-haul and a foundation to accelerate growth.

→ 90 Day Sales Accelerator: Hands-on coaching built around your pipeline and growth objectives.

→ Team Workshops: Live team training built around real friction points in your sales process.

→ Fractional Sales Leadership: Ongoing leadership for startups growing out of founder-led sales