The 'Helpful' Thing Sales Reps Do That Accidentally Kills Late-Stage Deals

Good Morning. Nobody won the Powerball last night, so the jackpot just hit $1.5 billion… the sixth largest prize in history. Look, we all love crushing quota, celebrating wins, and closing deals. But let's be honest: $686.5 million in cash (amount you’d get after taxes, still generational wealth) for matching six numbers sounds pretty appealing too. Your odds are 1 in 292.2 million, but hey, that still feels better than your chances of getting a response to that cold email you sent to a F500 CEO. Maybe swing by the gas station on your way to that 10am discovery call, just in case. Now, let’s get into today’s Follow Up. (:

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Take one option away and watch momentum come back on its own.

Your deal is at 90%. Budget approved. Champion engaged. Technical fit confirmed.

Then it just... stops.

No competitor swooped in. No budget got slashed. The buyer still likes you. They're just "reviewing options internally."

Translation: You gave them too many choices, and now they're paralyzed.

Here's what actually happened. You tried to be helpful. You showed them the basic package, the medium tier, the premium tier, and because you're thorough, a custom option "just in case."

Four different packages. Seems reasonable.

Except now your champion has to defend not just why your solution, but which version of your solution. That's two separate arguments to six different stakeholders who all have opinions.

So the deal gets tabled for "further discussion." And you have to keep defending why that deal is still sitting in "Late Stage - Reviewing."

Psychologist Barry Schwartz spent years studying this. He called it the paradox of choice: more options don't make people feel empowered. They make people feel anxious.

When you have two options, you compare them and pick one. When you have three, you start wondering if you're missing a fourth.

In B2B, this gets worse. Gartner research shows buying groups now average 6-10 stakeholders. Each person brings their own risk tolerance, budget concerns, and political agenda.

Give that group three options and watch the calendar fill with "alignment meetings" you'll never be invited to.

Top performers understand that too many options kill deals.

Here's their framework:

Before the call, pick your two. Don't improvise options in real time. Based on discovery, decide which configurations actually solve their problem. Everything else stays in your back pocket.

If they ask about another option, acknowledge it exists, but don't present it formally. "We could do that, but given what you've told me about [specific constraint], I'd keep us focused on these."

Make the tradeoff stupid simple. Option A prioritizes speed. Option B prioritizes customization. Option A is cheaper upfront. Option B has a lower total cost of ownership.

The clearer the tradeoff, the easier your champion can explain it to Finance, IT, and whoever else is in the room you're not in.

Recommend one. Then shut up. Don't end with "what do you think?" or "any questions?"

Say: "If I were in your position, I'd go with Option A because [one specific reason based on their goals]. But I want to hear what makes sense to you."

Then stop talking. The silence is where they commit.

If a deal feels close but stuck, your instinct will be to add something. A new use case. A different pricing structure. A pilot program. A discount…

Do the opposite.

Email your champion: "I've been thinking about our last conversation. I want to simplify this. Here's the option I'd recommend and why."

And if they don’t agree, they’ll let you know why.

When buyers have two or three options, the question becomes "which one fits us better?"

When they have more than 3 options, the question becomes "are we making the right decision?"

That's the difference between a choice and an existential crisis.

Be their trusted advisor and recommend them the options that are best for their situation. It will save you a lot of time… trust me.