Another dead deal?
Maybe, maybe not but what I am learning to do to analyze, improve and maybe win that deal yet.
When a deal stalls or a prospect goes quiet, it rarely feels like just business. At least not for me.
It feels personal.
I’ve carried that feeling in my chest. The hollow space where hope used to be. I’ve felt the quiet shame of wondering if I said the wrong thing, or didn’t show enough value. I’ve had the thoughts: maybe I missed something, maybe I wasn’t enough, maybe I blew it.
And like a lot of people, I responded by doing more. I added more to the offer. I lowered the price. I promised faster delivery. I followed up. Then followed up again.
I told myself, “Just give them a reason to say yes. Do something. Anything.”
Sometimes that worked. But more often, it didn’t. It just left me feeling tired, confused, and a little further away from clarity and freedom.
That pattern, trying harder when things slow down, has been my default. It still tries to sneak in. If a deal isn’t moving, the natural assumption is that I didn’t do enough. So I do more. More value. More emails. More justification. More urgency.
But lately I’ve been noticing something else. In those moments, effort isn’t usually what’s missing. What’s missing is clarity. For the buyer, and honestly, for me too.
Because when a deal gets stuck, it’s often not about the proposal or the pricing or the timing. It’s that the buyer is still uncertain. The risk is too high. They’re still trying to make sense of something, and they haven’t figured out how to move forward.
I used to assume they were evaluating me. But most of the time, they’re evaluating themselves. They’re asking:
Is this really the right time to fix this?
Do we believe this can actually work… this time?
Are we ready to bet on this person?
And when even one of those questions feels unresolved, they pause. They pull back. Not because they’re rejecting you, but because they’re unsure of what comes next.
No amount of follow-ups can override that kind of uncertainty. I’ve tried. Maybe you have too. It doesn’t create motion. It just creates pressure.
Pressure doesn’t build trust.
What’s been more helpful for me, and I’m still learning how to do this well, is to treat those moments as signals. Instead of asking, “What should I do next?” I try to ask, “Where did the buyer get stuck?”
It’s usually one of a few places.
Sometimes they’re not fully clear on the problem they’re trying to solve, or how much it’s really costing them.
Other times, they’ve tried something similar before and it didn’t work, and they’re quietly worried this will be the same.
And sometimes, they like the idea but don’t yet trust that I’m the one who can help.
Any one of those can hold a deal in place. Ignorance and apathy remains my largest competitor.
So rather than do more, I’m learning to do less, but act precisely.
I look at the deal again and try to see where belief slipped. I ask myself:
Did they ever fully name the problem?
Did they believe it could be fixed, and that the effort would be worth it?
Did they feel confident that I was the right partner?
I search for their words, not my assumptions. If I can spot where they paused, then I can slow down too. I can ask a better question. I can return to the real decision they’re still trying to make.
Sometimes that opens a new conversation. Sometimes it doesn’t. But at the very least, I’m no longer throwing effort at a fog. I’m starting to see the shape of what’s actually missing.
This has been a shift for me. One I’m still working on. I still have moments where I want to fix it all by doing more. But more and more, I’m finding that what moves a deal forward isn’t pressure. It’s clarity.
So if you’re in the middle of something that’s stuck, here’s what’s been helping me.
Pick a deal that feels frozen. Ask yourself three questions:
*remember this is NOT about your assumptions but did they clearly and concisely state answers to these questions.
Did they name the real problem and why it matters now?
Did they believe fixing it was possible and worth the risk?
Did they feel that I was the person to guide them?
Wherever the belief wobbled, that’s your place to start. That’s the question they’re still trying to answer.
You don’t need to chase. You don’t need to add more. You just need to help them see what might already be true, but still unclear.
And if there’s one question I’m carrying with me more often these days, it’s this:
What if what this deal really needs is not more energy, but more clarity?
If this resonates, or helped you see something more clearly, feel free to send it to someone you respect.
Not to go viral. Just to be helpful.
Because maybe they’re facing the same question. Maybe they’ve been wondering if they’re doing something wrong. Maybe this gives them language for something they already knew but hadn’t yet named.
That’s how Unstuck grows, one honest signal at a time.
And for that, I’m deeply grateful.