2 weeks ago, a founder with a fancy degree and every logo on their resume you can imagine, came to me exasperated…

“We ran a process, and it didn’t work! What went wrong??”

This is a common exasperation that gets thrown my way. I get a few of these a week, it feels like. And with all of them, there’s no clean answer. It’s never just one thing. In this case, I lost count of the problems pretty quickly… They barely spoke to any investors; the story missed the mark, and *checks notes* raised too much money previously…

But there was one thing that stood out that was significant enough to write a full essay on it. While describing her “process”, she double underlined (in a vocal kind of way) one action she took that she was proud of. She said, “We started our process, contacted investors, and let them know we wanted term sheets in 2 weeks.”

It was obvious that she felt like the inclusion of a deadline made her process even more processy. The subtext there was “You know, I’m sure I messed things up, but at least I included the deadline!”

She certainly did include a deadline, but she applied the wrong intensity. Some might be turned off by it this early on, and others just might politely think they can’t move that fast; either way, it definitely didn’t help.

In my opinion, deadlines are important, but they come in different intensity flavors, and you have to apply the right one at the right time.

3 Levels of Deadlines

One of the hardest parts of fundraising is keeping investors moving without seeming desperate. The good news is that there are a few tools that founders can use to keep things on track. Deadlines are one of those tools that I always recommend. But using the appropriate deadline is key.

Here are 3 levels of deadline intensity and when/how to use them.

Level 1 - Soft Deadline (more of a light outline)

Start with soft deadlines early in the process when you’re just beginning conversations. These are descriptions of a timeline that you’re working with without drawing a super-rigid deadline.
"We’re scheduling all first meetings over the next two weeks and aiming to wrap things up in 6-8 weeks. We want to be efficient but also meet the right investors."

This has the positive effect of focusing the investor, showing you’re organized, and hinting at competition, but also puts enough time flexibility to not scare off an investor before they have time to learn enough to get truly excited.

Level 2 - Solid Deadline (still not aggressive)

After the obvious passes get filtered out from your first meetings, you’ll be able to gauge interest levels with your 2nd meetings. From there you can be more specific about a deadline. This will get investors to get serious and prioritize doing the work for your deal.

Realize that even this level of deadline shouldn’t be aggressive. You don’t have any sure things in hand at this point, so pushing people too hard is not advisable. Try something like this:

“We’ve had a great second meeting, so we are pushing to wrap this up without wasting time. I’m looking at getting to terms in about 2.5 weeks [mention a date]. Does that timeline work for you? Let me know what makes sense. I’d love to keep things on track.”

Level 3 - Ultimate Deadline

The ultimate deadline occurs when you truly have a drop-dead date. This means someone else has an exploding offer that you don’t want to let expire or some other deadline on your side that truly can’t be moved.

This is stressful but a good type of stress. This allows you to set an ultimate deadline, one that you truly don’t mind sharing because, you know what? You kind of don’t have another choice. It is what it is and if they want to play ball, they’re going to have to meet this deadline.

When delivering an Ultimate Deadline, I’d still keep things positive and polite.

“Hey there, the situation is moving quickly so we need to hear back from you by ________. If there’s anything I can do from our side to help you get the work done to engage, please let me know. I would love to be able to consider working with you!”

Final notes on deadlines

Deadlines can be scary because, in some ways, they are forcing people to pass. Just remember there are levels you can apply which give you different levels of flexibility. Start light and as things progress, tighten the deadlines and make them more intense.

The good thing is, if an investor is interested, a clear timeline won’t scare them off; they’ll either move forward or let you know they need more time. And if someone pushes back on timing, that’s actually a good sign; it means they care enough to ask for some flexibility. At that point, you can decide whether it’s worth adjusting the schedule for them.

Side note: Founders sometimes worry that setting deadlines will piss off investors. The thing to remember is, when communicated correctly, deadlines help investors prioritize their cluttered and busy schedules. If you’re polite and positive, you’ll have nothing to worry about.

Till next time…

Be chased,

Jason