Jan 10, 2025

Use the “next step” approach in your conversations. Instead of closing with a vague, “Let me know if you're interested,” end your conversation with a clear, actionable next step. For example, “It's typically helpful to see how it works in action with a brief demo. Can we set aside 15 minutes...” This directs the prospect toward taking immediate action and keeps the momentum going. And remember, whenever you're asking for their time, use this tip from a few months back.

Dec 18, 2024

Do not be the person scrambling around at the 11th hour on Dec 31st because your prospects who said they'd sign are nowhere to be found. Use the holidays to create urgency, highlight the hectic schedule, and offer an incentive to close before the holidays. For example,

Hi John,

Because of the holiday and end of year rush, we're incentivizing new customers to come on board before it gets too chaotic. As such, we're offering you an additional user license on the house if you can move forward before the end of this week.

Nov 27, 2024

Reach out and thank prospects who have already signed with you this past year. A simple “thank you for your business, it was a pleasure working with you” works. And then ask for any referrals they might have. Customers are happy to refer business your way, but salespeople simply do not ask. See this post from a few months ago.

Nov 21, 2024

Get ahead of upcoming holidays and use this to get a few minutes with a prospect sooner rather than later. For example, say “Hey Tom, with Thanksgiving coming up next week I’d love to connect prior to that break and iron out X, Y, and Z as previously discussed. Do you have 15 minutes on Tuesday or Wednesday at 10:45 or 11:45 PT?”. It gives you a reason for the outreach and the sooner than expected meeting request.

BONUS: If you’re able to get this meeting, make sure to map out your next steps with EOY urgency in mind. Again, there are more holidays coming up so ask for follow up meetings ahead of these holidays. Keep things like legal review and additional sign offs in mind.

Oct 31, 2024

There are 61 days left in the year. Just under 9 weeks. That's plenty of time to have a sizeable impact on your 2024, especially considering it's Q4. It's also short enough that you can see the end coming closer and closer each day. Every hour put in during Q4 is worth 5x the hours put in during the dog days of summer. It's crunch time.

If you're not sure where to start, use this simple play from a few weeks back.

And for those you're already engaged with, be sure to implement this tactic to avoid hiccups come December.

Oct 25, 2024

Friday afternoon is a great time to elicit a response to something simple. For example, “Hey John, thanks again for the time this week. You mentioned wanting to talk with your team and then schedule our next call. Did they have any questions we didn’t cover, and can grab 15 minutes Tues or Wed at 11:45 ET?”

Keep it simple. Don’t make a big ask Friday afternoon, but the data shows something simple like a quick next step can get checked off, as the week is winding down and people are looking to button things up before their weekend.

Oct 24, 2024

For Q4 deals, create and talk through a reverse schedule with your prospects. For example, “Our goal is to close this by Dec 31st, so we need to have this in legal’s hands by Dec 15th, which means we need to have the package and terms buttoned up by then. We need to make sure the trial is wrapped up by Nov 30th. To do this we need to kick it off by Nov 15th.” And continue with any and all important events that must take place between now and the deal closing.

Outlining this schedule does two things. It creates urgency. It also exposes trepidation on their part that may have been hiding. With the latter, you can easily get to the bottom of it by honing in on which step is giving them pause, and/or if this was never going to happen by EOY we want to know that as well.

Oct 2, 2024

Q4 is here. Get the ball rolling on any potential deals that have pushed out, asked to circle back at the end of the year, etc.. You can use something simple, for example...

Hey Barry,

It's been a few months since our previous conversation, and with the end of the year coming up, I'd love to reconnect, revisit A, B, and C, and talk through our next steps. 

NOW is the time to do this. Not in December. This cannot be stressed enough. If it's too soon, they'll tell you, and you can ask for a more firm date ex: how about I through 15 minutes on the calendar for early Nov? 

Q4 starts now, revisit all those opps and accounts from the year, and you'll reap the rewards come December

Sep 20, 2024

Friday afternoon is the perfect time to get a simple task done or get a "yes" from a prospect. Don't ask for something complicated, but if you ask for something easy they'll more than likely take care of it for you. For example,

Hey Tom,

I can't wait for the weekend to get here, I'll bet you're in the same boat. One of the last things on my todo list is finalizing that DocuSign with you. Do you think you could help me out and put that behind us before the days over? I appreciate your help in advance.

Simple. To the point. Easy. If your prospect isn't a complete a**hole, they'll help you out.

Sep 16, 2024

Follow up is crucial, and yet few salespeople follow up enough. 60% of buyers say no at least 4 times before saying yes, and yet 48% of salespeople fail to follow up even once. Do not follow up with a "checking in" email or god forbid, a "circling back" email. During your first meeting, you should note which pieces of collateral are relevant, and send one or two on your first follow up, but not all of them. This is for two reasons. First, your prospect will not look through four or five pieces of content (you'll be lucky if they look at one), and second, this leaves you with relevant content to share in subsequent emails and follow up so you can avoid the dreaded clichés above, and instead provide follow up that is actually valuable.

By simply following up more, you will close more business. The more relevant your follow up, the more effective it will be at getting you to the finish line.

Sep 12, 2024

Send a confirmation email after sending a particularly important email. We're looking for confirmation and a mutual understanding the ball is in their court. It's effectively the reverse of this play from Aug 3rd. We get confirmation, and it's their turn to act. Emails with a lot of attachments and links, as well as DocuSign, etc. often end up in Spam folders. Here's an example (send immediately after the email in question)...

SUBJECT: Confirmation of Receipt

Jane - I just sent you the follow up email we discussed. Please let me know if you did not receive it.

To be clear, I'm only asking for a response if they did not receive the email, but 95% of the time they'll reply saying they did get it. And of course if they didn't, we'll know and take care of it.

Sep 10, 2024

Ask your prospect/customers if they're open to setting up a Slack channel for communication. You'll be surprised how many buyers are open to this, and it sets you up for a much higher chance of gaining their business. You'll have a direct feedback loop with real time communication that will A) drastically speed up their buying process, and B) put you miles ahead of any competitors involved in your sales cycle.

If you don't use Slack, but want that more direct line of communication, run this play from awhile back.

Sep 9, 2024

Pitch to the catcher on the other end. Too many salespeople pitch a one-size-fits-all solution. You typically have 3 levels of buyers: end users, middle management, and executives. They have very different interests and needs. Tailor your pitch to whoever you’re speaking with at the time. For example, tell end users how your solution will save them time and/or energy. They do not care about how much money it will save their company, but executives absolutely care about this. Managers typically care about numbers related to their teams overall effectiveness, and while end users can extrapolate these numbers to their own job, don’t make them go through that exercise. Tell them directly.

Remember, always consider the person’s role on the other end and what they are most interested in. This will translate to positive next steps immediately.

Sep 7, 2024

Get a response from someone by legitimately offering to buy them coffee and donuts. You're only going to send a gift card / digital cash to someone who replies so it's ultimately a great ROI, and your company will almost certainly let you expense this (if $10 a lead isn't worth it, run). From there, the dialogue is open to ask for a meeting in the coming week. Example...

SUBJECT: coffee and donuts on me    

OR    

SUBJECT: starbucks or dunkin' (this one always gets people riled up)

Hey Travis,

Happy Saturday. I'd love to buy you a coffee and a donut if you're interested, let me know!

Sep 6, 2024

Schedule sales calls for the afternoon. Seems counterintuitive, but prospects are 46% more likely to show for a 3 or 4 PM call than an 8 or 9 AM call. They're far busier in the morning than the afternoon, hence the no-shows, and no-shows are productivity killers. 

Bonus: Not only will your show rate increase, afternoon calls last 38% longer than morning calls. And anecdotally, the vibe always seems light and friendlier. All good things.

Sep 5, 2024

Do not say "list pricing". Or "typical price" or "standard price" or anything along those lines. Instead, when introducing pricing, say "approved price". According to Gong.io, saying one of the no-no's above will result in your sales cycle taking 19% longer than average. "Approved price" suggests the price is set and it's been established by a higher authority, which results in an understanding that pricing will not easily change and ultimately a reluctance to negotiate. Change that one word and you’ll see benefits immediately.

Sep 4, 2024

When facing an objection, slow down. In fact, pause. Gather your thoughts, and speak calmly and with authority. You will gain trust simply by the manner in which you handle the objection, far more than the substance of your answer.

Most salespeople speed up, and often interrupt, during an objection. They get wound up and burst. This response does the opposite from above and erodes any trust you have. Remember, slow down, gather your thoughts, speak calmly. This will bear fruit right away.

Sep 3, 2024

When closing a call or meeting of any kind (see tip here), immediately send a calendar invite for whatever the next meeting is. Always. This cannot be overstated. The calendar invite cements the meeting and is like a contract. Numerous studies demonstrate a show rate improvement of ~55% when there is a calendar invite, as opposed to simply a verbal or email commitment.

Sep 1, 2024

Sunday evening is a great time to reach out to anyone you have a scheduled meeting with during the coming week, and ask them if there is anything in particular they want to cover and/or if they have any questions. For example,

John,

Looking ahead to our meeting this week, I want to make the most of our time. Is there anything you want to make sure we cover and/or do you have any questions you want to ensure get answered?

Looking forward to connecting,

Paul

Aug 31, 2024

Saturday is the perfect time strengthen your relationship with any prospect/client through a casual, low key message. This could be reigniting a conversation that's gone dormant, a quick note to someone near the finish line, or anything in between.

Use this play from a few weeks ago, but focus on a weekend/friend vibe rather than weekday/work. Your prospect is in weekend mode too, even though everyone is still checking their email, and will appreciate the friendly tone. Think of it as Casual Friday, but for work.