There is no definitive “too late” when it comes to sending LinkedIn messages. As long as the recipient is actively using LinkedIn, it’s generally fine to reach out at any time. However, certain factors like the relationship you have with the recipient, the purpose of your message, and how long it’s been since you last interacted can impact the appropriateness and effectiveness of sending a late message.
If you don’t know the recipient
If you have no existing relationship with the recipient, it’s best to send a connection request before directly messaging them. Messaging someone out of the blue who doesn’t know you can come across as intrusive. A connection request gives them the chance to learn who you are first and the option to accept or ignore your request.
An exception is if you share a mutual connection who can introduce you. A warm introduction goes a long way towards establishing trust and context for your outreach.
If you haven’t talked in a long time
If it’s been over a year since you last interacted with your connection, take some time to refresh yourself on their profile and recent activity before messaging. Look for updates about their work and interests to reference in your message to show you took the time to catch up. This demonstrates your message is personalized and not a spray-and-pray copy/paste attempt.
Also consider the reason for your message. Are you reaching out just to say a random hello after years of no contact? Or is there a specific professional reason like a job opportunity or relevant article to share? The former may come across as strange while the latter provides a logical purpose.
If you ghosted on a previous conversation
If you previously engaged with a connection but stopped responding for whatever reason, don’t wait too long to follow up or you may need to re-establish rapport. A few weeks go by is fine, but after a couple months your conversation may be too cold to pick back up where you left off.
When you follow up, apologize for the delayed response and provide any context needed. Then get right into the topic at hand or propose meeting for coffee/a call to properly catch up.
When you’re asking for something
If your message is asking for something substantive like a referral, job opportunity, or advice, timing takes on an added layer of importance. While you may have an existing relationship with the recipient, you want to be cognizant of reaching out at a time that is convenient for them to thoughtfully consider your request.
Avoid sending asks first thing Monday morning or late Friday afternoon when people are usually ramping up for or winding down from their work week. Mid-week tends to be best for professional requests.
Also consider what the recipient has going on based on their profile activity feed and recent posts. If they just started a new job or are preparing for a big conference, they likely have limited bandwidth to assist others.
When you need a timely response
If your message pertains to an opportunity with a tight deadline or upcoming event you want the person to attend, give them enough lead time to respond and take action. Last minute asks just 1-2 days before your deadline may go unanswered simply due to bad timing versus lack of interest.
A good rule of thumb is to reach out at least 1 week in advance for time-sensitive asks. Any less and you risk the recipient having competing priorities and not being able to engage with your request meaningfully.
When you’re following up after meeting someone
After meeting someone in-person like at a conference, event, or mutual friend gathering, follow up with a message soon after while the interaction is still fresh. This could be the next day or within the same week.
Waiting too long makes it awkward to reference the get-together, and signals you weren’t actually that interested in connecting on LinkedIn after meeting.
When you want to reconnect
For old colleagues, classmates, or other dormant connections you wish to reconnect with, any time is fine to reach back out as long as you share a baseline relationship. The strength of your original relationship dictates the acceptable latency of your outreach.
For instance, messaging an old close friend or teammate from 5 years ago out of the blue is completely fine. But messaging a loose acquaintance you haven’t spoken to since college 10+ years ago requires more warming up.
In summary…
There is no definitive point at which it becomes too late to send a LinkedIn message. But factors like your existing relationship, the purpose of your message, time sensitivities, and simply using common sense etiquette all play a role in determining effective timing.
With the right context and approach, an overdue message can pick right up where you left off or reignite a lapsed connection. Be mindful, personable, and considerate of the recipient and your outreach is likely to be well received regardless of how long it’s been.