DM 101: FUNDAMENTALS OF DIRECT MESSAGE FOR CAREER BUILDING JOURNEY

By Yohannes Haile

How to initiate conversations through DMs

Career

7 minutes read

|

May 25, 2026

Read on medium.com

Originally posted on Oct 7, 2024

DM 101: FUNDAMENTALS OF DIRECT MESSAGE FOR CAREER BUILDING JOURNEY

DM is vital in forming a meaningful connection/partnership/relationship with someone we barely know online. Therefore, the way we slide into someone’s DM or the way we respond to others’ initial message is something that needs intentional care.

Cold emailing, cold reach, and cold DM are much different than the topics we are trying to discuss in that they tend to be formed with no prior impression of the platform they are on. For instance, LinkedIn and other business groups send you offers out of the blue and expect you to be interested in their ads and buy their products or services.

By DM, we mean the Direct Message someone initiates in the need of friendship, mentorship, partnership, relationship, or other forms of help and support. While it is a well-laid-out fact that we all need to consider DMs in some way at some point in our career-building journey, it is otherwise an overlooked concept to understand the nature of reaching out to someone we know online for the first time without ruining the first impression and losing their attention and focus.

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Before trying to learn what can be done to achieve a better result with our initial DMs, we need to get on the same page about the major challenges in DMs and the things we need to avoid while texting someone for the first time carefully.

DM Common Sense

1. Knowing the platform!

DMs are everywhere. We are starting from social media, such as Instagram or X, to dating apps like Tinder and Bumble, up to professional sites and apps like LinkedIn. The first issue to consider is where we are. Based on the platform we are on, we can understand what our intention in reaching out to people for the first time should be, or at least align with.


  • Social Media: friendships, romantic relationships, or fandom | rarely professional
  • Dating Apps: romantic relationships, casual or long-term
  • Professional sites: strictly professional, including mentorship, business partnership, and creative or academic collaboration

Most people in some professional niches on LinkedIn miss the point in engaging solely for professional reasons and tend to create discomfort in others by expecting more. This brings down the interest of others who are learning from you and also makes it a lot harder for people to trust others in their journey of building a career out of their passions and education.

2. Due Diligence

Doing your research about someone’s profile or expertise before going to their direct message helps you have an appropriate expectation and objective for your potential conversations.


3. Have a concrete objective for starting a conversation!

Some people slide into your DM for no apparent reason. The reason they initiated the conversation doesn’t get any clearer to both of you, despite desperately trying to keep the dialogue at the expense of your time and valuable energy. Know your why before you send the first text to someone you have known well online for the last couple of months. If you don’t have a valid reason to reach out, it is better to keep engaging with their public content through reactions and some polite comments until you find that introducing yourself to the person becomes an important thing for your professional endeavors.


3. Lower your expectations!

Don’t expect people you find online to be as cooperative and polite as you. Regardless of the platform you are using, people have different kinds of bad approaches when it comes to online communication through direct messages.


  • Ghosting: leaving your texts unopened or unread, or not opening your messages in the first place
  • Short responses: texts that you will find difficult to engage with and keep the convo flowing
  • Breaking promises: not behaving as they told you or seemed at first

DM — The Shoulds

How to Craft The LinkedIn Pick-up Lines

Who said the only text you need to craft is the one you send to the person you want to impress romantically? First impressions matter! We, humans, tend to stick with the first knowledge we have about a thing or a person, even though it is proven otherwise through time (anchoring bias/first impression bias). This shows us why we need to dedicate all the time there to come up with the nicest option for the first text while sliding into someone’s DM, despite the platform.


Here are a bunch of things we all need to do when we initiate a conversation through LinkedIn DM:

  • Have a LinkedIn profile that explains who you are and what you do.
  • Be authentic yet approachable.
  • Learning their profile before deciding to DM them helps you have a substantial conversation starter.
  • Greetings from a stranger online are not worth it.
  • Make your first texts concise and readable.
  • Mind your grammar and spelling.
  • Be polite, but don’t overkill it.
  • Be curious and learn more about the person.
  • Don’t bring money/numbers on the first few texts.
  • Don’t oversell yourself in the first few texts.
  • Be on point. Don’t beat around the bush
  • Try incorporating appropriate humor if you can. (Optional)
  • Reply as fast as you can.
  • Carefully read their messages. Don’t rush into responding without understanding their points.
  • Ask for additional clarification when you cannot understand them. (Politely)
  • Feel free to let them know and stop texting if you see the conversation isn’t bringing real value.
  • If the conversation begins to fade away from being professionally intoned and goes up to a friendship or romantic spectrum, ask them to switch to other platforms. (Phone number or Messaging apps)
  • Beware of the impression you are creating in the name of your professional brand, and consider a careful approach in whom you are texting.
  • Follow up wisely by mentioning some part of your previous conversation to keep the natural flow of the communication.

Being strategic about the way you approach people you admire, want to work with, or learn from online would benefit your career growth when it comes to creating meaningful connections via LinkedIn. Learning the DM tricks and applying them takes time and consistent practice, but that shouldn’t stop you from dedicating your energy to improving your texting skills. By following the tips mentioned above and experimenting with what works for your case, I hope you can see a great result in your online presence and the number and quality of opportunities for all the things that matter to you professionally, and you secure.