Most outbound messages and cold DMs are a tragedy.

I get about 10-20 a day on my Twitter DMs and ever since I started BIPF, my email inbox is flooded too. Here are a couple gems:

(these are 2 of the random examples of cold DMs from two separate people)

It’s clear to me that the founders and sales reps who’re sending us these terribly ineffective pitches have great intent in their heart.

But the way these messages are crafted screams a very transactional, desperate and “me-me-me” tone. It’s an off-putting way to strike a relationship with your prospect.

On the other hand, the truly compelling pitches signal thoughtfulness, warmth and a strong sense of “you-you-you” tone.

So, today, I intend to share a proven playbook that can come in handy for you whenever you need to write/re-write your high-stakes cold DM or outbound email.

My biggest meta tip is to view your pitch from the lens of:

• What’s in it for them?

• How will taking the action you’re suggesting (buy now or sign up etc.) benefit them clearly?

• Why should they believe you? What proof can you offer up front?

• Who else can co-sign on you? Are they relevant/important voices in the niche?

• How can you remove as much risk as possible and make the process friction-less?

For years, I struggled with getting my outbound pitches right too.

Mostly, I needed to shift my own mindset first. I used to assume you were either just courageous or you were not. I later learned that courage is a muscle, not a gift.

You can learn, practice and eventually master being courageous and bold. This will help a lot when you are a founder and have to pitch/ask a lot.

My turning point came when I accidentally published the below public tweet directed at Gary Vee. It was my 1st big time “shoot my shot” move that changed the game for me.

As you can see, Gary took up my ask and joined my fledgling podcast for the 5th episode and practically catapulted my career. (Now, I’m at 62 episodes btw as of June 20, 2023)

Here are 4 takeaways from that tweet which you can apply in your own way:

Tip 1: Leave an easy exit

The best pitches are those which don’t come with an obligatory tone. Make it easy for someone to take the exit door and say “No”. This sounds counter-intuitive but the more freedom you offer to the other person in the conversation, the more likely they will give the proposal a real consideration. It signals professionalism. No one owes you anything. Act like it.

Tip 2: Find a warm personal connection/common ground

We all have a lot more in common than we like to think. Be intentional about what specific areas your prospect and you see the world in the same way. In my above example, Gary is a 1st gen immigrant like me. He’s explicitly shared that throughout his content. I am a proud immigrant too so it was easy to start here. Spend time researching your prospect’s content to learn about their worldviews, likes, passions etc.

Tip 3: Make a direct and clear ask

Always be direct and bold in your ask. Don’t bury the lede. Don’t beat around the bush. Don’t second guess yourself here. You can’t expect the prospect to spend time piecing the puzzle together. Make the decision a binary one for them.

Tip 4: Get the timing/relevance right

This is probably the hardest to get right. Your ask has to align with the timing and priorities for the prospect. So you may have to be patient and wait weeks/months for the right timing. With Gary Vee, I wanted to ask him in January/Feb but I waited months until I saw him tweet a lot about NFTs and Vee Friends. I noticed he was trying to amplify and promote the topic of NFTs a lot in May (which is timed with his big public launch of VeeFriends) so I made my ask in the same week. It worked great! I’ve done this with other top authors too by pitching them during their book promo tours because to me their top priority was obvious. Time your ask well.

Tip 5: Show the stakes

Lastly, don’t be one of the ones who isn’t super excited for the ask. Show your enthusiasm. Let your gratitude and zeal shine. If I could pick 1 person to say ‘YES’ to among 100, I’d pick the one who I know is really thrilled to have me. Versus someone who treats this transaction as a chore. Show what the “YES” means for you. Show the stakes.

I shared much of this in a live session we recorded at BIPF (2nd cohort) recently. The response has been incredible and I loved sharing real examples and “showing the receipts.”

To close this out, as serendipity would have it, after my live session, I got a pitch from someone (not a founder I know, not in my network) with an ask to be on their podcast.

That pitch was masterclass. Here’s that cold DM I received on LinkedIn which applies all these tactics effectively.

5 observations from Harshita’s message:

Tip 1: Cut to the chase

Don’t waste time with pleasantries or weather talk. Your prospect might be super busy and inundated with requests. It’s not rude to cut to the chase and just open strong. This shows that you respect their time and attention.

Tip 2: Signal the relevance very early

She quickly touched on “stories of immigrants”. Clearly it’s relevant to my background and things I care about.

Tip 3: Share your why

She then moved on to share her “why”. Her why was inspiring and made me buy into her vision. This was actually a breath of fresh air. I’ve since learned to incorporate this into my future asks. The “Why” often has a powerful emotional pull to it. It signals that we’re doing this for beyond transactional reasons.

Tip 4: Make the ask super clear

She opens the next paragraph by straight up showing me the ask: “I’d love to have you on the pod”. No dilly dallying. No awkward pauses. I really love it.

Tip 5: Why me? (build the bridge)

I wasn’t ready to commit to saying ‘YES’ yet though. Because I was trying to evaluate if I can squeeze this in my busy schedule.

But she swept me away with this section “Why me”. She built the bridge of connection between my back story (which many people don’t know so she did her research) and to her podcast’s vision. I learned to include this section in my future pitches as well.

Tip 6: Share your stakes

“I’m personally excited to chat with you” is an ok way to show your stakes. I’d have said something like “I’d be incredibly thrilled” etc. Make the prospect feel really special. This is your kill shot. Go big!

Tip 7: You-centric CTA

This was another refreshing learning for me too. I thought she’d end the whole note by simply saying “would you be interested in joining my pod”. Which is often what I do. But she turned it around and make it seem even more prospect-centric. “Would you be interested in sharing your story”? What?!! Of course! She’s such a persuasive writer.

PS: Anyway, I had so much fun tearing this DM apart and sharing with you. I eventually jumped on a call with Harshita and shared my brief analysis with her. She was shocked and I think she will be again when she reads this piece.

One huge caveat:

Ultimately, all the preparation and tactics in the world can’t make the other person take you up on your shot. People may still ghost you or say “No” to your proposal. I’ve had my share of public failures using the above method. But the rejection didn’t sting me as much because I walked away feeling like I did all I could. Over time, I’ve learned to do my best (especially what’s within my control) and not take things personally.

That’s it. I hope this was helpful.

If you do end up leveraging some or all of the tactics in this playbook, I would love to hear how it went. Feel free to share your learnings and feedback with me so we can all improve the way people take their shots.

Often, one simple “shot” alone can lead to life-changing outcomes. I’ve leave you with this: courage is a muscle, not a gift. So the more you practice, the more resilient you become. All the best!