Writing Clear Email Updates

Your sales emails suck. And guess what? I know because I get 30 of them a day. I see the same mistakes over and over...the boring intros, the endless rambling, and the generic pitches that make my inbox feel like a nightmare. Want to know why? Because your email has 3 seconds to make an impression. THREE. Seconds. That's how long you have before I hit "delete" So if you’re not cutting through the noise, you’re just part of the problem. Here’s why your outreach isn’t working: 🚫 Cut the fluff, now – “Hope you’re doing well” or “Just checking in” is a one-way ticket to the trash. No one has time for that. If you don’t get to the point within the first 5 words, you’re done. ✂️ Get to the point fast – Lengthy emails are a killer. Research shows emails under 50 words see 83% more replies. That means if you're writing a novel, you’re already losing. 📚 Personalize (like actually personalize) – "I see you're in [insert job title here]”—that's not personalization, it’s lazy. Do your homework and show that you understand my specific challenges and goals. If you don’t, I’m clicking delete before you even finish your sentence. 🎯 Relevance matters more than anything – If your email isn’t directly tied to what I’m trying to accomplish, it’s not going to get a reply. I don’t need a generic pitch; I need to know how you can help me solve my problems today. 🔥 Stop the lazy copy-paste – If I can tell you’re sending the same message to 100 people, I’m out. Your outreach should feel like you’re speaking to me, not to the entire world. Personalization isn’t just a buzzword. You’ve got 3 seconds to grab attention and show value. If you’re still using the same tired tactics, you’re wasting your time...and mine. 🎤 🫳 ALSO MASSIVE SHOUTOUT to the folks using video to prospect, can say that personalized video messages get a response from me every time. I LOVE them.

One minute, you think you’ve got a sale. The next, you’re getting ghosted. If you’re tired of chasing or begging, I got you. First, why does this happen? Same reason you tell a friend, “I’m not feeling well,” when you just don’t want to hang out. It’s awkward to say no directly. Ghosting doesn’t mean you did something wrong. It’s just how people are. So what do you do? Detach. Retreat. How? Send a simple, one-sentence email like: “Have you deferred the cold call workshop?” “Have you deferred looking at [product]?” “Have you deferred fixing your roof?” The Psychology It leverages cognitive dissonance. The tension people feel when their actions don’t match their self-image. By implying they’ve already made a decision (“deferred”), you’re gently asking them to either correct you or accept it. Here’s the best part: No response is a response. That’s why the response rate is 100%. If they don’t reply, move them to your nurture track and move on. Because now you’ve got time for prospects who are motivated to continue the conversation. Remember: It takes two to make a sale. You can’t play catch with someone who won’t throw the ball back.

I received two separate cold emails this morning. One featured a photo of Donald Trump giving my agency the "Best Agency" award. The other showed Bill Gates crowning me the "greatest business mind on the planet." Both emails used the exact same phrase: "Legends recognize legends." We can all agree this is bad outreach. But why is it bad? It's the lack of insight. Even if an AI had written it, saying, "I see 2Stallions Digital Marketing Agency works with clients in the finance sector," it would still be missing the most important part. The most important part is the "So what?" You saw I work in marketing. 𝐒𝐨 𝐰𝐡𝐚𝐭? You noticed I liked a post on SEO by Neil Patel. 𝐒𝐨 𝐰𝐡𝐚𝐭? You know what projects I've worked on. 𝐒𝐨 𝐰𝐡𝐚𝐭? The connection is missing. The unique perspective is missing. Good outreach doesn't just state a fact; it builds a bridge from that fact to a relevant, compelling idea. It shows you've done your thinking, not just your research. Before you send your next cold email, whether it's written by you or an AI, apply the "𝐒𝐨 𝐰𝐡𝐚𝐭?" test. If you don't have a compelling answer, you're just creating spam. #MarketingStrategy #B2BMarketing #SalesStrategy #LeadGeneration #CriticalThinking

Buyer: Thanks for meeting with us, we've decided to go a different direction. Rep: Silence 😑😑😑😑😑😑😑😑😑😑😑😑😑😑😑😑 If someone fits your ICP today, there's a good chance they will again or will serve as a path to your next deal one day. Here are two common places I see reps and front line leaders take actions that are a disservice to their future selves: 1. The above. You don't get your way so you don't reply. "Well, no money there, on to the next." 😒 2. Your buyer replies to your cold outreach, "Thanks for the note, not a fit for the moment.", and we don't reply. "Not the right time or person, on to the next!" In both cases, our silence sends a message: taking the time to reply isn't worth my time because I didn't get what I wanted from you. Yeeeesh. In both cases, practice what we @ #samsales call being a Gracious Loser. 1. If you already invested the time in a call, invest the time to understand the change in their direction. Don't squander this lead - your reply can keep comms open, can help you learn, can help you figure out if there's a chance to sell down the line, or simply show that you're a good sport. 2. Your buyer did the first thing we'd all kill to get - A REPLY! But ignoring it not only sends the above message, it kicks you out of the opp to send this: "Really appreciate the reply - I'm sure you get dozens of emails each day. Might there be a better time to touch base, or is there someone else on your team or across a different division that shares this challenge and might make good use of seeing what we have to offer? I'll say hello on LI to keep in touch in the meantime - thanks for considering sharing the additional context!" The above is different, unexpected, client-centric, and polite - what a refreshing take to get from a buyer that usually gets the opposite. Sales is an incredibly long game and the bar these days isn't even low, it's on the ground. All we have to do to stand out is to step over it, and this is one of hundreds of ways we can do that + build those relationships for the long haul. #samsales

Are your sales emails so ‘nice’ they’re costing you deals? Here’s the brutal truth: wimpy, apologetic emails get ignored. If you’re typing 'sorry to bother you' or 'I hope this finds you well,' your prospects are already scrolling past. Weak vibes don’t win. Confidence does. After working with hundreds of clients (and seeing countless sales pitches), I’ve spotted the fix. Ditch the fluff—try these rewrites: Weak: 'I’d love to show you our software sometime.' Bold: 'We cut ABC Corp’s downtime 50% by locking out ransomware. Want that? Let’s talk.' Weak: 'I think our solution could help…' Bold: 'Our solution stops IT-OT chaos cold.' (No 'think.' Own it.) Weak: 'Just wanted to share some info…' Bold: 'Here’s how we’ll save your production line—based on your last earnings call.' Prospects skim. TL;DR kills deals. Short, punchy, problem-solving emails win every time. CEO tip: Write like your product’s a game-changer. It is. Stop tiptoeing—clarity and guts close sales. This hit home? Smash that Like, drop your best email hack in the comments, or share this with your team. Let’s kill the 'nice' epidemic together! #SalesTips #EmailHacks #Copywriting #BusinessGrowth #Leadership

You are wasting your time with discovery calls, if you don't follow up with an email. The re-cap email is very important, especially after an executive meeting. You need to capture the conversation so both parties are on the same page and can be held accountable. Take your time with these. It’s common to spend an hour to write, edit, and proof-read the note. Status and other general business meetings can be a simple email re-capping next steps.  Important meetings, like discovery, need more effort. Why spend time on the email follow up? 1. Shows that you are listening = trust 2. Helps the seller synthesize the information  3. It will get forwarded to people on both sides 4. You can forward it as a reminder of what they agreed to Email format: - Current Situation - Desired Situation - Value Drivers - Business Areas Impacted - People that need to be involved - Next Steps YOU CAN PUT THIS ON A SEPARATE DOCUMENT THAT IS ATTACHED TO THE EMAIL ------------------------- EXAMPLE EMAIL: Mark,   It was great meeting you on Thursday. Thanks for taking the time to explain your role, responsibilities, priorities. We appreciate the work you have done to evaluate the partnership.   From our discussion, I gathered the following notes. Please let me know if I missed anything.   𝐂𝐮𝐫𝐫𝐞𝐧𝐭 𝐒𝐢𝐭𝐮𝐚𝐭𝐢𝐨𝐧 - [Company] has an initiative to reduce operational expenses by $2B - Pressure from Amazon continue to drive down margin - New acquisition has created integration challenges - Top initiatives: Consolidate vendors, reduce cost, re-org design - Current process for X is manual and is impacting the business by Y - Delays in delivery, rising processing costs, and unhappy customers 𝐃𝐞𝐬𝐢𝐫𝐞𝐝 𝐒𝐢𝐭𝐮𝐚𝐭𝐢𝐨𝐧 - Digital transaction that is automated using Ai - Set up a central service across the enterprise - Flexible deployment options - Integration with Oracle, Ariba, Salesforce - Conduct a value assessment to determine the cost/benefit analysis   𝐕𝐚𝐥𝐮𝐞 𝐃𝐫𝐢𝐯𝐞𝐫𝐬 - Reduce [use case] from 2 weeks to 2 days - Reduce processing costs by 80% - Improve customer experience NPS by 10pts - Improve compliance through better visibility and tracking 𝐁𝐮𝐬𝐢𝐧𝐞𝐬𝐬 𝐀𝐫𝐞𝐚𝐬 𝐈𝐦𝐩𝐚𝐜𝐭𝐞𝐝: - Real Estate - Sales - Marketing 𝐏𝐞𝐨𝐩𝐥𝐞 𝐭𝐡𝐚𝐭 𝐧𝐞𝐞𝐝 𝐭𝐨 𝐛𝐞 𝐢𝐧𝐯𝐨𝐥𝐯𝐞𝐝: - Chris Pine, VP Real Estate - Leo Barley, VP Sales - Jay Johnson, VP Marketing - Rob Smith, Exec Sponsor - John McConnell, VP IT Architecture 𝐍𝐞𝐱𝐭 𝐒𝐭𝐞𝐩𝐬 - Mark will be the exec sponsor for the assessment project - Meet with Mike Green, IT Operations to assign IT owner - Complete the revised assessment in the next 1-2 months - If the value is high, then Rob and Alan will mandate the solution I will work with your EA to set up a check-point meeting in 2 weeks. We look forward to partnering with you.   Best,   Mike

Sending updates on your company to VCs is like getting a pet scorpion. Here's why. 1. Appropriate frequency. As a VC, I get at least five emails a week from founders and CEOs asking if it's OK if they send me a monthly progress update. WIth 1-2,000 pitches a year, that means maybe 5,000 live companies at any given time. If I accepted a monthly email from each, I'd need to start every working day by reading 25 updates. That's not going to happen. As a founder or CEO, you should match the needs of your audience. Some extra-keen VCs, or those learning the ropes, may jump at once a month; most will be happier with quarterly or half-yearly, especially if you've just raised and aren't going to be coming back for more money until mid-2026. 2. Short and sweet. The people who are definitely interested in every twist and turn of your journey are mostly your parents. Others will prefer bullet points, not an essay -- and when they want more detail, they can reply to your email and ask. It's good to begin with a TL;DR. Since your audience will be seeing dozens or hundreds of other companies between each of your updates, you can't assume they remember who you are and what your company does. So remind them in one sentence at the top. 3. Regularity trumps detail. As with most things, consistent effort brings rewards. Whatever frequency you set, stick to it. Clockwork but scrappy is better than beautifully thoughtful but irregular. 4. Scorpion bites. Maybe the most basic reason for sending an update is to make sure the VC remembers you -- it's a forget-me-not. But like the forget-me-not flower (whose Latin name is Myosotis scorpioides) your updates can come back to bite you. If you do them right, you'll have shared clear objectives at the start, which means you may have to admit that you didn't hit them. Final thought There's a case for saying updates matter less than they used to. In the past, only the best-resourced big VC firms had the staff to map their entire target market and keep tabs on everything that moved. Today, cheap software and tools help investors to follow companies easily. If you start showing signals of traction, they'll often find out by themselves and call you -- even if you don't send out a single email. Links in comments below.

Got an executive too busy to talk to you? Same. That’s why your weekly roundup email needs to be working overtime. In a world where your exec is triple-booked and skimming more than reading, a well-structured weekly email becomes survival. For you and for them. It cuts down the noise, keeps things tight, and makes you look like the organized genius you are. Here’s how to pull it together like a pro: 📬 Subject Line: Keep it tight and specific. Example: Weekly Update: Sales Ops – Week Ending June 14 👋 Greeting: Professional but warm. Example: Hi Jamie, hope your week’s been productive. 📝 Opening Line: Set the tone and purpose. Example: Here’s a quick roundup of this week’s key updates and priorities. 📌 Key Highlights: What went well. What moved forward. Keep it bullet-style. Completed onboarding for three new hires Finalized Q2 budget and submitted for approval Closed out logistics plan for annual meeting ⚡ Priority Actions/Decisions Needed: This is your call-to-action zone. Be clear. Be bold. Add deadlines. Decision Needed: Approve travel expenses by Friday Action Required: Feedback on draft deck for client meeting 🚧 Challenges/Issues: Don’t just bring problems. Bring potential solutions. Issue: Software update delay – ETA Tuesday Solution: Use current version until rollout 📅 Upcoming Events/Deadlines: Quick scan of what’s coming up. Help them stay ahead. Monday: Team strategy session – 10AM Wednesday: Stakeholder presentation – 2PM Friday: Finance report deadline 🔗 Quick Access Links: No hunting through inboxes. Link it once, link it right. Q2 Budget Report Client Meeting Agenda ✅ Wrap it Up: Let them know what’s next and how to respond. Example: Let me know if you’d like more details on anything above. Looking forward to your feedback on the action items. And if your exec says, “Wow, that weekly email is so helpful,” take the win. But if they don’t say anything but actually read it? Still a win. Streamlining communication like this not only supports your leader, it builds trust, shows initiative, and reinforces your strategic value. Anyone else swear by weekly roundup emails? Or thinking of starting? Let’s swap tips 👇 #evolvedassistant #administrativeassistant #executivesupport #administrativeprofessionals #executiveassistant

I've been told by investors that I give good updates, so I wanted to share a simple recipe for giving timely, relevant, and brief investor updates. The goals of giving investor updates are: - Celebrate the wins - Share in the struggle - Build trust - Get help I've found that investors are more than willing to help, but they often don't know how. And because they have invested in potentially dozens of companies, it's hard for them to be proactive. For this reason, I suggest a monthly cadence. Put a 1 hour recurring monthly meeting with yourself on your calendar. An investor update should take no longer than an hour to put together. Ideally less. IMHO, quarterly updates are too infrequent as startups move too fast and you're missing out on an opportunity to build trust so that when you do ask for help, there's already context as to why you need it. Keep it simple. This is not a board meeting, so you don't need a deck. Investors would rather receive less more often than more less often. A simple email with bullet points is the best and most digestible way to share an update (unless you're building a messaging app...then use that :) The simple format should be: 1. The good 2. The not-so-good 3. Needs Let me break those down. The good (3-5 bullets) Go ahead and brag a little. You've worked hard, so it's OK to celebrate the wins. But, no fluff here. Investors can spot vanity metrics a mile away. Go right to the heart of the matter with updates on revenue, churn, conversion rates, and successful experiments, new hires, new customers, etc. The not-so-good (2-3 bullets) Be honest. Investors know that it's not always sunny in a startup. The more vulnerable you can be, the more likely you are to build trust. Lose a key customer? Tell that story and what you learned. Most likely, one of your investors has run into the exact situation before. Needs (1-2 bullets) This is your opportunity to leverage the combined wisdom and connections of your investors. Shoot straight. Be specific. You'll be surprised how helpful your investors can be when you have a clear ask. That's why this section should really only be one or two things. Anything more is muddy. If you can accomplish sending this simple update to investors once a month, giving an honest view of your business, you've achieved elite status as a venture funded entrepreneur (as most suck at giving regular updates).

After writing cold emails for 2000+ businesses and booking 1000s of sales calls, I'm sharing my best copy tips to help you book more meetings: 1. Keep it short Your emails shouldn't require any work or over-thinking from the prospect. Keep it to 50 words or less - if they can't read it in ~5 seconds, you've already lost them. 2. Relevancy and specificity "I help watch brands in the UK" will always outperform "I help brands." The market needs to see real value, not generic statements. 3. Switch up your CTAs Skip the boring "hop on a call" pitch. Instead: "Mind if I send a 2-minute Loom explaining how we do this?" "Worth a chat to go over how you can achieve something similar?" 4. The 2:1 rule For every 1 thing you say about yourself, say 2 things about your prospect. People are naturally selfish - they care more about what you can do for them. 5. Focus on getting replies first Cold email is NOT for closing deals.  Your goal is to kick start a conversation and take your prospect from cold to warm then book a call. 6. Benefits over services Don't pitch Facebook ads - pitch the 55% increase in website conversions you delivered for your last client. 7. Stand out from competitors If everyone's pitching "more sales" with influencer marketing, position yourself as "making you go viral." 8. Keep your sequence flowing Your follow-ups should build on previous emails. Keep your offer and messaging consistent throughout.