Strategies for Remote Client Meetings That Work

I might get hate mail for this: Appearances and first impressions still matter—big time. Zoom calls and remote work culture erupted over the past decade, and somewhere along the way, we stopped caring about the 'little things'. Salespeople, missing the details = lighting cash on fire 🔥. 💰 Every call on your calendar costs your marketing team a few thousand dollars. Each meeting could be thousands in commission for you. That CMO you’re meeting with? Her 30 minutes is worth $500. When she brings her team, they spend $3k in salary just showing up. So, why do we show up like we don’t give a sh*t? Sweating the details can often be a waste of time, other times it's worth the effort. 💡 Here are 6 details you should never skip: 1) Do your research.  Asking where they live or what their company does—things you could Google in 5 seconds—doesn’t build rapport; it just makes you look unprepared. Instead, come in with a point of view on something you've already researched. 2) Use a good webcam & mic.  Who would you rather spend 30 minutes with in the screenshot below? You don’t need to break the bank—a solid cam/mic setup costs under $100. 3) Get your lighting right.  Clear the shadow from your face. Sit in front of good lighting. A $20 ring light can do wonders. 4) Dress like you care.  Would you rather be over-dressed or under-dressed when you're presenting to the C-suite of a $2billion dollar company? Toss the wrinkly T-shirt and baseball cap. Throw on a button-up or polo. Maybe even take a morning shower and comb your hair. 5) Send a follow-up the same day.  Buyers appreciate a quick recap they can share internally. Tools like WINN.AI, Gong, or Sybill can automate this, so you can get the email out in minutes instead of hours. 6) Send a pre-meeting brief.  An engaged audience = a better meeting. Prime their brains before the call. *Bonus tip: Send personalized messages to each stakeholder - this takes more effort, but it's worth it. A CMO has different interests/problems than a Sales Manager. Make it clear that you took the time to curate messages for each person. These details might seem trivial, but it's worth it if they make you even 1% more engaging. I get it—some of you will think I'm an old-fashioned grandpa. (Probably true.) Some will think, "it’s 2025, and this stuff doesn’t matter anymore." 🎲 But are you willing to gamble your company's hard-earned pipeline (and your own commission) on that? Deals are won or lost by tiny margins. Skimp a little here, skimp a little there, and watch your win rates suffer. (Legit, I had a rep almost lose a deal because he presented a deck using the customer's outdated logo <- the CMO was not smiling about it. We did damage control for 2 weeks.) ⚖️ My stance: obsess over the details. Alone, they might seem minor, but together, they will tip the scales and split success from failure. Would love to hear what details you swear by? 

“Don’t tell your customers something they don’t know about you. Tell them something they don’t know about them.” This is a quote from sales guru Jeffrey Gitomer. If you’ve ever reached out to a client to book a meeting and flaunted your new features as a reason to meet, you’re doing it wrong. Reviewing your cool new features can be helpful, but that is your value-add. It may get you the meeting, but it most likely won’t get you the next one. You need to teach your customers something about themselves to deepen your relationship. There’s a tech vendor I’ve used (I won’t name names), and the meeting with the CSM will go something like this. We would both jump on the meeting and after some nice pleasantries, the CSM would ask me, “So, what do you want to cover?”. It wasn’t long until I started canceling the meeting. It was rare that the CSM had shown up to talk about my needs and that was only if I had emailed them a topic ahead of time. These meetings provided no value and it wasn’t long before I started taking calls from competitors that could provide me insights I wasn’t aware of. With the advent of AI, meeting preparation has become much easier. Today, I fire up UpdateAI and grab a quick AI-generated synopsis that summarizes where we left off with the client from a previous meeting. With that context in hand, I can quickly scan the client’s metrics, compare them against their stated outcomes, and start making recommendations. If I don’t know their business outcomes, I can compare their key metrics against the benchmark metrics we gathered. Then, I’ll pull out a playbook that provides suggestions on some strategies they can use based on how they compare to the benchmarks. I’ll use AI to create a three-sentence hook that I can use for my client outreach. This should take less than five minutes. To go a step further, dive deeper into how your client has set up your application. Look for a few ways they can optimize their use of your products that you’re fairly sure they weren’t aware of. Include just one of those in your client outreach and let them know that there’s more of that you want to share when you meet. This is the kind of value that they are looking for from their CSM. It’s what will differentiate you from 90% of your CS peers. Teach your clients something they didn’t know themselves. Spend those extra few minutes building that value. That will get you noticed. You can then leverage that opportunity to learn more about your client’s business and really transform yourself into more of a strategic customer success manager. Yes, this takes some extra prep time, but trust me, it will be worth it. What are ways that you provide your clients with insights? ****** If you are interested in more practical CS tips, subscribe to the link in my profile.