🤝 how to network w/ awkward people

tips for awkward convos, address "that one coworker", and moving on when you screw up.

Subscribe here | Unsubscribe here | OG Tuesday Mar 25, 2025 ✅ Today's Checklist:  How to Make Networking Less Painful (for Everyone) When "They've Always Been Like That" Isn't Cutting It Mess Up & Move On 🤔 Riddle me this: A woman goes to a restaurant and orders iced tea. She drinks half her tea and leaves. Everyone else who ordered iced tea dies. How did she survive? (Find the answer on the bottom). QUICK LINKS 🧠 Leading projects shouldn't feel like herding cats—these top PM tools actually help you get sh*t done. 🎤 Booked your first speaking engagement? Congrats! Here's how to prep long before the mic goes live. 🔄 These apps and hacks turn ADHD patterns into effective time-management moves. 🧘‍♀️ Addressing grief in a group setting may be the best way to move forward. NETWORKING     How to Make Networking Less Painful (for Everyone) I recently went to an all-female networking event and met a variety of personalities and professionals. It was fun! But it also came with a few awkward interactions—people who were uncomfortable, nervous, or just difficult to talk to. As an ADHD girly, I've learned to do something called masking—where you adjust your behaviors to fit social norms. In everyday life, this can be mentally exhausting. But in networking? It's a superpower. Not everyone is a natural conversationalist. Some people ramble, some give one-word answers, and others forget to ask anything about you. Over the years, I've mastered how to navigate these situations so that both of us walk away feeling good. If They Seem Uncomfortable or Shy Some people just need a warm-up before they get comfortable. Make it easy for them by asking low-pressure, open-ended questions: "Is this your first time at this event?" "I love your [shoes/jacket/accessory]! Where'd you get it?" "What's been the highlight of your day so far?" "How did you first get into [industry]?" If they're giving you short, dead-end answers, switch to open-ended questions that require more than a simple "yes" or "no." Instead of asking, "Do you like your job?" try, "What's the most exciting part of your job?" This gives them more room to respond and keeps the conversation flowing. If They Don't Actually Answer the Question Nervousness often leads people to go on tangents or forget the original question entirely. Instead of awkwardly waiting for them to come back around, gently redirect: "That's really interesting! So circling back, I'd love to hear more about…" "I love that story—so how did you end up in [industry] again?" This keeps the conversation flowing without making them feel bad. If They Pause Too Long or Struggle With Silence Some people take longer to gather their thoughts. If you're a fast talker, this can feel awkward but don't rush to fill the silence. Instead: Smile and maintain eye contact to show you're engaged. Give them a beat to respond—some people just process slower. If it drags on too long, say, "No pressure! Take your time." Letting the other person set the pace makes them feel safe instead of scrutinized. If They Struggle to Open Up If someone struggles with self-disclosure, try sharing more about yourself first. Leading with your own story can make it easier for them to follow suit: "I used to work in [field], but I switched to [current industry] because…" "One of the most surprising things I've learned in my career is…" "I'm a huge fan of [interest/hobby]—do you have any favorite hobbies outside of work?" This takes the pressure off them while giving them something to respond to. If They Never Ask You a Question Some people just aren't good at conversational reciprocity. If they never ask about you, you can subtly work yourself into the conversation: "Oh wow, that's awesome! I'm similar in that I do XYZ." "That's so cool! I'm in a totally different industry—I do XYZ." "Funny enough, I just worked on something like that in my role at XYZ." This makes sure you're also part of the conversation without waiting for them to initiate. If It's Been Too Long and You Need to Move On You don't have to stay in a conversation that's dragging. Here's how to exit gracefully: "It was great learning about what you do! I set a goal to meet three new people today, so I'm going to keep mingling, but let's stay in touch!" "I really enjoyed our conversation. I'm going to circulate a bit more, but here's my card if you ever want to connect!" This gives them a positive takeaway while giving you an out. If It's a Creepy Dude Giving You Weird Vibes There's a difference between awkward and straight-up uncomfortable. If someone's giving off ick vibes, shut it down: "Sounds like you've got some exciting things happening at [Company]! I'm making sure to meet a few more people before the event ends—wishing you success at [event name]!" No need to offer your card, continue the chat, or justify leaving. Just walk away. Networking can feel awkward, but you don't have to. By guiding the conversation, being patient, and having go-to exit strategies, you can turn even the most uncomfortable exchange into a positive experience. And who knows? That quiet, socially awkward person might just be a hidden gem of a connection. Thania (TA Content Mgr) CRM CLEANUP     🧼 The Weekly CRM Cleanup You Actually Need   Keeping your CRM clean shouldn't be a once-a-quarter panic project. Just like your inbox, it's way easier to maintain if you stay on top of it regularly. Here's a weekly routine you can use to keep your CRM from turning into a digital junk drawer: ✅ Step 1: Run a "Dead Weight" Filter Search for contacts or deals that haven't had any activity in 30+ days. Most CRMs have this filter baked in. Do this: Add a tag like "Needs Review" or move them to a holding stage like "Stale Lead" If you know the deal's dead, close it out. Don't let it linger. If you want to revive it, schedule a follow-up or drop them into a re-engagement email sequence. Tip: In Pipedrive, you can create a custom filter for deals with no activity in X days—super fast to review each week. ✅ Step 2: De-dupe and Merge Duplicates are silent killers. They mess up your reporting, segmenting, and email sends. Do this: Most CRMs have a "merge duplicates" function—run it weekly. If not, sort by email or phone number and manually scan for matches. Merge the contacts and combine notes so no info gets lost. Tip: In Thryv, you can easily identify duplicates based on contact details and merge them with one click. ✅ Step 3: Update Notes + Contact Fields Pretend someone else had to pick up your pipeline—would they have a clue what's happening? Do this: Add context to contact records: recent convos, client preferences, quirks. Clean up fields: remove random test entries, fill in missing info. If your CRM has tags or custom fields, make sure they're consistent. (e.g., are you using "VIP Client" or "High-Value Client"? Pick one.) ✅ Step 4: Automate What You Can Don't wait to do everything manually. Your CRM can do some of the heavy lifting for you. Try this: Set up automatic task reminders when a deal moves to a new stage. Create autoresponder templates to follow up with no-shows or missed calls. 💼 CRMs We'd Trust With Our Rolodex Pipedrive: built for sales teams who want clarity without chaos. Visual pipelines, automated follow-ups, and powerful filters so nothing slips through the cracks. Thryv: Perfect for small business owners juggling it all. CRM + scheduling + payments + marketing in one place, so you can stop duct-taping 5 apps together. 💡 Make it a habit: Block 15-30 minutes every Friday on your calendar and name it "CRM Cleanup Party." Bonus points if you do it with lo-fi beats and a latte. Your future self will thank you. BIGGEST CHALLENGE     When "They've Always Been Like That" Isn't Cutting It "My biggest challenge right now is leading an employee who has an overall bad attitude that has been left unchecked for the past 2 years." One negative employee can slowly erode your team's morale, impede productivity, and create an overall toxic work environment. But how can you turn things around when a lack of correction has made their behavior seem almost acceptable for so long? 1. Assess Before taking any action, assess the extent of the issue. Separating their behavior from their performance helps to identify the specific disruptors rather than relying on subjective impressions or emotions. Ask yourself: How does this behavior affect the team? What specific actions or patterns contribute to the negativity? 2. Address It's time for a direct but empathetic conversation. Rather than making it personal, frame the discussion around the behaviors and their impact: 🚫 "You have a bad attitude." ✅ "I've noticed you've been a bit resistant to feedback and dismissive in our team meetings. Unfortunately, this is affecting the team's collaboration and productivity, so I'd like to have an honest discussion with you about what's going on." 3. Set Expectations Negativity often builds when expectations are vague, but expecting things to change overnight is unrealistic. Setting practical and achievable goals helps the employee "eat the elephant" one bite at a time. 📈 Specify the behaviors you expect to change and link them to performance metrics to help them better understand what success looks like. ⏳ Establish detailed timing for the employee's goals to provide structure as well as a sense of urgency for the start and completion of their objectives. 4. Coaching and Support Attitude problems can often stem from deeper issues like burnout, lack of support, or challenges at home. Give them an opportunity to speak freely, then offer correlating resources: mentoring opportunities stress management resources EAP contact information additional training role adjustments if necessary 5. Progress and Accountability Consistent accountability eliminates ambiguity and sets a precedent for professionalism. Follow up regularly to monitor their progress and provide both positive reinforcement and constructive feedback. Ideally, this strategy will realign the employee's attitude with your expectations and the organization's values. Yes, leadership is about managing performance. But you're also responsible for shaping the workplace culture for the better. Define what professionalism and teamwork look like in your workplace and make it clear that attitude matters just as much as results. PAYROLL     Stop Wasting Hours On Payroll   Let's be real—payroll probably isn't your favorite task. But it also doesn't need to be the headache it is for so many teams. Too many businesses are stuck manually calculating hours, tracking down timesheets, Googling tax rates, and hoping they're compliant. It's time-consuming, error-prone, and honestly...a little outdated. OnPay makes all of that almost effortless. It handles the heavy lifting for you—automating taxes, benefit deductions, garnishments, and compliance with the latest laws. No more stress about staying up to date or catching every tiny change. It's all done for you, accurately and on time. The best part? It works with the tools you already use. No need to change your entire workflow or onboard clunky software. Just plug it in and get going. So if you're still spending hours on payroll each month, constantly double-checking your math, or hoping your system doesn't break—there's a better way. Try OnPay. You might never dread payroll again. SUBSCRIBER SPOTLIGHT   Mess Up & Move On "'No one died, did they?' Don't stress about mistakes—learn from them and move on." —Brenda (Administrative Assistant to the Division) ⭐️ Share your best career advice here so we can feature it in a future newsletter. STAFF PICKS Stuff We're Loving This Week   ✨ Transform brittle strands into silky locks through Hers' personalized hair care—good hair days, delivered. 🥤 Cameron's solution for organizing all her straws—metal, paper, bendy, and crazy! 😍 Get luminously hydrated skin this summer by going "poreless!" 💸 Invoicing doesn't have to be a mess—FreshBooks makes it ridiculously easy to track time, send polished invoices, and get paid faster. JUST FOR FUN   JOB LEADS   Your Next Gig = One Click Away WuXi AppTec is hiring for a Senior Project Manager (Philadelphia, CH). Sally Swanson Architects, Inc. is hiring for a Marketing Coordinator (San Francisco, CA). Optimum Media is hiring for a Small To Medium Business Account Executive (Natick, MA). Pegasystems is hiring for a Director of Internal Communications (Waltham, MA). Aveanna Healthcare is hiring for a Hospice Sales Account Executive (Andalusia, AL). ⭐ View more jobs here > SPILL THE TEA Take Our Poll     Have more feedback? 💌 Reply to this email and tell us. ⭐️ Answer to the riddle. 👉 See all of March's OG Tuesday Riddles. ✨ P.S. Want more inspiration and positivity to kick off your week? Sign up for our Motivational Monday texts (U.S. only). 👀 Want to see if your company is a good fit for our 100k+ ambitious readers? Join our Sponsor Waitlist here. Catch up on all OG Tuesday newsletters here. We send 4 emails a week — update which issues you receive at any time. Never want to hear from us again? Break our hearts and unsubscribe. Visit our Etsy shop for awesome templates. THE ASSIST, LOS ANGELES, CA 90045, UNITED STATES