Essential Check-Ins for Remote Pre-Sales Leaders

If your weekly 1:1s with sales reps sound like “So, how’s it going?” - you’re not leading, you’re babysitting. Too often, these meetings turn into casual status updates - or worse, get skipped entirely. But done right, a consistent 1:1 builds alignment, accountability, and momentum. Want results? Start running meetings that build killers, not comfort zones. Here’s what should really be on the table every week 1. Review of KPIs & Metrics • of leads generated • of estimates delivered • Follow-ups completed • Closing rate • Sales pipeline value vs target • Weekly booked revenue 2. Open Conversation • What’s working well? • What deals are stuck, and why? • Where do you need support? • Any internal roadblocks? 3. Action Plan • Specific next steps for key deals • Follow-up strategy 4. Coaching Moment • Roleplay a tough objection • Refine sales messaging • Improve time management or follow-up cadence Remember, the goal isn’t to micromanage - it’s to develop, motivate, and hold accountable. When done consistently, these check-ins become one of your most powerful tools for building a high-performing sales team. What’s in your weekly sales 1:1s? Let’s compare notes.

I lead a remote team of 20+, and none have said: ‘I don’t understand or value them’ That’s a key reason TransforMe Learning & Leadership Solutions is growing fast. Here are 9 practices I follow to guide my remote team (without being rude), I: 1/ Never use "ASAP" ❌ "Need this ASAP" ✅ "Could you complete this by [TIME]?” Respect breeds respect 2/ Add context, not just tasks ❌ "Update the dashboard"  ✅ "Update the sales dashboard with Q1 figures - this will help us make decisions in Friday's strategy meeting" Purpose drives motivation 3/ Use voice messages for complex directions Trust me: ✅Quick 60-second explanations save hours of back-and-forth 4/ Acknowledge time zones actively ❌ "Let's meet at 9 AM"  ✅ "Would 9 AM EST (your 7 PM) work for you?” Since it's a remote culture now. 5/ Focus to create decision tree ✅"If X happens, proceed with A” ✅”If Y occurs, do B" Builds confidence and autonomy 6/ Use visual guides Make a habit to send: ✅ Quick Loom videos  ✅ Annotated screenshots  ✅ Process flowcharts After all, a picture saves a thousand messages 7/ Set expectations two ways ✅ What you need from them and… ✅What they can expect from you Because authentic communication goes both ways 8/ Maintain response windows ❌ Expecting instant replies ✅ "No rush - please respond within 24 hours so we can stay on track" Respects focus time while maintaining momentum And if there's still a delay… 9/ Follow up professionally ❌ "Why isn't this done yet?" ✅ "I noticed the deadline passed - are you facing any blockers I can help with?" Remember, support drives completion P.s: What would you add as 10th? Let’s learn from each other experiences↓ TransforMe Learning & Leadership Solutions https://transforme.in/ #remotework #leadership #communication #teammanagement #respect #autonomy #trust #teambuilding #productivity #virtualteams

I’ve been leading a distributed team since 2015... And I’ve learned a few things. If you want to be a good leader – one that understands their team, support the needs of their team members, and helps everyone row together in the same direction – then there are some areas you have to level up on. In a nutshell, here are 6 of the most important things I focus on for running a remote team. 𝐒𝐡𝐨𝐰𝐢𝐧𝐠 𝐠𝐞𝐧𝐮𝐢𝐧𝐞 𝐞𝐦𝐩𝐚𝐭𝐡𝐲 𝐚𝐧𝐲 𝐭𝐢𝐦𝐞 𝐭𝐡𝐞 𝐭𝐞𝐚𝐦 𝐦𝐞𝐦𝐛𝐞𝐫 𝐞𝐱𝐩𝐫𝐞𝐬𝐬𝐞𝐬 𝐚 𝐩𝐫𝐨𝐛𝐥𝐞𝐦 𝐨𝐫 𝐟𝐫𝐮𝐬𝐭𝐫𝐚𝐭𝐢𝐨𝐧. 📋How to: Use The Empathy Formula to acknowledge the team member’s feelings based on facts. Here’s the formula: “It sounds like you’re (feeling) because/about (fact). “Here’s a real-life example: “It sounds like you’re feeling overwhelmed (feeling) because of the reduced number of people on the team (fact).” 𝐄𝐬𝐭𝐚𝐛𝐥𝐢𝐬𝐡 𝐚 𝐧𝐞𝐰 𝐨𝐧𝐞-𝐨𝐧-𝐨𝐧𝐞 𝐦𝐞𝐞𝐭𝐢𝐧𝐠 𝐫𝐨𝐮𝐭𝐢𝐧𝐞. 📋How to: Have a scheduled meeting at least twice per week over video conference. If these meetings are currently less frequent, use the same amount of overall time divided up over more meetings. Always have your camera on and ask that the employee does the same — it’s a way to build connection. 𝐓𝐚𝐥𝐤 𝐭𝐨 𝐲𝐨𝐮𝐫 𝐭𝐞𝐚𝐦 𝐦𝐞𝐦𝐛𝐞𝐫𝐬 𝐞𝐯𝐞𝐫𝐲 𝐬𝐢𝐧𝐠𝐥𝐞 𝐝𝐚𝐲. 📋How to: If a meeting is not scheduled, call them on the phone and talk to them. Sometimes just a quick check-in call is all it takes for some days. One of the most important elements of being an effective manager is keeping lines of communication open with your team members, especially when it has nothing to do with assignments or project statuses. 𝐃𝐞𝐦𝐨𝐧𝐬𝐭𝐫𝐚𝐭𝐞 𝐲𝐨𝐮𝐫 𝐚𝐯𝐚𝐢𝐥𝐚𝐛𝐢𝐥𝐢𝐭𝐲. 📋How to: End your meetings with team members by encouraging the team member to contact you by phone or to request an unscheduled meeting. Answer the call if at all possible. 𝐄𝐬𝐭𝐚𝐛𝐥𝐢𝐬𝐡 𝐥𝐢𝐧𝐞 𝐨𝐟 𝐬𝐢𝐠𝐡𝐭 𝐚𝐧𝐝 𝐜𝐨𝐧𝐭𝐢𝐧𝐮𝐞 𝐭𝐨 𝐫𝐞𝐢𝐧𝐟𝐨𝐫𝐜𝐞 𝐢𝐭. 📋How to: Ensure work assignments, expectations, and deadlines are perfectly clear. Break down current goals into smaller chunks that are measured on a more frequent basis. Find opportunities during your one-on-ones to talk about how the specific work they do contributes to a specific team or company objective. This is not as obvious to them as it might be to you. 𝐃𝐨 𝐧𝐨𝐭 𝐡𝐨𝐥𝐝 𝐡𝐲𝐛𝐫𝐢𝐝 𝐦𝐞𝐞𝐭𝐢𝐧𝐠𝐬. 📋How to: For those leading hybrid teams, level the meeting playing field so all team members can contribute equally. This is best practice in general, and particularly important for the struggling team member. If some of the team members are in the same location and some are remote, have the onsite team members split up and join from their own computers. It equals the playing field. Tell me ⬇️ some of your best tips for leading distributed teams!

Leading sales teams remotely isn't easy Neither for the leaders nor for salespeople One important thing I learned leading > 30 salespeople all over Europe over the last 2 years: You should schedule time together rather often Here are a few regular sessions I usually put in our calendars: 1️⃣ Cold Calling Day (once a month): The whole team (SDRs, AEs, Operations) meets to call for one full day. Set a target for the day and see what the team can achieve together We often booked > 25 meetings on one day. Also helped us getting closer to the revenue target 2️⃣ Outreach / Cold Calling Sessions (2-3 hours, two times a week): The whole team focuses on outreach. These blockers are important for all salespeople so as to not lose focus on pipeline creation You might as well be doing it with the whole team? At the beginning of the session, we usually do a warmup with some mock calls 3️⃣ Weekly Sales Team Meeting (1-1.5 hours): Everybody shares what they achieved last week (most important advancements and new pipeline) There is usually a list of topics that needs to be discussed And knowledge should be shared (especially in early-stage companies) Everybody contributes 4️⃣ Weekly Call Coachings (1 hour): A sales rep is sharing a recorded call with everyone beforehand And the whole team is giving feedback on that call By showing parts of the recording 5️⃣ Weekly or Bi-weekly 1on1s wither every sales rep (30 min) Agenda: 1. How are you doing? 2. What is going well / where do we have room for improvement? 3. What do you need help with? 4. Career & personal development 5. Other topics? 6️⃣ Weekly 5-Ps coaching with the whole sales team (60 min): Someone prepares a late-stage deal by answering the questions below 👇🏻 The team asks questions Result: 2-3 immediate action items that help mitigate the risk to lose the deal Any other regular meetings you deemed useful with the sales team?

Regular 1-on-1 check-ins are essential for keeping your team engaged and aligned. Asking the right questions fosters connection, clarity, and progress. Here are 10 questions you should ask during every check-in (and what to listen for): 1/ "What’s going well for you this week?" ↳ Listen for highlights 2/ "What challenges are you facing right now?" ↳ Listen for obstacles 3/ "What’s one thing you’re excited about in your work?" ↳ Listen for passion 4/ "Do you have everything you need to do your best work?" ↳ Listen for clarity 5/ "How do you feel about the priorities we’ve set?" ↳ Listen for alignment 6/ "Where do you think you could use more support?" ↳ Listen for needs 7/ "What feedback do you have for me or the team?" ↳ Listen for insight 8/ "What skills would you like to work on next?" ↳ Listen for growth 9/ "How are you managing your workload?" ↳ Listen for balance 10/ "What’s one thing we could change to improve your experience?" ↳ Listen for improvement 1-on-1 check-ins are more than just status updates. They’re opportunities to connect, address challenges, and foster continuous growth for your team members and yourself as a leader. What questions do you ask during your 1-on-1s?

Is "management by walking around" still relevant for sales teams working remotely? I’ve always loved those spontaneous conversations on the sales floor. You can catch potential issues early, provide real-time feedback and coaching, boost morale, and have a good handle on what's happening. But with so many sales teams now remote, is this approach outdated? Not at all. The essence of “walking around” is being present, accessible, and in touch with your sales team. And you can still achieve that, even virtually. Here’s what I’ve learned: 1/ Hold informal check-ins Schedule quick, casual video calls. Don’t wait for your normally scheduled weekly coaching session to have a quick video call. 2/ Be visible and active in digital channels: Regularly engage in team chats or Slack channels. Celebrate wins, ask questions, and keep the energy high. 3/ Provide near real-time call coaching: Put time on your calendar to listen to samples of the last hour's of calls and provide feedback to your reps. 4/ Foster a culture of accountability and trust: Just because you’re not physically “walking around” doesn’t mean you can’t set expectations and hold your team accountable. 5/ Greet your reps in the morning It doesn't take much to send a dozen, short, 30 second video messages to each member of your sales team each morning. Remote doesn’t have to mean distant. Keep walking around, even if it’s in a virtual hallway. What other killer tips do you have for sales "management by walking around" in a remote selling environment? PS: If you want to step up your coaching sessions with your reps, check out my free Playbook for Running an Effective Salesperson Coaching Sessions. The link is in the first comment.