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In Today’s Market, Knowing Your Competitor Is Half the Battle
Deals are harder to win right now because buyers are more cautious and competitors are hungrier. That’s why knowing your competition isn’t optional—it’s deal insurance. One practical way to stay sharp: Set up a Google Alert for your top 3 competitors. You’ll automatically get updates on new press releases, funding news, or…
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The Missing Link in Carefrontation: Accountability With Compassion
We’ve spent a lot of time in this community talking about Carefrontation—caring personally while challenging directly—and how it transforms feedback into growth. We’ve explored pitfalls, feedback rhythms, workshops, and practical tools to make it stick. But there’s one piece of Carefrontation I see people wrestle with time…
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How I use AI to research competitors without crossing a line
Competitor knowledge has always been a cornerstone of good selling. But if we’re honest, it’s also one of the trickiest areas to navigate. On one hand, you want to walk into a call knowing how you stack up. On the other, you don’t want to spend hours piecing together fragmented insights or worse, risk crossing an ethical…
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The Current Environment Demands Forecast Precision. Here’s How to Get It!
In today’s market, leadership isn’t just asking for a forecast—they’re asking for a forecast they can trust. That means you need more than gut instinct. Three quick steps for Q3 pipeline accuracy: Re-qualify your active deals—buyer priorities may have shifted since the start of the year. Double-check decision…
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Audit Your Communication Style
In sales, communication is everything—and not just with customers. The way you interact with teammates, managers, and leaders can shape how you’re perceived, how quickly you grow, and how much trust you build across the org. Too often, though, we push through the fast pace of deals and meetings without ever stopping to…
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Not committing to learning AI isn't really an option, anymore
Over the past few months, I’ve shared a few posts about how my team and I are using AI. Whether it’s to uncover customer pain points more effectively, avoid cultural missteps in international deals, or refine our discovery questions with better prompts. The more I experiment, the clearer it becomes: understanding how to…
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What London Taught Me About “Hail Marys” and “Meat & Potatoes
I recently spent a week in London working with our international sales and solutions teams—and it was one of the most enlightening trips I’ve had in a while. Not just for the quality of the conversations, but for what I learned about how easily we, as Americans, can unintentionally confuse (or alienate) people in business…
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Still Time to Win: 3 Ways to Rethink Your Plan in Today’s Market
Deals are slower. Budgets are tighter. But that doesn’t mean goals are out of reach. If you want to finish strong, now’s the time to zoom out and get intentional with your day-to-day strategy. Three quick ways to reset: Re-prioritize your accounts—double down on ones with urgency or in-cycle timing. Map multithreading…
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How you can own the feedback process (even if no one else is doing it)
Not every company has a rock-solid system for giving and receiving feedback. There are lots of reasons this can fall behind. You might be focused purely on sales and not interested in making time for it. Your enablement team might be stretched thin. Maybe your manager doesn’t always make time. Or maybe the “feedback…
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Your Copy-Paste Friendly Personal Action Plan Template
If you’re running (or attending) a Carefrontation workshop, having a clear and simple personal action plan helps turn good ideas into lasting habits. This template is designed to be copy-pasted into a doc or email so participants can fill it out and refer back to it easily. Whether you're a rep, manager, or…
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Using AI to Navigate Cultural Nuance in Sales and Leadership
I just got back from a trip to London where I had the chance to work closely with some of our EMEA teams and sit in on a few in-region sales conversations. Every time I travel internationally, I’m reminded how easy it is to assume alignment—when in reality, subtle cultural differences can impact everything from how we sell…
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One Contact Isn’t a Strategy—Why Multithreading Wins in This Market
Buyers are being more cautious. More people are weighing in. That means single-threaded deals are getting stuck or lost—fast. Multithreading isn't about politeness; it’s about deal health. If you’re only talking to one person, your deal is vulnerable to delays, org changes, and internal politics. Build out multiple…
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In This Market, Relationships Are the Real Deal Insurance
Budget cycles are longer. Buying teams are bigger. And trust is harder to earn. That means your relationships matter more than ever—especially if you want to stay top of mind through multiple quarters. Make it a habit to check in even when nothing is moving. Share an insight, a relevant story, or even just a note of…
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Plan for Q4 Now
We’re barely into summer, and I can already tell who’s going to have the best Q4 on my team. It’s the people who are already planning for it. Not just with pipeline numbers, but with strategy, skills, and execution. As someone who works closely with AEs and SEs across multiple industries, I get a front-row seat to what’s…
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Bring the SKO Back to Life: Why Managers Should Reignite Those Big Topics
Remember that energy from Sales Kickoff (SKO)? The shared goals, the sharp strategies, the new ideas everyone swore they’d implement “first thing Monday”? If your team is like most, a few of those key messages got buried under Q1 chaos and Q2 quotas. That’s why now is the perfect time for managers to bring SKO topics back…
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How I Help My SE Team Create Better AI Prompts (and 5 You Can Steal Today)
When we first started using generative AI on my Solutions Engineering team, most people asked the same kind of prompt: “Summarize this call” “Give me ideas for my demo” That’s fine, but it barely scratches the surface of what AI can do in a revenue environment. Over time, I realized our team didn’t need more tools. They…
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Win the Prep Game: Using AI to Save Time and Stay Relevant
In today’s environment, every minute matters. AI can help you cut through research clutter and get to what actually matters in a deal faster. Here’s a great prompt we've seen some success with: “Summarize [Company Name]’s hiring trends and product announcements from the last 6 months. Identify any indicators of growth or…
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Want to Run a Workshop? Here’s How to Bring the Idea to Your Manager
If you’re a sales rep who’s been following along with our Carefrontation series and thinking, “I’d love to get my team talking about this," then you’re not alone. One of the best ways to build a stronger team culture is to be the spark that gets the conversation started. And no, you don’t need a manager title to lead the…
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3 AI tools I actually use with my SE Team & how we use them to get better
There’s no shortage of AI tools out there. But in a high-velocity pre-sales environment, I’ve found that it’s not about stacking tools, but about choosing the ones that make your team more effective, without slowing them down. I’ve spent the last year experimenting with different AI-driven tools across call prep, coaching,…
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Coaching My SE Team to Uncover Customer Pain Faster with AI
One of the highest-leverage skills in any sales process, especially in technical sales, is the ability to uncover customer pain. The kind that’s beneath the surface, not listed on the website or in the RFP. That skill is becoming even more essential as buying committees grow and sales cycles stretch. And while there’s no…
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Sellers in the Trenches: Thriving in a Longer, Tougher Sales Environment
We’re all seeing it with deals taking longer, more people are getting involved, and approvals are tighter. The best reps aren’t just grinding harder because they’re getting smarter about how they move deals forward. Here’s one tip: Treat every week like a micro-cycle. Ask: “What action am I driving this week?” Whether it’s…
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Three Ways to Run a Carefrontation Workshop, No Matter Your Role
These are some practical outlines for enablement leaders, managers, and team champions, but remember: Get approval before trying to just launch into something. If you're an individual contributor, yourr manager should sign off on the content! One of the best parts about Carefrontation is that it doesn’t require a massive…
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Making Carefrontation Workshops Stick: Tips for Impactful Sessions
Running a Carefrontation workshop isn’t just about presenting slides or reviewing the Carefrontation framework with new terminology. It’s about helping teams practice the skill of giving honest, direct feedback while showing genuine care, and actually feeling comfortable doing it. If you're planning or leading a…
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How I Coach My Team to Actually Use AI (Without the Hype)
I used ChatGPT to help me write this, but I used my examples. Let me know what you think in the comments! 1. Use AI to Prepare for Complex Demos Before any big demo or POC, we drop the customer's public website and relevant call notes into GPT and ask: “Based on this info, what’s the best angle to show value with our…
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Kick It Off Right: Crafting a Strong Workshop Introduction
Whether you're running a Carefrontation workshop or diving into any other sales enablement topic, your introduction sets the tone. It's your first chance to earn attention, build trust, and create energy in the room. A strong start can make the difference between a session that lands and one that drifts. So, what makes a…
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Designing Your Carefrontation Workshop: Exercises That Build Confidence and Connection
When it comes to running a great Carefrontation workshop, content matters, but so does delivery. The way you structure your session has a huge impact on engagement, learning, and follow-through. While you don’t have to include every type of exercise, incorporating a mix of formats keeps energy high and gives participants…
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We Want to Hear From You: What Should We Build Next?
Hey everyone! As we plan our upcoming webinars, playbooks, and enablement resources, we want to make sure we’re creating content that actually helps you, the people doing the work every day. Whether you're coaching reps, building onboarding tracks, or in the trenches with MEDDICC and Command of the Message, your…
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How to Write an Effective Workshop Invite Email for Carefrontation
Getting people to attend a workshop starts with the invitation and a well-crafted email can make all the difference. Whether you’re hosting a session on Carefrontation for your sales team or inviting a cross-functional group, your invite should be clear, compelling, and communicate the value of the session right away.…
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Setting Strong Objectives for Your Carefrontation Workshop
When you're planning a workshop, especially one centered on feedback, clear, practical objectives are everything. They guide the flow of the session, give participants a sense of purpose, and help measure success. For those of us focused on Carefrontation, the goal isn’t just to talk about feedback, it’s to build the…
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Running a Carefrontation Workshop: Why It Matters
If you’ve been following our series on Carefrontation, you already know the power of honest, caring feedback. But understanding the concept and actually putting it into practice are two very different things. That’s where a team workshop can make all the difference. Bringing your team together to learn, practice, and…