-
Helping My Team Navigate Higher-Level Stakeholders
One of the most significant shifts I’ve noticed in the sales landscape recently is the growing number of board-level stakeholders involved in the buying process. A few years ago, many deals could be influenced primarily by directors, VPs, or department leads. Today, especially in larger or more strategic deals, it’s…
-
Why Managers Need to Revisit Feedback Motions—Even When Things Feel Great
When things are going well on your team, it’s tempting to let feedback habits run on autopilot. Deals are closing, morale feels high, meetings seem productive. You may look around and think, “Why mess with something that’s working?” But here’s the truth: the best time to revisit your feedback motions isn’t when something…
-
Strategic Manager Involvement for Tough Deals
In today’s environment, deals are harder, buying groups are larger, and scrutiny is higher. That means your ability to bring in your manager at the right time can be a competitive advantage. Customers don’t just want to hear from you—they want proof your whole company is behind the partnership. Manager involvement shows…
-
Outside-In Selling: Earn the Right to Be Heard
Too often, I see sellers jump into solution mode before they’ve earned the right to be heard. If you want to build real trust and drive meaningful conversations, start with an “outside-in” mindset, make it about them first. Their business, their challenges, their language. You earn the right to share your solution by…
-
Carefrontation and Collaboration: Unlocking Team Success Across the Organization
One of the most common themes I hear in conversations with sales teams is that collaboration—real, productive collaboration—doesn’t happen nearly as often as it should. Marketing builds resources sales doesn’t use. Product rolls out features that don’t get communicated clearly to customers. Operations creates processes…
-
Partnering with Enablement: How Feedback Turns Resources Into Game-Changers
One thing I’ve been reflecting on lately is how much better our sales process becomes when we treat enablement as true partners, not just a team that “hands us stuff.” Too often, salespeople see enablement as a resource factory: they give us decks, playbooks, or tools, and we either use them as-is or let them collect…
-
Spot and Support Talent Before You Lose It
This is more for managers, but might be helpful if you're in an IC role. It's important to remember that you own your career and can speak up. Taking proactive steps can only help you! Like everyone, I've had my share of discussions about turnover. In many cases, it’s not about comp packages or titles. It’s about something…
-
Elevating Above the Noise
In today’s market, your buyer is likely evaluating more vendors than ever — and doing it faster. To win, you must go beyond features and pricing, showing you understand their business context better than anyone else. Why this matters: Buyers choose the seller who “gets them” over the seller with just a better spec sheet.…
-
How to Capture Meaningful Feedback After a Session or Meeting
Meetings, workshops, and sessions are only as valuable as the outcomes they drive—and the learning they inspire. Too often, though, we treat meetings as “done” once the calendar notification disappears. That means we miss out on rich opportunities to improve the way we run them. The truth is, better meetings don’t happen…
-
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…
-
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…
-
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…
-
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…
-
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…
-
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…
-
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…
-
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…
-
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…
-
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…
-
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…
-
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…
-
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…
-
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…
-
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…
-
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…
-
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…
-
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…
-
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,…
-
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…
-
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…