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Leading Vs. Convincing: The Art of Questioning
It is crucial to guide a business conversation with insightful questions, as this enables prospective clients to identify their own needs rather than being told what their problems might be. The key here is to lead rather than convince. This approach leads to more productive discussions than merely pushing solutions on…
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Mastering Carefrontation: Avoiding the Pitfall of Brutal Honesty
When it comes to Carefrontation, being honest and direct is essential, but there’s a fine line between candor and cruelty. One of the most common pitfalls sales professionals encounter is mistaking Carefrontation for brutal honesty. In the rush to provide feedback or challenge ideas, it can be easy to come off as overly…
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Driving Value in a Selective Market
Navigating today’s cautious spending environment requires a sharp focus on cost efficiency and clear value delivery. While some budgets are set to grow, decision-makers are prioritizing ROI from prior investments, making every deal more scrutinized. This puts added pressure on us to highlight not only how our solutions…
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What exactly is Carefrontation?
Carefrontation isn’t just about how we communicate. It’s about the mindset we bring to every interaction. At its core, it’s a commitment to balance honesty with care, challenge with support, and results with relationships. This approach isn’t confined to leadership roles; it’s a shared responsibility for everyone in an…
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Take the Stairs: The Only Path to Real Success
Last week, I shared a quick video about how the only way to get to the top is to climb. Throughout my career, I've learned there are no shortcuts to success. You can’t bypass the grind, skip the failures, or leap past the challenges. The truth is, there’s no elevator to success—every step you take is necessary, and every…
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Leveraging Trap-setting Questions During Discovery
The insights on leveraging discovery and trap-setting questions have transformed my sales approach by connecting solutions to prospects' business problems, driving urgency, and securing funding. This article provides you with a fantastic overview of what questions you should be asking during the discovery phase in order to…
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Customer Success is the key driver of Net Revenue Retention (NRR) in 2024
A must-read for anyone looking to stay ahead as more boards become focused on customer success’ critical nature. This article brilliantly captures the evolving landscape of customer success. Emphasizing proactive engagement, hyper-personalization, and AI-driven insights, it paints a vivid picture of how businesses are…
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Don’t Lose Sight of Why the Deal Started
One thing I’ve noticed lately in coaching my team is how easy it is to lose sight of why a customer came to us in the first place. Every deal starts with a reason. A problem. A goal. A frustration. A gap. Something wasn’t working, and they came to us to help fix it. But as the sales process unfolds, things get messy. New…
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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…
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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…
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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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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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Success Isn’t Given. It’s Owned.
If you want to win consistently, you have to take full ownership of your knowledge, your skills, and your character. Knowledge is where it starts. Your company owes you clarity on the problems you solve and how you’re different from the competition. If you don’t fully understand that, ask? Dig in. Make it your mission to…
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Navigating the Balance of Carefrontation
When it comes to Carefrontation, the magic lies in balancing honesty with empathy. It’s not just about giving direct feedback or holding people accountable. It’s about doing so while showing genuine care for the person you’re addressing. Neglecting the “care personally” aspect can quickly turn well-intentioned feedback…
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The Power of Practice
Staying at the top of our sales game requires the same level of dedication as elite athletes. Just like the pro players hit the gym after hours or run extra drills when the stands are empty, we have to commit to practicing our craft when no one is watching. It’s the work you put in after the workday that separates the good…
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Prospects withholding details of pain
We have a new logo team of mostly young sellers. They are mostly new to Force Management and are improving. We are noticing a trend of prospects withholding hard numbers. An AE had a call yesterday with a COO of a small company (under 200 employees). The first TED question around the pain was answered a bit vaguely as…
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Boosting B2B Sales with Effective AI Prompts
This blog post from Force Management on writing effective AI prompts for B2B sales offers insightful strategies to enhance engagement and efficiency in the sales process. I appreciated how it emphasizes the importance of clarity and specificity in AI prompts to yield actionable and relevant responses. By leveraging these…
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Customer Obsessed Culture
This article from Salesforce highlights the critical role of cultivating a customer-obsessed culture for sustained business growth and customer loyalty. Embracing this mindset ensures that every team member prioritizes customer needs, leading to exceptional service and long-term satisfaction. By aligning organizational…
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Unlocking Sales Success: The Art of Solving Business Challenges Through Strategic Questioning
As a successful seller, understanding that the key to effective sales is solving a significant business issue for your potential customer. This blog post reaffirms this notion, highlighting the importance of pinpointing a major business challenge to create urgency and secure funding in deals. John Kaplan's timeless advice…
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Follow up to questions from our January Webinar!
Hey Ascenders! I’ve gone through each and every question that was asked during our January Ascender Insights webinar (replay linked here), and wow! There were some great ones in here! I’ve listed the questions with my answers below and hope you take the time to read them and process them. It’s really powerful stuff you…
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Customer Success and Sales Teams
Customer Success Managers have improving NRR via up-sell/cross-sell as a responsibility and key performance metric. I'm eager to work collaboratively with Sales Teams to achieve these goals and excited for the empowerment this training will bring. I've been in the SaaS industry for the last 7 years - previously at Oracle,…
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Finding energy heading into Q4
As we turn the corner from summer into fall, I’ve been reflecting on how I need to shift gears and help my team do the same. The summer months always have a different rhythm. Vacations, lighter schedules, and a slower pace in some industries can make it easier to lose momentum. But Q4 doesn’t wait for anyone. It’s often…
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Protecting Quota During the Holidays
The holiday season often means fewer selling days, more out-of-office replies, and a harder push to hit year-end numbers. In today’s environment, where cycles are already longer, waiting until December to realize this is too late. The smartest sellers are building their holiday game plan now. Three things you can do today:…
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Carefrontation Workshops: How to Handle the Follow-Up
We’ve talked a lot about running Carefrontation workshops and how to make them engaging, valuable, and actionable. But here’s the truth: the workshop itself is only half the battle. What really matters is what happens after. If the insights, exercises, and action plans end the moment the session closes, you’ll see little…
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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…
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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…
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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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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…