-
Raising the Overall Discovery Standard
Enablement pros often see trends across deals that reps don’t — repetitive shallow questions, failure to follow up, or missing the chance to dig deeper. Raising your discovery standards is one of the fastest ways to improve pipeline health, deal velocity, and win rates across the board. Your reps need clear examples, safe…
-
The Secret Sales Skill Hiding in Plain Sight
When we talk about sales skills, we tend to default to the usual suspects: discovery, qualification, negotiation, storytelling, objection handling, and all the frameworks that guide us through the motions of a deal. But there’s a force that sits underneath all of those skills—one powerful enough to transform not just our…
-
Discovery in a Tougher Market
In this environment, every conversation counts. Customers are inundated with outreach and have little patience for sellers who don’t bring insight. That’s why great discovery questions are becoming a superpower. They help you stand out, build connection, and move the deal forward without force. Customers don’t want a…
-
Wrapping Up Carefrontation: My Top 10 Moments (Number 1)
After counting down through ten incredible moments from our Carefrontation series, we’ve reached the most important takeaway—the one thing I hope every salesperson and leader carries with them long after the series is over. Number 1 is this: Carefrontation is a mindset, not a checklist. #1: Embrace the Mindset, Not Just…
-
Handoffs That Build Trust Fast
In this market, the customer expects flawless execution the moment they sign. Their timeline is compressed. Their tolerance for misalignment is near zero. And they’re judging your entire company based on how you transition them from sales to the next team. A next-level handoff is the fastest way to prove that your company…
-
Wrapping Up Carefrontation: My Top 10 Moments (Number 2)
We’re getting close to the top of the list now. At number 3, we talked about how Carefrontation shapes your reputation as much as your results. For number 2, I want to highlight something that doesn’t always get enough attention in sales: the role of emotion in feedback. #2: Carefrontation Isn’t About Hiding Emotion—It’s…
-
Buyers Are Skeptical—Here’s How You Break Through
Buyers today come in with shields raised. They’re stretched thin, overwhelmed by vendor noise, and constantly measuring whether a conversation will be worth their time. That’s fertile ground for Seller Deficit Disorder and a tough setting for a seller who isn’t prepared. In this environment, the path forward is simple:…
-
How I’m Approaching My New Role — And What I’ve Learned About Starting Strong in Sales
Starting a new role is one of the most energizing and disorienting experiences you can have in your career. You walk in with a fresh title, fresh expectations, and a fresh chance to redefine how you show up. But you also walk into a maze of unfamiliar processes, new teammates, shifting priorities, and the unspoken dynamics…
-
Year-End Reality Check: Making Account Review Time Count
Between holiday travel, out-of-office messages, and end-of-year pressure, it’s tempting to go into autopilot. But the reps who win early in the new year are the ones who use December wisely. A solid account review isn’t about paperwork — it’s about clarity. Now’s the time to assess which accounts are truly ready to grow,…
-
Wrapping Up Carefrontation: My Top 10 Moments (Number 3)
At number 4, we explored how clarity is a form of kindness, and vagueness only holds people back. Now, let’s move into number 3, where the conversation gets a little bigger than just one-on-one interactions. This moment stood out to me because it connects Carefrontation to something most salespeople underestimate: your…
-
Getting Ready for the Holidays Before They Sneak Up on You
It’s that time of year again — the stretch between October and the end of the year where everything seems to speed up and slow down at the same time. Customers are busy, internal teams are distracted, and everyone’s juggling end-of-year goals with personal holiday plans. If you’re in sales, you know this season can be…
-
Discovery in Today’s Selling Environment: Make Every Minute Count
The modern discovery call isn’t an hour-long exploration anymore. Buyers come with information, and time is short. You need to maximize the impact of every minute you get. Discovery today is about earning the right to go deeper. If your prospect doesn’t see value fast, you won’t get another meeting. That means your…
-
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…
-
Wrapping Up Carefrontation: My Top 10 Moments (Number 4)
At number 5, we talked about silence and how it can trick us into thinking we’ve reached agreement when really, we’ve just reached the end of someone’s willingness to speak. For number 4, we’re moving into a tougher but vital truth about Carefrontation: it takes courage to be clear. #4: Clarity Is Kindness, Vagueness Is…
-
Finding Another Gear When You’re Tired
I’ve had a few of those weeks lately — the kind where you feel like you’re pushing uphill every day. The meetings keep coming, deals keep changing direction, the inbox never stops filling up, and somehow you’re still trying to keep yourself motivated through it all. It’s easy in those moments to tell yourself to “dig deep”…
-
Wrapping Up Carefrontation: My Top 10 Moments (Number 5)
When we talked about emotions at number 6, I said that one of the keys to Carefrontation is grounding yourself before you speak. At number 5, we’re moving into a different—but equally tricky—territory: silence. #5: Mistaking Silence for Agreement One of the sneakiest pitfalls in a Carefrontation moment is assuming that no…
-
Finding the Power in Today’s Selling Environment
In today’s environment, budgets are tighter, hierarchies are flatter, and approvals are more complex. That means deals often stall unless you’ve engaged the right level early. Sellers need to navigate carefully — building credibility, uncovering priorities, and demonstrating business acumen before asking for the meeting.…
-
Staying Steady When the Flow of a Deal Changes
If there’s one thing I’ve learned in my years as a solutions engineer, it’s that no deal ever follows the exact path you expect. You can build the perfect mutual plan, outline your decision criteria, and map out every stakeholder — and then one conversation, one reorganization, or one new face in the room shifts…
-
Wrapping Up Carefrontation: My Top 10 Moments (Number 6)
We’ve talked about consistency in feedback at number 7. Now, number 6 touches on something that makes or breaks a Carefrontation moment. It’s not about timing or frequency—it’s about emotional control. #6: Letting Emotions Run the Show One of the quickest ways to derail a productive conversation is letting your emotions…
-
Wrapping Up Carefrontation: My Top 10 Moments (Number 7)
We’ve talked about the importance of creating a safe environment at number 8. Now, number 7 is one of those subtle pitfalls that creeps up more often than we’d like to admit. It’s not about whether you give feedback, but how often. #7: The Pitfall of Inconsistent Feedback Inconsistent feedback is one of the quickest ways…
-
Finding energy when I just don't have it
I’ll be honest — the last few days haven’t been my strongest. Not in a catastrophic way, just in that subtle, dragging kind of way where the energy isn’t quite there. You wake up, you hit the alarm, and you feel like you’re running at 70% capacity. It’s not burnout, it’s not crisis — it’s just… heavy. But I’ve been…
-
Social Selling in Today’s Environment
Budgets are tight. Inboxes are full. But online networks are open 24/7. In this market, social selling isn’t optional — it’s essential. Buyers are doing more research and building trust online before engaging sellers. You can meet them there. Authentic engagement on LinkedIn builds mindshare. When prospects already see…
-
Wrapping Up Carefrontation: My Top 10 Moments (Number 8)
We’ve already talked about the importance of following up after feedback at number 9. Now, let’s move to number 8 on my list of favorite Carefrontation moments. This one has to do with something that often goes overlooked, but it can make or break whether your feedback actually lands. #8: Creating a Safe Environment for…
-
The Courage to Ask Up
Deals are more complex, budgets are tighter, and cycles are longer. That means you can’t afford to stay low in an account. To change deal momentum, you need to work higher and create urgency with people who actually have the authority to prioritize your solution. It takes courage, but the payoff is worth it. Three things…
-
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…
-
Wrapping Up Carefrontation: My Top 10 Moments (Number 9)
Last time, we kicked off this Carefrontation countdown with number 10: the power of icebreakers in workshops. Today, we’re moving to number 9 on my list of favorite moments from this series. This one has less to do with the start of conversations and more to do with what happens after they take place. #9: Following Up…
-
Identifying Customer Problems and Leveraging Technical Sellers for Big Wins
One of the most important lessons I’ve learned over the years is this: the best deals don’t get closed because we had the flashiest demo or the most persuasive pitch. The best deals get closed because we understood the customer’s pain better than anyone else. When we can pinpoint the real problem and articulate it back to…
-
Adapting to AI’s Pace
The current environment rewards sellers who move quickly and stay relevant. AI has changed dramatically in just the last three months, giving you more tools to accelerate prep, research, and outreach. But speed doesn’t matter if the quality isn’t there. Sellers who can combine efficiency with insight will stand out. Three…
-
Helping Without the Ask
In today’s environment, prospects are more protective of their time than ever. They don’t want another meeting request in their inbox unless it’s tied to something meaningful. That’s why offering value—without a request attached—is the easiest way to stand out. It shows you’re focused on their success, not just your quota.…
-
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:…