Sales Leadership Q&A: Real Answers to Tough Sales Management Questions

If you like blunt truth about sales and sales management, you will LOVE this conversation between Mike and sales leadership expert and author, Kelly Riggs.  Enjoy hearing these truth-tellers finish each other's sentences as they tackle several biggies, including… The fact that "the system" sales managers are dropped into is often what gets in the way of success The crime that so many successful sellers get promoted into management roles with exactly ZERO preparation, training, or clarity about their new roles Why newer leaders are not leading, but instead becoming what Kelly calls "SuperDoers" jumping into every sales call, presentation, negotiation, etc. This may sting but listen in as Kelly declares that just about every problem in corporate America is a leader problem – the type of problem that cannot be solved with tactical solutions and flavor-of-the-day initiatives! Near the conclusion of the episode, Mike has Kelly share why he wrote his captivating new book, The Five Power Moves: How Struggling Sales Managers Become Transformational Sales Leaders. It's short, powerful, entertaining, and packed with both truths that hurt and the fixes (power moves) to overcome many of today's toughest sales management challenges. RESOURCES MENTIONED IN THIS EPISODE: Kelly's book, The Five Power Moves _________________________________ This episode is sponsored by Pursuit Sales Solutions. If you are looking for help adding A-player talent to your team, contact Mike's friends at pursuitsalessolutions.com/weinberg

Mike is back after a break and as blunt as ever in Episode 112.  Listen in as he shares his concerns that way too many sellers are defaulting (or acquiescing) to the buyer's process or getting trapped playing to procurement people. The consequences are devastating, particularly when you sell premium offerings at a premium price!  As Mike often reminds sales teams, THERE IS NO LAW that the prospect/customer gets to dictate our relationship terms or rules of engagement. Just because a buyer (or procurement weenie) asks you to do something that does not mean it's the right thing to do or the right time to do it. Professional, mature, consultative sellers OWN THEIR PROCESS and do everything in their power to come across as true advisors and value creators, not as yes-men/women, order takers, vendors, or commodity sellers.  As teased in the episode title, Mike shares that one of the big keys to defeating procurement and winning bigger, tougher deals is for the salesperson to get close to, and demonstrate as much value as possible to, the senior stakeholders who care deeply about (and likely own) the outcomes that your solutions produce. RESOURCES MENTIONED IN THIS EPISODE: Episode 19 (originally released December 1, 2021):  Salespeople Who Act Like Obedient Order-Takers and Yes-Men/Women Don't Win More Business.   Listen on Mike's site at https://mikeweinberg.com/podcast/episode19/ or find the episode on your favorite platform. Mike's book Sales Truth   This episode is sponsored by Pursuit Sales Solutions. If you are looking for help adding A-player talent to your team, contact Mike's friends at pursuitsalessolutions.com/weinberg

In Episode 111, Mike offers a "stream of consciousness" delivering observations and takeaways from leading recent cohort sessions for sales leadership teams implementing the RPA accountability framework. A senior executive asked:  "As we roll out the RPA meeting as prescribed, what are two pieces of advice (the two keys) that will guarantee success? Without hesitating, Mike responded with:   Cadence  Consistency Mike explains why the regular rhythm of the manager-salesperson 1:1 accountability meeting is what actually changes behavior (and culture), and why consistency across managers is critical. Throughout the organization, sales leaders must conduct the RPA meeting  with a similar tone, progression, and rigor. Mike also cautioned leaders about confusing a "fat" pipeline with a healthy one. A pipeline packed with stale, aging, going-dark deals may at first glance appear "full," but not one that will necessarily translate into closed business. He goes on to make the case that a "fresh" pipeline may actually be more valuable than a fat one filled with stalled, old opportunities that are growing mold! And that is exactly why Mike believes the single most important accountability question sales leaders can ask every rep is: "What NEW opportunities did you create last month? What new deals are in your pipeline that were not here during our last RPA meeting?" If you are serious about strengthening accountability, (without micromanaging or demotivating sellers), improving sales management effectiveness, and driving MORE New Sales, this episode is for you. ____________________________ The final Supercharge Your Sales Leadership Event of the year is October 7th at The Porsche Experience Center in Atlanta. Join Mike and 55 driven sales leaders tackling the biggest topics in sales management.   Learn more and register here:  www.mikeweinberg.com/atlanta2026 ____________________________ This episode is sponsored by Pursuit Sales Solutions. If you are looking for help adding A-player talent to your team, contact Mike's friends at pursuitsalessolutions.com/weinberg

In Episode 110, Mike shares a sad personal update and tackles one of the most important and most misunderstood sales leadership issues: Sales DNA.  Prompted by client work, fresh research, and a painfully honest post-race interview from the Indy 500, Mike challenges sales leaders to stop pretending that your "nice," relational salespeople are going to be successful hunters! Mike also breaks down several aspects of selling (the sales process/cycle) that demonstrate why top new-business salespeople must be highly resilient in the face of rejection, and comfortable with conflict. From prospecting and handling objections to negotiating, displacing incumbents, and closing, he makes the case that sales hunters face risk, rejection, and conflict every single day—and if your people aren't wired for that, no amount of coaching, compensation, or accountability will magically turn zookeepers into new business development killers. __________________________________ This episode is sponsored by Pursuit Sales Solutions. If you are looking for help adding A-player talent to your team, contact Mike's friends at pursuitsalessolutions.com/weinberg

In this special Q&A-style episode, Mike Weinberg is joined by sales leadership coach Matt Ferguson for a practical, fast-paced conversation tackling real-world sales management challenges submitted by sales leaders and reps. Mike and Matt dive into topics like: Transitioning from top rep to first-time sales manager Coaching underperformers back to quota Why most pipeline reviews fail Creating proactive hunters instead of reactive order-takers Managing large, geographically dispersed sales teams Helping executives understand complex enterprise sales cycles Packed with honest insights, practical coaching advice, and a few laughs along the way, this episode is full of actionable ideas for sales leaders looking to build stronger teams, healthier pipelines, and a culture of accountability. RESOURCES MENTIONED IN THIS EPISODE: Matt's website:  MattDFerguson.com The October 7 Supercharge Your Sales Leadership Event   This episode is sponsored by Pursuit Sales Solutions. If you are looking for help adding A-player talent to your team, contact Mike's friends at pursuitsalessolutions.com/weinberg

In episode 108, Mike hosts outbound sales guru, Jason Bay, founder and leader of Outbound Squad. Jason and Mike get in the "Way Back Machine" looking at the evolution of SDRs, what went wrong with that model, and why prospecting is so damn hard today. If your team is struggling to book meetings and create new opportunities, this episode is for you as Jason shares strategies that are working right now and what the very best reps are doing to self-generate pipeline! Learn how to become "too good to ignore" by focusing on the right targets, crafting compelling offers, and creating emotional connections with prospects. Tune in and you'll immediately hear why Mike regularly points new business development sellers and sales teams to follow Jason Bay! RESOURCES MENTIONED IN THIS EPISODE: Jason Bay's Free Outbound Masterclass The October 7 Supercharge Your Sales Leadership Event _________________________ This episode is sponsored by Pursuit Sales Solutions. If you are looking for help adding A-player talent to your team, contact Mike's friends at pursuitsalessolutions.com/weinberg  

In Episode 107 Mike shares a personal update on his social media sabbatical and one of his biggest observations after participating in so many Q1 sales team kickoff meetings. Listen in as Mike unpacks his frustration and confusion about how few salespeople are conducting professional, consultative, value-delivering, opportunity-creating, conversational meetings with prospects and customers. He briefly reviews his common sense outline (from New Sales. Simplified. Chapter 11) for structuring winning sales calls and then dives deeper into both how to start and end the meeting well. 1. Hear a simple technique for how sellers can take control, share their plan/agenda, get buy-in and input from the prospect/customer, reduce tension, create comfort and remove that awkward, adversarial dynamic…all while making the buyer feel that the meeting is all about them!  2. Ensure that sellers define, secure, and SCHEDULE the prospect/customer's committed-to next step! Too many salespeople are concluding sales calls with assignments for themselves but not getting agreement to (and scheduling) what the prospect/customer will do next. RESOURCES MENTIONED IN THIS EPISODE: The October 7-8 Supercharge Your Sales Leadership Event   Mike's 12-year bestseller, New Sales. Simplified.     This episode is sponsored by Pursuit Sales Solutions. If you are looking for help adding A-player talent to your team, contact Mike's friends at pursuitsalessolutions.com/weinberg

Mike gets asked to read a lot of books about sales and sales management. Most recently, he read Focused – from his Canadian buddy, sales management expert, and former fantasy football adversary, Steve Rosen. Mike was so blown away that he actually asked Steve if he could provide the foreword and help promote the book. Truly, it was that good. So good, in fact, that this was Mike's visceral reaction… The Bold Statement (from Mike's foreword):  FOCUSED is the single best and most helpful book for sales leaders to be published in years! If you lead a sales team, or lead leaders of sales teams, the introduction to this book will take your breath away. It will stop you in your tracks.  I am serious: Do NOT read FOCUSED unless you are ready to be smacked in the face with the cold, hard truth and willing to address what is arguably the biggest challenge in sales today. Truly, by page 2 my chest tightened as the all-too-real scenarios described by Rosen perfectly depicted exactly what I see every. single. day. in companies where I speak, train, consult and coach. The Big Issue:  Sales managers live in reactive mode, often overwhelmed, and are regularly distracted and diverted from their highest-payoff activities. Rosen not only calls it out, but provides practical help for overcoming this massive challenge. Enjoy this engaging conversation between Steve and Mike. But beware, if you lead a sales team, it may cause you to laugh, cry, or scream.  Be sure to grab the free copy of the Foreword, Table of Contents, and the Introduction that Mike mentions in the episode! RESOURCES MENTIONED IN THIS EPISODE: FOCUSED: The Leadership Discipline That Protects Performance from Distraction (on Amazon HERE)   Mike's Foreword  along with the Introduction that took his breath away   Supercharge Your Sales Leadership October 7 event   This episode is sponsored by Pursuit Sales Solutions. If you are looking for help adding A-player talent to your team, contact Mike's friends at pursuitsalessolutions.com/weinberg

Episode 105 starts with a startling proclamation as Mike reveals what feels like a seismic decision to pull the plug on LinkedIn. He transparently shares what's going on in his mind and heart, along with what he's reading and experiencing, that prompted this bold (and surprising) move. The episode concludes with a simple, practical sales management checklist that Mike will be working through during a large client's upcoming annual learning conference. Listen in as he briefly unpacks these Sales Management. Simplified. Fundamentals: Master the 1:1 Accountability Meeting (and the RPA progression) Get a True Hunter (DNA) in a Sales Hunting Role Identify and Address Underperformance Quickly (coach-up or out) Ensure Every Sales Rep Is Targeting a Strategic, Finite List Observe and Coach Your Salesperson (get your head out of the CRM & spreadsheets)  RESOURCES MENTIONED IN THIS EPISODE: Mike's LinkedIn post  The hospice nurse's article about the final thoughts from 300 patients It's Sales Management Malpractice to Ignore Underperformance podcast episode Just Announced: October 7 Supercharge Your Sales Leadership event _____________________________ This episode is sponsored by Pursuit Sales Solutions. If you are looking for help adding A-player talent to your team, contact Mike's friends at pursuitsalessolutions.com/weinberg

Dennis Sorensen is back! A former super successful senior sales executive who has built a thriving, multifaceted sales improvement firm, Dennis is embedded inside companies doing real transformational work around sales leadership, playbooks, process-driven selling, and unlocking crazy potential through his concept of Ambition. In this episode, Dennis shares what he's seeing on the front lines — what's working, what's not, and how challenging times are forcing sales leaders to become better coaches and skill developers. We dig into talent gaps, the idea of "everboarding" (not just onboarding), strategic sales planning, and why too many teams limit their potential by focusing on how far they think they can climb instead of asking, "How big is the mountain?" Dennis also recently launched his own podcast, Think Big. Win Bigger. — and I had the privilege of being his guest on the inaugural episode. You'll want to check that out as well. Guaranteed you walk away with  a handful of BIG IDEAS after listening to (or watching) our dialogue! Enjoy this powerful conversation with one of the most strategic and driven sales leaders I know.   This episode is sponsored by Pursuit Sales Solutions. If you are looking for help adding A-player talent to your team, contact Mike's friends at pursuitsalessolutions.com/weinberg