『Sales and Cigars』のカバーアート

Sales and Cigars

Sales and Cigars

著者： Walter Crosby
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今ならプレミアムプランが3カ月 月額99円

2026年5月12日まで。4か月目以降は月額1,500円で自動更新します。

概要

 How do you increase sales in your organization? Host Walter Crosby sits down with cigar in hand and has growth minded conversations proven to boost sales. Crosby sets the table by identifying areas where you can excel by first acknowledging the misunderstandings. Like every great sales person he takes time to reflect, strategize and execute. Sit back, listen in, and puff that cigar because Walter Crosby will light you up!2021 Walter Crosby マネジメント マネジメント・リーダーシップ リーダーシップ 経済学
エピソード
  • The Sales Problem You Can't See: Storytelling, Positioning, and False Momentum

    The Sales Problem You Can't See: Storytelling, Positioning, and False Momentum
    2026/04/21

    Most CEOs think they have a sales hiring problem, a sales performance problem, or a pipeline problem.

    But often, the real issue is deeper—and harder to see.

    In this solo episode of Sales & Cigars, Walter Crosby breaks down one of the most expensive hidden problems in growing companies: a lack of shared sales story and positioning clarity.

    This is not usually a problem caused by bad salespeople. In fact, it often shows up inside experienced sales teams. Reps sound confident. Conversations seem productive. Deals appear to move forward. But underneath the surface, the team is defaulting to pitching instead of guiding buyers through a clear story.

    Walter explains why pitching is often a coping mechanism, how false momentum shows up in the pipeline, and why this issue compounds as companies grow.

    Episode Highlights

    • Why many sales leaders misdiagnose messaging problems as hiring or performance problems
    • How experienced sales teams can still create confusion in the buying process
    • Why pitching feels productive—even when it is actually damaging deals
    • The hidden cost of collapsing context in sales conversations
    • How false momentum creates misleading pipeline and forecasting confidence
    • Why this issue gets worse as companies scale and add new people
    • The difference between a people problem and a visibility problem
    • Why you cannot coach alignment into existence—you have to extract it
    • How a shared sales story gives leadership more control over language, promises, and buyer expectations
    • The practical questions leaders should ask to evaluate whether this problem exists in their business

    Key Takeaways

    Pitching is often a symptom, not the root cause.
    When salespeople default to pitching, it is not always because they are lazy, untrained, or ineffective. Often, they are filling a gap. Without a shared sales story to anchor them, they rely on explanation, compression, and persuasion.

    False momentum is dangerous.
    Deals can look like they are moving when they are really just drifting. The pipeline feels active, forecasts appear reasonable, and leadership assumes progress is happening—until deals suddenly stall or disappear.

    The real issue is often visibility.
    The founder usually holds the origin story. Leadership holds the strategy. Marketing holds the brand language. Sales holds the buyer friction. But no one person sees the full picture clearly, which makes alignment difficult.

    This problem compounds as a company grows.
    New reps interpret the company differently. Marketing evolves. Strategy shifts. Language starts to drift. The result is not always immediate failure—it is inconsistency that becomes more expensive over time.

    You cannot solve this with surface-level fixes alone.
    More training, more scripting, or another sales hire will not fix the core issue if the underlying story is still unclear. Companies need to extract the real story already living inside the business and make it usable for the team.

    A shared story improves more than messaging.
    When sales teams know exactly what they are carrying into buyer conversations, deals become more grounded, forecasts become more trustworthy, and leadership regains control over promises, expectations, and positioning.

    Who Should Listen

    • Founders who feel like sales should be working better than it is
    • CEOs frustrated by stalled deals and inconsistent pipeline movement
    • Sales leaders trying to understand why experienced reps still default to pitching
    • Companies struggling with messaging drift as they scale
    • Anyone trying to improve sales clarity, consistency, and predictability

    Links & Resources

    • Free storytelling and positioning resource mentioned in the episode
    • Helix Sales Development

    Subscribe to Sales & Cigars

    If you want real conversations about selling, leadership, and the hidden issues that impact growth, subscribe to Sales & Cigars on Apple Podcasts, Spotify, or YouTube.

    The only smoke we blow is from cigars.
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    8 分
  • Your Story Is a Sales Advantage: A Conversation with Bill Blankschaen

    Your Story Is a Sales Advantage: A Conversation with Bill Blankschaen
    2026/04/07
    Bill Blankschaen joins Sales & Cigars to explain why entrepreneurs need a clear origin story, how storytelling builds trust, and why consistent messaging gives companies a real sales advantage. Episode Overview Most companies already have a story. The problem is they are not telling it clearly, consistently, or in a way that actually connects with customers. In this episode of Sales & Cigars, Walter Crosby sits down with Bill Blankschaen, author of Your Story Advantage, to talk about why storytelling is not just a marketing tool — it is a business and sales advantage. Bill shares his own journey from leading a private school to taking a major entrepreneurial risk in order to become a writer and storyteller. That decision eventually led to building Story Builders, where he now helps entrepreneurs, authors, and businesses clarify their messaging and tell stories that stick. The conversation explores the difference between an origin story and a brand story, why sales teams need a consistent narrative, and how leaders can create messaging their teams can actually use. Episode Highlights Bill's transition from school leader to entrepreneur, writer, and storytellerThe risk of leaving stable work to pursue a callingWhy every entrepreneur's breakthrough begins with understanding their own storyThe difference between a company's origin story and its broader brand storyWhy inconsistent storytelling creates friction for sales and marketing teamsThe importance of helping the whole company "sing from the same hymnal"Bill's five-part storytelling structure: attention, tension, connection, solution, and actionWhy salespeople often jump to the solution too earlyHow strong storytelling helps buyers feel understood before they ever hear the pitchWhy storytelling should be customer-centered, not company-centered Key Takeaways Your story matters more than you think. Many founders and entrepreneurs downplay their own story because it feels normal to them. But your story is often the very thing that helps customers trust you, relate to you, and understand why your company exists. An origin story creates context. A strong origin story explains where the business came from, why it was started, and what problem or calling led to its creation. It gives customers and employees a deeper understanding of the mission behind the company. Your story is about you — but it is not for you. One of Bill's most important points is that while your story may start with you, it must be framed for the customer. The goal is not self-expression for its own sake. The goal is connection. Sales teams need a shared story. When every salesperson tells a slightly different version of the company story, trust erodes and the message gets diluted. Clear storytelling gives the team a shared framework they can deliver in their own voice without drifting off-message. Storytelling should start with the customer, not the product. Too many companies jump straight to features, benefits, and solutions. But buyers care first about their own goals, problems, and frustrations. The best storytelling starts there. A simple structure makes storytelling usable. Bill's five-part framework gives companies a practical way to shape their messaging: Attention — what the customer wantsTension — what is getting in the wayConnection — why you understand and can helpSolution — what you offerAction — what they should do next Good storytelling makes scaling easier. When the founder is the only one who can tell the company story well, growth gets stuck. A clear story helps the whole team communicate consistently across sales, marketing, and leadership. Who Should Listen Entrepreneurs trying to clarify their company messagingFounders who know their story but struggle to get it out of their headSales leaders who want their team speaking more consistentlyCompanies where sales and marketing are not aligned on the messageAnyone who wants to turn their story into a real business advantage Links & Resources Your Story Advantage by Bill BlankschaenStory BuildersBill Blankschaenyourstoryadvantage.com Subscribe to Sales & Cigars If you want real conversations about selling, leadership, and building a message that actually connects, subscribe to Sales & Cigars on Apple Podcasts, Spotify, or YouTube. The only smoke we blow is from cigars.
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    32 分
  • Short-Term Pressure Is Killing Great Sales Leadership

    Short-Term Pressure Is Killing Great Sales Leadership
    2026/03/24

    In this episode of Sales & Cigars, Walter Crosby sits down with Darren Mitchell, host of the Exceptional Sales Leader podcast, for a sharp conversation about sales leadership, short-term thinking, and what it really takes to build sustainable sales teams.

    Darren shares his path from engineering to telecommunications sales to sales leadership, and explains why too many organizations still confuse high-performing salespeople with high-potential leaders. The conversation digs into the pressure sales leaders face to hit short-term numbers, the damage that comes from product-first selling, and why the best leaders focus on building teams that can succeed without them.

    From The Infinite Game to Atomic Habits, this episode is packed with practical leadership wisdom for anyone trying to build a stronger sales culture—one rooted in service, discipline, and long-term thinking.

    Episode Highlights

    • Why The Infinite Game is a must-read for sales leaders under quarterly pressure
    • How short-termism damages customer relationships and long-term revenue
    • Why Atomic Habits matters for sales teams and leadership development
    • Darren's transition from engineer to salesperson to sales leader
    • The danger of promoting top reps into leadership without proper development
    • The powerful lesson Darren's manager gave him on his very first day as a sales leader
    • Why the goal of great leadership is to make yourself unnecessary
    • How sales leaders accidentally train customers to bypass their salespeople
    • Why product training is not enough to create great sales teams
    • The importance of understanding buyer psychology instead of pushing product

    Key Themes & Takeaways

    • Great sales leaders play the long game.
      Organizations obsessed with quarter-to-quarter results often sacrifice trust, relationships, and sustainable growth.
    • Leadership is not the same as top performance.
      Being a great salesperson does not automatically prepare someone to lead, coach, and develop others.
    • The best leaders build teams that can thrive without them.
      Sales leadership is not about being the hero in every deal. It is about creating an environment where the team can perform independently.
    • Habits drive long-term success.
      Small daily disciplines compound over time and create the consistency great sales teams need.
    • Customers do not care about your product first.
      They care about their problems, their priorities, and what happens if those problems remain unsolved.
    • Sales is service when done correctly.
      The role of the salesperson is not to push product, but to help a customer recognize a problem and evaluate a solution.
    • Coaching and mentoring are essential.
      Without guidance, many new sales leaders default to control, ego, or problem-solving for their team instead of developing them.

    Who Should Listen

    This episode is especially valuable for:

    • Sales leaders feeling trapped by short-term revenue pressure
    • Founders and executives trying to build stronger sales leadership
    • Organizations promoting top reps into management roles
    • Sales teams that rely too heavily on senior leaders to close deals
    • Anyone who wants to build a more sustainable, service-driven sales culture

    Links & Resources

    The Infinite Game by Simon Sinek
    Atomic Habits by James Clear

    Exceptional Sales Leader
    https://exceptionalsalesleader.com

    Darren Mitchell on LinkedIn

    Exceptional Sales Leader Podcast

    Subscribe & Follow

    Sales & Cigars is hosted by Walter Crosby of Helix Sales Development.

    The only smoke we blow is from cigars.

    Subscribe on Apple Podcasts, Spotify, YouTube, or wherever you listen.
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    54 分
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