Episode #523 – John Klymshyn
Meet
John Klymshyn
John Klymshyn has written extensively about Enterprise Sales and how to INSPIRE High Performers through practical techniques outlined in his book: “The Ultimate Sales Managers’ Guide”, available in hardcopy AND audio, which John himself narrates. He has guided sales teams to scale across the globe, and is currently out speaking about his New book: “Open The Valve; The New Path To Creative Play.”Available NOW in English AND Spanish! Multi–instrumentalist, composer, performer, speaker, and coach, Klymshyn lives to explore creativity in all forms.
Our Mission Is To Change The Negative Perception Of Sales People
Our Vision Is A World Where Selling Is A Profession To Be Proud Of
On the show this week, I’m joined by John Klymshyn—multi-instrumentalist, composer, acclaimed author of The Ultimate Sales Manager’s Guide and Open the Valve, and a seasoned leader in enterprise sales. We discuss the nuances of sales leadership versus sales management, exploring how culture, vision, and practical coaching distinguish the most successful teams. John shares his strategies for building high-performance sales teams, the critical traits of effective sales leaders, and why humanity, humor, and high expectations are the pillars of sustainable sales excellence.
Outline of This Episode
- [00:00] Distinction between sales leadership and sales management
- [03:42] Sales as a performance profession
- [06:45] Three key concepts: humanity, humor, and high expectations
- [09:25] Building a high-performance sales team
- [13:12] Importance of regular team check-ins
- [16:20] The impact of technology and AI on sales leadership
- [19:52] Real-world example of leadership transformation
The Essence of Sales Leadership
Sales leadership isn’t about day-to-day oversight or hand-to-hand combat in the trenches. It’s about shaping the culture and vision of the sales organization, emanating from the top and permeating to every client-facing role—even those not carrying traditional sales titles.
For John, robust sales leadership starts with articulating how the organization wants to be perceived—by clients, partners, vendors, and even internally. This top-down ethos inspires pride, integrity, and service, enabling a healthier and more growth-oriented company. Sales management, by contrast, is the ongoing daily interaction between leaders and salespeople, focused on performance and tactical guidance.
The Characteristics of Great Sales Leaders
John identifies three core traits in high-impact sales leaders: humanity, humor, and high expectations.
- Humanity: The best leaders relate authentically to their teams, recognizing the real challenges, aspirations, and lives of their salespeople.
- Humor: Lightness and laughter are not frivolous—they “soften the heart, which opens the mind”. Humor makes feedback less threatening and keeps morale high, especially when the stakes are high.
- High Expectations: Top leaders don’t settle for mediocrity. They maintain demanding standards, pushing each team member to stretch and grow.
Combined, these three traits build environments where trust, engagement, and accountability thrive, paving the way for sustainable success.
Achieving High Performance—and Harmony—on Sales Teams
One myth John dispels is the idea that every sales team can be stacked solely with “A-players.” In reality, any team of five or more will naturally include top performers, reliable “B-players,” and some underperformers. The key to consistency isn’t seeking perfection but identifying the five essential attributes of your ideal contributors, then cultivating and hiring for those.
That way the focus shifts from unattainable balance to the healthier concept of harmony, which is more sustainable and realistic—especially in sales, where there isn’t always a clear-cut separation of work and life.
Coaching and the Human Connection in a Digital World
While AI, CRM platforms, and sales enablement tools are transforming the profession, John points out that nothing replaces the impact of a live conversation. Regular coaching sessions—his “15 minutes of fame”—give salespeople a moment to shine, discuss wins, articulate upcoming goals, and voice their needs. Coaching is most effective when it goes beyond metrics, focusing on the person rather than just the pipeline.
Leaders should recognize the individuality of each team member and resist the urge to create clones. The best thing to do is aim to harness diverse strengths, not impose your own methods.
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Learn More About John Klymshyn
1. Leadership Journey: What was the defining moment in your career that transformed your approach to leading salespeople?
I remember it specifically it occurred when I was building a North American sales team for a Norwegian manufacturer. One of the salespeople came to me and was talking about the fact that he could not get a prospect “to come over to our side of the fence”… My gut reaction turned into something that has been a process and a phrase that I have relied on for many years period my response to him was: “We’re not looking to get people to do anything. All we’re here to do is to Move Conversations Forward.”
I immediately wrote the phrase down and have since trademarked it and it has led to the publication of my first (of several) books.
2. Practical Advice: Can you share a leadership framework, coaching model, or management system that has consistently helped you build high-performing sales teams? Please include a practical example.
Yes the leadership framework is for a sales leader to operate as though they are emulating what I refer to as the ultimate sales manager. This is someone who loves what they do, is productive at what they do, is liked both by management and direct reports and is also someone who can hold people accountable. There are 52 attributes of this person so let me share a couple with you here.
Attribute #3: Hire people who you hope will surprise you. Develop them into people who surprise themselves.
Attribute # 11: Lead with the intent to elevate the team
And the Ultimate Sales Management Rule of Three:
* Hit Your Number * Maintain Low Churn (Clients and employees) * NO DRAMA.
3. Overcoming Challenges: What has been your most difficult sales leadership challenge, and what did you learn from overcoming it?
Teaching myself to NOT expect people Love what they do for the same reasons that I do or to think about the work the way that I do. This is when I started approaching leadership as a creative process. What I mean by that is that my role as a band leader and band member as a musician is to draw the greatest performances out of all of the other members of the band. That means that I am a great listener, a patient collaborator, and I go out of my way to prepare. One of my 17,342 aphorisms is: Practice does not make perfect. Practice makes prepared.”
4. Building Great Teams: Recruiting, developing, coaching, and retaining top talent are all critical leadership responsibilities. What advice would you give to leaders looking to build world-class sales teams?
When you conduct interviews, make sure that you are learning who the person is as opposed to what they can recite from their resume. I am mildly cynical, and after eight years in the recruiting industry, I’m convinced that 62.37453% of every salesperson’s resume is a work of fiction. That’s not a negative. What I’ve learned, though, is that I ask questions that are designed to engage a deeper conversation. I discuss much of this in my audiobook “Deeper dialogue; Conversations That Inspire.”
One of my go to questions has two parts. The first part is asked and the responses listen to all the way to the end. Then I ask the second part. First part is: “What’s the toughest thing you’ve ever done?” Sometimes people hesitate. Sometimes they will take a deep breath in. What I’m really interested in is what sort of story they decide to share. And at what level of detail. Folks that are very, very guarded are probably not going to work on my team. People that immediately go to an emotional experience and talk about it openly have a better shot. The second question to ask, and again I remind the reader this is asked only after a long and/or detailed answer has been listened to. The next question is: “What did you learn about yourself from that experience?”
5. Future Trends: Looking ahead over the next five to ten years, how do you see Modern Sales Leadership evolving, and what capabilities will distinguish tomorrow’s most successful Sales Leaders?
It certainly is my hope that modern sales leadership will evolve to become more human while maintaining high expectations. After 40-plus years of being a sales leader, managing other sales leaders, teaching sales leaders, and coaching sales leaders of billion-dollar organizations, I have to say that the capabilities that will distinguish tomorrow’s most successful sales leaders have been demonstrated consistently, which are: Humor, Humanity, and High Expectations.
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