Real Sales Manager

Steve Hoyle

A regular podcast for new sales managers where we interview practising sales leaders in complex B2B. In conjunction with realsalesmanager.com

  1. Sep 11

    2.5 Dilemmas: The retiring salesperson

    This episode 2.5 of the Real Sales Manager podcast features the dilemma of what to do about a salesperson nearing retirement whose performance is declining. The discussion looks at how to evaluate a situation by looking beyond surface-level data. Stephen Fowler and Richard Bounds focus on what the numbers reveal, Sophie Steel emphasizes the need to question assumptions, and Steve Hoyle adds the importance of having skilled, motivated people who are doing the right thing for customers. We also explore what to do when your boss demands that you increase your forecast, and whether or not to grant leave when the 'rules' say no. In the three dilemmas we discuss judgment, motivation, and reading the signals underneath the obvious metrics. It matters because bad decisions often come from incomplete context and wrong assumptions, not just bad data. Key topics ·      Stephen Fowler shares a data-first approach: review activity, pipeline creation, deal velocity, account plans, CRM accuracy, and whether opportunity plans are live, dead, or stale ·      Richard Bounds adds that motivation matters too, and asks what success should look like for a salesperson over the next two years ·      Sophie Steel warns that relying only on surface data leads you to “come a cropper” and says you have to question, explore, and go beneath the surface ·      Steve Hoyle highlights that having good, skilled, motivated people doing the right thing for customers is more than half the battle ·      The group frames the conversation around understanding what is really happening before drawing conclusions and making decisions ·      The discussion suggests that operational data and human context both matter, and neither should be ignored Guests Richard Bounds: Richard brings more than three decades of sales and leadership expertise across startups, scale-ups, and global enterprises, with experience leading teams of 30+ sellers and driving consistent, high-impact growth. His track record includes doubling turnover at Box-it by transitioning to a cloud-first model, scaling a business from zero to $4M in just 18 months before a successful trade sale. Built a $25M partner channel at Software AG and delivered record results at OpenText as VP EMEA. Today, Richard supports technology companies as a Board Advisor and Fractional Leader, helping organisations build stronger sales functions, implement best practices, and accelerate revenue through structured coaching, advisory, and modern sales approaches https://www.linkedin.com/in/richardbounds1/ Sophie Steel:  Sophie is a coach, trainer, and recovering sales manager who now spends her time figuring out what actually makes people perform. She loves mindset, behaviour, and all that good stuff, but mainly she enjoys calling out the gaps between what we say we do… and what’s really going on. She’s an ICF PCC coach, EQ-i qualified, and specialises in brain and behaviour change, working across sales teams and senior leaders to turn insight into actual behaviour change, not just good intentions. https://www.linkedin.com/in/sophie-steel-72218817/ Special Guest, Stephen Fowler: Stephen is an Advisor and Coach helping market leaders drive performance by leading, managing and coaching their people, as well as building teams that focus on customer outcomes and value rather than products, features and functions. He is a Partner at Positive Momentum while undertaking PhD research focused on value-based selling in B2B SaaS organisations. He brings more than 25 years of experience from SAP, Oracle, Accenture, Salesforce, Microsoft, QAD and UiPath. He has sold in the field, built and led sales organisations, managed teams across EMEA and Asia Pacific and run regional P&Ls. https://www.linkedin.com/in/scfowler/ Sound Bites “Data is the first lens, not the full truth.” “You can’t lead from the dashboard alone.” “The real story is in the behavior behind the report.” “Motivation is a strategy variable, not a soft extra.” “If you stop at the surface, you’ll miss what’s really happening.” “The best diagnosis starts below the dashboard.” “Skilled, motivated people doing the right thing for customers—that’s more than half of it.” “Use metrics as a map, then go looking for the human context behind them.” Keywords sales management, leadership, performance, data, motivation, retirement, forecast, rules, listening

    2.5 Dilemmas: The retiring salesperson
  2. Aug 7

    2.4 Dilemmas: Top salesperson frustrations

    In this episode of the Real Sales Manager podcast series 2, we explore complex sales management dilemmas, including handling top salespeople's frustrations, resource allocation during large deals, and managing underpaid employees considering resignation. Our expert panel shares practical insights and strategies to navigate these challenges effectively. Topics ·      Managing top salespeople's frustrations ·      Resource allocation during large deals ·      Handling employee resignations due to pay ·      Balancing short-term wins with long-term strategy ·      Building trust and consistency in leadership ·      Understanding underlying causes of sales person behavior ·      Effective communication and coaching strategies Guests Richard Bounds: Richard brings more than three decades of sales and leadership expertise across startups, scale-ups, and global enterprises, with experience leading teams of 30+ sellers and driving consistent, high-impact growth. His track record includes doubling turnover at Box-it by transitioning to a cloud-first model, scaling a business from zero to $4M in just 18 months before a successful trade sale. Built a $25M partner channel at Software AG and delivered record results at OpenText as VP EMEA. Today, Richard supports technology companies as a Board Advisor and Fractional Leader, helping organisations build stronger sales functions, implement best practices, and accelerate revenue through structured coaching, advisory, and modern sales approaches https://www.linkedin.com/in/richardbounds1/ Sophie Steel:  Sophie is a coach, trainer, and recovering sales manager who now spends her time figuring out what actually makes people perform. She loves mindset, behaviour, and all that good stuff—but mainly she enjoys calling out the gaps between what we say we do… and what’s really going on. She’s an ICF PCC coach, EQ-i qualified, and specialises in brain and behaviour change—working across sales teams and senior leaders to turn insight into actual behaviour change, not just good intentions. https://www.linkedin.com/in/sophie-steel-72218817/ Special Guest: Phil Loudoun Phil Loudoun is Head of Sales for the Private Sector at Boxxe - having been with them and CAE who they acquired for over 15 years. He’s been an Account Manager and had various Sales Management positions  before taking on his present position some 18 months ago. He describes himself as A results driven sales leader with a reputation for integrity, loyalty and high performance. He says that he thrives on building strong relationships and collaborative cultures that energise teams, strengthen customer partnerships and deliver exceptional results.  https://www.linkedin.com/in/philip-loudoun-58284826/ Sound bites "Let the content dictate the format." "Think through the consequences of your actions" "The brain loves certainty." "We must support our people" "Money is not the only motivator" "Treat the issues, not just the symptoms." "Consistency for a leader is key" Keywords sales management, leadership, team dynamics, resource allocation, employee retention, sales strategy

    2.4 Dilemmas: Top salesperson frustrations
  3. Jul 10

    2 3 Dilemmas: Hunter or Farmer

    In this episode, we explore key dilemmas faced by sales leaders, including can you transition from farmer to hunter, handling 'creepy' behaviour, and managing client presentation pressures. Our expert panel offers nuanced insights and practical advice for navigating complex situations in sales management. Topics ·      Transitioning account managers to new roles ·      Hunters vs Farmers ·      Handling uncomfortable workplace behaviour ·      Managing client presentation pressures ·      Leadership strategies in sales dilemmas ·      Importance of transparency and communication Guests Guests Richard Bounds: Richard brings more than three decades of sales and leadership expertise across startups, scale-ups, and global enterprises, with experience leading teams of 30+ sellers and driving consistent, high-impact growth. His track record includes doubling turnover at Box-it by transitioning to a cloud-first model, scaling a business from zero to $4M in just 18 months before a successful trade sale. Built a $25M partner channel at Software AG and delivered record results at OpenText as VP EMEA. Today, Richard supports technology companies as a Board Advisor and Fractional Leader, helping organisations build stronger sales functions, implement best practices, and accelerate revenue through structured coaching, advisory, and modern sales approaches https://www.linkedin.com/in/richardbounds1/ Sophie Steel:  Sophie is a coach, trainer, and recovering sales manager who now spends her time figuring out what actually makes people perform. She loves mindset, behaviour, and all that good stuff—but mainly she enjoys calling out the gaps between what we say we do… and what’s really going on. She’s an ICF PCC coach, EQ-i qualified, and specialises in brain and behaviour change—working across sales teams and senior leaders to turn insight into actual behaviour change, not just good intentions. https://www.linkedin.com/in/sophie-steel-72218817/ Special Guest: Scott Cassie Scott brings a different perspective to our discussions. He is a seasoned and very successful sales person and sales leader, with vast experience in the financial services sectors, leading teams in both client management, what many people call account management, and also new business. He has great experience of the North American market as well as Europe. In my experience, having worked with Scott in different ways over the last few years he is a consummate professional as a sales person and sales leader and has particular skills in developing sales talent. https://www.linkedin.com/in/scottcassie/  Sound bites "Can account managers become successful hunters?" "Handle uncomfortable behaviour with HR support." "Always be transparent with your team and clients." "we kid ourselves sometimes" "we should ask the sales person" Chapters 00:00 Introduction to Sales Dilemmas 02:04 Navigating Team Dynamics: The Case of Andy 17:18 Addressing Workplace Behaviour Concerns 22:32 Navigating HR Dilemmas in Management 28:27 Handling Client Presentations and ROI Expectations 34:05 Key Takeaways from Complex Scenarios Keywords sales management, account transition, workplace behaviour, client presentations, leadership dilemmas

    2 3 Dilemmas: Hunter or Farmer
  4. Jun 10

    2.2 Dilemmas: Account Allocation & Interviewing

    Dilemmas explores difficult situations faced by sales managers.  In this episode we look at deal allocation, team development, and hiring decisions. Featuring insights from experienced sales leaders, it offers practical strategies for effective sales leadership. Key topics Deal allocation strategies between A and B playersBalancing fairness and performance in team decisionsThe importance of rules and transparency in sales managementCoaching and developing struggling salespeopleThe role of intuition and gut feeling in hiring decisions 𝗚𝘂𝗲𝘀𝘁𝘀 Special Guest: Sami Ammous Sami is the Founder and Chief Change Maker at kyadah, a B2B SaaS fractional sales advisory, based in Singapore, which helps companies achieve their potential through building & executing sales and go-to market strategies and fractional leadership for senior roles.  Before running kyadah, Sami spent several years in senior leadership roles in tech companies in the APAC and Middle East, navigating nuanced cultures, economic turmoil, and the shift to XaaS solutions. He has been entrusted with resolving the most complex challenges the companies he worked with had, and consistently executed successfully. His focus was always creating environments where teams performed to their maximum ability.  https://www.linkedin.com/in/sami-ammous/  Richard Bounds Richard brings more than three decades of sales and leadership expertise across startups, scale-ups, and global enterprises, with experience leading teams of 30+ sellers and driving consistent, high-impact growth. His track record includes doubling turnover at Box-it by transitioning to a cloud-first model, scaling a business from zero to $4M in just 18 months before a successful trade sale. Built a $25M partner channel at Software AG and delivered record results at OpenText as VP EMEA.  Today, Richard supports technology companies as a Board Advisor and Fractional Leader, helping organisations build stronger sales functions, implement best practices, and accelerate revenue through structured coaching, advisory, and modern sales approaches  https://www.linkedin.com/in/richardbounds1/  Sophie Steel Sophie is a coach, trainer, and recovering sales manager who now spends her time figuring out what actually makes people perform. She loves mindset, behaviour, and all that good stuff, but mainly she enjoys calling out the gaps between what we say we do… and what’s really going on.  She’s an ICF PCC coach, EQ-i qualified, and specialises in brain and behaviour change—working across sales teams and senior leaders to turn insight into actual behaviour change, not just good intentions.  https://www.linkedin.com/in/sophie-steel-72218817/ Sound bites  "Establish the rules up front" "Customers are not the training ground"  "Star performers also need development"  "Team perceptions of favoritism matter"  "Listen to your gut in sales decisions"  "I spend more time with people who need help"  "Fairness and consistency and communication is really critical"  "if you're not 100%, don't do it" (hiring)  "You always want more information; dig deeper"  Further information Dilemmas is brought to you by Real Sales Manager. For more details of our coaching, consulting, training and research go to https://www.realsalesmanager.com/  Please get in touch with any dilemmas that you are facing that you would like us to discuss. 𝗞𝗲𝘆𝘄𝗼𝗿𝗱𝘀 sales management, lead allocation, team dynamics, recruitment, leadership, integrity, performance management, sales team culture, sales manager coaching

    2.2 Dilemmas: Account Allocation & Interviewing
  5. May 13

    2.1 Dilemmas: the disruptive salesperson

    In this first episode for series 2 of the Real Sales Manager podcast we explore the complex dynamics of managing disruptive salespeople, the importance of character and integrity in sales leadership, and practical strategies for handling challenging situations in sales teams. We explore two typical dilemmas for sales managers: ·      you have a good, reasonably well performing salesperson, but who is being incredibly disruptive to the team; what will you do? ·       you have a major bid, where you appear to be the preferred supplier, beating other competitors on functionality and ROI. Your team discover that actually they could reduce the cost to the customer by substituting some less expensive components, without sacrificing needed functionality or performance. Do you tell the customer? Key  topics Managing disruptive salespeopleThe importance of character and integrity in sales leadershipStrategies for early intervention and performance managementBalancing short-term results with long-term team healthThe impact of senior management decisions on team dynamicsGuests Richard Bounds: Richard brings more than three decades of sales and leadership expertise across startups, scale-ups, and global enterprises, with experience leading teams of 30+ sellers and driving consistent, high-impact growth. His track record includes doubling turnover at Box-it by transitioning to a cloud-first model, scaling a business from zero to $4M in just 18 months before a successful trade sale. Built a $25M partner channel at Software AG and delivered record results at OpenText as VP EMEA. Today, Richard supports technology companies as a Board Advisor and Fractional Leader, helping organisations build stronger sales functions, implement best practices, and accelerate revenue through structured coaching, advisory, and modern sales approaches https://www.linkedin.com/in/richardbounds1/ Sophie Steel:  Sophie is a coach, trainer, and recovering sales manager who now spends her time figuring out what actually makes people perform. She loves mindset, behaviour, and all that good stuff—but mainly she enjoys calling out the gaps between what we say we do… and what’s really going on. She’s an ICF PCC coach, EQ-i qualified, and specialises in brain and behaviour change—working across sales teams and senior leaders to turn insight into actual behaviour change, not just good intentions. https://www.linkedin.com/in/sophie-steel-72218817/ Special Guest: Steve Mortimer Steve is a Sales Leader at BT who believes that being a good person and building genuine relationships are the foundations of commercial success. A natural challenger who makes the complex simple, he brings real curiosity to every customer engagement — always seeking to understand the "reason why" before aligning solutions to the outcomes that matter most. https://www.linkedin.com/in/stevenmortimer/  Sound bites "Disruptive behavior is data telling you something's off" "Set non-negotiables from day zero" "Build long-term trust through integrity" Keywords sales management, team dynamics, disruptive behavior, leadership, integrity, performance management, sales team culture, sales manager coaching

    2.1 Dilemmas: the disruptive salesperson
  6. 08/15/2025

    27. Rob Herbst and the changing role of Sales Managers

    In this episode of the podcast Steve Hoyle interviews Rob Herbst about the evolving role of sales managers and the essential traits that contribute to their success. Rob shares insights from his extensive experience in sales leadership, emphasizing the importance of personal development, accountability, and building trust within sales teams. The discussion also touches on the impact of technology and data on sales management, the necessity of coaching and feedback, and the mindset shifts required to thrive in a tumultuous business environment. Rob concludes with advice for new sales managers, highlighting the value of embracing change and learning from mistakes. Contact You can see Rob's profile at https://www.linkedin.com/in/robherbst/ You can contact Rob through https://www.spireselling.com You can watch Rob on YouTube at @spire.selling  Key Takeaways ·      Sales managers are pivotal in shaping sales culture. ·      Successful sales managers enjoy being with their salespeople. ·      Accountability in sales comes with responsibility and authority. ·      Sales coaching should be a collaborative process. ·      Trust is built through genuine human interaction. ·      Sales managers must adapt to the changing landscape post-COVID. ·      Feedback culture is essential for strong sales teams. ·      Sales is an adventure that requires a growth mindset. ·      Data should be used to examine and interpret sales performance. ·      Personal development is crucial for both salespeople and managers. Sound Bites "Sales Managers are the pivot point" "Three anchors: personal development, clear expectations, achievement orientation" "They own the culture" "What can you depend on me for?" "What can I depend on you for?" "Friends don't let friends fail" Accountability comes together with Responsibility, Autonomy, Authority" "Trust can't happen that way." (digital only communication) "I can't do that by text" "Be with your salespeople." "Sales is a lonely place if you're not part of a sales team" "Get your team together" "A one-on-one is my sanctuary" (for a sales person) "The world is tumultuous, and it's doing us a favour" "Keep the easy parts easy" "We are now examining truth much more deeply" "Truth is hard work. Fiction is easy" "A real relationship is disruptive, intrusive and disturbing" "Sales is a fantastic vocation." Books Rob referred to his two books: both available on Amazon and at Barnes & Noble Cheating Death, https://www.amazon.com/dp/B0F3JG9VZR/ Spire Sales Culture: Your Guide to Developing a Thriving B2B Sales Force Keywords accountability, trust, sales leadership, sales management, characteristics of managers, team culture, authentic leadership, growth, mistakes, success, team building, sales strategies, personal development, coaching

    27. Rob Herbst and the changing role of Sales Managers
  7. 07/15/2025

    26. Lennart Sigterman Leadership and Planning

    In this conversation, Lennart Sigterman, a hugely successful and experienced sales leader, shares his journey into leadership. He emphasizes the importance of understanding team dynamics, building a strong team culture, and the role of vulnerability in effective leadership. He discusses the challenges of transitioning from a sales role to management, the significance of clarity in leadership, and the characteristics that make a successful manager. Lennart also highlights the essence of sales planning, the balance between structure and autonomy, and the importance of learning from mistakes. He concludes with insights on the pride that comes from seeing a team become self-sustaining and the challenges faced by first-line sales managers. You can see Lennart's  profile at https://www.linkedin.com/in/lsigterman/ Key Takeaways ·      Leadership is an attitude, not just a title. ·      Act like a leader before you have the title. ·      Understanding team dynamics is crucial for success. ·      Building a strong team culture fosters collaboration. ·      Vulnerability in leadership encourages trust and openness. ·      Sales planning provides structure without micromanagement. ·      Effective planning translates strategy into action. ·      Balancing structure and autonomy is key to team success. ·      Navigating resistance requires creating a safe environment for dialogue. ·      Authentic leadership involves sharing personal values and experiences. ·      Coaching team members leads to their growth and success. ·      Learning from mistakes is essential for growth. ·      Creating an environment where every opinion is valued is important. ·      The hardest job in the company is often that of a first-line sales manager.  Sound Bites  "Leadership is not a title or a job." "You can't make a hockey team out of football players" "If the team do not see the value, they will not do it" "Have those tough conversations" "The hardest job in the company." "It's all about transparency." "Under big trees, nothing grows." "You can coach their potential."  Book Lennart referred to: 'Dare to Lead: Brave Work. Tough Conversations. Whole Hearts' by Brené Brown He also recommends: 'Authentic Leadership' by Bas Blekkingh Keywords attitude, leadership, sales management, team dynamics, vulnerability, planning, characteristics of managers, team culture, resistance, authentic leadership, growth, servant leadership, mistakes, success, team building, sales strategies, personal development, coaching

    26. Lennart Sigterman Leadership and Planning
  8. 06/24/2025

    25 Andrew Smyth: Leadership and Customer Relationships

    In this podcast conversation, Andrew Smyth shares his unique journey from being a tradesperson to becoming a successful sales person, sales manager, and senior leader. He emphasizes the importance of understanding customer perspectives, effective communication, and the need for visibility in leadership roles. Andrew discusses the characteristics that make an effective sales manager, including listening, involvement, and recognition of team members. He also highlights the differences in managing employees versus contractors and the significance of maintaining relationships in both contexts. The conversation concludes with insights on how recognition and motivation play crucial roles in driving sales performance. We discuss the importance of building strong customer relationships, and the role of sales managers in engaging with customers. We also explore strategies for effective joint calls, the intelligence a managers needs in customer interactions, and the responsibilities of salespeople in maintaining accountability. The conversation emphasizes the need for appreciation, communication, and understanding in the sales process, highlighting how these elements contribute to overall sales success. Andrew also shares his insights on transitioning from a peer to a sales manager, emphasizing the importance of establishing the identity of the Sales Manager while maintaining authenticity. He discusses the challenges of managing experienced salespeople and the necessity of addressing issues with empathy and openness. Andrew highlights the significance of making mistakes as a learning opportunity and the importance of celebrating successes, no matter how small. He reflects on his own experiences, sharing powerful valuable lessons learned from making decisions in his management role, and concludes with a powerful message about the importance of kindness and authenticity in leadership. You can see Andrew's  profile at https://www.linkedin.com/in/andrew-smyth-06a54677/ Key Takeaways • Listening and involving team members in decisions is vital for new sales managers. • Recognition for salespeople can take many forms, including incentives and personal acknowledgment. • Sales managers should balance data analysis with personal engagement. • Salespeople value autonomy and recognition for their achievements. • Building relationships with contractors requires a different leadership approach. • Recognition can come from simple words of appreciation. • Joint calls should focus on adding value to the salesperson. • Sales managers must respect the salesperson's relationship with customers.. • You need to cast your identity as a sales manager. • What you walk past, you condone; set clear standards. • Own your mistakes instead of blaming your team or others. • Celebrate successes, no matter how small. • Recruiting the right people is a significant triumph. • Be brave, bold, authentic, and kind in leadership. Sound Bites "You still need to be visible." "You need to be able to engage your manager." "You can't beat being together." "A customer doesn't need to understand. They have a choice" "Be super, super interested in the customer." "Make your problem my problem." "You have to cast your own identity." "What you walk past, you condone." "Don't be afraid to make a mistake." "Celebrate success, it can be simple." "Be brave, be bold, be authentic, be kind." "Kindness can help business grow." Keywords sales management, leadership, employee engagement, contractor management, recognition, sales strategies, sales recognition, customer relationships, joint calls, sales accountability, leadership, sales motivation, sales management, leadership, mistakes, success, team building, authenticity, kindness, coaching

    25 Andrew Smyth: Leadership and Customer Relationships

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A regular podcast for new sales managers where we interview practising sales leaders in complex B2B. In conjunction with realsalesmanager.com