By
Simon Hazeldine
Sales leadership is not just about driving revenue. It is about shaping culture, holding people accountable, and making the tough calls that others avoid. Yet many sales leaders hesitate when it comes to difficult conversations. They soften the message, delay the dialogue, or sidestep it altogether.
The result? Underperformance lingers, bad habits spread, and credibility erodes.
If you want to be an elite sales leader, you must master what I call Commercial Courage: the willingness and ability to have the tough leadership conversations that protect performance, values, and long-term growth.
Here are the five conversations that matter most.
1. The Underperformance Conversation
The most avoided conversation in sales leadership is also the most necessary. Allowing consistent underperformance sends a message to the entire team that mediocrity is tolerated.
How to handle it:
- Start with clarity. Be specific about where performance is falling short.
- Be direct but supportive. “Right now, you are 27% below target and this trend has been consistent for three months. Let’s discuss the changes you need to make to turn this around.”
- Agree on an action plan. Define milestones, timeframes, and support available.
Failing to address underperformance quickly turns a performance issue into a cultural issue.
2. The Unethical Behavior Conversation
Sales leaders sometimes spot behaviors that might technically “deliver results” but undermine trust. Examples include sandbagging, manipulating CRM data, or making promises the company cannot keep.
How to handle it:
- Zero tolerance. Be clear that results achieved through unethical means are unacceptable.
- Focus on principles. “Our reputation is worth more than any deal. If we sacrifice integrity, we destroy trust with customers and colleagues.”
- Redirect to standards. Reinforce the values and code of conduct, not just the numbers.
When leaders dodge this conversation, they silently condone the behavior.
3. The Strategic Alignment Conversation
Sales teams often waste energy on opportunities or activities that do not align with the company’s strategy. A courageous leader must challenge reps, or even senior colleagues, who are pulling resources in the wrong direction.
How to handle it:
- Link to the bigger picture. “This opportunity is attractive, but it diverts us from our core market focus. Here is why we need to prioritise differently.”
- Back decisions with data. Use win rates, pipeline analysis, and customer lifetime value to illustrate the point.
- Make trade-offs explicit. Great leaders help teams understand not just what to do, but what to stop doing.
4. The Ambition-Setting Conversation
Sometimes, the tough conversation is not about pushing back, but about raising the bar. Many reps underestimate their potential, settling for “good enough” performance. The best leaders challenge people to aim higher.
How to handle it:
- Frame it positively. “You consistently hit quota, but I believe you are capable of achieving more.”
- Provide evidence. Highlight strengths, past performance spikes, or unique skills.
- Offer stretch support. Pair ambitious goals with resources, coaching, and recognition.
This is not about applying reckless pressure. It is about helping people see possibilities they cannot yet see themselves.
5. The Peer or Executive Challenge Conversation
Perhaps the hardest conversation for many sales leaders is not with their reps, but with peers or senior executives. Whether it is pushing back against unrealistic targets, challenging poor cross-functional collaboration, or questioning a flawed strategy, commercial courage means speaking truth to power.
How to handle it:
- Ground in data. Emotion alone will not persuade, but evidence combined with conviction will.
- Position as business-focused. “My concern is not personal. It is about the risks to revenue, customer satisfaction, and long-term growth.”
- Stay calm under pressure. Model professionalism even when disagreeing.
When sales leaders bite their tongue with executives, the entire sales team suffers the consequences of misaligned decisions.
Why Commercial Courage Matters
Sales leadership is a privilege, not just a position. The real test of leadership is not when things are easy, but when conversations are tough. If you shy away from these five dialogues, you fail to protect your team and your business.
If you embrace them, you set the tone for a high-performance culture rooted in accountability, integrity, and growth.
So ask yourself: Which of these conversations are you avoiding? And what is it costing your business every day you stay silent?
Commercial courage is not optional. It is the defining characteristic of sales leaders who drive sustainable success.
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About the author
Simon Hazeldine works internationally as a revenue growth and sales performance speaker, consultant, and coach. He empowers his clients to get more sales, more often with more margin.
He has spoken in over thirty countries and his client list includes some of the world’s largest and most successful companies.
Simon has a master’s degree in psychology, is the bestselling author of ten books that have been endorsed by a host of business leaders including multi-billionaire business legend Michael Dell and is co-founder of leading sales podcast “The Sales Chat Show”.
He is the creator of the neuroscience based “Brain Friendly Selling”® methodology.
Simon Hazeldine’s books:
- Neuro-Sell: How Neuroscience Can Power Your Sales Success
- Bare Knuckle Selling
- Bare Knuckle Negotiating
- Bare Knuckle Customer Service
- The Inner Winner
- How To Lead Your Sales Team – Virtually and in Person
- Virtual Selling Success
- How To Manage Your People’s Performance
- How To Create Effective Employee Development Plans
- Virtual Negotiation Success
