246 (Lead) Challenging Your Reps on Their Deal Risks (Chris Surdi, Ascend)

This is an except from the Daily Sales Show by Sell Better with Will Aitken Check out the full show here: https://sellbetter.xyz/daily-show/how-to-book-more-meetings-with-these-cold-call-strategies

Mark & Armand link up live and in person to discuss the when, how, and who of promoting sales reps to sales managers ACTIONABLE TAKEAWAYS: Efficacy in Sales Management: A sales manager’s primary job is to ensure team efficacy while fostering a supportive environment. Effective managers don’t just oversee but actively build up their teams. Conscious Competence: It’s crucial for managers to understand the "why" behind their actions. Recognizing the reasons behind effective strategies allows managers to drive consistent, purposeful change. “Taste Test” Before Promotion: Before fully promoting someone to a managerial role, conduct a "taste test" over a quarter to assess fit. Evaluate if they enjoy the role, excel at it, and if their team gravitates toward them as a leader. Avoid Common Frictions: Avoiding favoritism, limiting who can apply, or promoting based on performance alone (i.e., “super reps”) can lead to friction. Open opportunities for all and emphasize leadership skills over individual sales metrics. RESOURCES DISCUSSED: Join our weekly newsletter Things you can steal

ACTIONABLE TAKEAWAYS: Provide Hypotheses, Not Generic Questions: Instead of broad questions, offer informed hypotheses to invite deeper discussion. Ask Questions to Guide Next Steps: Use questions to guide the process without being pushy, keeping the prospect engaged. Teach Process Over Just Problems: Beyond identifying issues, recommend processes (like a custom demo over a POC) to build trust. Uncover Intent Behind Extra Steps: When extra steps are requested, ask what they aim to learn to suggest simpler options. DAN'S PATH TO PRESIDENTS CLUB: Senior Vice President of Global Sales @ Challenger VP of Sales, Account Management @ Challenger VP of Sales, Major Accounts @ Challenger Managing Vice President, Sales & Community @ Evanta RESOURCES DISCUSSED: Join our weekly newsletter Things you can steal

Free Guide: 3 Tactics to Drive Mid-Funnel Deals to Close FOUR ACTIONABLE SALES TAKEAWAYS Do not spend excessive time researching when sometimes calling the account may be the fastest way to get information Be like the restaurant that is calling you to make a reservation to avoid no shows, send reminders, and set an agenda ahead of time When telling a customer story describe the persona who felt the problem, the annoyances they felt, the scenery they were in when they felt the problem, and the emotions they felt If confirming a meeting within one week send a reminder the day before if confirming a meeting more than a week out do a 1 week and day before reminder PATH TO PRESIDENT’S CLUB VP of Sales @ Boomerang Chief Revenue Officer @ Table Needs VP of Fundraising & Business Development @ Table Needs Head of Sales & Business Development @ Table Needs RESOURCES DISCUSSED Join our weekly newsletter Things you can steal

ACTIONABLE TAKEAWAYS Foster belonging to engage the prefrontal cortex: Sales reps thrive when they feel they belong, as it activates their prefrontal cortex, leading to passion—a key trait in top reps. Start with one-on-one exercises before group activities: Begin with individual sessions like "Rosebud Thorne" to ease reps in before moving to larger group exercises. Use the 'Four H's' to build deeper connections: Ask reps to share four things—history, a hero, a heartbreak, and hope—to foster trust and authenticity. Gradually share personal insights: Start by setting the example, then have reps journal, share one-on-one, and finally share with the group, building comfort step by step. ALEX'S PATH TO PRESIDENTS CLUB Founder & CEO @ Alluviance Director of Sales Commercial @ Outreach Director of Sales Corporate @ Outreach Territory Account Executive @ Microsoft RESOURCES DISCUSSED Alex's Arise Retreat Join our weekly newsletter Things you can steal

ACTIONABLE TAKEAWAYS Know Competitors' Fiscal Periods: Be aware of when your competitors’ fiscal periods end to anticipate price drops and position yourself better. Phased Approach: When price matters, propose only the essentials for day one to make your quote smaller and easier to accept. Timeline Stack: Identify key timeline drivers, like contract end dates or business seasonality, to create urgency. Turn Want into Why: During discovery, dig deeper to find the real business problem behind a customer’s desire for change. JOHNNY'S PATH TO PRESIDENTS CLUB Commercial Account Executive @ Talkdesk Enterprise Sales Development Manager @Talkdesk Team Lead, Enterprise Sales Development @ Mimeo Enterprise SDR @ Mimeo RESOURCES DISCUSSED: Join our weekly newsletter Things you can steal

TOP FOUR ACTIONABLE TAKEAWAYS Incorporate GIFs or Venn Diagrams in prospecting emails to capture attention effectively. When prospects mention a competing solution, ask how long they've used it and what prompted their choice to uncover their unresolved needs. Direct prospects back to email in voicemails; keep initial messages brief and contextual, saving detailed information for follow-ups. Structure emails to expand on voicemail content, addressing specific pain points or presenting case studies to encourage engagement. LYLLE'S PATH TO PRESIDENTS CLUB Senior Manager, Business Development @ RocketReach Manager, Business Development - Enterprise @ Shopify Manager, Business Development - Enterprise @ Angi SMB Account Executive @ Angi RESOURCES DISCUSSED 8 Ways to Triple Your Phone Connects and Email Opens Join our weekly newsletter Things you can steal

ACTIONABLE TAKEAWAYS: Signal Prioritization: Categorize signals (e.g., high-intent, time-based) with different response SLAs to ensure timely outreach. Call Blitz Culture: Multiple weekly call blitzes with a virtual sales floor create a high-energy, team-building cold calling environment. Effective Personalization: Don’t rely on signals alone; combine them with company insights to craft personalized, compelling outreach. 80/20 Email Framework: Provide reps with an 80% completed template (signal, company insight, ideal state, light CTA), letting them personalize the final 20%. FLORIN'S PATH TO PRESIDENTS CLUB: Head of Sales Development @ Common Room Director of Sales @ Barley Senior Manager, Sales Development @ Loopio Manager, Sales Development @ Loopio RESOURCES DISCUSSED: Join our weekly newsletter Things you can steal

ACTIONABLE TAKEAWAYS: Facial Expressions Control Tone: Your facial expressions influence your tone. For example, leaning in creates a concerned tone, while tilting your chin up can convey curiosity. Slow Down Your Questions: Asking questions too quickly leads to poor answers. Slow down the second half of your question to give prospects time to think and respond meaningfully. Master the Five Types of Tone: Use different tones—curious, confused, concerned, challenging, and playful—to guide conversations and elicit the right responses. Challenge Prospects with a Direct Tone: A challenging tone helps push prospects to take action, especially when addressing tough issues like low-quality leads. JEREMY'S PATH TO PRESIDENT'S CLUB: Founder @ 7th Level VP of Sales @ Pinnacle Security RESOURCES DISCUSSED: Join our weekly newsletter Things you can steal

FOUR ACTIONABLE TAKEAWAYS To learn about what’s going on in other parts of your organization, get on the email alias distribution lists. Build out your go team of people that you can rely on in legal, product, marketing, deal desk, etc. so that you’re never stuck trying to figure out how to get a function to help you with a deal. To determine the next steps and what’s important to a buyer, ask, “Say you’re evaluating a few technologies, and they’re similar. What are the things that make you pick one over the other?” When dealing with technical buyers, always under promise so you don't lose credibility. PATH TO PRESIDENT’S CLUB Named Account Manager - Digital Natives UK @ Databricks Named Account Manager - Digital Natives @ Databricks Snr Manager, Commercial Sales, ANZ @ Databricks Enterprise Account Executive @ Databricks RESOURCES DISCUSSED Join our weekly newsletter Things you can steal