Navigating Leadership Challenges: From Ask Holes to Pre-Mortems

You’ll be hard pressed to find a more energetic and experienced sales expert than our special guest, Maria Boulden!

Maria Boulden has spent over 3 decades creating and leading world-class sales teams at leading enterprise organizations like DuPont and Gartner. She brings her incredible experience in multiple verticals and truly unstoppable energy to one of the best conversations yet with co-hosts Matt Amundson and Craig Rosenberg. Maria drops some serious insight bombs in this one, including why steak dinners aren’t the deal closer that they once were, why top execs need to get down to the frontlines to talk with employees, and why ‘not broken’ is not good enough for your company to succeed. 

Additionally, there is some great advice in here about effectively leading change management efforts in your organization, why building personal relationships in SaaS has become so important for B2B sellers, and why you shouldn’t hold a deal signing at a Japanese gentleman’s club. Fueled by an ungodly amount of Coke Zero, Maria really brought it this episode and delivered some incredible stories, which make this a must-watch!

Also, Craig tests out a new hat and Matt admits he can be bought with a burrito. 

Critical Takeaways

• Senior leaders need to be visibly and vocally present with front-line sellers periodically. This not only boosts team morale but also ensures the leader understands the day-to-day challenges and can directly impart strategic guidance.
• Sales teams should focus on providing value and building genuine connections rather than relying on traditional wining and dining strategies.
• Waiting for 'normalcy' to return so you go back to old tactics is not viable. Leaders must guide their teams to adapt to the current market conditions and be prepared for continuous change.
• Conducting “pre-mortem” sessions can be an effective way to anticipate potential failures and mitigate risks before executing significant strategic changes. This approach can foster an environment of proactive problem-solving and better preparedness among the team.
• Helping clients understand their own business better and providing insights creates stronger, more trusting client relationships.

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Chapters

00:00 Intro

00:44 Craig’s Special Hat

02:35 Introducing Maria Boulden

10:39 The Challenge with Channel Partners

19:31 Brazenly Baring It All

23:03 A Quick Conversation Regarding Caffeine

23:43 Steak Dinners have Gone Stale in Sales

33:42 Stories from the Signing Party & Where NOT to Hold One

36:48 Taking a Hands-on Approach to Leadership in Sales

38:17 Unbatten the Hatches & Adapting to Market Changes

41:56 How Executives Should Engage with Their Sales Teams

50:59 Delving into some Delicious Additions to Business Dictionaries

55:30 Wrapping Up

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Epic Quotes

• “ It was not my aspiration that they would have world-class sales skills, it was my expectation.” - Maria Boulden
• “ Not broken is not good enough in this environment.” - Maria Boulden

New Terms

• Donut Run (v): When a rep brings a box of joe and a box of donuts to meet with their distributor and ‘shoot the breeze’ for an hour.
• Ask Hole (n): Someone who continuously asks the same question, but never does anything with the suggestions they receive.
• Pre-Mortem (n): A proactive meeting held before executing a decision, campaign, etc., where the risks are clearly laid out along with what indicators should be monitored to determine real-time progress and what actions need to be taken mid-course.

Connect with Maria

• LinkedIn: https://www.linkedin.com/in/maria-boulden-8a778b11/ 
• Website: https://www.jsjrehoboth.com/ 

Shoutouts

• Dan Gottlieb: https://www.linkedin.com/in/danielpgottlieb/ 
• Dan’s Post: https://www.linkedin.com/posts/danielpgottlieb_good-luck-with-that-ai-theres-no-ai-on-activity-7293698734540955648-rNIz 
• Dan’s Episode: https://open.substack.com/pub/thetransaction/p/triple-t-pov-with-dan-gottlieb?r=3iae7z 
• Nick Toman: https://www.linkedin.com/in/nicktoman/ 
• Nick’s Episode: https://thetransaction.substack.com/p/the-commercial-efficiency-crisis?r=3iae7z 
• Neil Rackham
• Spin Selling: https://a.co/d/1FSFtS1 
• Mark Gustaferro: https://www.linkedin.com/in/mark-gustaferro-3894aa1a5/ 
• Kyle Porter: https://www.linkedin.com/in/kyleporter/ 
• Kyle’s Episode: https://thetransaction.substack.com/p/startup-stunts-and-loving-your-customers?r=3iae7z 
• Brent Adamson: https://www.linkedin.com/in/brentadamson 
• Brent’s Episode: https://thetransaction.substack.com/p/reframing-b2b-sales-to-drive-buyer?r=3iae7z 
• Ted Purcell: https://www.linkedin.com/in/tedpurcell/ 
• Bill McDermott: https://www.linkedin.com/in/billrmcdermott/ 
• Gartner
• DuPont
• Salesforce

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