The Transaction

Steak Dinners Don’t Close Deals with Maria Boulden - Ep 47

Mar 20, 2025

Join Maria Boulden, a seasoned sales expert with over 30 years leading sales teams at DuPont and Gartner, as she shares her energetic insights on modern sales. She humorously debunks the myth that steak dinners close deals, emphasizing the need for authentic connections instead. Maria advocates for senior leaders to engage directly with front-line sellers and adapt to today’s B2B dynamics. With stories of leadership challenges and the importance of personal relationships, she offers invaluable advice for navigating the evolving sales landscape.

58:42

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Episode guests

Maria Boulden

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Episode notes

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Quick takeaways

Steak dinners are no longer effective for closing deals as buyers prioritize substantive value and insights over casual interactions.

Sales leaders must engage with frontline sellers to build trust, boost morale, and ensure alignment with corporate strategies.

Companies must proactively adapt to evolving market dynamics rather than relying on outdated methods or hoping for a return to normal.

Deep dives

The Shift in Sales Techniques

Traditional sales methods, such as securing deals through casual interactions like steak dinners, are now considered outdated. In the current business climate, relying on established relationships or informal dinners for closures is ineffective, especially when addressing significant deals. Recent trends show that buyers expect more substantive value and insights rather than mere social engagements. This shift calls for a transformation in sales strategies that focus on providing genuine, impactful solutions rather than relying on outdated social techniques.

Intro

2min

Evolving Sales Strategies and Leadership Insights

21min

Is the Steak Dinner Tradition Outdated in Modern Deal-Making?

3min

Evolving Sales Strategies in B2B

26min

Navigating Leadership Challenges: From Ask Holes to Pre-Mortems

4min

Lighthearted Reflections and Sports Celebrations

3min

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.

Sponsored Segment

The Transaction is sponsored by Ringmaster, on a mission to create connections through Branded podcasts. Learn more at https://ringmaster.com/

Interested in becoming a sponsor of The Transaction? Contact thetransaction@samguertin.com

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

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.

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