Coaching Enterprise Sellers on Managing Multi-Million Dollar Tenders
Designed for Senior Sales Managers coaching enterprise sellers responsible for strategic, high-stakes deals involving multi-million dollar public and private sector tenders to spark real collaboration and high-energy learning.
A 3-hour in-person workshop with senior sales leaders responsible for coaching enterprise sellers on high-value opportunities. These leaders often struggle to move beyond surface-level deal reviews, face resistance from confident sellers, and lack confidence in how to coach through lengthy, high-pressure tender cycles. The session is held in a dedicated training suite, with mixed tables to spark cross-team learning.
Tender Tales: Mystery Case Teaser
Participants receive a one-page anonymized deal summary, with select details redacted, from a real Fortune 500 tender that went sideways. They work in pairs to jot down three burning questions they want answered. The facilitator then reveals the true outcome, building intrigue for the session.
Tap to view the full activity.
Why this works
This primes curiosity and stakes by hinting at complexity and uncertainty, and makes the relevance of coaching tangible.
The Winning Myth: Spot the Trap
Show a series of bold statements (e.g., ‘Lowest price always wins’, ‘If the RFP is published, it's too late to influence’) on slides. Participants vote ‘myth’ or ‘reality’ using colored cards, then discuss real-world counterexamples in small groups.
Tap to view the full activity.
Why this works
Confronts deeply held misconceptions that block effective coaching, and opens up space for unlearning.
Silent Coaching Carousel
Participants rotate in trios. Each shares one sticky coaching challenge they face (e.g., ‘My seller is too reactive to RFPs’), while the others silently write down clarifying questions or first-step advice. No talking—just written notes passed along at each rotation.
Tap to view the full activity.
Why this works
Reduces pressure to perform, encourages thoughtful peer feedback, and surfaces common patterns without judgment.
Accelerated Bid War Game
Teams are given a fictional, high-stakes RFP scenario and 15 minutes to plan a coaching approach for their 'seller.' Midway, a 'surprise' email (e.g., new competitor, shifting budget) disrupts their strategy. Teams must quickly adapt and pitch their revised coaching plan in 60 seconds.
Tap to view the full activity.
Why this works
Simulates real-world urgency, uncertainty, and the need for agile coaching—engages competitive and collaborative energy.
The Fork-in-the-Road Decision
Present a true-to-life coaching dilemma: e.g., ‘Your seller is pushing to discount heavily to secure a deal, but you sense the buying committee values long-term partnership. You have a 30-minute 1:1—what do you coach on?’ Participants debate in two groups, then defend their stance.
Tap to view the full activity.
Why this works
Anchors learning in messy, real-world dilemmas where there’s no single right answer, sharpening practical judgment.
My Coaching Playbook: Signed & Sealed
Each participant fills in a ‘Coaching Playbook’ worksheet: one actionable commitment for each tender stage (pre-bid, bid response, negotiation, post-award), plus a ‘red flag’ to watch for in their next deal. They pair up to exchange and sign each other’s playbook as a pact.
Tap to view the full activity.
Why this works
Personalizes learning, creates accountability, and bridges workshop insights to real deals.
Sign up to unlock 3 more activities
Get the full pack, facilitation flow, and more ready-to-run ideas.