Deal Strategy Conversations Banner

The Art of Holding Deal Strategy Conversations

By Les Yuen, DealCoachPro

Three Impactful Approaches High-Performing Enterprise Sellers Practice for Deal Strategy Conversations

Deal pursuit has never been more challenging than it is right now. The number of stakeholders in a deal continues to rise. Today, there are an average of 7 decision-makers involved in the B2B buying process. Buyers tend to be more risk-averse, which further extends the sales cycle. For those of us in high-value pursuit, failing to get just one of our commit deals over-the-line on time results in missed quota. The sad news, it is happening a lot!

Sellers need more help with deal strategy and execution to make quota. According to Gartner, “High performing managers focus coaching on customer-facing, deal-level activities as opposed to long-term skill-building.”  In this article, we examine what is wrong with status quo, why sales management must commit to a better way, and three practical approaches for optimizing deal strategy conversations and focusing sellers efforts on deal activities that close deals.

The Status Quo is Your Biggest Threat

As a sales leader, coach and seller, I have been on both sides of deal reviews and strategy conversations. Three everyday observations I have witnessed during these conversations actively encourage wrong behaviors, inaccurate forecasts and waste sellers time:

  1. Assume the outcome of the conversation is to build the win-plan
  2. Put sellers in the hot-seat and make them “defend” the Deal
  3. Gut-feel is the basis for strategy conversations

Assume The Outcome of the Conversation is Enhancing the Win-Plan

Most sales operations adopt a formal deal qualification at kick-off using a framework such as MEDDICC, BANT and others.  Given we have established that the status of a deal can change in a heartbeat, it is astonishing that so few deal strategy conversations start with “let’s check that it still makes sense to pursue this deal.” A deal can move from closing this quarter to dead overnight. Who has not lost a late-stage deal because a critical stakeholder moved on or a new buyer with a different agenda or preferred vendor stepped in?

Sellers Have to ‘Defend’ the Deal

Asking sellers to defend deals is the classic case of “motivation drives (wrong) behaviour.” Be careful what you wish for. Ask sellers for a 3X pipeline, and that is what they will give you (without regard to quality). Ask them to ‘defend’ their deal, and that is what they will do. Instead of asking “where are the weaknesses in our win-plan?” and “what assumptions do we need to challenge?” Sellers ask themselves, “how should I respond to a challenge from my boss” or worse, “what information do I need to hide?”

Sellers need the help and the experience that sales leaders hold. Ask yourself: What is the most effective way of working with sellers that adds value, builds trust and delivers results?  Attacking a deal win-plan and poking holes in it is an old-school mentality, and it does not work with me!

Gut-feel is the basis of strategy conversations

Back in the day, sales teams would pile into a ‘war room’ for a deal strategy conversations. We used hard copy company reports to discuss the opportunity and deal strategy and capture the plan on a whiteboard (yes, I am that old.)  We eventually upgraded to using information from CRM and manually stripping it out into spreadsheets, blue sheets and the dreadful PowerPoint as the basis for a strategy conversation. Today, many organizations are still using these old-school methods, enhanced by using online conference rooms rather than meeting rooms, of course.

The sales stage in the CRM and gut-feel of the sellers are a poor indicator of true deal health and position. Asking your sellers to take time out from selling activities to manually fill out a presentation and then defend it for an hour is unlikely to create the conditions for an engaging and productive session.  Sellers and teams spend more time collecting and talking through the data then having thoughtful, strategic conversations and deal collaboration sessions.

The Better Way to Impactful Deal Strategy Conversations

We have explored some fundamental flaws with the traditional approach to holding deal strategy conversations and how that impacts sellers’ performance and perpetuates the friction between sellers and leaders. Sales leaders that have mastered the art of holding deal strategy conversations approach these conversations differently. Below are three impactful approaches to adopt today to optimize deal strategy conversations and maximize seller’s success rate:

  1. Create the right conditions that naturally drive the right behaviors
  2. Act like a deal coach rather than a boss
  3. Apply a standard framework

Create the right conditions that naturally drive the right behaviors

Abandon outdated practices and expectations that drive wrong behaviors and perpetuate friction, such as expecting sellers to maintain a 3X pipeline is. Do not set unrealistic expectations. Sellers are more open to qualifying out weaker deals following a deal conversation to focus on the more winnable ones. Start every conversation with “OK, first let’s check where we are in this deal and with the key stakeholders today and decide if it is worth continuing to pursue.”

Act like a deal coach rather than a boss

During the conversation, forget you are the boss! Walk in your sellers’ shoes. If this was your Deal, would you invest your time in it? Can you genuinely see it closing as forecast?

Instead of simply poking holes in the win-plan, ask great coaching questions. This builds trust and helps to develop skills they can apply to the next deal. Contribute to advancing the deal – sometimes, a call from you to a key stakeholder can unblock a stalled deal. Roll up your sleeves. Your sellers will appreciate it.

Apply a standard framework and measures

It is easier to reach an agreement about deal strategy (including the outcome of “let’s qualify this one out”) when everybody is working to the same standards.

Using agreed measures to evaluate deal status, strategy, and next steps in place of CRM stage and sellers and leaders opinions reduces friction and drives consistency.

Mastering the art of holding deal strategy conversations is a straightforward concept. It starts with a decision by leaders to challenge the status quo. Changing behavior may seem daunting. Take small steps: Start with a few sellers and apply your new approach. Be bold and win faster!

Lesheadshot Circle Png

Les Yuen

VP Sales, DealCoachPro

DealCoachPro’s data-driven deal coaching software drives deal execution for modern pursuit teams. Our patented framework brings rigor and rhythm to deal pursuit, helping send better signals about deal health. Visual heat maps bring more clarity to deal legitimacy and buyer relationship status, while the framework guides sellers on the next actions to pursue to strengthen relationships and advance deals. Our data-driven deal-coaching software boosts sales effectiveness and win-rates. DealCoachPro is a private SaaS company headquartered in Delray Beach, Florida.