Skip to main content
The Conversation Roadmap is a step-by-step engagement plan that moves an opportunity from initial discovery to a final decision. Each step is a targeted interaction with specific goals, stakeholders, and outcomes. Start with the end in mind when considering your steps. Be prepared to pivot your roadmap based on the intelligence you gather with each conversation. For example, you may learn of new stakeholders, or you may discover that a client has a strict security or CIO screening process you need to incorporate. Don’t forget to add this new intelligence as an Account Plan Note. ShiftUp Conversation Roadmaps provide a strategic framework, not a rigid checklist. The following decision points will help you align situational reality with the roadmaps found in ShiftUp. Having this roadmap keeps you on track and guides the sales process. Ground Rules for Engagement Before engaging in any conversation, these ground rules should always apply:
  • Who: Who do you specifically want to meet with?
  • What: What is the desired outcome of this conversation?
  • Why: How will this move the conversation forward?

Choose Your Entry Point

Your starting point is determined by the level of insight you currently hold. Choose based on what you need to achieve in that conversation and how to drive to your overall goal. Using the Strategy Hypothesis, consider these points:
  • Active Problem Solving: Is the company actively working to solve the problem stated in your hypothesis? If yes, determine who owns that mission.
  • Validation vs. Discovery: Do you want to validate the hypothesis and gather more information? If yes, you will likely start with a discovery call with a non-executive.
  • Value Point of View: Does the hypothesis provide a strong point of view on the value your company can bring? If yes, you may want to start at the executive level, prepared to discuss successful outcomes with similar companies.
  • Existing Relationships: Have you done business here before? Strategize on complementary approaches, leverage previous success, or gain access through established stakeholder relationships.

Choose Your Initial Stakeholders

Your entry point decisions influence who you engage with initially.
  • Influencer or User: Start here if you are in “data gathering” mode or unsure whether a legitimate opportunity exists.
  • Functional Lead (Director/Manager): Start here if you have a proven track record with similar projects and need to validate a specific initiative.
  • Project Owner - Gaining access to these stakeholders is critical for alignment if an active project exists.
  • Executive/C-Suite: Start here only if you have enough business intelligence to share a fresh perspective on their high-level strategy. Align conversations with the goals of any recent leadership changes.

Choose Your Next Move

Reflect on previous conversations to determine if outcomes were achieved. Consider:
  • Problem/Solution Alignment: Is there agreement on the problem and proposed solution? The business case is a primary document for this alignment.
  • Stakeholder Expansion: Were new key stakeholders identified that you need to connect with? 
  • Gatekeepers: Are there gatekeepers or specific approval layers (like Technical/Security) you need to get past to advance?
  • Proof Points: Does the customer need proof points to be comfortable moving this forward? This could be case studies, demos, POCs, or referrals.

Risk Mitigation

Prevent pursuing unqualified deals or extending cycles through missteps.
  • Agreed Business Case: Have you finalized on a business case with clear success metrics? 
  • Organizational Alignment: Have you met with all key stakeholders, including gatekeepers, to ensure broad alignment? Have you identified the buying committee and process?
  • Ability to Drive Change: Do your contacts have the authority to drive change, or must you engage their leaders? 
Qualification Framework: The MEDDPICC framework is a useful tool to identify risks and the steps needed to de-risk your deal.