Stepping into a new enterprise organisation as a sales leader is no small task. Expectations are high, and the pressure to deliver results quickly can be overwhelming. To navigate this transition successfully, you need a clear, methodical approach. The framework outlined below is designed to help you diagnose your sales organisation’s strengths and weaknesses in the first 90 days, enabling you to build a solid foundation for growth without falling into the trap of trying to fix everything at once.
Days 1–30: Team & Pipeline Deep Dive
In the first month, your focus should be on understanding the current reality of the organisation. Resist the temptation to make big moves at this stage; instead, prioritise listening, observing, and identifying patterns.
Key Actions:
- 1:1 Meetings with Reps
- Conduct individual meetings with each sales representative.
- Explore their approach to deal inspection and client relationship management.
- Focus on listening to uncover how they sell rather than just what they sell.
- Pipeline Audit
- Dive deeply into the sales pipeline, examining not just the numbers but the stories behind them.
- Evaluate forecast accuracy by scrutinising deals labelled as “about to close.”
- Win/Loss Analysis
- Review the last six months of win/loss data.
- Pay special attention to lost deals, as they often reveal systemic issues that may be impacting sales performance.
Red Flags to Watch For:
- Sales reps who struggle to articulate their customers’ business problems.
- A pattern of massive end-of-quarter deal pushes.
- Over-reliance on discounting as a tactic to close deals.
Days 31–60: Systems & Process Analysis
Once you have a clear understanding of the team’s dynamics and the state of the pipeline, shift your focus to examining how the work gets done. This phase will highlight inefficiencies and gaps in the sales processes and systems.
Key Actions:
- Shadow Discovery Calls
- Observe sales representatives during discovery calls.
- Evaluate their ability to ask insightful, relevant questions rather than focusing on pitch delivery.
- Audit Tech Stack Usage
- Assess the adoption and effectiveness of existing tools.
- Low adoption rates often indicate broken processes rather than faulty tools.
- Review Account Plans for Top Customers
- Analyse the account plans for your organisation’s top 10 customers.
- Look for evidence of strategic thinking, such as long-term goals and actionable insights.
Warning Signs:
- Inconsistent sales methodologies across teams, leading to unpredictability in outcomes.
- Misalignment between sales and customer success teams, particularly if the latter is surprised by closed deals.
- CRM systems with missing or outdated documentation, reflecting poor data hygiene and process discipline.
Days 61–90: Strategic Realignment
With a comprehensive understanding of your organisation’s people, processes, and tools, the final phase involves connecting the dots and creating a strategic plan for improvement.
Key Actions:
- Align Ideal Customer Profile (ICP) with Closed Deals
- Map your ICP against actual closed deals to identify where your positioning and targeting may be misaligned.
- Assess Competitive Intelligence
- Evaluate your team’s understanding of why they win or lose against competitors.
- If this knowledge is missing, it’s a critical gap that must be addressed.
- Review Territory Design and Quota Capacity Planning
- Analyse how territories are defined and whether quota assignments align with realistic opportunities.
- Misalignment in these areas is often a root cause of underperformance.
Why This Framework Works
Many incoming sales leaders fail by trying to address every problem simultaneously. The key to success lies in understanding the nuances of your organisation before taking action. This phased approach ensures you diagnose problems accurately, prioritise effectively, and build trust within your team.
By the end of 90 days, you’ll have a clear understanding of your sales organisation’s strengths, weaknesses, and opportunities for growth. Most importantly, you’ll have a roadmap for driving sustainable success while avoiding the pitfalls that trip up so many new leaders.
