Qualification Worksheet

A structured set of questions to qualify, shape, and win complex opportunities.

• Client:

• Opportunity:

• Date:

• Team Lead:

• Primary Competitor(s):

• Estimated Value:

• Stage:

• Next Milestone:

1. Why Would They Buy? (Pain & Value Proposition)

·  Do their stated priorities truly drive decisions and behavior—or are they mostly messaging?

·  Are those priorities reflected in what they measure, fund, and reward?

·  What have you observed that confirms their real values and priorities?

·  What evidence supports this, and how can you help them advance what matters most?

·  Have you validated your understanding externally (customers, analysts, partners, public sources)?

·  Can you link this opportunity to relevant industry trends?

·  Are the client’s issues primarily driven by industry-wide forces or company-specific circumstances?

·  Which KPIs matter most to the client?

·  Are any KPI shortfalls symptoms of deeper (dormant) pain?

·  Do they need a culture or behavior shift to meet the challenges they face?

·  Who are the internal catalysts for culture change?

·  Are requirements defined—by whom—and what business drivers sit behind them?

·  What issues matter most right now, and what’s likely to matter next?

·  Can you ethically and credibly reframe the issues in your favor?

2. Differentiation

·    If this is an existing client, what criteria are you using to evaluate their level of satisfaction?

·    Do you know how the company views your competitors?

·    If there is no relationship, how will you learn how they view you (and the market)?

·    Are you doing work for any of the client's customers?

·    Are you doing work for competitors of the client?

·    Are you doing work for a business partner of the client?

·    Do you have relationships with these organizations (outside forces on the client) that can be leveraged in the sales effort? Does your competitor?

·    Have you considered collaborating with other business partners to strengthen your position?

·    Why have you chosen your winning strategy?

·    How will the competitor try to neutralize it?

·    Do these strategic benefits tie directly to the critical business issues you identified?

·    How will you state these benefits in a compelling, client-specific way?

·    Why have you proposed this solution?

·    Are you proposing what the customer says they want - or what they truly need?

·    If there are potential showstoppers, have you identified and assessed them?

·    Have you assessed mutual fit (technical, functionality, professional services, methodology, price, culture)?

·    What could cause your strategy to fail - and what is your mitigation plan? 

3. Why Now? (Their Urgency)

·    What is the client trying to accomplish, and how do you fit?

·    Why are these issues important to the client right now?

·    How do you know these are critical issues? What is your source?

·    Is this what senior management is focused on? Who verified it?

·    Do you understand the impact of these issues on their business (financial, operational, reputational, strategic)?

·    What impending event, deadline, or risk is driving action now?

·    Have you confirmed the source of urgency with someone who has power?

·    What could cause the urgency to change or fade?

·    What is the consequence of delay (business impact or political fallout)?

·    What is the cost of lost benefits if the client does not move forward?

4. How Much Is the Opportunity?

·    Value, discount, and scope - what is the current estimate?

·    How confident are you in the estimate, and what assumptions drive it?

·    What is the client's experience buying and implementing similar solutions?

·    Is that experience an advantage or a disadvantage for you?

·    Is the project budgeted? If not, can funding be made available - and by whom?

·    Is the business problem large enough to motivate the client to buy?

·    What stage of evaluation are you in right now?

·    Is your sales cycle in sync with the client's buying cycle?

·    When will they decide?

·    Is momentum increasing or decreasing? Why?

·    Given the decision process and urgency, does the process advantage you or a competitor?

·    Are there other projects or events that could threaten or delay this initiative?

5. Who Cares?

·    Have you spoken with people across the client organization (beyond your immediate contacts)?

·    Who will personally benefit from the outcomes you are proposing?

·    What criteria do they believe will be used to differentiate vendors?

·    In whose opinion?

·    Are the criteria prioritized?

·    Who are potential influencers (formal and informal)?

·    How confident are you in this stakeholder intelligence?

·    Who is giving you inside information, and why?

·    Have you confirmed this information with multiple sources?

·    Have you personally called on all of these people? If not, how do you know this information is accurate?

·    Do you have a power sponsor - and are they politically astute?

·    Do they have the power to influence the decision?

·    Who supports your competitors - and why?

·    What is your strategy for managing them (change preference, outvote, disconnect, or discredit with facts)?

·    Does this project have a political sponsor?

6. Who Matters? (Decision Process & Politics)

·    How do the benefits tie to the agendas of powerful stakeholders?

·    Are the requirements likely to change in the 'crucible' stage?

·    Do you have access to the right people to address major blind spots?

·    If the client had to vote today, would you win or lose? Why?

·    Is there a defined decision-making process?

·    What phase of the client's decision-making process are they in?

·    How do they think they will decide?

·    In whose opinion?

·    What could change the process?

·    What is their approval process?

·    Who else could become involved?

·    Is corporate or board approval required?

·    If and when the decision-making process turns political (the 'Crucible Effect' - see below), what do you predict will happen?

·    Who have you not called on that could have major pain or power to influence the decision?

7. What Next? (Action Plan)

·    What is your sales objective (frontal, flanking, fractional)?

·    If it is too early to set one, when will you decide? (Add to the tactical action plan.)

·    How will you gain and document a client commitment?

·    How will you communicate the plan to the rest of the team?

·    Do you have the resources to execute your strategy?

·    Do you have the right people to execute the strategy?

·    Are your tactics consistent with your strategy?

·    Are your tactics helping you gain control of the sale - or are you reacting to the client/competitor agenda?

·    Do the action plans address the major blind spots?

 Key Concept: The Canyon and the Crucible

The 'Canyon' and the 'Crucible' describe critical, high-pressure phases in complex competitive evaluations where deals often fail due to political misalignment or buyer indecision.

The Canyon: The Information Gap

·    Momentum loss: early excitement fades and the deal enters a 'limbo' state where stakeholders lose focus.

·    Political disconnect: the sale stalls when the team relies on a funnel instead of understanding the political power of the internal champion.

·    Probability trap: pipelines may assign 10-20% probability here, but if momentum has not crossed a threshold, the true probability can be near zero. 

The Crucible: The Pressure of Decision

·    Stakeholder division: buying organizations form divided camps with conflicting priorities, creating a political battleground.

·    Indecision and fear: many losses are due to inability to commit, not preference for a competitor.

·    JOLT response: high performers reduce indecision by judging it, offering recommendations, limiting exploration, and taking risk off the table. 

Strategies to Cross the Canyon and Survive the Crucible

1. Identify the power champion: ensure your sponsor has the political capital to push the deal through when momentum fades.

2. Focus on loss aversion: address fear of messing up (FOMU) in addition to fear of missing out (FOMO).

3. Limit research late in the cycle: prevent analysis paralysis by limiting new exploration and keeping the team aligned.

4. Control the narrative: use clear storytelling to frame the decision as a necessary evolution, not a risky disruption.

Notes / Observations