At our October Connect To Market Growth Roundtable, Steve Kahan, Marketing Advisor at Insight Partners, joined us for a lightning talk on creating urgency. His message was simple but powerful: stop leading with features and functions, and start helping buyers understand the size, magnitude, and urgency of the problem you solve. The conversation sparked so many great questions from our community that we couldn’t fit them all in. So we asked Steve to answer a few more here.
Question: How do we get prospects beyond surface-level requirements?
Answer: I’d ask: “Beyond the requirements you’ve listed, what business problem are you really trying to solve and what happens if you don’t solve it?” Then: “Who feels that impact, and what does it cost?” You want the buyer talking about consequences, not checking boxes.
The Key: If buyers define the conversation around features, they’ll compare you on features. Help them see the cost of the problem, and they’ll evaluate you on value.
Question: How do technical champions sell identity recovery to leadership?
Answer: Give the technical champion a business conversation, not another technical deck. Ask: “If identity services went down tomorrow, which operations stop? How long could you function? How fast could you recover?” Put the answers on one page: exposure, consequences, confidence in recovery, and next action. Help the champion speak the CFO’s language.
The Key: Your technical champion doesn’t need more product knowledge. They need a business case that gets the CFO’s attention.
Question: Why is cost-of-inaction modeling less common than ROI?
Answer: Mostly because we’ve trained teams to prove what a product is worth, not what the status quo costs. ROI asks, “What do I gain?” Cost of inaction asks, “What do I keep losing if I wait?” The second takes better discovery and credible customer inputs. Start with three to five cost drivers. Don’t make it a science project.
The Key: ROI gives buyers a reason to invest. Cost of inaction gives them a reason to invest now.
Question: Does cost of inaction have to be financial?
Answer: Not at all. Lost time, burnout, anxiety, frustration, customer experience and risk can be just as compelling. Ask how often the problem occurs, whom it affects, and what people can’t accomplish because of it. Measure what you can without forcing a made-up dollar value onto every human consequence.
The Key: Not everything that matters can be measured in dollars. But everything that matters deserves to be understood.
Question: How do we put a dollar value on process improvements?
Answer: Start with the work: how often, how long, how many people, and how much time could realistically be saved? Twenty people saving three hours a week is roughly 3,000 hours a year at 50 weeks. At $60 fully loaded per hour, that’s $180,000 in potential labor capacity - not automatically cash savings. Then ask what the business would do with that capacity.
The Key: Don’t sell hours saved. Sell what the business can accomplish with those hours.
Question: How do we do this with a multi-person buying team?
Answer: Build one business case but connect it to each person’s priorities. IT sees downtime and workload. Operations sees continuity. Finance sees exposure and payback. Leadership sees strategic risk. Ask the team together: “If nothing changes over the next 12 months, what does each of you stand to lose?” Validate the assumptions with everyone.
The Key: You don’t need six different value propositions. You need one important business problem six people can understand in their own terms.
Question: What stops every rep from articulating cost of inaction crisply?
Answer: We tell reps to sell value, then leave them to invent the math. Give them three common problems, Three discovery questions per problem, a simple model, and examples they can use. Put it into deal reviews. Have managers challenge unsupported assumptions. Make it part of how you sell, not an optional slide.
The Key: If cost of inaction depends on an exceptional salesperson, you don’t have a sales strategy. You have a few exceptional salespeople.
Question: Should we use a consultant or AI to build an ROI tool?
Answer: I’d start with AI and a small cross-functional team. Build a simple model with three to five value drivers, pilot it on ten real deals, and check the assumptions with customers and finance. Bring in a specialist or analyst if you need deeper economic research or independent validation for complex enterprise sales. AI can build the tool; it can’t manufacture trust in the numbers.
The Key: AI makes the calculator easier to build. Credibility is what makes buyers believe it.
Question: Do influencers and decision-makers need different ROI versions?
Answer: One model, different views. The technical influencer needs to see feasibility, operational risk and workload. The CFO needs assumptions, payback and downside exposure. The executive sponsor needs business outcomes and why action matters now. Never give different stakeholders contradictory math.
The Key: One business case. Multiple perspectives. One compelling reason to act.
Question: What if our biggest differentiator is service and experience?
Answer: Translate “better service” into the problems it prevents. Ask: “When your current provider lets you down, what happens to your people, customers, operations and deadlines?” Then use evidence - resolution times, escalation performance, customer outcomes to show what changes with you. If service isn’t a real pain point for that buyer, don’t force it.
The Key: Better service isn’t the value proposition. What better service makes possible and what poor service costs is the value proposition.