Last Updated: October 16, 2026
The Inspire Podcast — Practical Leadership for People Who Run Companies
How Client Insights, Conferences, and AI Shape Your Next Strategy
What do your customers really think of you, and what do they want to achieve next year?
In this episode of The Inspire Podcast Executive Series, Jason Diamond Arnold, Director of Leadership Solutions at Inspire Software, sits down with Chris Wollerman, CEO and Co-Founder of Inspire Software, to talk about why your clients belong at the center of your strategic planning, and how to gather what they are telling you before you set next year’s plan.
Watch Inspire’s recent How-To Series Episode related to this podcast: https://youtu.be/7J1igMEtKds
HOW DO YOU BRING YOUR CUSTOMERS INTO YOUR STRATEGY?
- Crowdsource your SWOT analysis through the people who talk to customers most: customer success, sales, and project managers.
- Know who you are serving. The sponsor who buys your product and the users who work in it often want different things, and your strategy has to account for both.
- Don’t wait for a formal score. Lagging signals like a contract performance report or a bad G2 or Capterra review arrive late. Regular face-to-face check-ins help you see problems coming.
- Go where your customers go. Industry conferences show you the trends and priorities your clients are hearing from their own leaders.
- Use AI to find patterns across your client meeting transcripts, and seed your quarterly business reviews with questions about next year’s roadmap.
- Keep the survey simple. A one-question Net Promoter Score survey, plus a follow-up on what would make it a 10, gives you easy-to-benchmark data.
QUESTIONS THIS EPISODE ANSWERS
- Why should customer insight shape your next strategy?
- How do you gather customer input for a SWOT analysis?
- How is what a sponsor wants different from what end users want?
- How do you find out how customers really feel before a bad review lands?
- Where should a small or mid-sized company start collecting customer data?
- Why do industry conferences matter for strategic planning?
- How can AI help you spot trends across client conversations?
- How do you make a quarterly business review worth a CEO’s time?
WHO THIS VIDEO IS FOR
CEOs, executive teams, and strategy leaders at small and mid-sized B2B companies planning their 2027 strategy, plus the client success and sales leaders who hear from customers every week.
CHAPTERS
- 0:00 Highlight: put your customers at the center of planning
- 0:42 Welcome: Jason and Chris
- 0:59 The Executive Series and the SWOT analysis
- 2:12 Why customers belong in your strategy
- 2:47 Crowdsourcing customer insight for your SWOT
- 4:41 Customer strengths, weaknesses and opportunities
- 5:13 What are customers actually saying about you?
- 5:42 Understanding your customer’s business
- 6:43 Sponsors vs. end users
- 10:01 Don’t wait for the formal score
- 11:21 Where to start: face time with customers
- 12:45 Go where your customers go: conferences
- 14:19 HR Tech and the B2B view
- 15:05 Common themes across your clients
- 15:58 AI’s role in understanding your clients
- 17:41 Final advice for CEOs
- 18:39 Make your QBR worth attending
- 19:13 Net Promoter Score: one simple question
- 19:59 Wrap-up
ABOUT INSPIRE SOFTWARE
Inspire connects strategy to the OKRs, performance, recognition, leadership development, planning, and task management that carry it out, in one platform, with coaching from the Inspire team.
Talk with an Inspire expert: https://meetings-na2.hubspot.com/bill-pappa?utm_source=youtube&utm_medium=inspire-podcast&utm_campaign=client-insights
What leaders say on G2: https://www.g2.com/products/inspire-software-inspire/reviews
Subscribe to The Inspire Podcast: https://www.youtube.com/@inspiresoftware
#CustomerInsights #StrategicPlanning #StrategyExecution #SWOTAnalysis #CustomerSuccess #VoiceOfTheCustomer #NetPromoterScore #QuarterlyBusinessReview #AIforBusiness #B2B #CEO #ExecutiveLeadership #2027Planning #InspireSoftware #InspirePodcast
Related Resources
For More on How AI Can Help Executive Leaders Create a Strategy Execution Engine through Continuous Performance Management, read this Inspire article: https://inspiresoftware.com/the-execution-engine/
For More Insights on how to Turn Strategy into Action Through OKRs, read this Inspire article: https://inspiresoftware.com/ai-for-planning-toward-okrs-helps-organizations-turn-strategy-into-action/
Download the free eBook — The Six Steps to a Winning Strategy: https://inspiresoftware.com/resources/ebook-the-6-steps-to-a-winning-strategy/
Get the State of Strategy Execution in 2025 report: https://inspiresoftware.com/resources/the-state-of-strategy-execution-in-2025/
Featured Guest / Co-host: Chris Wollerman — CEO and Co-Founder, Inspire Software. Chris has spent his career helping organizations connect strategy, goals, performance, and leadership into a single execution system. About Inspire Software Inspire helps companies align strategy with performance to drive effective execution and employee engagement through meaningful, measurable results. The platform connects strategy, OKRs, continuous performance management, leadership development, and recognition to turn intent into action.
#CustomerInsights #StrategicPlanning #StrategyExecution #SWOTAnalysis #CustomerSuccess #VoiceOfTheCustomer #NetPromoterScore #QuarterlyBusinessReview #AIforBusiness #B2B #CEO #ExecutiveLeadership #2027Planning #InspireSoftware #InspirePodcast
