We’re halfway through the year. The plans we made in January have either taken root, unraveled, or been quietly replaced by reality. It’s the perfect time to step back, recalibrate, and ask: Where are we now, and where are we going?
One of the best ways to do that isn’t by staring harder at dashboards, it’s by talking to your customers.
But here’s the catch: most people have the wrong kind of conversation.
They default to product validation.
Do you like what we built?
Are you using it?
What features do you want next?
If you want to shape the second half of your year with real intelligence, shift the conversation. Stop asking about your product. Start asking about their problems.
Orient Around the Problem, Not the Solution
When you lead with “What do you think of our service?”, you get answers that keep you in your comfort zone. But when you ask, “What’s your team’s biggest challenge right now?” or “What keeps you up at night?” you open the door for insight and opportunity.
Here are a few problems I’ve been hearing again and again in customer conversations lately. They signal at something beyond what any one solution would solve:
1. Disengaged mid and senior leaders
Many organizations are suffering a slow leak from the middle. Leaders are burned out. They’re running on autopilot. As a result, strategy isn’t translating downstream. People don’t know the “why” behind the work and that vacuum is breeding disengagement.
2. Critical talent walking out the door
Highly skilled, high-context employees are transitioning out, and the organization has no clear succession plan. Often, these are niche roles built around specific talents that can’t be easily hired for. These exits expose the absence of a real bench, and a long-overdue investment in internal talent development.
3. Change fatigue
Organizations are caught in a frenzy of reinvention: new tools, new processes, new sales plays, new org charts. Employees are exhausted. Cynicism creeps in. People stop believing that the next initiative will be any different from the last.
Questions Worth Asking
If you want to surface the real dynamics underneath the surface, try these questions in your next customer conversation:
On leadership and engagement:
- What signals do you use to know whether your managers are actually leading—or just executing?
- How confident are you that your leaders could clearly articulate your current strategy?
- Where do you see energy in your org right now? Where do you see people checking out?
On succession and talent risk:
- If your top three performers left tomorrow, what would break?
- Who are you actively developing for bigger roles? What’s getting in the way?
- Are there roles in your organization that have quietly become “unfillable”? Why?
On change fatigue:
- What’s something your team is “over” right now?
- When was the last time a change initiative actually made work easier for your team? What was it and why did it work?
- What would it take to restore trust in the change process?
Don’t Wait Until December to Reflect
June is halftime. Use it.
This is your chance to stop pushing the same playbook harder and start asking better questions. Good questions will reveal what really needs fixing. That knowledge will help you stay relevant, useful, and worth paying attention to.
The right questions surface what’s broken, and what’s possible.
Success Labs is a leadership development and management consulting firm in Baton Rouge, Louisiana. For 40 years, our expert team of consultants has worked with hundreds of companies to grow leaders, build teams, and drive results through great people strategy. Contact us to get proactive about expanding your company’s potential and stay up-to-date with our latest news and leadership development updates here.
By: Adrian Owen Jones
