Get to the ‘Heart of the Matter’ with 2 Powerful Questions

Tags: Leadership Worth Sharing Blog, Organizational Culture, Organizational Leadership, Situational Leadership

Have you ever been part of a leadership program that energized everyone with ‘feel good’ traction only to have it fade away in a matter of weeks? What happened? Didn’t we all leave with good intentions, make solid commitments, and agree to be different?

The short answer is, ‘absolutely,’ but just like a new year’s resolution, leadership programs and retreats that don’t get to the ‘heart of the matter’ are just like motivational speakers. They make you feel good but the ‘high’ quickly fades once you return to your daily hustle and bustle. Before long, you don’t even remember the experience.

What’s my point here? Regardless of what ‘mode’ you use to tackle ‘people issues,’ make sure you are diving deep enough to actually get to the source. Otherwise, you are just wasting your time and money.

In my 30,000 hours of working in the trenches on people issues, I have discovered two powerful questions that get to the ‘heart of the matter.’ Read on for these questions.

The 2 Most Powerful Questions

The ‘heart of the matter’ questions are . . .

  1. What’s working
  2. What’s not working

To the casual observer, these questions appear simple, even pure common sense. However, when used correctly, they have the power to help heal teams, departments and whole organizations more quickly and more resolutely than anything I have ever encountered before.

Let me give you a case-in-point. I just completed an ‘inter-departmental optimization session’ out West this week. Two flagship departments were not ‘playing nicely in the same sandbox.’ What’s the negative ramification to these departments not getting along? Potentially billions. What’s the upside to them getting along? Again billions. I only had 3 hours to resolve an issue that had been percolating for the past 6 months.

Was I able to solve the issue in 3 hours? The answer is both a ‘yes’ and a ‘no.’ This was a long-standing issue that had escalated creating barriers and breakdowns. But in just 3 hours, we were able to agree and align on the following:

Mind you, these questions aren’t the only approach I take but it is certainly one of the primary things I do. Why? People care about two things when it comes to work . . . ‘What’s working’ to create areas of satisfaction and ‘what’s not working’ that is generating pain points. Guess which one is more top-of-mind with people? Pain points, of course!

I’ve often called myself an ‘Organizational Healer’ because I genuinely care about resolving people’s pain at work. And 9 times out of 10, much of work ‘pain’ revolves around people issues.

Now here comes the hard part! We, meaning anyone and everyone who is willing and has the courage to ask these two questions, must also have the discipline, accountability and follow through to ‘stick it out’ until the identified pain is resolved! Don’t even ask these two questions unless you are really serious about trying to make things better.

So how do you invoke the courage to ask these questions of your team, department or organization and bring about fundamental change? The answer is to hold an optimization session either conducted by an external Organizational Leadership consultant, or by you, yourself. I strongly recommend a 3rd party facilitator if the issues are deep and you’re potentially ‘part of the problem.’

But if you’re simply course-correcting, consider trying it on your own with these pointers to get you started. Remember, the likelihood you resolve everything the first time around is NOT high. But you can definitely make a positive ‘dent’ in the right direction.

How to Conduct Your Own Optimization Session

I’d Love to Help You, Really

Privately send me your challenges, questions and comments at I can’t guarantee I’ll have all the answers, but I will be candid, truthful and genuine at all times with you. All of us deserve to be inspired and joyful in our lives. We simply need to work towards it.


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