The Importance of Having Difficult Conversations

Leaders who avoid difficult conversations eventually create average cultures

This is the first article of a three-part series assessing how intentional leaders pursue clarity

while the more typical and average leader may pursue comfort.  In this probe, we look at how leaders ask questions.

One of my amazing leadership mentors is Mark Cole, CEO of Maxwell Leadership. He is amazing because he learned to push himself into situations that forced growth. He willingly stepped into environments where he would either sink or swim — and he learned to swim fast.  

I admire that. I am learning to push myself as well, but if I’m being honest, it is not always easy to push beyond comfort. What has become even more difficult over time is helping others push themselves beyond their own comfort zones.  Actually, difficult is probably too soft a word. Sometimes it is disappointing.  Even frustrating.

Many people say they want growth, better results, stronger culture, improved communication, or greater success. Yet underneath the conversation, many are really searching for the “easy button.” They want improvement without discomfort. Change without confrontation. Better outcomes without deeper questions.  I often call this the Hope Strategy.

“I hope next year is better.” “I hope the team improves.” “I hope communication gets better.” “I hope things turn around.”

Let’s realize the truth - Hope is not a strategy.

One thing I have learned over the years is that average results often come from average questions — or worse, from no questions at all.  I cannot believe the number of leadership discussions I have participated in where the team’s biggest challenges were painfully obvious. In many cases, the root issues centered around communication problems, unhealthy culture, lack of leadership development, or unresolved team tension. 

The fascinating part is not that the problems existed. Every organization has problems. The fascinating part is that leaders often struggled to assign enough value to solving them. I remember conversations with both a construction company and a church administrative team where the symptoms were obvious:

• communication breakdowns,

• frustration between departments,

• declining morale,

• unclear expectations,

• and leadership inconsistency.

Yet when the conversation turned toward investing in leadership development or team culture improvement, hesitation immediately appeared.

Why? Two reasons.  The first is because culture is difficult to measure on a spreadsheet. Communication problems rarely show up as a single line item on a financial report. But poor communication always costs something:

• productivity,

• trust,

• retention,

• momentum,

• execution,

• and eventually revenue.

The second reason is that there is a cost involved to address the problem.  Costs = Expense, right?  Sometimes.  And at other times, when we spend money, it’s really an investment.

The irony is that organizations often spend enormous amounts of money reacting to problems they refused to address proactively through leadership. That is why asking better questions matters. Leaders who ask better questions create better cultures and better results. Questions create clarity. And clarity can be uncomfortable.

Sometimes leaders avoid questions because they are afraid of what the answers may expose:

• weak leadership,

• inconsistent communication,

• lack of accountability,

• unhealthy culture,

• or misplaced priorities.

But avoiding difficult questions does not eliminate problems. It simply delays their consequences. We must realize that we are already wasting money on the current state of affairs. Any conversation that starts with the misleading question, “Do we have money budgeted to address this problem and/or develop our people?”, focuses on the problem as a potential win-lose scenario. If we have extra funds, we can address the problem; and if not, well, then we cannot address the problem.  

Here’s another perspective to consider.  If you can identify approximately how much a particular problem is costing you right now, and you were willing to redirect (ie. invest) 10% of those funds to address the problem, would getting 90% of those misdirected funds back to your bottom line be a win for you and your organization? Of course!  Framed that way, it's almost a silly question. 

Additionally, spending 10% to get a 90% return can easily be converted to an ROI of 9.  Putting that in terms of a financial market return, most of us would love making that kind of a return. And yet, many times, people choose to wait until funds become available.  

Wise leaders ask more questions. They seek perspective before making conclusions. They understand that the first answer is rarely the complete answer. Unfortunately, many people settle for average because they stop asking questions too soon. Growth-minded leaders do the opposite. They lean into the discomfort of clarity.

They ask:

• What problem are we avoiding?

• Where is communication breaking down?

• What conversations are we unwilling to have?

• What is this dysfunction actually costing us?

• What would happen if we intentionally developed our leaders instead of simply managing problems?

Those questions may create temporary discomfort, but clarity creates momentum. Over time, I have learned something important about leadership:  Comfort and growth rarely coexist.

The leaders who create exceptional cultures are usually willing to ask the questions others avoid. They are willing to challenge assumptions, confront reality, and create honest conversations. Not because they enjoy tension. But because they value growth more than comfort. And that is quite interesting… because few people ask questions.

Reflection Questions

• What questions am I avoiding because they create discomfort?

• Where have I accepted average results?

• What conversations need greater clarity within my leadership or organization?

• Am I hoping things improve, or intentionally leading improvement?

• What’s the worst that would happen if I invested in my team?

• What’s the best thing that could happen if I invested in my team?

Closing Thought

Leaders who avoid difficult questions eventually inherit difficult outcomes. 

I'd love to have more conversations about this.

Brian