The Leadership Skill Most Organizations Underestimate: Having the Difficult Conversation
The Leadership Skill Most Organizations Underestimate: Having the Difficult Conversation
I've seen organizations invest considerable time and money in developing their leaders' strategic thinking, financial acumen, operational expertise, and technical capabilities.
All worthwhile investments. But after more than four decades in business, including over twenty years in senior executive roles, I've come to believe that one of the most important leadership capabilities receives far less attention than it deserves.
The ability to have a difficult conversation.
I'm not talking about being confrontational or unnecessarily blunt. I'm talking about the willingness to sit across from someone and address an issue both parties likely know exists, but neither particularly wants to discuss.
An executive who consistently underperforms. A colleague whose behavior undermines the team. A strategic initiative that isn't delivering despite considerable investment and organizational commitment.
I've participated in those conversations many times. I've also delayed a few that I should have had sooner.
And I've learned something along the way. The conversation you're avoiding today is often the problem you'll spend much more time managing tomorrow.
The Hidden Cost of Avoidance
One of the interesting things about avoiding difficult conversations is that, at first, it can feel like good management. You don't want unnecessary conflict. You want to give someone another chance to improve. Perhaps you believe the issue will resolve itself. Sometimes those instincts are reasonable. Not every disagreement requires immediate intervention.
But there's an important distinction between exercising patience and shirking responsibility.
When an executive consistently misses commitments, the problem rarely stays confined to that individual. Others make up the shortfall. Deadlines slip. Frustration builds. Strong performers question why they're being held to standards that don't seem to apply to everyone.
People notice. They notice when poor performance goes unaddressed and when disruptive behavior is tolerated because someone delivers strong financial results.
Over time, that inconsistency can do more damage to organizational credibility than the original problem itself.
What might have been resolved in one candid discussion becomes a much larger leadership challenge.
Why Capable Leaders Avoid Difficult Conversations
I've both worked with and coached accomplished executives who are exceptionally comfortable making complex business decisions yet surprisingly uncomfortable addressing interpersonal problems. These are people who negotiate multimillion-dollar agreements, make major investment decisions, and navigate challenging market conditions without hesitation.
Yet telling a respected colleague that their performance is unacceptable can be extremely difficult.
Sometimes it's personal. The executive values the relationship. Other times, it's organizational. The individual has influence, longstanding relationships, or specialized knowledge that's difficult to replace.
And sometimes the leader simply isn't confident that the conversation will yield a constructive outcome.
There's also a tendency among experienced executives to believe they already know how to handle these situations.
But leadership experience doesn't automatically eliminate discomfort. Managing the human side of leadership can be considerably more complex than managing the numbers.
Candor and Confrontation Aren't the Same Thing
One reason difficult conversations are postponed is that leaders anticipate conflict. But candor and confrontation are not the same. A productive conversation doesn't start with assigning blame. It starts with building a shared understanding of the issue.
What is happening? Which expectations aren't being met? What are the business consequences? What needs to change?
Consider an executive whose department consistently misses key deadlines. Questioning the individual's competence right away makes the conversation personal and invites defensiveness.
A more effective approach focuses on observable facts, business impact, and expectations for the future.
That doesn't mean every conversation ends on a positive note. Sometimes the appropriate outcome is a difficult personnel decision. But even then, people deserve clarity and respect. Being candid and being respectful aren't competing leadership responsibilities. They're complementary.
The Higher You Rise, the Harder It Gets
There's another dimension I've come to appreciate after more than two decades in senior executive roles. The higher you rise in an organization, the fewer people are willing to tell you what you need to hear. Direct reports may hesitate to challenge your judgment. Colleagues have their own priorities. Even board members may lack sufficient visibility into day-to-day operations.
Executives can unintentionally contribute to the problem. When someone challenges your thinking, do you become curious or defensive? When people raise concerns, do you listen or immediately explain why your decision was correct? I've seen executives discourage candor simply through their reactions to uncomfortable information. Eventually, people stop bringing them difficult issues. The absence of disagreement can start to look like organizational alignment, even though it may reflect something far less healthy. Silence.
The Value of an Independent Business Advisor
This is one reason I believe an experienced, independent business advisor can add considerable value to a CEO or senior executive. Not because the advisor necessarily knows the business better than the executive. The value comes from combining an independent perspective with practical operating experience.
Someone who has spent years making difficult decisions, managing performance issues, navigating organizational politics, and being accountable for results understands that leadership problems rarely have clean-cut solutions.
A good advisor can challenge assumptions without getting entangled in internal politics. They can ask questions others may hesitate to raise.
Are you tolerating this behavior because the individual produces strong financial results?
Have you clearly communicated your expectations?
Are you postponing the conversation because the timing is genuinely inappropriate, or because you're uncomfortable with the consequences?
Perhaps most importantly, what conversation do you know you need to have but haven't?
Sometimes, that question alone changes the direction of a discussion.
An advisor's responsibility isn't to make the executive's decisions. It's to help the executive see the situation more clearly, consider alternatives, and prepare to act with confidence.
That kind of trusted counsel can be especially valuable when the issue involves another senior executive, a longstanding relationship, or a decision with significant organizational consequences.
Preparing for the Conversation That Matters
Difficult conversations rarely benefit from improvisation, especially when the stakes are high. Before entering one, I believe leaders should consider four questions:
What's the real issue? Separate observable behavior and business consequences from personal frustration.
What outcome are you seeking? Are you correcting performance, resolving a disagreement, or establishing accountability?
What might you be missing? The other person may have information or perspectives you haven't considered.
Are you prepared to listen? Too many difficult conversations turn into rehearsed speeches rather than genuine exchanges.
You may enter the discussion convinced you understand the problem, only to discover that the circumstances are more complicated than you realized. Listening doesn't mean abandoning accountability. It means ensuring your judgment is informed before deciding what to do next. The objective isn't to win the conversation. It's to improve the outcome.
Leadership Requires the Courage to Be Uncomfortable
Looking back on my career, I can recall difficult conversations that led to meaningful improvements in performance, relationships, and organizational effectiveness. I can also recall situations where waiting too long made the eventual discussion considerably more difficult. We don't always get the timing right, and we don't always handle every conversation as well as we should. But we can improve at recognizing when a difficult conversation is necessary and at approaching it constructively.
Organizations need leaders who can develop strategy, allocate capital, manage operations, and deliver results. They also need leaders willing to speak up, especially when it is uncomfortable. Because leadership isn't measured only by the decisions we're willing to make. It's also measured by the conversations we're willing to have. The difficult conversation rarely gets easier over time. But the cost of avoiding it almost always increases.
