The Power of Strategic Conversations

(Third instalment of the Conversational Leadership series)

The way a leader communicates with their team largely defines the quality of their leadership. Effective communication is not just about transmitting information—it is about influencing, inspiring, and fostering genuine commitment. Every conversation has the power to build trust, align expectations, and enhance performance, or, conversely, to create confusion, resistance, and demotivation.

Strategic conversations are not superficial exchanges or aimless meetings. They are intentional, structured interactions with a clear purpose, designed to improve decision-making, support professional development, and strengthen organizational culture.

What Makes a Conversation Strategic?

For a conversation to be truly strategic, it must have the following characteristics:

• Clear, objective, and structured: Based on facts and observable behaviors, rather than subjective interpretations.
• Assertive and growth-oriented: Respectful, empathetic, and focused on continuous improvement and problem-solving, without personal judgments or ambiguity.
• Centered on shared responsibility: Encourages agreements and commitments instead of imposing orders, making excuses, or enforcing authority.

When strategic conversations become a regular part of a team’s dynamic, motivation, productivity, and trust naturally increase.

How to Master the Art of Strategic Conversations?

By consistently practicing six key skills that will allow you to positively influence the performance and culture of your team and organization:

1. Assertiveness: Direct and Effective Communication

Assertiveness is the foundation of any strategic conversation. An assertive leader expresses ideas clearly, directly, and respectfully, without being aggressive or passive.

It is important to note that “aggressiveness” in organizational communication tends to occur when the leader is more focused on tasks than on people or when leadership is exercised from a place of positional power rather than personal power.

Conversely, “passivity” occurs when the leader is overly focused on people, resulting in messages that are overly softened or vague, leading to confusion.

Assertiveness, therefore, strikes the right balance between focusing on people and tasks and allows leaders to exercise influence through personal power, not positional authority.

How to Improve Assertive Communication?

• Use a kind and authentic tone of voice.
• Base statements on objective facts, not assumptions.
• Focus on the problem, not the person—describe the situation, its impact, and why it needs to be resolved.
• Avoid vague language and communicate expectations precisely.
• Balance listening and expressing your point of view.
• Use open-ended questions to foster dialogue.

Example of Different Communication Styles:

• Aggressive Communication: “You always leave things for the last minute—this is a disaster.”
• Passive Communication: “I just wanted to mention that the client isn’t very happy with the delays… I’m not saying it’s your fault, but…”
• Assertive Communication: “I’ve noticed that the last three deliveries were delayed. This affects not only your performance but the entire project. I’d like to understand what’s causing these delays. How can we adjust deadlines to ensure timely delivery and improve efficiency?”

2. Effective Feedback: Driving Growth

Strategic conversations should always include elements of feedback. Well-delivered feedback strengthens commitment and performance, while poorly handled feedback generates resistance, confusion, and disengagement.

Key Principles for Strategic Feedback

• Focus on specific facts, not assumptions or generalizations.
• Describe the impact of actions and why a behavior should be changed or reinforced.
• Encourage dialogue and problem-solving rather than one-way criticism.
• Make feedback timely and consistent.
• Provide both corrective (improvement-focused) and positive (recognition-focused) feedback.

Example of Strategic Feedback:

• Ineffective Feedback: “Your presentation was confusing and made no sense.”
• Effective Feedback: “In your presentation, I noticed that some key points were unclear to the team. How do you think you could structure it better next time?”

3. Active Listening: Understanding Beyond Words

The most powerful conversations do not always depend on what is said but on how well we listen. A leader who practices active listening can identify needs, anticipate problems, and build trust.

Additionally, paying attention to both verbal and nonverbal communication is essential.

How to Strengthen Active Listening?

• Silence your mind—listen to understand, not just to respond.
• Maintain eye contact and use nonverbal cues to show interest.
• Be mindful of your own body language—your facial expressions and posture matter.
• Paraphrase what you hear to ensure understanding: “If I understand correctly, you’re saying that…”
• Avoid interrupting—let the other person fully express their thoughts.
• Ask open-ended questions to deepen the conversation.

Example:

If an employee says, “I’m not sure if I can finish this project on time.”

• Poor response: “Just do your best.”
• Better response: “It sounds like you’re concerned about the deadline. What challenges are you facing?”

4. Strategic Support: Guiding Without Taking Over

Many leaders make the mistake of trying to solve every problem for their team. Strategic support does not mean doing the work for others—it means guiding, mentoring, and facilitating growth.

Failing to do this undermines two essential leadership responsibilities:

1. Delegation
2. Fostering professional development

Often, when leaders say, “I don’t delegate because I don’t trust the work will meet my standards,” it is because they have not invested in properly developing their team—but that is a topic for another discussion.

Principles of Strategic Support

• Ask questions instead of giving answers—help others think critically.
• Let go of control when necessary—trust your team’s ability to solve problems.
• Encourage autonomy and confidence—help your team develop their own judgment.
• Serve as a mentor—share knowledge and support skill-building.

Example:

• Ineffective leadership: “Let me check your presentation. I’ll correct it before we send it.”
• Effective leadership: “Before you submit it, review it using these three key criteria and let me know if you need any help.”

5. Establishing Clear Agreements: Defining Expectations with Precision

A strategic leader leaves no room for interpretation. Well-defined agreements reduce uncertainty and reinforce individual and collective accountability.

How to Set Effective Agreements?

• Clearly define what is expected and by when.
• Explain the purpose and importance of the agreement.
• Identify potential obstacles and strategies to overcome them.
• Establish who will follow up, when, and how.

6. Managing Unmet Agreements: Addressing Issues Without Conflict

When an agreement is not fulfilled, how a leader addresses the situation can either correct the course or damage the relationship.

How to Handle Unmet Agreements Effectively?

• Avoid emotional confrontation—focus on observable facts.
• Use dialogue to uncover reasons behind the issue.
• Reinforce the importance of the agreement and its impact.
• Collaborate on a solution rather than imposing a consequence.
• Create a revised agreement following the steps above.

Final Reflection: Leadership Through Strategic Conversations

If you have been following this series on Conversational Leadership, you are beginning to see that effective leadership is not just about results—it is about the quality of the relationships and conversations that drive those results.

A leader who consistently engages in strategic conversations achieves:

• Teams that are more committed and motivated.
• An environment of trust and collaboration.
• Fewer conflicts and greater clarity in objectives.
• A positive impact on both performance and organizational culture.

Ask Yourself:

• Do your conversations bring clarity or confusion?
• Do you listen actively or just wait for your turn to speak?
• Are your agreements explicit or open to interpretation?
• Do you follow up on agreements or assume they will be fulfilled?
• Do you have a clear strategy for handling unmet commitments?

The power of strategic conversations lies in their ability to transform teams, strengthen culture, and drive results. Are you fully leveraging this power in your leadership?