A Collaborative Journey to Success: How Direct Reports Can Talk Truth to Power and Help Their Boss Be More Effective

direct reports

Summary: In the workplace, a hierarchical dynamic often characterizes the relationship between direct reports and their leaders. These power differences can create challenges regarding open and honest communication. But speaking truth to power is essential for a transparent and collaborative work environment. This can significantly enhance a leader’s effectiveness. Direct reports hold valuable insights about team morale, operational bottlenecks, and the reality of day-to-day operations, which can substantially benefit their boss. But how can direct reports effectively communicate feedback in a way that drives positive change?

Dear Dr. Sylvia,

I finally did it!

I told you I would tell you when I ultimately “pulled the ripcord.”

Yup, I was ready to get off at the miserable bus ride at the next stop.

I am now free from the most challenging work situation of my career.

And I want to thank you for stopping me from saying too much in my resignation letter.

I am putting a synopsis of the letter here for others to see.

There are better ways to resign than ‘spilling your guts’

This is so others can learn and avoid a conundrum of poor choices.

I wish I had better communication skills to share more honestly with my boss. However, he is the Founder and CEO of an entrepreneurial company, and rather intimidating.

None the less, I now have a deeper and more effective way to tell truth to power moving forward.

I love what you are saying about how less can be more. I also love that when I am ready to say “and furthermore,” that is the time to tell myself to choose silence.

Here is the long form resignation letter.

But first, here is the short form one:

Dear XXXXX,
After long deliberation I have decided to resign from XXXX. This is effective
immediately. Please know I will be here for two weeks to make sure you have everything
you need moving forward.
I will also be available for the next month if any emergencies occur.
I want to wish you great success and thank you for all I learned in the two years I was with this organization.
Signed,
XXXXXX

When in Doubt, LESS is MORE

So, here is the first version of the email. This is the one I was going to send to my boss.

I’m glad your voice in my head says LESS is MORE.

Dear XXXXX,

This is to inform you that I have decided to resign from XXXX Company. I have taken a week to think about this decision from every angle, and I can no longer find the purpose I once had to continue here.

For example, in the sales meeting last week, almost everyone in the room expressed anger, hurt, and resentment—not just me. My colleagues and I talked about it after the meeting ended.

While I cannot and will not speak for others, the way you voiced your demanding questions created a sense of hopelessness.

Everyone was looking for a safe place to hide. No one, including me, was willing to “speak truth to power.” You know how finger-pointing and yelling made us all shrink.

We became little kids fearing punishment when yelled at

Sadly, this was not the first time (nor will it be the last) when you set the tone and belittle your employees in front of each other.

I could go on and on. I do not think you and your “favorite person, the COO,” really care what we worker bees think. Several weeks ago, you said at a meeting, “Our culture is fair. We pay you, to do as you are told. Clear and even exchange.”

I am choosing a different type of environment. This is NOT it.

I wonder if you even have a slight idea of how others view you as a leader.

I am sure you dont even care.

In any case, maybe now you will get a coach or someone else to help you see that there is a better way.

And with that said, I wish you and the company success. I would like the same from you to me.

Signed,

XXXXXXXXX

Sylvia, when you suggested it was not the time or place to vent to make myself less anxious or to prevent my boss from making the same mistakes over and over.

You helped me craft a simple resignation letter. I’m glad I took the high road.

Now I realize I wish I had done coaching earlier in my career. Then I would have developed the courage and skill to speak up.

What I would appreciate now is a short tutorial to remind me how to speak truth to power.

Signed,

Truth seeker

The truth shall set you free if done without JUBLA, judgment, blame or attack

Dear Truth Seeker,

Firstly, I am glad we could work together when you were ready to learn more effective communication skills.

I’m also delighted you acknowledged the benefit of doing personal work. This is the core for long-term leadership success.

Let’s explore strategies that empower employees to speak candidly with their leaders. This fosters a relationship that ultimately helps leaders and direct reports grow and succeed.

These insights will also highlight the importance of creating a safe, respectful, and solution-focused dialogue.

Here are the basics for “truth to power talks:

Cultivate the Right Mindset for Constructive Conversations

One of the first steps toward speaking truth to power is overcoming the fear associated with hierarchy.

Many direct reports hesitate to speak up due to concerns about backlash, job security, or being perceived as critical.

However, it’s essential to recognize that leaders, too, are human and can benefit from feedback that helps them see blind spots they may have missed.

Approaching feedback with the right mindset—one that is centered on growth rather than criticism—can help ease the tension.

Be Solution-oriented to Win in Communicating with Others

When giving feedback, frame it in a way geared toward solving problems rather than merely pointing them out.

For instance, if the leader’s communication style is causing confusion, instead of saying, “Your communication is unclear,” reframe it as, “I’ve noticed that there are often misunderstandings in the team when we receive instructions. Perhaps we could explore a new method for providing updates that allows for more clarification.”

Speak Out with Both Empathy and Intention

Remember that leaders are under constant pressure. They may need to know how their decisions or behaviors impact the team.

Empathy and understanding of their position can create a more productive conversation.

When approaching a leader, it’s helpful to communicate the intention behind the feedback—to improve the team’s performance, create a better working environment, or enhance overall communication.

I just wanted to let you know that this is NOT to be done when you are ready to hand in your resignation. It is too far down the road and will not make permanent positive changes for either your boss or you.

Establish Trust with Your Leader

Before attempting to speak candidly with your leader, it’s crucial to build a foundation of trust. Leaders are more likely to be receptive to feedback from direct reports they trust.

Trust is built over time. It develops through consistency, reliability, and demonstrating that you have the organization’s best interests at heart.

Prove your Credibility Before You Speak Out

One of the most effective ways to establish trust is by consistently delivering results.

When your leader sees that you are competent, solution-oriented, and invested in the team’s success, they will be more inclined to take your input seriously.

Contribute regularly to team discussions, provide well-researched and thoughtful insights, and show that you commit to mutual goals.

Make Sure to Have Frequent, informal check-ins

Rather than waiting for formal reviews or meetings to offer feedback, try to engage your leader in frequent, informal conversations.

This not only makes feedback less daunting but also creates opportunities for regular, ongoing dialogue.

During these interactions, you can offer positive reinforcement as well as subtle feedback that doesn’t feel confrontational.

A Basic Dictum in Life: Timing is Everything

When it comes to giving feedback, timing plays a critical role.

Even the most well-intentioned feedback can fall flat or be perceived negatively if delivered at the wrong moment.

Before initiating a conversation, direct reports should be mindful of the leader’s current workload, stress levels, and emotional state.

Request a private conversation. Do not, deliver feedback in front of other team members or during public meetings.

This can cause embarrassment or defensiveness, creating a barrier to effective communication. Instead, ask for a private conversation where the leader has the space to process and respond thoughtfully.

Be Clear, Specific, and Respectful. When offering feedback to a leader, it’s essential to be clear, specific, and respectful.

Vague comments can lead to confusion or misinterpretation, and overly harsh feedback may cause defensiveness or a communication breakdown.

Use concrete examples: To avoid ambiguity, provide specific examples to support your feedback. Instead of saying, “You don’t delegate enough,” you could say, “In the last few projects, I’ve noticed that you’ve taken on many tasks yourself, which has caused some delays in meeting deadlines. It might be beneficial to delegate more responsibilities allowing us to contribute more effectively.”

Maintain a respectful tone: Respect is key in maintaining a healthy dialogue. Avoid accusatory language or making it personal. The goal is not to criticize the leader as an individual. It is to improve behaviors or actions. Phrases like “I’ve noticed,” “Perhaps we could,” or “I believe it could benefit us if…” can help maintain a neutral and collaborative tone.

Present Solutions Alongside Feedback

One of the most effective ways to help leaders grow is by presenting solutions alongside any feedback. Simply pointing out problems can come across as unconstructive.

However, offering potential solutions shows that you are engaged in problem-solving and are actively contributing to the leader’s success.

When you raise concerns, please present it as an opportunity to work together to find a solution. For example, if team meetings are too long and unproductive, you could suggest a new meeting format or agenda style that prioritizes action items and follows a tighter schedule.

If the issue is within your control, could you offer your assistance? If a leader is overwhelmed by tasks, suggest, a redistribution of workload. Demonstrate your commitment to improving the situation.

There are Many Faces to Feedback

Once feedback is delivered, could you follow up and maintain open communication? This will help you keep track of progress and demonstrate your ongoing investment in the team’s growth and success.

After some time, have a follow-up conversation to see how things are progressing. Express appreciation for any changes that have been implemented and provide additional feedback if necessary.

Acknowledge positive changes. Celebrating wins—whether small or large—reinforces positive behavior and strengthens the leader’s willingness to remain open to feedback in the future.

A Collaborative Journey Toward Success

In conclusion, speaking truth to power is not just about offering feedback; it’s about contributing to the growth and effectiveness of the entire team.

Direct reports can play a vital role in helping their leaders become more effective by approaching conversations with empathy, respect, and a solution-oriented mindset.

Ultimately, a leader willing to listen and grow in response to feedback from their team fosters a healthier, more collaborative, and high-performing work environment.

Your leader can grow, and you certainly will grow. Worst case scenario, you can resign if no change happens, knowing you did the best you could.

To your success,

Sylvia Lafair

PS. Please check out my webinar, “Communicate to Captivate” for more information.

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