4 Ways To Dramatically Increase Honesty On Your Team

Mar 25, 2025 | Employee Retention, Employees, Leadership, Management, Strategy, Training

Lessons from a Leadership Retreat:

I recently led a 2-day retreat for a 5M landscaping firm where the owner wanted to step out of day-to-day operations and fully embrace his role as a visionary.

One of the most impactful exercises we did was a “What I need from you?!” conversation.

Each attendee had the opportunity to express what they needed from everyone else, in order to be successful this year.

We held this exercise at the end of the retreat, after everyone was feeling loose and open.

Start With the Owner.

Each team member shared openly about what they needed the owner to start doing more of—and what habits needed to change.

They shared things like

  • “Stop the machine gun communication style”
  • “Reduce the intensity”
  • “Not everything is drop-dead urgent”

This required vulnerability from both sides.

  1. Employees had to step up and voice their concerns honestly—something that isn’t always easy when addressing the boss.
  2. In turn, the owner had to listen openly and commit to changes that would benefit the team.

Once we finished with the owner, we repeated the process with each of the other leaders.

The result: A room filled with WAY MORE trust and understanding.

Surprise At the End.

As we wrapped up, one of the newest leaders took a deep breath and shared his biggest professional weakness with the team, and where he needed the most help.

“Wow!” His honesty surprised everyone and was a testament to the safe space we had created.

While not everyone reading this newsletter can hire our firm to facilitate your strategic planning sessions, you can take steps on your own to foster greater honesty.

4 Ways to Build Greater Honesty in Your Business

1. Lead With Vulnerability

As the owner or leader, openly share your own challenges, mistakes, and uncertainties. When employees see vulnerability at the top, they’ll feel safer being honest themselves.

Exercise: Ask your team what you can do personally to encourage more honesty in team discussions. It all starts with you.

2. Encourage a ‘Problem-Solving’ Culture

Shift from finding fault to problem-solving. Create a culture where the team is focused on process improvement and not personal blame.

Exercise: Discuss this concept with your team; have everyone grade the team (1-5) how well they live this value.

3. Make It Safe to Give Critique

Make sure that employees feel safe being critical without fear of retaliation. “Thanks for sharing that”is the response when someone gives you a critique.

Exercise: Have a discussion with your team: how good are we at receiving critique? What can be done to improve it?

For more insight on training honest critique, read the book, “No Rules Rules”

4. Regularly Ask for Constructive Feedback

Leaders can create a feedback loop with their teams and peers. When feedback becomes a normal part of company culture, it becomes easier to accept it.

Exercise: Ask each of your direct reports what you should “keep doing, start doing, stop doing .” Meet with them in private to fully understand their perspective.

After you meet with everyone, report back to your team what you plan to change.

Your Challenge – Improve Your Team’s Courage and Compassion

The best (most honest) teams will win this year: Those that can safely cut to the chase and say what’s really on their mind, but in a compassionate fashion.

Start by reading this newsletter with your team and pick a jumping off point.

Just remember, If the captain of the Titanic had created an open culture amongst his crew, they could have missed that dang iceberg.

Empower your team to ‘feel something, see something, say something!’

Regards, Jeffrey

Would you like to meet a high performing team that knows how to win?

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