How to let go of the past and move forward—together
Does your organization have baggage—mistakes from the past that keep being dredged up again and again?
You’re not alone. And you're not alone in wondering why the team won't let it go.
There are usually a few reasons in the mix:
- Past mistakes can be an easy scapegoat to point to instead of being held accountable.
- Baggage is a great way to avoid unwanted change—“we’ve already tried that, and look at what happened.”
- The old guard wants to be recognized for their loyalty, strength, and grit—for earning their stripes, for walking two miles through four feet of snow to get to the IT department. They have lived to tell the tale. And they will tell it, over and over again.
- The past skeletons that continue to arise were never truly laid to rest. They have not been forgiven and thus will not be forgotten.
This is toxic for your organization. If your team continues to bring the past into the present, your future will be a repeat of the past. There will be very little progress. Old school and new school will become more and more divided.
The good news is it’s never too old, and it's never too late. The baggage at hand could have been created 10 years ago. If it wasn’t handled well and the aftermath acknowledged, it is still haunting your organization. Now is the time to address it.
So how do you get your team to let go of the past and move forward?
Hold two intentional meetings to guide your team through a shift. Don’t try to rush or shortcut the process—while we would all rather have one meeting than two, trust us on this one. You'll want both.
In the first meeting
Describe the gory details. Yes, really. Everyone already knows the story—they need to know you know it, too. If you weren’t there, share what you’ve heard.
Don’t explain or defend. Resist the urge to explain why the issue was handled the way it was. This hasn't worked before, and it’s not going to work now. It simply makes you appear defensive and sounds like “I’m sorry, but…”
Acknowledge the impact. While you’re over it, they’re not. Time often sharpens pain, not dulls it. So take this up a notch—the impact was deeper than you think and/or it’s gained depth as the pain of time has continuously carved through the organization. Speak to how hard it was for everyone.
Genuinely apologize. If you were in leadership at the time, own it. If you weren’t, apologize on behalf of those who were. It is much easier to forgive and forget when a genuine apology has been offered.
Recognize those who endured. Acknowledge your long-tenured team members for sticking through the hard times: “We wouldn’t be here without you.”
Then end the meeting. “That's all for this meeting—we're done. I just needed you all to hear that from me.”
Exit without fanfare, and pat yourself on the back for doing something very few leaders have been able to do. You're halfway home!
In the second meeting
Bridge this meeting to the last. Set the tone by saying something like:
“Today it’s time to let go of the past and create a future we can all be proud of.”
“Old mistakes cannot continue to hold our organization back.”
“We have learned from our mistakes, and it’s time to finally move on and start fresh.”
Speak to the future. Now that this is behind you, what can the future look like? Feel like? Sound like—what will people be saying about your team? Authentically speak to possibility, to the potential that you see. Make it real, not abstract. What will it feel like working here? What will meetings be like now?
Invite commitment. Say: “Everyone who’s aligned with this vision—please stand up.”
(Or online: “Please raise your hand.”)
Pause and check alignment. Pause and gently notice if anyone does not have their hand raised. Most people will. Oftentimes, everyone will stand up, as there's a desire to be part of a community contributing to creating a better future.
Speak to their concerns. But first, thank them for having the courage to speak up. This reinforces that you mean what you say (that asking them to raise their hands wasn't just a gimmick) and that you are a leader whose team can feel comfortable raising concerns.
Say something like: “Thanks for being honest.” Then ask: “Will you share what’s holding you back?”
Listen with curiosity and your undivided attention.
Then speak to their concern as best you can in that moment—which may mean saying, “Good question. I don't know. I'll look into that piece and will report back to everyone what I find out.”
Pro tip: Do NOT try to accomplish both of these meetings in one meeting.
This is critical. The content of the second meeting needs to be a separate meeting. If you stack the second meeting on the first, it will feel manipulative and disingenuous—and it will leave you worse off than you were before.
You’ll see the shift
Within weeks of the first meeting—and often just days after the second—you’ll notice the change. The team starts focusing on the future instead of recycling the past.
Because now they’ve been seen, heard, and invited to co-create something better.
That’s how to let go of the past and move forward—with courage, care, and clarity.
Want support guiding your team through the past and into the future?
