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's usually a few reasons in the mix:

1. Past mistakes can be an easy scapegoat to point to instead of being held accountable.

2. Baggage is a great way to avoid unwanted change—“we’ve already tried that and look at what happened.”

3. 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 to the tale. And they will tell it, over and over again.

4. 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.

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?
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Conduct two meetings in which you bring your whole team together.

In the first meeting:

1. Describe the gory details of what happened. Really. Yes, everyone already knows them—they want to know that YOU know them. Even if you weren't there at the time, you can describe what you have been told.

2. Do not 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…”

3. Acknowledge the impact of the issue. While you’re over it, they’re not. 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.

4. Genuinely apologize. If you were part of leadership when the issue was created, own the issue. If you weren’t there, apologize on behalf of those who were in leadership at the time. It is much easier to forgive and forget when a genuine apology has been offered.

5. Recognize and thank those who went through the difficult times. Acknowledge your long-tenured team members contribution for the success and growth of the organization today - "We wouldn't be here without you."

Then end the meeting.
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In the second meeting:

1. Bridge the last meeting to this one. Share something along the lines of:

• 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.

2. Speak to the future. Visually, with authentic expression, sentiment and feeling, paint the picture of your vision. Speak to the potential and possibility that's now available working from a clean slate. Make sure to speak not only to outcomes but also to how it will feel, what it will look like and even how it will sound (what will people be saying.)

3. Give your team agency to opt into participating in creating this future. Request, “Everyone who is aligned with supporting this vision, please stand up.” (Or if you're online, "Please raise your hand.")

4. Measure alignment. Pause and gently notice if anyone does not have their hand raised. Oftentimes everyone will stand up as there's a desire to be part of a community contributing to creating a better future.

5. Speak to concerns. If there are individuals who do not stand up or raise their hands, first thank them for their honesty and courage. Then ask them, "Will you please share with me your hesitation or concern?" Come from a place of curiosity and give them your undivided attention. Then speak to their concern as best you can in that moment - which may mean answering with, "Good question, I don't know. I'll look into that piece and will report back to everyone what I find out."
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PRO TIP: Do try to accomplish both of these meetings in one meeting. The content of the second meeting needs to be a separate meeting. If you tack it on to the first it will make everything you share feel disingenuous and like manipulation.
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You will notice within weeks of the first meeting, and within days of the second meeting, your team is making progress towards the future vision rather than remaining stuck in the past.