Leading through change

How to lead a reorganization without wrecking your culture

Restructuring is something almost every leader will do, and it’s consistently mishandled. Here is the process we use with leaders to make hard structural decisions in a way that builds trust instead of spending it.

Sam Franklin

You’ve decided the structure has to change. Maybe roles have drifted, maybe funding shifted, maybe the organization simply outgrew the chart. Whatever the reason, you’re about to make decisions that will change people’s jobs, and everyone will be watching how you do it.

Restructuring is something almost every leader will do. Yet it is consistently botched. Trust is compromised and people are left confused about why decisions were made. Sometimes they’re even left to figure out what it means for them on their own, while leaders share vague messages and high-level talking points about how the reorg will benefit the organization.

The way you manage the reorg is the culture

It is as if leaders think they can execute the reorganization quickly and fix the culture later. What they miss is that the way they manage the reorg is the culture. Culture shows up in actions, especially the actions that affect people’s lives and responsibilities. You can’t botch a reorg and fix it with a movie night.

If you want a culture of integrity, care, and hard work, the reorg had better exemplify those things. There is simply no faster way to damage your culture than with a poorly managed restructuring.

Before the steps, it helps to get the mindset right. We’ve written about seven mindsets for leading an organizational redesign. This piece is the practical process.

Why reorganizations go wrong

Beyond underestimating how much it matters, there are two simple reasons restructuring is so often mishandled. First, doing it well takes time. It requires a real investment of attention and resources. Second, it inevitably involves difficult one-on-one conversations, which most of us fear and some leaders avoid entirely.

No wonder the typical process looks like this: leaders make decisions behind closed doors, announce them in one fell swoop, assume people understood the plan (even though it took the leaders weeks to work it out themselves), and move on as quickly as possible, as if it never happened. Then they wonder why there’s a “culture problem.”

A better way: five steps, and one leaders skip

Fortunately, there is a better way, and it isn’t especially complicated. Here is the process we typically recommend to leaders preparing for a reorganization.

The process at a glance
  1. Name the change and set a windowTell everyone change is coming, why, and when the uncertainty ends.
  2. Listen before you decideOne-on-ones with everyone affected: what they want, what they’re thinking.
  3. Make the decisionsTest your hypotheses against what you heard.
  4. Share decisions one-on-one firstStart with the people most affected. Direct, factual, respectful.
  5. Tell the whole team clearlyWhere you landed, why, and when it takes effect. Leave time for questions.
  6. Keep talking about itThe step leaders skip: keep making space for questions, and check back in.

1. Name the change and set a window

Explain that you are willing to live with a period of uncertainty because it allows for new conversations and possibilities that will lead to a better outcome for everyone. Uncertainty is a necessary place to visit and a hard place to live, so tell people exactly how long the visit will last.

Let people know that by engaging them, you hope to reach an outcome that is positive for as many people as possible, while also being clear that it is ultimately your responsibility to make hard decisions that are best for the organization.

2. Listen before you decide

Sometimes the most important decision a leader can make is not to decide yet. Once the window is announced, people’s wheels will be turning. Hear them out.

You likely already have strong hypotheses. These conversations may confirm them or change them for the better, and they can reveal information that changes the shape of the problem entirely. More than one leader has lost sleep over a difficult decision about someone, only to learn in that conversation that the person was already planning their next step.

There is also the undeniable benefit of everyone feeling heard and included. These conversations are a chance to reassure the people you most want to keep, and they give you a realistic sense of how many conversations will actually be hard in the next round. Usually it’s fewer than you think.

3. Make the decisions

Combine your hypotheses with what you learned in the one-on-ones. Sometimes the answers will be obvious. Other times there will be details to work through, information to track down, or new ideas to consider. You may want to talk with someone again to see whether a particular outcome would work for them.

4. Share decisions one-on-one with the people most affected

Hold a second round of one-on-ones with the people who will be most affected, and with anyone you expect to react strongly even if they aren’t personally affected much. These conversations will include people who see themselves as winners and people who see themselves as losers in the change.

When you have to deliver bad news, get to the point and stick to the facts. Don’t tell the person how they should or shouldn’t feel. Treat them with dignity and respect throughout. This is trust over comfort in practice: the honest conversation, held with care, rather than the softened version that leaves people guessing.

5. Tell the whole team, clearly and directly

There’s no need for a long preamble. Tell the team where you landed and why:

“As you know, I’ve been considering some important decisions about how we move forward. We began this process three months ago, and I want to share those decisions with you today.”

Thank people for how they engaged in the process, and give the date the changes take effect. Leave time for questions, and anticipate the ones people will ask, especially “Why?” and “What does this mean for me?”

Equip people to answer questions from others. Accepting change is much easier when I have a clear reason to share with my family and network, understand the details, and was treated like a smart, thoughtful person throughout.

Then keep talking about it

Leaders often blow past this step, hoping to move beyond difficult feelings quickly. Instead, keep creating space for discussion. Ask the team, “How is it going so far?” and “What new questions are coming up?” Remind them why the decisions were made. Don’t make it a taboo subject. If you create space for questions to surface and tension to be released, it will be. After a few weeks, check back in one-on-one with the people most affected.

Before you announce anything
  • Can you explain, in two sentences, why the structure needs to change?
  • Have you chosen a date by which the uncertainty will end?
  • Have you blocked time for a one-on-one with everyone affected, twice?
  • Do you know who you most want to keep, and how you’ll tell them?
  • Have you planned the follow-up conversations, not just the announcement?

Actions create culture

This process will need to be adjusted to your context: the size of the organization, the magnitude of the change, how long you’ve been in the role, and more. Whatever the context, we’ve found it effective because it reflects the culture most leaders genuinely want: one where people’s ideas and voices are heard, hard decisions are made for the good of the mission, and people are treated with care.

When leaders’ actions and words align, the culture they want takes hold. That is true day to day, and it is even more true with the hard stuff. A reorganization is one of the biggest culture-building opportunities a leader gets. Handle it in a way that models what you want, and people will remember. Handle it poorly, and no amount of free snacks or early Fridays will fix it.

See it in practice.

Joyful Reading Co.

A culture that can grow—and a team that can carry it.

From Zoobean to Joyful Reading Co., Outside Angle helped build and evolve an operating system through growth and combination. The organization is now taking greater ownership of its systems, with Outside Angle shifting toward guidance and targeted support.

Read the Joyful Reading Co. story

HCM Strategists

Building the next version of the firm.

Over three years, Outside Angle partnered with HCM Strategists as the firm moved from HCM 2.0 to 3.0. The work connected leadership development, ways of working, and shared ownership. HCM is now moving toward 4.0 with greater independence and more selective support from Outside Angle.

Read the HCM Strategists story

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