Every week, Built. Not Born. examines an assumption about work or leadership that deserves a harder look. We use current research, practical experience, and timeless principles to help you build better teams, stronger organizations, and, most importantly, a life by design.

I've watched leaders make difficult decisions that were absolutely necessary for the business. I've also watched those same leaders become frustrated when their people didn't immediately get behind them.

The assumption is that if the strategy makes sense, people should support it.

I don't buy that.

Someone can understand exactly why a decision is good for the company and still have legitimate concerns about what it means for them.

So here’s my question:

How a leader responds to that tension often determines whether a reorganization succeeds.

Recently, HubSpot announced plans to eliminate approximately 660 positions, or 7% of its workforce, while restructuring its product teams around customer outcomes and reducing management layers.

CEO Yamini Rangan explained the business rationale: move faster, get closer to customers, and give teams clearer ownership.

Those are reasonable objectives. Whether the changes achieve them remains to be seen.

But the announcement illustrates a challenge leaders face whenever they change how an organization operates.

The business case for change and the human experience of change are two different things.

Imagine you're a CRO reorganizing sales territories.

You've analyzed market opportunity, account distribution, coverage, and revenue potential. The numbers tell you the current structure isn't working.

You make the change.

One salesperson loses accounts they've spent three years developing. Another inherits a territory with unfamiliar buyers. A manager suddenly has a different team and the same quarterly target.

From your perspective, you've made a decision that gives the company a better chance to grow.

From theirs, you've changed the conditions under which they're expected to succeed.

Both can be true.

Here's where leaders get into trouble. They interpret frustration as a failure to understand the strategy.

So they explain the strategy again.

But the salesperson isn't necessarily confused. They may understand the decision perfectly well. They just don't agree with what they're being asked to give up.

You can't explain away a consequence someone has to live with.

I've never believed that good leadership means making everyone happy. Sometimes the right decision is unpopular. Sometimes people lose something they worked hard to build.

That's part of leading a business.

But leaders make a mistake when they expect employees to respond to organizational change the same way the executive team does.

The executive team has often spent weeks or months evaluating options, debating tradeoffs, and preparing for the decision.

Employees may be hearing about it for the first time.

Then we wonder why they aren't excited.

The leader's responsibility isn't to manufacture enthusiasm. It's to acknowledge what's changing, explain what isn't negotiable, and give people a fair opportunity to succeed under the new conditions.

For a sales organization, that means addressing practical questions. What happens to existing opportunities? How will commissions be handled? Are targets being adjusted? Who owns customer relationships during the transition?

Those aren't objections to the strategy. They're questions about whether the organization has thought through the consequences.

A reorganization isn't successful because the new org chart looks better or the financial model works on paper.

It's successful when the people operating within it can produce better results.

That requires more than an announcement.

Leaders need to understand what they're asking people to give up, what uncertainty they've introduced, and what support people need to perform.

You don't have to reverse a difficult decision to respect the people affected by it.

But you do have to lead them through what happens next.

Here's something I think more leaders need to hear: Making the right decision doesn't automatically mean you've done your job as a leader.

If you're leading organizational change, ask yourself three things before announcing it:

If you're an individual contributor or preparing to become a manager, learn to separate the business rationale from your personal reaction. You can disagree with the consequences while still understanding why the decision was made.

You don't have to earn everyone's approval. You do have to earn their confidence that you've thought beyond the decision itself.

On On the Shoulders of Giants, we explore the leadership decisions that look straightforward on paper but become complicated when real people are involved.

Whether you prefer to watch or listen, we'd love to have you join the conversation.

🎙️ Listen on Apple Podcasts, Spotify, or wherever you subscribe to podcasts.

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If this week's argument made you reconsider how you're leading people through change, pass it along to a manager, salesperson, or future leader who might benefit from the conversation.

For years I’ve said: Poor leaders hurt people. Great leaders change lives.

Sometimes leadership requires making decisions people won't like. That doesn't make the decision wrong.

But being right about the business doesn't relieve you of responsibility for the people affected by it.

The org chart is the easy part. Leading people through what it changes is the work.

Until next week, keep building.

- Jeff Wells

Source: HubSpot, A Message From Our CEO: Important HubSpot Team and Business Changes, October 6, 2026.