What CHROs Can Learn from the Team I Built Before a 7-Week CEO Sabbatical

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Most CEOs think the problem is talent.

It’s not.

It’s the system the talent operates in.

I learned that the hard way.

At one point, I had a team where maybe 20 percent were true top performers. The rest looked strong on paper but didn’t operate like a high-performing team.

There was backstabbing. Finger pointing. Low accountability.

And I own that.

I overvalued resumes. I undervalued attitude, aptitude, and appreciation.

We also didn’t have a strong employer brand. We were early, not well known, and didn’t have big benefits.

So we couldn’t rely on inbound talent.

We had to build differently.

Years later, I took a seven-week sabbatical as CEO.

Nothing broke.

Here’s what actually changed and what CHROs should be doing right now.

What actually allows a team to run without the CEO?

A team runs without the CEO when decision-making, accountability, and priorities are built into the system, not dependent on the leader.

Before, everything flowed through me.

After, it didn’t.

• Leaders owned decisions within clear guardrails
• Hiring didn’t require layers of approval
• Priorities were defined and visible
• Trade-offs didn’t need escalation

Stop being the system. Build the system.

If your CEO is still in the middle of everything, it’s not just a people issue. It’s a design issue.

Why hiring alone doesn’t build a high-performing team

Hiring improves inputs. It does not fix a broken system.

I hired smart people.

My roots are in executive search and recruiting.

And the mindset there is very clear.

If you just hire the right people, everything else takes care of itself.

Hire hard, manage easy.

That was the environment I grew up in.

Very high bar for talent.
Very little focus on development.

And to be fair, that approach works in certain environments.

In a startup, when the team is small and moving fast, you can get away with hiring a group of strong A players and letting them run.

But it breaks when you try to scale.

Because even great people need:

• Clarity
• Structure
• Consistent expectations

Without that, you still get:

• Politics
• Inconsistency
• Low accountability

That’s exactly what happened.

We had talented people.

But the environment allowed behavior that didn’t scale.

We started hiring for:

• Can-do attitude
• Raw aptitude
• Appreciation for the opportunity

But hiring only worked once the system reinforced the right behaviors.

If your team isn’t performing, don’t just look at who you hired.

Look at what you’ve built around them.

What systems actually create a high-performing team?

These are the eight pillars that changed everything.

1. What is a real playbook and why does it matter?

A real playbook defines how the team operates, not just what tasks they complete.

We documented:

• How we behave
• What success looks like
• How performance is measured
• Financial goals
• Development expectations

This removed guessing.

Here’s what that looked like in practice.

On the sales side, we built full go-to-market playbooks.

• How territories were defined
• How to run a discovery meeting
• What good questioning looked like
• What activity levels were expected

On the operations side:

• How to source
• How to evaluate candidates
• How to interact with clients
• Who to pull in and when
• How to close

Everyone was trained the same way.
Everyone was measured the same way.

That alone removed a lot of chaos.

What I would do differently?

I would spend more time helping the team understand the why.

Because process creates consistency.
But purpose creates commitment.

CHRO takeaway:
If “great” is not clearly defined, teams will default to their own version of it.

2. How do you make culture real, not optional?

You measure it.

We added culture accountability alongside performance.

Not just what you did, but how you did it.

We introduced a “culture checkup” as part of performance reviews.

You were evaluated on:

• How you worked with others
• How you handled conflict
• How you contributed to the team

It was a 360-style view.

We got this from Aileron, founded by Clay Mathile from Iams.

And it changed behavior.

Because people realized:

You could perform.

But if you created friction or mistrust, it would show up.

We were very intentional about avoiding “brilliant jerks.”

CHRO takeaway:
If culture is not measured, it becomes optional.

3. How do you turn strategy into daily execution?

You translate it into operating discipline.

At one point, we had too many priorities.

I remember an advisor asking,
“How does this align with your strategic plan?”

And I thought… what strategic plan?

Through Aileron and an external expert, we built one.

• Mission, vision, core values
• SWOT analysis
• Competitive analysis

But the real shift was focus.

We narrowed down to a few priorities.

• One year: scale the sales organization
• Another year: increase gross margin

Then we tied compensation to those priorities.

That’s what made it real.

CHRO takeaway:
Your CEO needs clarity and execution, not more abstract alignment exercises.

4. Why is a talent pipeline a discipline, not an activity?

Because waiting creates bad decisions.

We learned this the hard way.

When we didn’t have the right talent, everything became a fire drill.

So we made a decision.

We would never stop recruiting.

Even when fully staffed, we kept building relationships.

We told candidates:
“We’re not hiring right now, but we want to build a relationship.”

That gave us something most teams don’t have.

Choice.

Leaders weren’t picking the best of the worst.

They were choosing from strong, pre-vetted candidates.

We also adjusted expectations by market:

• In one market: 10 interviews to hire 2
• In another: 10 interviews to hire 8

This didn’t require a huge team.

Roughly half a headcount sustained the pipeline.

CHRO takeaway:
If you only recruit when there is a req, you are already behind.

5. How do you remove the CEO as the bottleneck?

You fix governance.

At the start, I was the bottleneck.

Every decision flowed through me.

The shift started when I promoted a COO from within.

She ran the day-to-day business.

We also changed decision rights:

• Leaders owned budgets
• Hiring required only one level-up approval
• Leaders priced deals without me

For bonuses:

• I approved the pool with the board
• Leaders decided distribution

That autonomy increased speed and ownership.

CHRO takeaway:
If everything still runs through the CEO, the structure is broken.

6. Why does financial transparency matter for performance?

Because people cannot drive what they do not understand.

We shared:

• Revenue
• Gross margin

Not everything. Just what people could influence.

For example, the delivery team owned margin.

They learned:

• Keep the bench low
• Maintain utilization
• Cover work during absences

We tied bonuses to margin.

So behavior changed.

One year, we set a stretch goal.

“If we hit it, everyone gets an iPad.”

The team became so focused, they hit the annual goal early and didn’t even notice.

That’s when people understand the business.

CHRO takeaway:
If your leaders do not understand the business, they cannot drive business outcomes.

7. What does real development actually look like?

It’s built into how you operate.

• Weekly 1:1s
• On-the-job coaching
• Shadowing
• Real-time feedback

Our COO ran weekly one-on-ones. No skipping.

We had structured meetings across levels.

We developed future leaders:

• Leadership programs
• External coaches

We even created an advisory board for leadership development.

And we made a key decision.

Our human capital team focused on:

• Recruiting
• Talent management
• Development

Administrative work like benefits sat elsewhere.

That kept HR focused on revenue and margin impact.

CHRO takeaway:
Your team does not need more content. They need better coaching rhythms.

8. Why does the leadership inner circle matter so much?

Because truth drives performance.

When you become CEO, people stop telling you the truth.

I remember a sales leader telling me:

“People don’t like you.”

That feedback traced back to how the previous leader communicated tough decisions “Cindy is making us do this”.

It wasn’t easy to hear.

But it was necessary.

From that point on, I paid attention to who would:

• Push back
• Call out issues
• Offer better solutions

That group became my inner circle.

We also exposed them to our advisory board.

Because I knew I wasn’t the only one who could develop them.

CHRO takeaway:
If your leadership team is not telling you the truth, you are operating with blind spots.

The outcome that actually matters

I stopped managing problems.

I started leading.

I had time to develop people.
I enjoyed the work again.

And eventually, I took a seven-week sabbatical.

Nothing broke.

That’s the outcome.

Not just hitting your numbers.

But building a team that can run without you.

Closing

A high-performing team is not built on hiring alone.

It is built on structure, clarity, and discipline.

If you’re a CHRO, your CEO doesn’t just need better talent.

They need a system like this.

And this is exactly the kind of work we do inside CHRO Mastermind groups.

Not a CHRO Mastermind member yet? Learn more at: www chropartners com

Or DM me to schedule a CHRO Clarity call.