Is your business navigating the messy middle?
If you're scaling, you've likely experienced this phase or you're in it right now.
Most conversations about the messy middle focus on the founder’s experience.
What often gets overlooked is how the team moves through that same stretch.
As the business hits complexity and change, your team feels it too.
The way you lead during this time plays a big part in whether your people remain engaged or begin to disengage quietly.
Learning the following will also help you with navigating the messy middle:
• Understanding the Messy Middle
• Importance of Transparency from Founders
• Navigating Change and Growth Pains
• Investing in Team Development
• The Costs and Benefits of Team Empowerment
• Advice for Teams and Founders in the Messy Middle
In episode 231 of the Simplify to Scale Show, Annie P. Ruggles and Jessica D.Maine also share their perspective on what the messy middle looks like for team members. They’ve supported multiple founders through growth phases and understand what creates stability through transition.
Tune into Episode 231 of the Simplify to Scale Show or keep reading below.
Transparency Builds Trust and Alignment
When growth brings challenges, it’s natural for a founder to want to protect the team from the pressure.
That instinct often shows up as putting on a brave face and saying everything is fine.
The problem is that your team can feel when things are off.
If their workload increases or priorities shift, and they don’t understand why, they may start to feel like they are operating in a different business than the one you're describing.
Clear and honest communication about what’s happening builds alignment.
It also helps your team feel valued and informed.
You don’t have to share every detail, but you can give enough context for people to understand the direction, even when the path feels messy.
Your Team Wants to Grow Too
Growth often comes with the need for new capabilities.
That growth doesn’t just apply to you as the founder. It also applies to your team.
A common hesitation among founders is the fear that investing in a team member’s development will lead to them leaving.
While that’s possible, it’s not the most likely outcome.
People tend to stay where they feel supported and seen.
When you give your team the tools, training, and opportunities to grow, they can rise with the business.
Most team members want to get better at what they do. They want to add more value.
By helping them do that, you’re not just supporting their development, but you’re also strengthening your business from the inside out.
Let the Team Learn Through the Process
When your team is navigating change, they need space to adjust and implement.
Creating that space allows for better thinking, clearer decision-making, and stronger execution.
This may look like building in time buffers when testing new systems.
It may mean communicating with clients about updated timelines to allow for proper integration.
It could even be as simple as pausing to regroup before rushing to the next initiative.
When people have room to figure things out, they are more likely to bring their best thinking forward.
This creates a more stable and consistent outcome for the business overall.
Ownership Comes from Trust, Not Control
One of the reasons the Lean Out Method team has been able to move through multiple evolutions successfully is the way leadership shows up.
I give my team room to work through challenges, trust their capabilities, and stay involved without micromanaging.
This approach helps people feel empowered. It encourages them to think critically and own their roles fully.
Instead of stepping in to direct every move, effective leaders provide a clear vision and then give the team the space to make decisions and solve problems.
This builds confidence and commitment.
Plus, it also helps develop leadership capabilities within the team, which creates greater capacity over time.
Long-Term Loyalty Comes from Investment
Annie and Jess both highlighted how deeply they trust and respect me.
That trust was earned through consistent investment, open communication, and space to grow.
They’ve been with the business through significant changes.
Their commitment didn’t come from a single moment, but rather it came from being valued, challenged, and supported consistently.
When people feel like they’re part of something meaningful and that their contributions matter, they stay.
They also tend to go above and beyond during high-growth periods because they understand the bigger picture.
Leading Through the Messy Middle Starts with Intentional Support
Here are a few ways to help your team feel supported through the challenges of growth:
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Communicate clearly and often, especially when things feel uncertain
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Provide context for shifts in strategy, priorities, or workload
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Offer training and development so your team can grow with the business
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Allow time for learning and implementation rather than pushing for constant urgency
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Build trust through consistent support and space for ownership
These actions help create stability, even when the business is evolving.
They also help build a team that grows stronger through every phase of the journey.
If you're looking for ways to simplify your operations and lead more effectively during times of growth, join the Scale Smarter, Not Harder interactive workshop. You'll walk away with clarity and actionable steps, and you’ll have a chance to ask your questions live.
Head to strategicopsinstitute.com/scalesmarter to get registered.
by Crista Grasso
Crista Grasso is the go-to strategic planning expert for leading global businesses and online entrepreneurs when they want to scale. Known as the "Business Optimizer", Crista has the ability to quickly cut through noise and focus on optimizing the core things that will make the biggest impact to scale a business simply and sustainably. She specializes in helping businesses gain clarity on the most important things that will drive maximum value for their clients and maximum profits for their business. She is the creator of the Lean Out Method, 90 Day Lean Out Planner, and host of the Lean Out Your Business Podcast.
