Trailhead Thoughts

“Leaders are only as good as the teams they build.”

- Douglas Gerber

Trail Map - Learn. Think. Act. ™

Building Scalable Teams

📚Learn

Building a scalable team starts simple by breaking work into smaller jobs to be done. In this scenario, each job has one clear outcome. As your business grows, you need to be able to stop doing everything and start assigning these jobs to others. Then specialize roles so people focus on what they do best. The key idea: you can’t force the wrong person into the right job. Fit matters more than effort. Keep in mind, you cannot manufacture fit.

Hiring follows a clear path:

  1. Quick check - can we work together?

  2. Real scenario - can they actually do the job?

  3. Team/executive alignment

  4. Offer and onboarding

Keep in mind, onboarding isn’t random. It is built backward from a 90-day success goal.

🤔Think

Where are things breaking in your team right now?

  • Are roles too vague? People are doing “a bit of everything.”

  • Are you hiring based on resumes instead of real ability?

  • Are people struggling because success isn’t clearly defined?

And the big one:

  • Do your people enjoy the work they’re assigned or are you forcing fit?
    *** or, worse. Are they forcing fit because they want to hold on too long?

💪 Act

Try this today:

  1. Pick one role on your team.

  2. Write down 3-5 clear jobs to be done (small, specific outcomes)

  3. Ask, who is naturally good at each of these?

  4. Redesign the role around specialization and jobs to be done, not convenience.

Bonus step:

Define what success in 90 days looks like for that role.

Small clarity → better fit → scalable team

Beyond the Trailhead

Why Most Teams Break as They Scale

You don’t feel the problem at first.

Early on, everything works. One or two people doing everything. Decisions are fast. Nothing gets missed because there isn’t much to miss.

Then you grow.

And things start to slip. Work overlaps. Priorities blur. Important pieces fall through.

It’s easy to blame people.

It’s almost never the people.

It’s almost always a lack of clarity around the work.

The Work Is the System

We find that teams struggle because no one has clearly defined the work.

A “job to be done” isn’t a title. It’s the smallest unit of work that produces an outcome.

Something happens → it creates a result.

When you define work at that level, hiring changes. You stop looking for broad roles and start looking for someone who can produce a specific outcome, in a specific context, within a specific timeframe.

That clarity removes guesswork.

Growth Forces a Tradeoff

In the beginning, everyone is a generalist.

They have to be.

But as the business grows, the work expands. Eventually generalization becomes the bottleneck.

So you split the work. You specialize. And this is where things get uncomfortable.

Now people have to give up parts of the job they enjoy to focus on what matters most.

Some people lean in. Some don’t.

Most teams try to solve this by pushing harder. Coaching, nudging, convincing.

You can’t force someone into work they don’t want.

You can’t manufacture fit.

Fit Is a Match

Fit isn’t intuitive. It’s structural.

It’s the alignment between:

  • The work - the what, not the how.

  • The person - the who.

  • The timing - the when.

Miss one and you’ll feel it. Slow execution. Rework. Frustration.

But, when all three align, the work moves without constant oversight.

That’s what scale actually looks like.

Hiring Should Look Like the Job

Most hiring processes rely on conversation.

Unfortunately, conversation doesn’t prove capability.

A better approach is simple.

Start with validation. Can we see a scenario where we might work with each other?

Then move to reality.

Put the person in a scenario that reflects the actual work.

Watch how they think. How they communicate. How they respond when things aren’t clean.

Offer feedback. Adjust the direction. See if they adapt.

Skill matters. But in a growing business, the ability to be coached matters more.

It’s not the conversation, it’s the conversion.

Speed Signals Clarity

Long hiring processes don’t produce better outcomes.

They typically signal uncertainty.

If it takes too many steps to decide, the role likely isn’t clear.

Clear work leads to clear decisions and clear decisions move faster.

Where Good Hires Fail

Hiring gets attention.

Onboarding gets rushed.

That’s the intersection where good hires fail because no one defined what success looks like.

A strong onboarding process makes the first 90 days clear.

What needs to be true by the end?

Then work backwards.

  • What do they need to learn?

  • What do they need to see?

  • What do they need to practice?

You build structure so they can succeed.

If you throw everything at them at once, you’re not testing capability, you’re testing endurance.

Culture Follows the Work

This might be cliche, but culture isn’t what you say. It’s how you do what you do.

It’s how the work is designed.

  • If roles are unclear, culture feels chaotic.

  • If expectations shift, culture feels political.

  • If fit is forced, culture feels heavy.

When the work is clear, people know where they fit. They know what good looks like. They know how to win.

Start Here

Don’t try to fix everything.

Pick one role.

Define the real job to be done - the outcome, not the title.

Then ask:

  • Do we have the right person for this work?

  • Or are we trying to force it?

  • If we hired today, would we know exactly what we need?

If the answer isn’t clear, that’s the work.

Start there.

Voices from the Trail

From Burnout to Breakthrough - don’t miss this awesome conversation with Jamie Vinck.

  1. Redefining Addiction

  2. The Impact of Cross-Addiction

  3. Danger in Life Transitions

  4. Healthy Coping isn’t Always Health

  5. Exposure Creates Possibility

Hitting the Trail

Mike works with GTM and revenue leaders who know their capable of more, but need space to think, recalibrate, and align at a higher level.

Through executive retreats, leadership offsites, strategy sessions, and curated peer discussions he creates the room senior trams rarely give themselves. Room to surface assumptions, name friction, and make decisions that move their teams and business forward.

If your leadership team needs to create space for strategic thinking, let’s talk.

Announcements

If this quarter felt off, this is for you.

We’ve been having the same conversation with a lot of leaders lately:

“I’m busy, but I’m not where I expected to be.”

So, we’re rolling out the G.A.M.E. Plan™ Intensive: a focused reset to help you get clear, cut the noise, and execute on what matters next.

Not more ideas.

Not more planning.

A real plan and follow-through.

We’re opening a limited number of these as we head into Q2.

If you want next quarter to feel different, this is the place to start.

That’s it for this week.

Keep putting one intentional step in front of the other - the view gets better and better as you climb.

We’d love if you would share this with someone who is ready to build their sprints for the new year.

The Find My Catalyst Team

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