12/19/2024

A battle-tested perspective on why executives must continue doing the core work that got them their role, and how stepping away leads to organizational failure

Written by: Jonathan Haas

The Executive Trap

I’ve seen it happen a dozen times: A brilliant engineer becomes CTO and suddenly decides their job is “managing the engineering organization.” A phenomenal salesperson takes the CRO role and declares they’re now focused on “sales strategy.”

And just like that, you’ve lost what made them valuable in the first place.

The Hard Truth

Here’s the lesson I learned the painful way: The moment your executives stop doing the work that got them their position, your company starts dying. It’s slow at first, then all at once.

Why This Happens

The pattern is devastatingly predictable:

1. Star performer gets promoted to executive role
2. They believe “leadership” means stepping away from the hands-on work
3. Their skills begin to atrophy
4. They lose touch with the daily reality of their team
5. Decision quality plummets
6. The entire organization suffers

The Real Job of an Executive

Let’s be crystal clear: Your job as an executive isn’t to “manage” your function. It’s to:

• Set the standard for excellence
• Stay deeply connected to the work
• Understand the real challenges
• Make informed decisions based on direct experience

The Rules That Matter

After multiple startups and countless battles, here are the non-negotiable rules I’ve learned:

For CTOs

• Code for at least 2-3 hours every day
• Review pull requests regularly
• Be involved in critical technical decisions
• Ship features alongside your team
• Experience your own technical debt

For CEOs

• Keep running sales calls
• Stay involved in key customer relationships
• Handle support tickets regularly
• Experience your product’s pain points firsthand
• Close deals

For CROs

• Keep a personal quota
• Run sales calls weekly
• Work directly with challenging customers
• Close deals alongside your team
• Feel the pain of your sales process

”But I Don’t Have Time”

The most common pushback I hear is “I don’t have time to do the work anymore. I have to focus on strategy/management/meetings.”

This is precisely backwards.

If you don’t have time to do the work, you’re doing the executive job wrong. Period.

The Real Costs of Disconnection

When executives stop doing the work, the damage is profound:

1. Decision Quality Suffers

   • You make calls based on abstractions rather than experience
   • You lose the gut feel that comes from daily involvement
   • Your solutions become increasingly disconnected from reality

2. Team Respect Erodes

   • Your people know you’ve lost touch
   • Your feedback carries less weight
   • Your ability to mentor decreases
   • Your understanding of challenges becomes theoretical

3. Innovation Stalls

   • You stop seeing opportunities for improvement
   • You miss the small details that lead to breakthroughs
   • Your strategic thinking becomes divorced from reality

The Right Way

Here’s what good executive leadership actually looks like:

1. Lead by Doing

   • Keep your skills sharp
   • Stay in the trenches
   • Experience problems firsthand
   • Build alongside your team

2. Delegate But Don’t Disconnect

   • Give others autonomy
   • But stay involved enough to understand
   • Keep your finger on the pulse
   • Maintain your operational excellence

3. Balance Strategy and Execution

   • Use your hands-on experience to inform strategy
   • Let real work guide your decision-making
   • Stay connected to the day-to-day reality
   • Keep your skills current

How to Stay Connected

Practical steps for maintaining involvement:

1. Block Sacred Time

   • Set aside non-negotiable hours for hands-on work
   • Protect this time fiercely
   • Make it known that this is a priority

2. Choose High-Impact Work

   • Pick projects that matter
   • Work on critical features/deals
   • Stay involved in key decisions

3. Create Feedback Loops

   • Regular hands-on sessions with your team
   • Direct involvement in critical projects
   • Personal experience with your product/service

The Warning Signs

Watch for these red flags:

• You haven’t written code/closed a deal in weeks
• You can’t remember the last time you used your own product
• Your calendar is all meetings, no doing
• You’re making decisions based purely on reports and dashboards
• Your team stops asking for your technical/practical input

The Path Forward

For executives reading this:

• Schedule hands-on work tomorrow
• Pick up a critical project
• Get back in the trenches
• Remember why you were good at this in the first place
• Lead by doing, not just directing

For founders and boards:

• Make this expectation clear
• Build it into executive roles
• Monitor for disconnection
• Act quickly when you see drift

The Bottom Line

Your executives need to keep doing the work. Not because they can’t delegate, but because their value comes from the combination of leadership and hands-on excellence.

The moment they stop, start looking for their replacement. Because they’ve already started becoming less effective, whether they realize it or not.

Leadership isn’t about stepping away from the work. It’s about setting the standard for how the work should be done.

Keep your hands dirty. Your company depends on it.