Work With Steve

When the leadership layer stops keeping pace with the org, the CTO absorbs what it cannot handle. Escalations pile up, delivery pressure becomes constant, and strategic work suffers. These engagements are built to change that structure.

What Changes When We Work Together

Escalations stop defaulting to the CTO (clear ownership + thresholds)
Decisions get made faster (decisions rights + decision cadence)
Managers own outcomes, not tasks (accountability without micromanagement)
Delivery gets calmer and more predictable (risk visible earlier, fewer late surprises)
CTO gets strategic bandwidth back (protected time for architecture + long term bets)

Individual Coaching

For CTOs and VPs of Engineering who are carrying the org but losing ground on the strategic work. Bi-weekly sessions focused on real problems from your week, not theory.

You bring a topic: a difficult direct report, a CEO concern, a delivery problem you cannot get ahead of. We clarify what better looks like, identify what is actually driving it, and build specific moves you can make before the next session. Light async support between sessions so you are not waiting two weeks to course-correct.

A fit if you:

  • Are facing growth, a new role, or an escalation load that is crowding out strategic work
  • Lead a team that needs to become more autonomous but are not sure how to get there
  • Are ready to look honestly at your own leadership patterns and change what is not working

Starts with a discovery call to align on goals and confirm fit. Clear coaching outcomes defined before we begin.

Advisory

For CTOs who need more than a thinking partner. Advisory is hands-on org design work: diagnosing what is actually driving the problem, building the fix, and supporting the rollout.

The engagement follows a consistent shape. Discovery first: conversations with you and key stakeholders, review of org structure, roles, and escalation patterns, identification of the two or three highest-leverage areas. Then recommendations: concrete options with tradeoffs, drafts of org structures, decision frameworks, or playbooks. Then implementation support: help communicating changes, shadowing key meetings, focused check-ins as you roll out and adjust.

A fit if you:

  • Are facing a specific org challenge: growth, reorg, post-merger integration, or chronic execution problems that keep recurring
  • Need a partner who can design and implement changes, not just advise on them
  • Have tried to fix this before and need someone who will stay until it holds

Starts with a consultation call to align on context and scope. Simple proposal with defined focus areas and success criteria before anything begins.

Organizational Coaching

For CTOs whose leadership layer is not keeping pace with the org. The work happens at the system level, not just with you, so the changes hold when you are not in the room.

We start with a diagnosis: org structure, decision flows, escalation patterns, where things are routing that should not be routing there. From that we run bi-weekly sessions with your managers and leads, working real scenarios from your org. Selected leaders get targeted 1:1 sessions alongside the group work. Every engagement produces practical tools your team can use immediately: decision frameworks, escalation paths, meeting templates, feedback scripts.

A fit if you:

  • See too many decisions and escalations piling up at your level
  • Have managers who are capable but still operating as individual contributors
  • Want teams that are autonomous and predictable without you driving every outcome

Starts with a scoping conversation to define goals and agree on how progress gets measured. Clear structure, defined cadence, no vague retainer.

Workshops

For engineering leadership teams that need shared tools and consistent habits, not another training that fades by Friday.

Each session is built around one or two concrete outcomes: reducing escalations, improving manager effectiveness, making better tradeoffs. We work your real situations, recent escalations, hiring decisions, cross-team friction, not generic case studies. Leaders leave with specific scripts, decisions, and commitments they can use the next day.

A fit if you:

  • Lead an org that is growing or restructuring faster than the leadership layer beneath it
  • Have managers who are capable but still operating as senior individual contributors
  • Want your leadership team aligned on how decisions get made, not improvising independently

Delivered virtually or in person. Sessions run 60 to 180 minutes depending on scope. Starts with a short discovery call to align on outcomes and who should be in the room.