493: Move Coaching from Theory to Practice, with Jason Weeman

Executive overview

Most organisations invest in coaching workshops but see little behaviour change because they skip the foundation: managers lack the actual skill to coach, not just the knowledge. Feedback becomes the entry point, and coaching becomes the infrastructure that makes all other learning stick.

At Upwork, building a coaching culture started before the first L&D hire even joined — coaching was a consistent theme across every interview. That executive alignment made it possible to move from proposal to execution on day one.

The real bottleneck is not knowledge but habit: leaders regress to directing and telling the moment they practise, even when they can articulate exactly what good coaching looks like.

Why coaching has to come before everything else

• Feedback is the natural entry point — it surfaces observed behaviour and opens the door to coaching.
• Without coaching as a foundation, training workshops produce no lasting behaviour change; there is no one on the front line connecting learning to behaviour.
• L&D teams default to "order taking" — delivering requested workshops — rather than building the underlying capability that makes all training land.
• Coaching is not a programme among many; it is the skill that enables every other programme to work.

What made Upwork's approach different

• Coaching was raised as a priority in every interview conversation, unprompted — a reliable signal of genuine organisational alignment.
• The L&D strategy proposed during hiring was adopted immediately; there was no 30/60/90-day discovery phase.
• Early adopters with a growth mindset raised their hands quickly; bringing them in early cemented credibility and momentum.
• Sessions were cross-functional by design — engineers, marketers, sales, recruiters, and executives in the same room.
• The former and current CEO participated in workshops alongside early-career managers, visibly struggling with the same things.

The "be lazy" problem

• "Be lazy, be curious, be often" (Michael Bungay Stanier) sounds simple; the lazy part is the hardest to sustain.
• Most leaders reached their roles by being exceptional individual contributors — the habit of solving and directing is deeply embedded.
• Letting go of rescuing feels counterintuitive; it requires trusting that a question helps more than an answer.
• Leaders need to pause before responding — the natural reaction is to insert a great idea, not ask a great question.
• Revisiting and getting honest feedback on whether you are actually coaching remains ongoing work, not a one-time shift.

The gap between knowing and doing

• Leaders can articulate what great coaching looks like; they cannot reliably do it under pressure.
• In practice sessions, people regress immediately to feedback, directing, or teaching — even minutes after discussing coaching principles.
• The basketball analogy: knowing the correct shooting form does not mean your shots land. Self-awareness and deliberate practice close the gap.
• A common confusion: managers cannot reliably distinguish in the moment whether they are coaching, giving feedback, mentoring, or just telling.
• Simplifying the goal helps — not "be a coach" but "show up more curious in whatever conversation you are already having."

How the Coaching Habit workshop was implemented

• All managers went through the Coaching Habit Workshop (Box of Crayons), facilitated internally by certified L&D team members.
• Internal facilitation mattered: facilitators understood Upwork's culture, had skin in the game, and could speak to what was actually happening across the business.
• Approximately 20-plus sessions were facilitated in the first year alone.
• Feedback workshops ran in parallel for all employees — not just managers — creating a shared language across levels.
• When employees knew their managers were doing this work, it created accountability; employees felt more confident giving upward feedback when they were not getting coaching.

What drove actual behaviour change

• Immediate application after sessions — not waiting for the "right moment" — was the strongest predictor of change.
• Proactive follow-up: leaders reaching out with questions, asking for coaching on where they were still struggling.
• Cross-level vulnerability: seeing a VP or CEO wrestle with the same skill made it acceptable to struggle openly.
• Common language across the organisation reduced defensiveness in feedback conversations.
• Four people almost skipped a session because they assumed it was not for their level — when they attended and saw executives struggling alongside them, it shifted their perception of what development looks like.

Advice for leaders building a coaching culture without executive support

• Start with your own behaviour — demonstrate curiosity consistently before trying to scale it.
• Do not build a proprietary programme when something proven already exists; the Coaching Habit is an accessible off-the-shelf starting point.
• Avoid overcomplicating what coaching is — the goal is not coach certification, it is being more coach-like in everyday interactions.
• One senior leader modelling the behaviour creates pressure for others to engage; it spreads without a mandate.
• Data supports the connection between coaching and performance — use it to make the business case internally.

What changed after joining Upwork

• The biggest mindset shift: moving from solo execution to genuine cross-functional collaboration.
• Getting support from teams with different expertise cements learning and reinforces behaviour change in ways a single L&D function cannot achieve alone.