The subtle art of timing: when to push and when to pause
The rhythm of leadership
Leadership isn’t just about what you say or do. It’s about when you say it, when you act, and when you hold back
Timing is the invisible dimension of influence. Push too early, and you are met with resistance. Push too late, and the moment will have passed. Pause for too long, and you will lose momentum. Move too quickly, you will burn trust
The product and transformation leaders who master the art of timing don’t just make good decisions, they make them at the moments when they are most impactful. They understand that leadership is less like a sprint and more like a rhythm. They know when the accelerate, when to hold steady, and when to wait
Why timing matters
Timing isn’t about luck. It’s about having awareness of:
stakeholder readiness. Even the best ideas fail if people aren’t ready to hear them
organisational cycles. Budgets, planning seasons, and board meetings create windows of opportunity
emotional climate. After a crisis, people may need stability before they can embrace change
momentum. Some initiatives need urgency, others need patience to build alignment
The risk of poor timing
There are consequences to either going too fast or too slow. With timing, you need to get it “just right” to win:
push too soon and you’ll trigger resistance because your stakeholders aren’t aligned
wait too long and you’ll miss the window and someone else will seize the opportunity
ignore your organisational context and your proposals will fall flat. Think of when you asked for money during a budget freeze or asked for a major strategic decision to be made during a leadership transition period
be overly persistent and you’ll get one everyone’s nerves and erode the goodwill that you’ve been painstakingly building
The opportunity of good timing
The opposite is true when you get your timing “just right.” You:
see reduced levels of resistance. Stakeholders are more open when the moment feels right
get faster decisions. Well timed proposals move quickly through approvals
achieve greater credibility. You’re seen as being commercially astute and attuned to the organisation’s rhythm
have a lasting impact. Initiatives launched at the right times are sticky
Example 1: Pushing too early
A General Manager in Technology pitched a major system overhaul just weeks after the executive team pulled the pin on a failed multi-year, multi-million-dollar investment program. The idea was strong, but the timing was wrong. Stakeholders, still bruised, rejected it. A year later, when trust had been rebuilt, the same proposal was made and it was approved as time had healed the wounds and trauma from their previous experience
Lesson: even the right ideas fail when introduced at the wrong time
Example 2: The missed opportunity
A General Manager in Product identified a market opportunity but waited too long to build consensus. By the time she presented it to the board, a competitor had already launched. The idea wasn’t seen as fresh, innovative, and a large revenue opportunity. It was seen as reactive because they had already started losing revenue to their competitor
Lesson: waiting too long can cost more than moving too soon
Example 3: The perfect pause
A Head of Product wanted to challenge a Chief Product Officer’s flawed proposal. Instead of speaking up in the heated meeting, she waited. Later, in a one on one conversation, she raised her concerns discretely with him based on clear data evidence and suggested some alternative solutions that would achieve an even better outcome. The Chief Product Officer changed course, he appreciated her discretion, and she became one of his trusted advisors after that experience
Lesson: sometimes the pause is more powerful than the push
Mastering timing
There are a few things you can do to set yourself up for success when it comes to the art of mastering your timing:
read the room. Observe the energy, mood, and openness. Ask yourself: are people ready to hear this now?
map organisational rhythms. Know when budget, planning cycles, and reviews happen. Align your proposals with these windows
gauge stakeholder readiness. Test ideas informally before formal proposals are made. Look for signals of openness or change fatigue
balance urgency and patience. Push when momentum is high. Pause when resistance is strong
choose your moment. Sometimes the best time is not in the meeting, but in the coridoor, during the coffee chat, or in the one on one conversation
For those who want extra finesse:
use micro-timing. In conversations, wait for a beat before responding. Silence can create space for others to reveal more
leverage external events. Tie your initiatives to market shifts, customer demands, or competitor moves
ride the wave. Align with existing momentum instead of creating it from scratch
anticipate fatigue. Don’t launch change when people are overloaded
Common mistakes leaders make
Timing is hard and it’s easy to miss the right moment. Look out for these common mistakes that product and transformation leaders make:
confusing urgency with importance. Not everything urgent is so important that it deserves immediate action
assuming readiness. Just because you’ve done your research, seen the data, and are ready to move on your idea doesn’t mean others are
waiting for too long. Perfectionistic tendencies and paralysis by analysis are real problems that delays action. The window of opportunity could close before you’re done with dotting the i’s and crossing the t’s
mistaking silence for consent. Stakeholders may be quiet because they’re not ready or haven’t formed an opinion about your initiative yet, not because they agree
Balancing the push and pause
Timing is a dance between the push and the pause. Push without pause, and you’ll overwhelm and exhaust people. Pause without push, and nothing will move. The best product and transformation leaders:
push when momentum is high. They seize the window of opportunity when their stakeholders are experiencing positive feelings associated with progress and recent wins. This gives them the confidence to make bigger or bolder bets when they otherwise wouldn’t
pause when resistance is strong. They wait for the right conditions because they know how to conserve their energy and only spend it when the right impact and outcomes can be achieved. They prioritise other things that are right for right now instead
stay attuned. They read the signals, cycles, and climates so that when things change they can assess what that means for the current and future priorities they have
stay flexible. They adjust timing as contexts shift so that when things change they can adapt and pivot to capture the best opportunities for that moment
Example 4: The strategic delay
A Head of Product delayed the launch of a new initiative until after a major restructure. By waiting, she avoided being caught up in the political turbulence given this new initiative was a controversial bet that needed strong executive support to make it work. By having six months of informal conversations with the executive as they were formulating their strategy and having them input into the formulating of the initiative, she got the executive’s strong backing and her initiative was launched into a much calmer environment where people were ready to engage since they’d been given the time to stabilise after the major restructure
Lesson: sometimes waiting isn’t a weakness, it’s wisdom
Your homework for this week
What’s one initiative you’re considering right now? Is this the moment to push, or the moment to pause?
Things you could do to help you with this:
identify one initiative you’re leading
map the organisational signals and rhythms that affect it
test stakeholder readiness informally
decide: push now or pause strategically?
revisit timing regularly as conditions shift
Why this matters
Being politically savvy isn’t just about what you know or who you know. It’s about when you act
Product and transformation leaders who master timing don’t just avoid mistakes, they amplify their impact. They know when to push boldly, when to pause strategically, and when to wait for the moment that turns resistance into readiness
Timing is everything. The right move at the wrong time is the wrong move. The right move at the right time changes everything
Want to figure out if this the right time to push your initiative or it’s a moment where you need to pause in order to create the most impact?
Let’s work on this together. Here are three ways:
Influencing for Impact: This practical 2-day workshop is for you if you want to influence a decision maker, influence a change in customer or colleague behaviour, or influence someone to buy something from you
Executive and Leadership Team Coaching: Work directly with Lai-Ling to problem solve for your specific situation in a confidential setting. This is for you if you want to develop and execute on a game plan that is 100% tailored to you
Leadership Development: Invest in the product and transformation leaders in your company with leadership development that is customised for their role. This is for you if you want your people to learn about people and politics