The Power of a Repeated One-on-One Ritual

As leaders, we often obsess over trying to make each one-on-one meeting special, unique, and unpredictable. But real power stems from small, simple consistencies over time, not cleverness in every instance. Start each one-on-one the exact same ritualistic way to lay the groundwork for deeper understanding.

In this series, I’m exploring one-on-one best practices, many inspired by the Manager Tools podcast. Their wisdom has profoundly shaped my perspective, though I synthesize insights from many sources into my own coaching philosophy.

Single one-off meetings can be impactful. But over months and years, the cumulative effects of repetitive actions are what builds trust, insight, and retainment of top talent. Don’t get distracted trying to reinvent the wheel or show off your wit every time. Thoughtful, predictable rituals create fertile ground for sustained growth.

Why Ritual Outperforms Cleverness

It’s tempting to want each one-on-one to feel fresh, organic and completely unique. But this mindset misses the power of pattern recognition over time. A repeated simple ritual may seem boring, but it pays dividends.

Benefits include:

- You learn how different personalities express themselves based on their response style. Quiet employees may offer short vague answers. Big picture thinkers may not recite details. Over time, the pattern recognition ability you develop is invaluable.

- You start noticing subtle trends and changes in mood, energy, body language or tone that can signal emerging issues or opportunities worth digging into. Abrupt terseness from someone usually verbose quickly raises flags something is amiss.

- It reduces the mental effort of trying to conjure a novel, organic opening line every time, allowing you to funnel that brain power into focused listening instead. Energy goes into the conversation rather than the gimmick.

- The predictable rhythm comforts employees and eliminates uncertainties. One less thing to worry about puts them at ease and primes them for candor.

Rituals Build the Foundation, Insights Follow

Resist the urge as a leader to approach each encounter as a chance to impress. Put the emphasis instead on long-term pattern recognition and meaning derived through consistency over time. Establish a simple ritual, then work to discern insights within the comfortable structure it provides.

Optimal Opening Questions

Choose a standard opening question and use it start every one-on-one, every time, with every employee. For example:

- How are you?

- What's been going on this week?

- How are things?

- What's top of mind right now?

Don’t feel pressure to conjure something new or contemporary. The power is in the pattern itself, not the poetry of the words.

Capture Responses for Reflection

Write down or otherwise record your team members’ answers each week. Taking this small step allows you to:

- Easily refer back to check on progress of issues week-to-week. One-off problems become trends.

- See insightful patterns over months that you certainly would have missed in the moment.

- Not rely solely on memory, which fades quickly when managing a team.

- Quiz people about inconsistencies between their own responses that they may not recall offhand.

Don’t view it as imposing tedious structure. You’re laying the groundwork for enhanced recall and insight over the long run.

The Big Picture Role of Management

It’s easy as a leader to slip into thinking your job is to “win” each individual one-on-one. But your real duty is noticing subtle trends over time, coaching others’ development, and ultimately retaining your best talent over months and years. A repeated simple ritual feeds that bigger picture focus on continuity.

Of course, eventually rituals can become rote. So periodically change the question, while still keeping it consistent for a sustained period to allow insights to emerge. Just don’t fall into the trap of trying to impress people with your wit and ingenuity each time. The power is in the pattern.

Invest in Your Growth as a Leader

Like all management skills, consistently practicing one-on-ones will boost your ability to cultivate trust, have meaningful exchanges, and strengthen connections over time. If you want additional support on your journey to management excellence, I offer executive coaching focused explicitly on upleveling leadership abilities like emotional intelligence and communication.

Please feel free to reach out if you would like to explore coaching for yourself or your team. We all get better together. Consistency compounds, in leadership and in life.