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.

Why Skip-Level One-on-Ones Undermine Rather Than Strengthen Connection

As managers rise through the ranks, it’s tempting to want direct, firsthand relationships with all employees, even well down the org chart. But conducting one-on-one meetings with direct reports of your direct reports—known as skip level employees—often proves to be an ineffective use of time that actually weakens critical connections.

I’m synthesizing the wisdom of the Manager Tools podcast, which has profoundly shaped my own coaching philosophy. I’ve experienced the dysfunction of skip-level one-on-ones personally during my career. When one-on-ones flow properly up and down the management chain, critical information bubbles up through trusted relationships. Attempting to short-circuit this chain through skip-level meetings then becomes redundant rather than value-adding.

Why Managers Are Tempted By Skip Level One-On-Ones

It’s understandable why managers are intrigued by the idea of skip-level one-on-ones. Some common motivations include:

- A desire for firsthand exposure to what’s happening on the frontlines to gain unfiltered perspectives.

- Suspicion that direct reports might not provide complete transparency, so wanting to verify stories.

- Belief that more access and visibility will improve skip-level employees’ engagement and connection to leadership.

- Feeling like informal, personality-driven connections are crucial for talent retention and development.

- Wanting to signal an open door policy and outlet for raising concerns.

- Curiosity about how policies and strategies are being implemented.

- Identifying high-potential employees who might not be visible through current processes.

These motivations are well-intentioned. But skip-level one-on-ones often fail to achieve the desired goals while creating unintended consequences.

The Pitfalls of Skip Level One-on-Ones

In practice, skip-level one-on-ones between managers and indirect reports frequently fall flat:

- They undermine the primary relationship between managers and their own direct reports, sowing confusion on where employees should devote time and attention.

- They tend to rehash much of the same ground already covered in other one-on-ones, wasting time without surfacing new insights.

- Employees can feel uncomfortable being fully candid with a more senior leader they don’t know well, impairing psychological safety.

- Even if issues are surfaced, subsequent follow-up is diffused across multiple parties rather than clear accountability.

- They signal a lack of full trust and confidence in the transparency and integrity of data flowing properly up through management channels. This reflects poorly on your team’s managers.

- As an employee, I’ve personally found them unproductive. The skip-level leader gains little meaningful new context about my work. And I leave unsure if my input sparked any substantive change or action plans.

- Conducting meaningful one-on-ones with indirect reports takes significant time. The opportunity cost of investing hours this way detracts from developing your direct reports.

In essence, skip-level one-on-ones disempower managers from building strong connections with their own employees. They also rarely provide meaningful new understanding for senior leaders. The juice is rarely worth the squeeze.

Strengthening Bonds Indirectly But Effectively

None of this means you must resign to distant, impersonal relationships with skip-level employees. But the most effective connections come indirectly by working through proper channels.

- Coach your managers to have excellent one-on-ones with their own direct reports. This cascades transparency and accountability up the chain.

- Conduct skip-level team meetings to hear collective, high-level perspectives without undermining individual managers.

- Maintain an open door policy so employees know they can surface unresolved issues.

- Make time during site visits for informal conversations and rapport-building across the organization.

- Celebrate successes publicly to indirectly fuel engagement at every level.

- Debrief regularly with managers on employee feedback themes so you know the pulse and culture.

The truth is, the relationship health of your skip-level team depends almost entirely on the relationship health between each manager and their direct reports. This means investing in your direct reports’ leadership abilities rather than circumventing them.

Why The Links In Your Chain of Trust Matter Most

Organizational relationships function like a chain. They are only as strong as the trust between each link. When you try to short-circuit the chain through skip-level one-on-ones, you implicitly signal a lack of confidence in its strength.

Instead, focus on fortifying each link:

- Coach your managers on having rich one-on-one dialogues with their people.

- Help them grow skills in building trust, providing feedback, delegating, and developing team members.

- Require and monitor the consistency of their one-on-ones.

- Role model transparent leadership yourself in your meetings with them.

- Work collaboratively on aligning priorities across levels.

- Celebrate, appreciate, and reward collaborative, empowering leadership.

The more you invest in nurturing the links closest to each employee, the greater the returns in engagement, innovation, and execution throughout the organization. Skip-level one-on-ones often nip these buds before they can bloom.

Invest in the Chain, Invest in the Organization

If you want additional support strengthening your chain of trust, I offer executive coaching focused explicitly on this management system connectivity. Feel free to reach out to explore how I can help you and your team develop the leadership abilities that translate to broad organizational health.

Empowered people empower people. With consistency and care, you can build an organization that actualizes this virtuous cycle at every level.

How to Make Your One-on-Ones More Conversational

One-on-ones are most effective when the conversation flows naturally in both directions. But transforming them from reporting sessions into genuine dialogue takes some finesse. Follow these tips to foster engaging, productive exchanges.

As always, I’m sharing guidance that has shaped my own coaching approach, and this topic again comes inspired by the Manager Tools podcast. Their wisdom on one-on-ones has proven invaluable time and again.

While structure provides consistency, the real magic of one-on-ones happens through candid, unscripted connection. When you and your employees can share openly without judgement, trust deepens on both sides.

Don’t Worry if Early One-on-Ones Feel Stiff

If you’re just launching one-on-ones, expect some initial awkwardness as you and your team adjust to the new format. Allow time for guards to fall as relationships strengthen through repetition.

Resist the temptation to force casual interaction. As long as critical information is flowing, view early discomfort as a necessary stage of establishing new habits.

Ask Questions to Spark Conversation

Don’t just listen silently during your employee’s portion. Jump in with clarifying questions and additional perspectives. Make it a dynamic exchange.

Interruptions and back-and-forth happen in most meetings. Apply that same principle to one-on-ones. Just take care not to dominate the conversation.

Address Shared Topics Together

If you and your employee plan to discuss the same issue, don’t wait your turn. Dive in when it arises and have a fluid discussion.

Still prioritize their concerns first, but take the opportunity to share, probe and gain alignment.

Add Time as Needed When Agendas Overlap

If you end up covering some of your topics while your employee is speaking, grant them extra time so you don’t cut them off early.

The goal is allowing enough space for both of you to get needs met, not rigid time splits.

Encourage Questions During Your Portion Too

Tell your employees up front that you welcome their questions and interruptions while you’re speaking. A conversation goes two ways.

Reinforce that it’s not a presentation - it’s a dialogue to gain mutual understanding.

Schedule Time to Build Rapport

Consider scheduling rapport-building time before diving into agendas. Those first unstructured minutes allow you both to shift gears into a conversational mindset.

With practice, you can transform one-on-ones into relaxed yet productive sessions where you both contribute fully. The openness will yield dividends.

Invest in Yourself as a Leader

As with all management skills, consistently practicing one-on-ones will boost your ability to connect. If you want additional support, executive coaching provides immense value in augmenting emotional intelligence.

Please feel free to reach out if you would like to explore coaching for yourself or your leadership team. Fostering growth and trust ultimately serves your whole organization.

How to Schedule One-on-Ones for Maximum Impact

One-on-one meetings are a cornerstone of great management. But with packed calendars, it can be challenging to find time for meaningful connections. Proper scheduling is key to making one-on-ones work. Follow these strategies to set up a cadence that demonstrates your team is a top priority.

I learned the importance of dedicated one-on-ones from an influential mentor of mine who followed the wisdom of Manager Tools, an invaluable resource for leaders. Now I pass on their guidance to help managers develop critical relationship-building skills.

While demands press in, one-on-ones create essential space to guide employees, exchange feedback, and foster growth. Done right, they boost trust, morale, and performance.

A 4-Step Process for One-on-One Scheduling

Scan your calendar first. Block off times for standing meetings and other commitments. One-on-ones take precedence as your most important meetings.

Offer at least 1.5 times slots as you have direct reports. Don’t just provide the exact number of slots - you need wiggle room.

Allow employees to choose the best time for them from your provided options. This demonstrates you value their needs.

It’s okay to request 1-2 time changes if certain slots end up overbooked. But overall, defer to employee preferences.

This balanced approach enables you to steer the ship while empowering your team to find optimal timing.

Key Considerations For One-on-One Scheduling

While there’s no single perfect way to schedule one-on-ones, keep these factors in mind:

Avoid Monday mornings and Friday afternoons due to common conflicts.

Earlier in the week allows more flexibility to reschedule if needed.

Standard meeting times tend to work better than off-times.

Morning, mid-day or afternoon slots have pros and cons - choose based on your and your team’s preferences.

Scheduling them all in one day provides focus, while spreading them out increases flexibility.

Some like back-to-back scheduling for efficiency while others prefer breaks between.

The priority is establishing consistent touchpoints, not finding an elusive ideal time. Test different approaches to see what works best.

The #1 Rule: One-on-Ones Are Sacred

Above all, once you commit to scheduling one-on-ones, make them a firm calendar commitment. Never cancel without immediately rescheduling. Defy attempts by others to schedule over this sacred time with your team.

Making one-on-ones a consistent presence demonstrates their immense value to your employees. It also reflects clear priorities on your part as a manager and enables the trust-building relationships that motivate great work.

Invest in Your People and Your Leadership

By dedicating time for one-on-one meetings and actively listening during them, you develop your team and strengthen your own emotional intelligence and coaching abilities.

If you want additional support for your management journey, executive coaching provides immense value. We can work together to refine your one-on-one approach and other leadership practices. Please feel free to reach out if you would like to explore coaching for yourself or your team. Developing leaders develop their people.

The Power of One-on-One Meetings: A Key Tool for People Leaders

As a manager, few things are more important than building strong relationships and trust with your team. But it’s easy to get caught up in the endless cycle of tasks and meetings, with little time left to connect. That’s why the most effective leaders consistently make one-on-one meetings a priority.

I first learned the power of dedicated one-on-ones from a director I worked for years ago. He structured our meetings based on guidance from the invaluable Manager Tools podcast, which has shaped my approach as a coach. Now I pass this wisdom on to help other leaders develop critical management skills.

While meetings proliferate and time disappears, one-on-ones provide consistent space to listen, exchange feedback, provide guidance, and demonstrate each employee’s value. Done right, they transform relationships and results.

Why One-on-Ones Are Essential

It’s tempting to view one-on-one meetings as just another item on your endless to-do list. But they offer immense benefits that impact your team’s performance and morale:

- Develops trust and stronger connections from quality focused time together

- AllowsSurfacing concerns early before they become major problems

- Provides a regular forum for delivery of praise and constructive feedback

- Keeps you closely in touch with the status of projects and any roadblocks

- Creates a space for brainstorming solutions and providing coaching

- Demonstrates the employee’s importance by giving them your undivided attention

Without regular one-on-ones, you miss critical opportunities to provide clarity, resolve issues early, and guide your employees’ growth and development. Don’t let the urgent undermine time dedicated to understanding your team.

How to Structure Effective One-on-One Meetings

To maximize the impact of one-on-ones, Manager Tools recommends this simple but powerful structure:

- Schedule them for 30 minutes once a week with each direct report

- Block them on your calendar to preserve the sacred time

- Give employees the first 10 minutes to talk about anything on their mind

- Use the next 10 minutes to address your agenda and questions

- Spend the final 10 minutes on coaching and discussing future goals

- Hold them in your office or a neutral space with no distractions

- Never cancel without rescheduling that same week – they are a top priority

This format enables your team to share ideas and concerns freely, knowing they have your full attention and support. This transparencybreeds loyalty and innovation.

Making One-on-Ones More Natural

At first, one-on-one meetings may feel awkward as you develop rapport. Here are some tips to help the conversations flow:

- Ask thoughtful, open-ended questions and listen deeply

- Focus on understanding, not immediately solving problems

- Share your own relevant experiences to find common ground

- Follow up on action items week-to-week to provide continuity

- Note key points and summarize conversations to show you were listening

- Find informal spaces like coffee shops to vary the scenery

As you learn about your employees’ needs and build understanding, the meetings will become more relaxed and valuable.

Why Investing in One-on-Ones Pays Off

Consistent one-on-ones clearly demonstrate that developing team members is a top priority for any great leader. The benefits include:

- Employees feel valued, heard, and invested in

- You gain critical insights into morale, challenges, and goals

- It keeps you connected to the team’s real experience day-to-day

- You strengthen coaching skills through practice and repetition

- Trust increases as people know they have direct access to you

- You quickly address frustrations before they become problems

- It allows recognition of achievements that might otherwise go unnoticed

- Your whole team gains confidence in your leadership and concern for them

By spending time in one-on-ones listening, learning, and connecting, you empower your staff to grow and do their best work. You also build vital management and communication abilities that make you a stronger leader.

Taking Your Leadership Development to the Next Level

While I firmly believe one-on-ones are a foundational management practice, executive coaching can provide immense value in augmenting your skills. Coaches work with leaders to:

- Set up scheduling systems and one-on-one best practices

- Develop strong listening and empowering feedback skills

- Learn to provide guidance while maintaining autonomy

- Improve executive presence and leadership communication

- Implement ongoing methods for relationship-building and mentorship

Everything rises and falls on leadership. Developing yourself is the highest-yield investment you can make, both for your own growth and to inspire your team to bring their best.

I encourage you to check out the Manager Tools podcast and community for more wisdom that has shaped my approach to management excellence. And please feel free to reach out if you would like to explore executive coaching for yourself or your leadership team. Helping leaders grow and serve their people well is my passion.

The Power of One-on-Ones: Building Trust and Encouraging Professional Relationships

In our quest to become more effective leaders, we often overlook the basic building blocks that form the foundation of great management. One of these basic but extremely powerful tools is the practice of one-on-one meetings. This practice is part of the Manager Tools Trinity, a set of core principles recommended to every manager looking to enhance their leadership skills.

The Aim of One-on-Ones

The primary purpose of one-on-one meetings is to cultivate professional relationships with your team members. Many managers might argue they already communicate with their team members regularly, but drop-in chats or brief updates don’t necessarily encourage professional relationships.

What is required is deliberate, regular communication that gives the team member a sense of predictability and trust. This trust is the cornerstone of a great team. A high degree of trust within a team can lead to improved performance and better results.

How One-on-Ones Foster Trust

Conducting one-on-ones might seem simple, but it’s surprising how many managers overlook this crucial practice. If you strive for a high-performing team, you must cultivate trust. Trust comes from relationships, and relationships are built and sustained through regular communication.

Human beings measure communication based on two criteria: quantity and quality. To foster trust, a manager needs to communicate frequently and meaningfully with their team members. That’s where one-on-ones come into play.

One-on-ones provide the quantity by ensuring weekly communication between the manager and each team member. But what about the quality? The key to high-quality communication is talking about things that are important to the other person. Hence, effective one-on-ones should always start with the direct — it’s their meeting.

The Impact of One-on-Ones

You might hesitate at the idea of spending half an hour every week with each of your team members, but consider this: it equates to only three days a year spent in deliberate, direct time with each person on your team.

One-on-ones are not just regular check-ins; they are an investment in building trust and fostering professional relationships. They are a way to understand your team members better, gauge their motivations and concerns, and ultimately lead them more effectively.

Remember, effective management isn’t necessarily about being the smartest person in the room or having in-depth industry knowledge. It’s about having great professional relationships with your direct reports. And one-on-ones are the simplest, most measurable way to foster these relationships.

If there’s one thing you can do today to enhance your management skills and effectiveness, start conducting regular one-on-ones. It’s a small step that can have a significant impact on your team’s performance and trust levels.