Working the Weekly One-on-One: A Primer on Coaching

There are a lot of work “rituals” that suck so badly you want to hunt down and interrogate whoever invented them. The dreaded weekly status email is one of them. The weekly one-on-one between a boss and a direct report can be another. What should be a chance to get on the same page with the person critical to your success is often awkward, overly chummy, or even skipped.

In my life, I’ve been a manager, a coach, and a teacher. You could argue they are all variations of management. All three share a common misconception, which is that the job is to tell people things—what to do, what to think, or what to know. But it’s not. If you want to be good at any of these, you have to become a facilitator in another human’s journey to self-management.

The job of a manager is to make yourself as unnecessary as possible.

A teacher who only lectures is no more valuable than a YouTube video. A teacher who asks great questions makes life-long learners.

A coach who tells you how to solve your problems is giving you a one-size-fits-all answer, creating dependency if the advice works, and blowing up in your face when it’s wrong. But a coach who pushes you to closely examine your situation and develop your own solutions is a great coach.

A boss who tells you what to do is a micromanager. As well as annoying the subordinate, a boss like that doesn’t scale. No CEO has the time to tell their direct reports what to do in every situation, much less all their employees. Although I know plenty of startup founders who try . . .

A manager has to learn to create a workplace where all employees feel comfortable both making decisions alone and asking for advice when it’s needed. The one-on-one is where that habit is built.

I recommend using an approach based on John Whitmore’s GROW model12 (based on the Inner Game13 approach). I could gush about the Inner Game approach to coaching for days. The big idea is that everyone can be their own coach, because everyone is an expert on themselves. Instead of an advisor, we need a thinking partner to help pull those insights out.

Here’s how that model works for one-on-ones:

Step Zero: Start with at Least a Little Prep

Before the one-on-one, scan the person’s status report. Is there anything there that you should address? A worry, a missed goal, a drop in confidence?

Or you might have something you need to discuss with your direct report, such as a concern about a behavior issue.

I told you you’d use your role canvas again—this is where. Before the one-on-one, review the Role Canvas. Are they making progress toward the goal? Are they fulfilling their responsibilities? Do they have the needed knowledge and skills to do their job?

Now pick the most important topic to discuss. That very well might be feedback you’ve heard about them from another team member or a skill you believe they need to learn.

Make a note to yourself on what the topic is and any salient details. Don’t trust memory. Emotion can disrupt it.

Try not to have more than one to three things on your list. Just one is best. Remember, you meet every week. Discuss fewer things better.

Consider going for a walk rather than sitting in a conference room. It will be easier to talk, more relaxing, and it will get you out of the building. Start the conversation by asking an easy personal question about an interest you and the person share, such as sports or entertainment. If you don’t know what they care about, ask! The best work is done when we all know each other as human beings.

Step One: Now You’re Ready to Coach

G is for Goals. Ask your report, “What would you like to get out of today’s meeting?” Let their topic lead the discussion. You can make space for your issues after.

R is for Reality (or Reflection). Ask questions about the topic they are struggling with: What facts do they have? What insights? What hunches? What is their reality? 

Some questions to try out from Coaching Mastery14:

O is for Options. Have the report come up with their own solutions to the situation. 

This can be tough if you are a “fixer,” like I am. As soon as I hear someone say they have a problem, I start thinking of solutions. But this keeps you as the holder of all answers. Sit on your hands, resist the urge, and ask, “Do you have any ideas for what to do about this?”

W is for Wrap-Up. If you have gotten through the issues you need to, you can discuss next steps, e.g., “Let me know how it goes,” “Email me that report,” or “Looking forward to learning more next week!” Ask, “How can I help?” Then you can restart the cycle or finish the conversation. 

Wrap-Up questions:

Step Two: Giving Feedback, Positive and Negative

Feedback is a word that strikes terror into many people’s hearts. Feedback is often used to mean, “I’m going to tell you what’s wrong with you.” I used to be terrified of feedback, because all I heard was, “You are a bad person.”

Over the years, I’ve studied feedback: How to give it, how to take it, and how to use it to live in a state of constant growth. It still scares me a little, but I value it because it makes me more effective. Feedback helps you see yourself as others see you.

When people engage in a behavior that upsets us, we often attribute intention: “They don’t care,” “They’re selfish,” “What a privileged asshole!” But intention is unknowable. Only through feedback and conversation can we create a common understanding that leads to better cooperation.

The prompt to give feedback is usually emotion. It can be anger, frustration, or resentment. People feeling strong feelings often vent or repress. You cannot do either, for the sake of your team.

This is the hard part. You have to transform your negative emotion into curiosity.

I feel angry. Why? What triggered the anger? What are the stories I’m telling myself about my anger? What other stories explain this trigger? Is the behavior appropriate in another context? Could it be personal? Have I seen this before, or is it atypical? Is this the individual, or is this how our culture asks us to behave?

The next step is to try to put the behavior into context via compassion.

Watch for High Context-Low Context Culture Clashes

Everybody has an internalized idea of appropriate behavior. It comes from multiple factors, from geography to family to corporate culture. When people grew up in one place, got jobs, and worked for one company for most of their life, there was very little cultural tension. In other words, your family played by the same rules as your country and your company.

As we become more global, we run into issues when people have to work together but are playing by different rules. When we see a behavior we think is inappropriate, it must be examined for context.

At Yahoo, we had a culture of passive-aggressiveness. At Zynga, we had a culture of aggressive-aggressiveness. I grew up in Iowa, which is a mix of high context and low (because of its Dutch-English mix). My family, however, were very non-confrontational. You can imagine which company I found easier to navigate.

Mind Your Motivations

From curiosity, change your emotional state to sympathy, then empathy, and finally compassion. Sympathy allows you to see they have a different experience; empathy allows you to feel their struggle as well as your own. Compassion is empathy with an action item. Compassion gives you the right posture to communicate feedback. When you move from wanting to give feedback because you’re hurt to wanting to give feedback to help them be more successful, then you are ready to shape your message.

Structuring Effective Feedback

Matt Abraham, lecturer at Stanford Business School, uses the four I’s as a model for structuring feedback. His steps are:

I shorten this to simple sentences like, “You’ve turned in your designs late three times now, and this means I don’t have time to code properly, or I have to stay up all night working, and my husband gets mad at me. How can we change this? Otherwise, I’m not sure I can continue to collaborate with you.”

The touchy-feely approach works, but you may wish to modify messaging to match your company and team culture. But no matter how you say it, keep feedback about the behavior and not the person or the intentions. For example, delivering promised work late can be called out as bullshit nonsense, but never call the person a jerk or assert, “You don’t care about my life.” People get upset if you judge them as a person or ascribe intent. They know you are making stuff up about them (even if you are right).

The only thing you can both be sure about is behavior. Talk about that, share your reactions, inquire about intention.

David Bradford, professor at Stanford University, calls this moving from your area of expertise (your feelings) and moving to your area of ignorance (their motivations). In Power Laws, he describes it thusly:

“Crossing the line between objective remarks about performance and judgments about the person is common in workplace feedback:

“Each of these statements contains assumptions about another person’s motives and intentions. None address observable behavior or its consequences. The person on the receiving end of this inept feedback will naturally become defensive.”

Stay with what you both know: This happened.

There are four strong ways you can stay with what you know, but still offer clear feedback:

  1. Tell them how the behavior affected you. This we’ve discussed.
  2. Tell them the behavior is not meeting their apparent goals. In the fable portion of this book, Mick wants Kendra to work faster. Allie has to point out this has the opposite effect.
  3. Your behavior may meet your goals, but it is costly to you. For example, being so persistent in pushing your agenda that another person might dig in out of sheer annoyance. The pushy individual may get a poor reputation and find it hard to accomplish goals that take cooperation.
  4. Ask, “In what ways am I part of the problem?” Perhaps Kendra could say, “Mick, I know I deliver late a lot, and I really want to fix this. But when you hover over my cube, I can’t focus, and it takes me longer to do my work. Can we find a way to make you more comfortable so I can settle down and focus?” Hopefully Mick and Kendra could find a way to find a balance, perhaps via short daily check-ins.

What if You Aren’t the Boss?

It can be tough when your boss isn’t the best coach. But you can still coach upward. Ask your manager what she wants to cover or suggest a topic, then ask her what she knows about the reality of the matter, share what you know, bounce options off her and so on. Help her help you.

As well, look for peer-to-peer coaching. You can read a book like Inner Game of Stress with a small group of coworkers and discuss it after. Then coach each other, using the GROW model. Question-based coaching with GROW allows you to coach anyone, even if you don’t have expertise in that area. That means a designer can coach an engineer or a QA person can coach a marketer. You might even get greater team cohesion along the way.

Managers, Avoid the Seduction of Bossing

Advice is thrust upon us so often in our everyday life. It’s kinder to ask first, even when you are the boss. Maybe especially when you are the boss.

If you do have advice, ask for consent first. Try saying something like, “I have an idea I think might help. May I share?” That little gesture of respect prevents you from appearing bossy and makes space for your report to hear what you have to say.

The combination of deep listening, directed questioning, and respectful and restrained advice changes the power dynamic in the employer-employee relationship. It becomes a partnership in which each person has a distinct role to play and in which both are responsible for each other’s success. Which they are.

This model is so effective I’ve been using it in my office hours with my Stanford students. When a student comes by, I ask them what’s on their mind. I ask them what they know about the situation, and if they had thought of any solutions already. I offer advice when I have it and when the student wants it. But often they figure it out just by talking it through.

My students are bright and passionate humans, and I won’t be teaching them for long. I’m better off teaching them to teach themselves.

12 Whitmore, John. Coaching for Performance: GROWing Human Potential and Purpose. Boston: Nicholas Brealey, 2009.

13 Gallwey, W. Timothy. The Inner Game of Tennis. New York: Random House, 1975.

14 Smith, David W. David Smith’s Coaching Mastery: The Ultimate Blueprint for Tennis Coaches, Tennis Parents, Tennis Teaching Professionals. St. George, UT: David Smith, 2008.