The guide this episode is built from
Coaching as a Leader: How to Coach Your Team and When Not To
For a friend in a search, start here
- The STAR Method Interview, and When It Fails Senior Candidates. The STAR method for interview answers, with examples, how STAR compares with CAR, PAR and SOAR, and why senior candidates need more than a tidy story.
- Passed Over for Promotion: Test This Before Working Harder. If you've been passed over, don't just work harder. Ask if you can do the next job, if the people who choose know it, and if a real path exists here.
Transcript
Welcome, friends, to The Operator's Playbook. One guide from my desk, cut down to what you can use this week. Thanks for giving me 11 minutes.
If you’re stuck deciding whether to ask a question or give a direct answer, this episode helps you see when coaching works and when you need to step in. It also gives you a simple structure you can use in any one-on-one or hallway chat.
Coaching as a leader is helping people think for themselves: ask before you tell, listen, and let them own the next step.
Coaching is a skill, not a personality trait, and it sits beside managing, not in place of it. Some moments need a question, some need a decision. I have been on both sides of that line. I founded a company, took it public, ran organizations of hundreds of people, and now coach CEOs and senior executives as an ICF and CEC certified coach. The leaders I have watched grow people fastest did not coach in every conversation. They knew which conversations needed it.
Gallup shows managers account for about 70 percent of the variance in team engagement, and global employee engagement has fallen dramatically in recent years. Engagement is falling, and managers are falling fastest. When people feel the gap, they tell you they would be more productive if their manager’s people skills got better. Coaching is how trust gets built. In DDI’s Global Leadership Forecast, leaders who said their manager coached them effectively were nine times more likely to trust that manager. As AI takes over reporting, the human part that remains is deciding what a team needs to hear, building trust, and developing people.
What coaching as a leader actually means can be boiled down to three habits. First, you ask before you tell. When someone brings a problem, your first move is a question, not an answer. Second, you listen for what they already know. People usually know more than they say, and your job is to draw it out. Third, they own the next step. The conversation ends with their commitment in their own words, not with your instructions. As Marshall Goldsmith puts it, managers work to get people to do what is needed, while leaders work to get people to want to do what is needed.
Coaching and managing are different tools. Managing is about the work: setting goals, giving people the tools to meet them, and judging the results. Coaching is about the person doing the work: their judgment, their confidence, and their next step. A leader who only manages wears people out; a leader who only coaches misses deadlines. The skill is knowing which hat to wear.
When you are asked for something, work out first what the person needs from you. If they need help thinking a problem through, coach. If they need a chance to build their own judgment, ask, even when you already know the answer. If they need clarity on what is expected, give it plainly. A question cannot stand in for an expectation that was not stated. If the feedback is that their work is below the standard, say “this is not the standard I need” first. Questions can follow, but they cannot replace it. If a decision has already been made, make it. Coaching someone toward a decision you have already made is manipulation, not coaching. If someone needs a confidential place to say something hard, that may not be you; help them find someone who can be. Direct, too, in a crisis, when accuracy is critical, and with someone new to the work, who needs the basics before they can generate their own options. Then coach in the debrief.
Two honest limits matter. First, when you coach someone who reports to you, the power dynamic does not disappear. You still write the review and decide the raise, so people will hold some things back, and that is not a failure of trust. Second, coaching works when the person can do the work, takes feedback, and wants to grow. When one of those has been missing for months, more coaching is a way of postponing a decision you already know you need to make, and your strongest people are watching what you tolerate.
A four-step coaching conversation follows the GROW model: Goal, Reality, Options, Way forward. Start by agreeing what the conversation is for. Ask whether they want to think it through or just want your answer. Then ask, “What would make this conversation useful for you?” If several issues are on the table, ask which one matters most right now. Keep the goal inside their control.
Next, look at what is really happening. Ask what they have tried so far, what is getting in the way, and what they are assuming. When something has gone wrong, ask “Walk me through how you decided” rather than “Why did you miss the number?” The first gets a real conversation about the call, the second gets a defense. Ask “what” and “how” more than “why,” which tends to sound like blame.
Then let them find the paths. Ask what could they do, what else, and if you weren’t there, how would they approach it. Use the favorite question: “What would have to be true to get to a yes?” That turns a dead end into a list of conditions you can work on together. Offer your idea only after theirs, and as one option among several.
Finally, commit and follow up. Ask what they will do, by when, and how you will know. Check the commitment by asking, “On a scale of one to ten, how likely are you to do this? What would make it a ten?” Write it down and follow up at the next one-on-one. Follow-up is where most coaching fails; without it, the conversation was a nice chat.
Among the 21 coaching questions the guide lists, the opening questions help you set the agenda: “What is on your mind?” and “What would make this conversation useful?” To understand the situation, ask “What have you tried so far?” and “What is getting in the way?” To find options, ask “What could you do?” and “What would have to be true to get to a yes?” To commit, ask “What will you do, and by when?” and “What support do you need from me?”
If you are a CEO, your value is what happens when you are not in the room. Coaching your executives is how you get out of the way without letting go of the result. Start with your own team. Coaching habits travel down an organization. When the executive team asks before it tells, the managers below start to copy it. Coach the decision-makers, not the decision. After you give direction, ask “What am I missing?”
Test whether you agree on where you are going. I ask leadership teams, “It’s a year from now. Describe what your team’s future state looks like and why it’s a must that you achieve it.” Most teams give wildly different answers. The differences are the coaching agenda. Back the person before they back themselves. Stretch work and a public vote of confidence do more than a feedback session.
Giving people a voice is the pattern behind coaching. I once watched a junior engineer’s proposal get dismissed in a meeting. I asked her to make the case again and made sure the room heard it. Her solution got the project back on track, and she went on to lead the company’s product engine. When a leader shows a red chart in a status review, thank them for the visibility and ask what can be done to help. That simple response invites more honesty and more coaching.
What coaching produces shows up years later. One person I coached became the CEO of their own company. Another, after a long sit-down about what they really wanted, changed careers and became a priest, saying that conversation gave them the courage to follow the dream. One went on to build a $100 million business. One brilliant but unsure person is now a senior vice president at a Fortune 100 company. None of those came from a formal coaching program. They came from a leader asking, listening, and making room.
Common mistakes leaders make when they coach include answering on the third question. Most managers ask two or three quick questions and then give the answer. Each time, the person learns to bring the next problem instead of solving it. Ask a few more questions than feels natural, and wait longer than is comfortable.
Another mistake is asking leading questions. “Don’t you think you should call the client?” and “Have you tried calling the client?” are both instructions wearing a question mark. Adding too much value is another trap. When a senior leader improves an idea by five percent and takes a large share of its ownership, the suggestion lands as an order. Before you add yours, ask whether it is worth it.
Coaching to avoid hard feedback is a mistake. Say the standard first. Coaching works when the person can do the work, takes feedback, and wants to grow. Building dependency instead of judgment is a third mistake. If the same person keeps coming back with the same kind of problem, your answers are the problem.
Coaching only in scheduled meetings is another error. The best moments are in the hallway after a presentation, when a project stalls, or when a person mentions what they want next. Skipping the follow-up is a fourth mistake. The commitment matters only if you ask about it next week. Coaching each person the same way is a fifth mistake. A new hire needs more direction; a seasoned executive needs harder questions.
Coaching and feedback in the moment should be brief. Most coaching by leaders happens in the two minutes after someone presents, when a project goes quiet, or when a person mentions what they want next. Look for a win, when you can name the behavior that caused it, and a stall, when one question can unstick the thinking. “That was strong. What made it work?” is a coaching conversation. So is “What is the one thing holding this up?”
Frequent feedback is worth the effort. Gallup found that 80 percent of employees who said they had received meaningful feedback in the past week were fully engaged. When the moment calls for feedback, keep it to three parts: the situation, the behavior, and its impact. Then ask what they were trying to do. “In this morning’s client call, when you committed to Friday before checking with the team, the team left unsure how to hit it. What were you aiming for?” Facts about the behavior get a conversation; a judgment about the person gets a defense.
To build the habit, put coaching into your one-on-ones. Spend the first part on their agenda, not yours, and include at least one open question that is not about status. Ask one more question before you answer. It is the simplest habit and it changes the most. Ask your team to coach you. For example, “When I hand something off, how clear am I about the outcome and the decisions you can make?” Or use Marshall Goldsmith’s feedforward: ask for two ideas for the future, listen, and say thank you, without defending yourself.
Get coached yourself. The fastest way to learn how to coach is to be coached: you learn what it feels like to be listened to and challenged. Measure engagement, not just output. I use seven yes-or-no questions with teams, and each “no” gets the same follow-up: what would have to be true to get to a yes?
Bring in an outside coach when a leader needs a confidential space to say “I’m struggling” without it affecting their review, when the issue is your relationship with them, or when you are the one who needs coaching. The higher a leader goes, the less honest feedback reaches them, so the confidential room matters most at the top.
This week, pick one upcoming one-on-one and use the four-step conversation, ending with a clear commitment and a follow-up date.
Here is my one ask. If you are carrying an outcome, a number, a team or a transition, and want a thought partner who has been in the seat, book a free forty-five minute discovery call with me. It is in the show notes, with the guide, the links and the full transcript. A working conversation, not a pitch.
And if you know someone in a transition, or thinking about one, I have written a few guides to help them land their next opportunity. Those are in the show notes too.
Thanks for listening. I am back next week.
Questions this guide answers
What does coaching as a leader mean?
It means helping the people who report to you find their own answers instead of handing them yours: asking before telling, listening for what they already know, and leaving them owning the next step. It sits beside managing, not in place of it.
What is the difference between coaching and managing?
Managing focuses on the work: goals, resources, deadlines and judging results. Coaching focuses on the person doing the work: their judgment, confidence and next step. Leaders use both and switch based on the moment.
Is coaching the same as mentoring?
No. A mentor has been where you are going and shares what worked, when asked. A coach helps you find your own answer and works on how you decide and lead now. A leader does both, and it helps to say which one you are doing: “Do you want my experience here, or do you want to think it through?”
What is the coaching leadership style?
A style in which the leader develops people through questions, feedback and support rather than instructions. It works best with people who are capable and motivated and when there is time to learn; it works poorly in a crisis, with people new to the work, or when a decision is needed now.
What are good coaching questions for managers?
Open questions that make the other person think: “What have you tried so far?”, “Walk me through how you decided”, “What else could you do?”, “What would have to be true to get to a yes?” and “What will you do, and by when?”
Can a manager be a coach to their own team?
A manager can and should use coaching skills, but the power dynamic remains: the manager still writes the review and decides on pay and promotion. That is why an independent coach is sometimes the better choice for confidential development.
What is the GROW model?
A four-step coaching structure: Goal (what the conversation is for), Reality (what is really happening), Options (what could be done) and Way forward (what the person will do, by when). It works in a long one-on-one or a five-minute check-in.
When should a leader not coach?
When the person needs an answer only the leader has, when a decision must be made, in a crisis, with someone new to the work, when a standard is not being met and has to be stated plainly, or when the person has shown for months that they do not want to grow in the role.
What are the benefits of the coaching leadership style?
People build their own judgment instead of waiting for answers, take more ownership of their work, and grow faster into bigger roles. For the leader, it means fewer problems landing on your desk over time, and a bench of people ready for the next job.
What are the core coaching skills for a leader?
Three skills do most of the work: listening to understand rather than to reply, asking open questions before offering answers, and giving specific feedback, followed by holding people to the commitment they made.
How do you become a good coach at work?
Start with one habit: ask one more question before you answer. Then give the first part of each one-on-one to the other person’s agenda, follow up on what they committed to, and get coached yourself so you know what good coaching feels like.
How often should a leader coach?
In short moments as they come, plus a regular one-on-one where the first part belongs to the other person. What matters more than frequency is follow-up on what was committed.