How to coach teammates: A key responsibility of effective leaders

A few months into my career at Facebook, my manager, Yishan, found out that I was rubbing my colleagues the wrong way. Turned out that I was a jerk, and I didn’t even know it!

Left unimproved, this would have thwarted my ability to contribute at Facebook. Fortunately, to my great luck and eternal appreciation, Yishan was determined to see me succeed. First, he asked all of my colleagues for specific feedback about how I was doing—the good, the bad, even the ugly. He then typed up that feedback, printed it out, and asked me to go through it in detail. My homework was to extract the major themes and write a short essay on each one.

While initially a hard pill to swallow, seeing such a clear reflection—and, more importantly, having space to reflect on how to improve—was ultimately both humbling and inspiring. The final list of essays read like a “Management 101” course: listening to feedback, sharing credit, focusing on “we” instead of “me.” I had my work cut out for me.

Effective coaching can have a profound impact on not only the lives of your teammates, but on your entire company.

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With Yishan’s help and support, I chose one theme to tackle first. Along the way, the two of us met regularly, during which Yishan “held space” for me, asked probing questions, and guided me toward specific goals, without interjecting his own ego. Once one theme was sufficiently addressed, I chose another, and then the next. Six months later, he asked the same colleagues what they thought of working with me, and many said they felt like they were working with a completely different person. They liked this person better.

That experience marked a major turning point in my life, fundamentally changing the way I relate to others and even myself. And it’s just one example of how effective coaching can have a profound impact on not only the lives of your teammates, but on your entire company.

Branches on the tree: what coaching is (and isn’t)

A company is a group of people who come together to achieve a goal. So it makes sense that helping the people you hire reach their full potential is an extremely effective strategy. In fact, one study found that leadership coaching delivers an ROI of 5.7 times the cost.

Companies traditionally draw org charts with the CEO at the top, an illustration depicting managers giving commands to reports. But a more empowering view is to think of an organization like a tree, with the CEO on the bottom. The individual contributors are the fruit—the people doing the work—and managers are their supportive branches. Coaching is a key tool for ensuring your teammates fully ripen.

Coaching can be defined as “a development process whereby an individual meets on a regular basis to clarify goals, deal with potential stumbling blocks, and improve their performance.” In other words, you can help people become better versions of themselves by holding space for them to solve problems and accomplish goals. This should happen over the course of a series of one-on-one sessions that occur at a regular cadence. Unlike your regular weekly 1:1s, these meetings should be specifically dedicated to coaching.

I’ve found coaching to be most effective in addressing three areas:

1. solving problems
2. developing and achieving long-term goals
3. improving performance

This takes patience and empathy: Always remember that your teammates are people, not computers whose software you’re upgrading. But it’s worth it. Not only will your team be more capable and better retained, but you’ll grow too, as teaching is one of the most effective ways to learn.

1. Problem-solving: Teaching your team to fish

When a teammate comes to their manager with a problem that needs solving, many leaders’ first instinct is to give them advice on what to do. If you’re good at something that someone else is struggling with, it’s only natural to say, “Here’s what I would do.” But that’s at best a short-term solution. When you simply give advice, your teammates never learn how to solve similar problems for themselves in the future.

Instead, you want to “teach them how to fish.” To adapt the famous saying, “Give your team a solution, and you empower them for today; teach your team how to solve problems, and you empower them for a lifetime.”

Start with active listening: when your teammate brings up the problem they need to solve, reflect back on what they’re saying (“What I hear you saying is…”). Sometimes just hearing a problem relayed back inspires someone to realize they already know the answer.

Think of an organization like a tree, with the CEO on the bottom. The individual contributors are the fruit—the people doing the work—and managers are their supportive branches. Coaching is a key tool for ensuring your teammates fully ripen.

Next, ask probing open-ended questions that can help them come to the answer themselves. Walk them through the thought process you would use. Tell them about your own experiences, and how you’ve seen similar situations go down. Give a specific solution to the problem only as a last resort.

I was once coaching a person on my team who was struggling with another teammate’s perceived unwillingness to take feedback. I asked her questions like, “Can you give me an example?” “Is there a chance the opposite of your assessment is also true?” “How do you want him to feel?” “How can you help him to feel that way?” Through this conversation, she came to her own conclusion about how to approach her teammate: Reassuring him about her respect for him without sacrificing directness.

2. Goal-setting: Big hairy audacious goals

Anyone on a career track should have concrete long-term goals. As a coach, it’s your job to help them identify those goals and then set them on a realistic path toward achieving them, with a timeline of concrete milestones along the way.

For example, a long-term goal might be to take on new responsibilities that are more aligned with their passions; you can help them identify the skills they need to develop to achieve that, and what projects they could take on to develop those skills gradually. As you do this, it’s important to align your teammate’s priorities with the wider goals of the team.

Different people have different goals, so you need to listen and probe to understand each person deeply. One person might want more responsibility, another may want to master their craft, or be a better communicator, or become a leader, or increase their productivity, or feel more confident. What obstacles will they need to overcome? What habits do they need to outgrow? You can ask them to introspect on these questions, and you can add your own answers based on your experience.

Many people need help figuring out possible goals, especially when they’re early in their careers; they may not know what their career options are. Throughout the course of these conversations, try to unearth their real goals, not just their stated ones. Many people will say that they want to become managers, when their real goal is to have more influence and recognition; you can help them identify other paths to achieving that goal.

Once goals have been identified, it’s your job to help set realistic expectations about how long it will take to achieve them. Create intermediate milestones and a plan for tracking progress towards them. Emphasize the value of the journey, rather than being focused on the particular outcome. Ultimately, they should develop their own framing and phrasing of the goal, but you should provide a lot of feedback and input.

I often like to set “BHAGs” with teammates—big hairy audacious goals, moonshot aspirations that at first seem impossible to reach. In early 2014, I was coaching Tyson, the designer on our mobile team. His goal was to do world-class design, but at the time, our mobile apps were only so-so. The BHAG we came up with was for Asana to be recognized as having one of the best mobile apps in the world. Since then, thanks to a team effort to which Tyson was central, we’ve won many mobile design awards, including Google’s own Material Design Award. This may never have happened if Tyson’s goal had been to just “make Asana mobile better.”

3. Performance improvement: Tough conversations

An inevitable part of any leader’s role is to give constructive feedback to a teammate when something isn’t going the way it should be. These can go poorly if done without mindfulness; if done well, they can be a huge source of growth and gratitude.

In these conversations, it’s important for them to know you’re on their side. Be empathetic and maintain eye contact in order to maintain a consistent and trustworthy presence. Disclosing your own weaknesses (“I totally get it; I’ve been there”) can help create a space of trust.

Energetically, you want to be centered. That is, you want to avoid leaning back: beating around the bush, sheepishly prefacing with “Oh, hey, this isn’t a big deal, but…” But you also want to avoid leaning forward: scolding aggressively, making the situation feel dire. Instead, remain in your center, like a calm mountain. Be direct, without judgment.

Speak objectively about what you’ve observed and about your own experience. “I see you doing X. When you do X, I feel Y.” Explain why this matters to you—how you think the issue is impacting their effectiveness or the success of the team. Listen deeply to their perspective on it, and be genuinely open to having your mind changed. Help them come to actionable steps about how they can change. Create homework. Then, check in on next steps, homework, and your sense of progress at every 1:1 until you mutually agree the issue feels resolved. Once it is, celebrate!

An inevitable part of any leader’s role is to give constructive feedback to a teammate when something isn’t going the way it should be.

I once worked with a leader who seemed to be lacking intellectual curiosity. I would see people share good ideas with them, and they would smile and nod, but the ideas never made it into the plan. I don’t think they even realized they were doing it. So I gave them feedback. I collected examples anonymously from several people, including their descriptions of what happened as well as how it made them feel. I set up a meeting dedicated to working through this feedback, and compassionately shared the examples I’d collected, as well as my own experience: “When I share an idea with you and don’t engage with it, I feel discouraged. I wish that when ideas were put forth, you took the time to actually consider them, and, if you don’t like the idea, to at least explain your reasoning.”

And it worked: they had been blind to this pattern and hearing how their behavior affected others stoked a new self-awareness. But had I given the feedback less skilfully, I’m not sure it would have landed: leaning too far (“You’re not listening!”) may have triggered unproductive defensiveness. Leaning too far back (mentioning the problem in passing without clear examples) may have just given them one more piece of feedback for them to ignore.

Coaching is a competitive advantage

In Atul Gawande’s TED talk on the importance of coaching, he recounts the origin of coaching in sports: “In 1875, Harvard and Yale played one of the very first American-rules football games. Yale hired a head coach; Harvard did not. The results? Over the next three decades, Harvard won just four times. Harvard hired a coach.”

The bottom line: As leader of a team, you want your team to succeed in accomplishing its mission. You’ve likely put in a lot of effort to find and recruit the talented people you’re working with. It’s worth it to continue investing in them, to help them be as great as they can be, both for the sake of your project, and for the sake of their natural desire to become great at what they do. Coaching is a highly leveraged way to up your team’s game, making you better and better at doing great things together.

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Ready to implement a few of these practices? Here are a set of questions to guide your coaching sessions:

Assessing how things are going:

• How are you feeling?
• What went well this week?
• What’s exciting to you right now?
• What’s bugging you?
• What are your priorities?
• What are your goals? Specific action plans for working toward each one?
• What are the biggest challenges you currently face?
• How can I and the organization can assist you? 
• Is there anything preventing you from an unqualified “yes” to the question, “Is this organization the place where I can do my best work?” What obstacles can we remove?
• How challenged do you feel at work? Do you wish you were more, less, or differently challenged?

Role reflection:

• How do you view yourself in your role?
• Is there an area we should give you more space, sheltered from the day to day, to shine?
• Are there new approaches you’re interested in experimenting with in how you do any part of your role?
• How would you appraise your current skills and abilities?
• What’s your pie chart of what you working on? What do you want it to be?
• Where are you being under-leveraged?
• Where would you like to develop? 

Career reflection:

• If you were having the best workday ever in your ideal role, what would your schedule look like?
• Where do you get your job satisfaction from? What do you find most fulfilling and rewarding? What matters to you most?
• What’s most unique in your skill sets?
• Where have you been most successful in the past? What do those experiences have in common?