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Five Tips to Improve Your Coaching Conversations

As a leader, you're responsible for coaching and growing your team, helping them be successful. To do this, you need to set the tone and example of the behaviors you want the team to have.

No matter how good of a team you have or how good of a leader you are, you will have to have a conversation about performance. Whether it's delivery, professional skills, or technology skills, you will have a moment where you need someone to change their behaviors.

Having these types of conversations can be scary, no matter how much experience in leadership you might have. However, when done correctly, these moments can greatly impact the other person, helping them grow tremendously.

On the other hand, poor coaching will do the absolute opposite. The other person can become confused or angry. They could even shut down and disengage altogether, making coaching them that much harder.

So what does good coaching look like? I can't guarantee that these steps will solve all your woes; however, I do guarantee that following these tips will increase the odds of the other person listening and at least consider your feedback. Remember, you want to do this coaching because some behavior has caught your attention, and you want to correct it. If the other person doesn't listen or want to engage, then you literally can't make this happen.

Step 1: Be Timely

The sooner you can have this conversation, the more effective it will be. Remember, the point of feedback is to let the other person know how they're doing and correct if needed. They can't do this if the behavior happened three weeks ago because there's no correlation at that point.

Imagine if you had a test suite that only told you about failing tests a week after the build started. There's no way you could make the right decisions, so why would we think that's the case for behavior?

If I've noticed a pattern and feel that it's time to coach, I will get that feedback to them that week, if not the next day.

Step 2: Be Specific

When giving this feedback, the behavior may be obvious to you but not even a thought for the other person. Because we can't control what the other person is thinking, we need to set the context for the feedback so they know what you're talking about.

Let's take my son, for example. He's particular about his food, so when he says that "dinner was awesome," that makes me feel great as I'm happy he enjoyed dinner. But I have no clue what he actually liked or why he thought that. Was it the food? The way it was served? The fact that we had a picnic? No idea, so I'd respond with, "What made it stand out to you?". When he mentions that he liked the pizza, I go "Ah! He enjoyed the food, nice!"

Providing this specific context is crucial for the other person because it lets them kow what caught your attention and drastically reduces the confusion in the conversation. For those who like more concrete details, sharing links to chats, emails, or other artifacts with the behavior can be helpful because you can use it as the foundation for the conversation.

Step 3: Explain Why

There's a reason that you're having this conversation. There's something that's important to you, and, in your opinion, it wasn't important to the other person. We've got to explain why it's important and why you're commenting on it.

I never want to remove someone's autonomy as I like to set the direction and let the team blaze a path, with me guiding to make sure we don't get lost in the wilderness. However, for someone to have autonomy, they need to understand the goals and the reasoning behind it.

If they don't have this knowledge, then it's that much harder for them to make the right decisions. Ensuring they know the why is a leader's responsibility.

Step 4: Seek To Understand

You're working with a team of professionals. A professional makes the right decisions based on their knowledge and experience. If the person is making mistakes, we need to understand why they made the choice that they did.

For example, let's say I'm coaching someone who's consistently missing meetings. I'm frustrated that they're unresponsive and that they don't care. The issue here is that it's okay for me to feel frustrated, but I can't make the judgment that they don't care. I don't know that, and it causes more problems than it solves. I won't vent my feelings to the other person because even though it'd make me feel better, it doesn't help the situation.

A better approach would be to understand why they're missing meetings. Is it something outside of work? Could it be that they don't know why they need to attend? What if they didn't receive an invite? In any of the above cases, there was a solid reason why they didn't attend, and I wouldn't have known that if I had not opened the conversation.

Don't assume malice or apathy when something happens. We are humans first, which means we're going to make mistakes.

Step 5: Working Together

The entire point of coaching is to help the person improve, and we also don't want to take away their autonomy. To make this happen, we need to work with the other person to come up with ideas that can help improve the situation. It's not any one person's responsibility, but it's your responsibility to brainstorm with them and help guide them down the correct path.

The key here is to have an open mind and really consider all ideas. One of my favorite leadership books, First, Break All The Rules, talks about how great leaders work with their people to have their strengths shine and to make their weaknesses a non-issue.

In the missing meeting example, I found out that the issue was that they didn't know why they needed to attend the meeting, so they didn't attend, in order to focus on their development work. Working together, I changed invites to include the reason for attending and encouraged them to chat with me so we could figure it out if they didn't know why they needed to be there.

Case Study - Bringing It Together

In this example, let's explore where we would need to do some coaching.

While reviewing a pull request from Bruce, you see a comment from Alvin, a member of your team, where they were particularly critical of the work. Reading through the pull request, you see Alvin has left more harsh comments about Bruce's work.

Talking with Bruce, they mention that they don't work well with Alvin as it seems like he's always critical of Bruce.

Based on this scenario, we know that Alvin has left some harsh words for Bruce, which makes them less likely to work together. If Alvin keeps this behavior up with other people, this will impact others wanting to work with him, reducing his effectiveness.

After collecting your thoughts, you reach out to Alvin to see if he's got a few minutes to chat about Bruce's pull request.

"Hey Alvin, I noticed you left some pretty harsh comments that in Bruce's pull request. For example, saying that 'this code is convoluted, rewrite it'. Even if that was the case, it's not clear why you think that. I'm more concerned with how the messaging came across because we work with others to accomplish our tasks, and that communication style can make people not want to work with us.

I don't believe you intend to alienate others, so can you walk me through your thought process here and why you thought this was the right approach?"

In this example, we've already hit four out of the five tips. Our feedback was timely and specific to the problem. We included why it caught our attention and started with an open-ended question for the conversation about the behavior.

In the follow-up conversation, Alvin mentions that he was having a rough day, particularly outside of work, and that he wasn't entirely focused on his tone. Given that this is the first time Alvin has done this, we want to focus on fixing the issue before it becomes a pattern.

"I understand that it can be hard to focus on your tone when you're having a rough time, however, we can't speak to others this way. I don't want this to become a pattern, so what are some things that we could do instead when we're not in the right mental head space for code reviews?"

At this point, we've acknowledged what was said and reaffirmed expectations. Using another open-ended question, we can start brainstorming things that we could do to help improve Alvin's tone. Since we're opening the conversation, Alvin is also giving feedback on what might work for him and what wouldn't work.

Wrapping Up

Giving critical feedback to someone is not the easiest thing to do, however, it can have the most impact for them. To help frame the conversation, our coaching should:

  • Be Timely
  • Be Specific
  • Explain the Why
  • Seeking to Understand
  • Be Collaborative

Building Relationships Through One-on-Ones

As a leader, one of your goals is to build a strong, high-performing team. To do this, you'll need to establish and develop relationships within the team and with each other. One approach I've found helpful to build and sustain these relations is through one-on-ones.

When most people think of one-on-ones, they typically think of some scheduled time, every so often, where they talk about work concerns or whatever is on the leader's mind. Some might find one-on-ones a waste of time and skip them.

Let's face it, we've all had bad one-on-ones where the conversation was forced and stiff. Or, it felt like the other person wasn't listening or cared about what was being talked about. If enough one-on-ones go down this route, it's no surprise that people don't want to have these conversations.

So, how do we improve the situation? In this post, I'm going to show you three things you can do to improve the one-on-ones you're having with the team by making sure that they're being heard, relationships are being built, and, just maybe, you might even get to know them better.

It's Not a Status Update

A common mistake is treating one-on-ones as status updates for work or projects. Even though it might be tempting to get an update (especially on important projects), remember this time is for the other person to talk with you about what's on their mind. They can't do this if you're asking for updates on work. If you're leveraging stand-ups or a task board, then you should be able to get updates from there. If this isn't sufficient, ask for updates outside this conversation. The one-on-one is where you give the other person your full attention.

Despite your best intent, this can be a tough habit to break. To help get out of this mindset, start time-boxing the updates to be a set period of time (e.g., ten minutes) with the goal of making this period shorter in subsequent one-on-ones.

Another technique I use is resetting, where I remind my teammate of the purpose and goal of the conversation. Doing this, it's a gentle nudge in the correct direction and reinforces that this time is for them, not for whatever is on my mind.

Don't Get Distracted

In the world of working remotely, it's easy to get distracted by chat notifications or emails. You're on the call, and you see the notification at the bottom of your screen, and before you realize it, you've read it and already thinking about a response. This may be great for you getting things done; however, for the other person, it's clear that you stopped paying attention. So what's important? Is it the notification or the other person?

pedestrians looking distracted in downtown
Credit to Matt Quinn via Unsplash

To help reinforce the focus, I put myself in Do Not Disturb mode, which will hide notifications from me until the meeting ends. If the issue is truly important, then someone would give me a call, in which case, I can excuse myself from the one-on-one to see what's up. In this rare case, I will reschedule our conversation as it's essential that we meet.

Allow Them to Set the Agenda

Another mistake I see leaders make is that they'll come to the one-on-one with a list of topics they want to discuss for the day. This can be particularly true if you're coaching this person and you want to provide concrete feedback. However, remember, the goal is to build and strengthen the relationship, and you can't do that if you're always setting the agenda for the conversations.

I find it amazing that you can learn quite a bit about the other person based on what they bring up. For example, if they're speaking about a conflict with another person, that lets me know that they're aware of relationships and how they're being perceived. On the other hand, if they're talking about a project and the concerns they have, then they're thinking outside of a task and are thinking at a higher level.

In one case, I was in a one-on-one with an engineer where they brought up their concern about supporting an API as they didn't know much about it. My first impression was that they didn't know how to read the code, but digging in, it turned out that they didn't see how the API fit into the bigger picture of the system. Learning this was a great fact check because I thought it was a technical issue, but in reality, it was a system question, which changed my perspective on them.

(Bonus) - Seeding a Conversation

I mentioned that the other person should own the agenda, but sometimes, they may not have much on their mind or a topic that sticks out to them. For these cases, I come prepared with a list of questions to help start the conversation.

pedestrians looking distracted in downtown
Credit to Markus Spiske via Unsplash

In Warren Berger's The Book of Beautiful Questions, he talks about the power of open-ended questions and how they can help people be more open. So instead of asking, "How's the project coming along?", which can be answered in a binary fashion, we could instead ask, "What's one thing about the project that stands out to you?", which could give us a richer response and allow you to learn more.

For those looking for questions, here's an excerpt of questions I've used to help seed a conversation:

  • What's one thing about the current project that turned out to be harder than you thought?
  • What was your biggest win last week, and why does it stand out?
  • What's something that happened in the past week that you want to learn more about?
  • I know you've been working more with this past week, talk to me about that experience
  • What's something that you're looking forward to?

Wrapping Up

To build great teams, you will need to foster relationships with the team and the individual members. Having one-on-ones can help with build these relationships, but only if you treat them like so. By allowing your teammate to set the agenda, giving them your full attention, and cutting out project updates, you can improve the quality of your conversations and get to know them better.

Building Relationships with Intent

As a leader, one of your superpowers is how you can connect your team with someone else. For example, if your team is struggling to work with an API and you know someone who's made recent changes or is a Subject Matter Expert, you can get your team unblocked and moving faster.

I've worked with leaders like this, and it's amazing how fast and helpful it is to get unstuck quickly. Don't get me wrong, sometimes it's the right strategy to "burn the time" to learn, but it's helpful to know someone who can get you unstuck if you need it.

With one leader, it seemed like they always knew a guy, no matter the topic, and I was amazed at how they did it. So like a lifelong learner, I asked, and they told me networking.

large group of people networking
Credit to ProductSchool via Unsplash


If you're like me, you hear networking and think about dozens (if not hundreds) of people milling around, introducing themselves, and sharing business cards. Don't get me wrong, that approach can work for some people, but to me, that sounds exhausting. Instead of a hummingbird, going from flower to flower, I'm more like a bear. I just want to sit down and eat my jar of honey.

So what am I supposed to do? How am I supposed to network if I don't like large groups?

Given time, you can work on becoming more comfortable in large groups. However, why fight your natural tendencies and what you're good at?

For me, it's small groups and one-on-one conversations. As such, that's my approach to networking. Though it takes a bit longer, I find that I build stronger relationships with those people, and in turn, can be just as successful. I like to think about one-on-ones as lazy river conversations as I never know where it will take us.

man sitting in inner tube
Credit to Kiara Kulikova via Unsplash

One Cup of Coffee

At a previous company, we used Slack and, as such, had an integration called Random Coffee that would pair the members of a channel up to get together for the week. Such a simple idea, but so powerful when you now have a built-in excuse to chat with someone.

Coffee Chat
Credit to Priscilla Du Preez via Unsplash

After a couple of weeks of getting to know people, I started learning what others did, what interests them, and who to go to about specific issues. Combine that with asking, "How did you know that?" I found that I could quickly fill gaps in my knowledge.

But something else happened. Once I knew the person, I didn't see them as a name in the chat anymore, I saw them as their selves. I'd find myself saying, "Oh, it's Chris, and Chris is cool, so I'll help him out," instead of thinking, "Ugh, another thing to do." In a way, these conversations humanized those I worked with, and I found myself caring more about them.

Caring By Knowing

To me, this is the most important thing about relationship building and networking. Deep down, I want to care about those I work with because I want them to be successful. I can't help them be successful if I don't know them both as a colleague and as a person.

Having one-on-ones is how I know my people and how I continue building care. It might be as simple as knowing what types of things they like to work on or what they did over the weekend. However, having these conversations helps both of us open up, and I get to know them so much better. Once I know them, I can guide and direct them better, looking for opportunities I wouldn't have thought of before.

How Do I Start?

If you want to start this for your own company, you don't have to have Slack to make this happen. The important thing is getting buy-in from others and explaining the why behind the exercise.

Once you have buy-in, you can start low-tech by using an Excel sheet and randomizing the list of names. This isn't the most robust solution, but it's a start and you can iterate as you figure out the timing, the frequency, and the other steps that setting this up would look like.

Once you've got something in motion, you can always work on automating the process later. Don't let a perfect solution stop you from starting with a good solution.

What I've found successful is having either a weekly or fortnightly scheduled message in our main channel that assigns the groups. From there, participants are encouraged to share something they've learned about their counterparts during their conversation. To help make sure that people meet, scheduling a set time during the week for all the groups can be helpful as it removes another barrier (e.g., if you know that you'll have coffee at 10:30 am on Tuesdays, you learn to expect it).

If you have a group that is just starting, it might be helpful to provide some starting questions to help jump-start the conversation. A good list of questions can be found in one of my gists.

Wrapping Up

To be a successful leader, you must cultivate and grow relationships with those you work with. Not only does it help your team be successful, but it allows you to have a richer experience with your work and helps solidify that we're all working together.

Telling the Story: The Pitfall of a Single Data Point

Let's say that you're sitting down to read a new book, and you come across the following:

The King's Knave Inn was but a short distance from the Alverston train depot, just outside the town proper. (excerpt from The Infernal Machine by John Lutz)

After reading this, a friend interrupts your reading and asks your thoughts on the book so far. What would you say?

Most likely, you'd respond that you need to read more, and it's still too early to decide if the book is good or not.

To honestly answer this question, you would need to read more of the book (ideally all of it) to get a full picture of the story.

When measuring an engineer's performance and effectiveness, why don't we take the same approach?

My experience has been that leaders look for one or more metrics to quantify a person. At the face of it, I understand why, as it's hard to compare people if there aren't numbers.

However, the mistake I see leaders make is what they're trying to measure. For example, do you measure the number of pull requests? What about the number of stories completed in a sprint? How about the number of bugs shipped to production? Something else entirely?

The problem is that even if you use all of the above (please don't do this), you're still not seeing the whole picture, but only bits and pieces. This would be like reading five chapters at random from a book and then giving an opinion.

The other problem with using metrics is that the measurement will cease to be effective as people will start gaming the system (see Goodhart's Law).

For example, if we measure effectiveness by the number of completed pull requests, then what stops someone from creating hundreds of single-line pull requests that don't accomplish anything?

On the other side, what about the engineer who reduced scope and time because they knew how to simplify the approach or came up with a more straightforward solution? This insight won't show up as a pull request or a completed story; however, this should be rewarded just the same.

To really determine how effective someone is, we need to look at things holistically, which can be done by examining how well someone does in these three areas:

  • Understanding the problem (e.g., why are we doing this?)
  • Understanding the system (e.g., how are we doing this?)
  • Understanding the people (e.g., whom are we doing this with?)

By looking into these areas, you will see what your team is good at and where they could use coaching, helping you be more effective. You might also realize that your team is doing things that aren't so obvious.

You can't write a report to generate these metrics. To understand this, you have to understand your team and how they work together. This involves paying attention, taking notes, and being engaged. Passive leaders will struggle if they use this approach.

Understanding the Problem (The Why)

To be successful, we first have to understand the problem that's being solved. Without this base knowledge, it's impossible to build the right solution or even ask the right question to the problem at hand.

How comfortable are they within the problem domain? Do they know certain terminologies, our customers, the users, workflows, and expected behaviors?

Besides quizzing, there may not be an obvious way to measure this; however, here's my approach.

First, you can look at the questions that are being asked. Are they surface level or are they deep? You can see these questions through chats and meetings, comments on the stories or pull requests, and interactions with others.

Second, look at the solution they came up with. Did they design it with domain knowledge in mind? For example, are things named correctly? Did their solution take care of the main workflows? What about the edge cases?

Third, how are they handling support issues? Being on support is a quick way of learning a problem domain and system. As such, I'm looking at how much help they need and how they communicate with others.

By using this approach, you can get a good sense of how knowledgeable someone is in the problem domain without quizzing them.

Understanding the System (The How)

There's always a push to deliver more things, and in order to do that, we have to understand the current system, its limitations, what's easy vs. what's hard, and from these constraints, determine the correct path to take.

In addition, once the system is live, we need to support it. If we don't know the moving parts, what it interacts with, and how it's used, we're going to have a bad time.

Like understanding the problem, we can measure system knowledge without quizzing them. In particular, I've found pull request comments and code reviews to be insightful on someone's knowledge of the system.

For example, do they call out that there's already something in the system that does this new piece of functionality? Do they suggest taking a simpler approach with what we have? Do they propose a different solution altogether because the system has a limitation? All of these are indicators of someone's system knowledge.

Another way to gauge system knowledge is by looking at how the person handles support requests. If you can understand the problem, find the cause, and create a fix, then by definition, you have to have a solid understanding of the system.

Understanding the People (The Who)

When it comes to the third part of being effective, we have to measure how they work with those around them. Most people think engineering is a solitary line of work, and that can be true when it comes to the development phase.

However, in reality, engineers work with others to design, develop, and iterate on a solution, and this can only happen when working with others. As such, building these relationships are paramount to being successful.

If you want to go fast, go alone. If you want to go far, go together.

Measuring team cohesion can be difficult (it could be its own post), however, we start simply be getting peer feedback on the person. We can also look at the communication between them and others through their comments, messages, or meetings.

Another way to measure this is through your company's recognition system. Whether it's an email or some other tool your company uses, you need to keep tabs on these recognitions, as you can use them as a talking point during 1:1s and review time.

Wrapping Up

So, how do we measure how effective someone is? We know that a single data point isn't sufficient and that if we limit ourselves to metrics, we can get a skewed sense of the person. To know, we have to take a holistic approach.

To accomplish this goal, I recommend measuring the following areas:

  • Understanding the problem (e.g., why are we doing this?)
  • Understanding the system (e.g., how are we doing this?)
  • Understanding the people (e.g., whom are we doing this with?)

In each of these areas, we can get a sense by observing their interactions they have, the questions they ask, the approaches they take, and how likely people want to work with the individual.

Three Steps to Better Interviews

At some point in your career, you're going to be conducting interviews. Regardless of the role, you have the opportunity to shape the future of the company as your recommendation controls whether this person is going to be a colleague or not.

What a lot of people don't realize is that an interview is can be the first experience that someone has with your company. As such, you want this experience to be fantastic, even if they're not hired, as they could be a future customer of yours.

With interviewing to be so important (there are whole books about the subject), it's confounding to me when companies don't invest in training or resources to help grow their leaders into being better interviewers. Especially, when making a bad hire can cause so much damage and is expensive to resolve in the long run.

Over my career, I've seen my share of good and bad interviews and have some tips and tricks to improve your interviewing skills. In this post, I'm going to share three tips that help me have better conversations with candidates.

1. Build Better Conversations Using Scenarios

The first mistake I seen interviewers make is that they have a set of questions that they want to pepper the candidate with, in an effort to figure out if they're going to be a good fit or not.

An ideal interview should flow more like a conversation where the candidate is getting to know you and the company and where you are learning about the candidate. As such, a never-ending list of questions makes the candidate feel like they're being interrogated and it doesn't allow for a natural conversation. A great interview should feel like tennis, each player receiving and sending the ball to the other side.

For example, let's say that I want to know a candidates familiarity with REST APIs. I could ask questions like

What's the difference between GET and POST?

What's the difference between a 404 and 400 response code?

Even though I'll get answers, this is not much of a conversation, but more of a quiz. Instead, I ask the following

In this scenario, I'm a newer engineer sitting down to make some changes to one of your APIs and I seem to be running into some issues.

For example, when I invoke the endpoint via GET, I'm getting back a 404 (Not Found). Doing some digging, it seems like it's related to the resource not being there, but I'm not sure how to troubleshoot. What would you recommend?

With the above, the candidate has a clear problem (e.g. can't communicate with the API) and has plenty of space to talk about what they're thinking (incorrect route, API not running, etc..). As the candidate is talking things through, I'm getting more insight on what they know and how they think about things. For example, if they mention that a firewall could be blocking the request, I could dig into that a bit more and learn that they have knowledge in networking or cloud technologies.

Another advantage of this approach is that we can add more steps. For example, here's one of the scenarios I ask to measure understanding of REST APIs.

In this scenario, I'm a newer engineer sitting down to make some changes to one of your APIs and I seem to be running into some issues.

For example, when I invoke the endpoint via GET, I'm getting back a 404 (Not Found). Doing some digging, it seems like it's related to the resource not being there, but I'm not sure how to troubleshoot. What would you recommend?

I've fixed the typo, made another request, and I'm now getting a 401 (Unauthorized). Looking up the response code, this implies that I don't have permissions, but I'm stuck on next steps. What would you recommend for troubleshooting?

Oh right, Bearer Token, I remember reading that in the README, but I didn't understand at the time. After generating the token and making another request, I'm now getting a 400 (Bad Request). Looking up the status code, it seems like it's something related to the payload or route. How would you troubleshoot?

Finally! After fixing that issue, I was able to get a 200 (Ok) response back, thanks for the help!

By using the above scenario, I can learn quite a bit about what systems an engineer has worked with, what gaps they might have, and how they troubleshoot issues. This is a lot more effective than knowing if an engineer can tell the difference between GET and POST.

2. Build Better Conversations Using Open-Ended Questions

Another common mistake I see is asking closed-ended questions to gauge knowledge. Even though these are binary in nature (Yes/No) or have a specific answer (What's the capital of North Carolina?), they come off as interogative instead of conversational. In addition, these types of questions are informational and could easily be looked up, where as open-ended questions are opinion based and come from experience.

For example, if we were to ask:

What's the difference between an Observable and a Promise?

We would know if the candidate knows the difference or not and that's about it. Even though this knowledge is helpful, we could learn this (and more) by rephrasing it to be open-ended instead.

For example, if we were to ask:

When would you use an Observable over a Promise?

With this question, not only do we learn if the candidate can talk about Observable vs Promise, but we also know if they know which scenarios to use one over the other.

For more effective questions, we could turn this question into a scenario, by asking the following

Let's say that we're working on a web component that has to call an API to get some data. It looks like we could call the API and have the value returned be either an Observable or a Promise. What would you recommend and why?

In this scenario, we get to learn if the candidate knows the differences between Observable and Promise, can reason about why one approach would be better than another, and explain that to another engineer. No matter their choice, we could follow up by asking why they wouldn't pick the other one option.

3. Build Better Conversations By Asking For Examples

For the final mistake, I see interviewers ask some form of a leading question, where based on the phrasing of the question, the candidate would be pressured or coerced into answering a particular way.

For example

This position involves mentoring interns to be associate engineers. Is that something you're comfortable with?

This is a leading question because if the candidate were to say "No", then they would believe that they wouldn't get the job. So they would always answer yes, regardless of how they feel, which makes this question useless as it doesn't tell us anything about the candidate. Most leading questions tend to also be close-ended questions, so a double strike for this style of interviewing.

But Cameron! I need to know this information as this person would be responsible for coaching up our engineers! Cool, then let's tell the candidate, but let's also provide some context and allow them to tell us their experience.

For example, we could phrase the question this way

One of the responsibilities for the role is to help grow interns into associate engineers so we can grow terrific engineers internally. With this context, can you walk us through a time where you had to coach someone up? What was your approach? What would you do differently?

With this question, you've still mentioned the skill you're looking for, however, you've added context on the "why" behind the question and you've set the candidate up to talk about their experience, which in turn, gives you more context about the person.