Approaching Sessions

Interviews with experienced domain-specific coaches about how they approach sessions.

Andy Scheff

Engineering leadership coach, CTO of BestPracticer, and lifelong teacher

Coach profile

How do you usually approach your coaching sessions?

Let's talk about an average session in the middle of a coaching relationship, as opposed to the first session, because that one's special. The most important thing that I do is review the notes from the last session. And I find that that's usually all I need to do because that helps me to remember all the context. Even if we've been working together for a year or more, it just helps me to refresh all of those threads and get me into the learner's mindset and what their concerns of the day might be. I'll also take a look at the goals that we've set to refresh my memory on a slightly more zoomed-out view — What are the long-term and short-term things that we're looking forward to that might be a little more zoomed-out than what happened in the last session.

How much do you guide the session and how much is fluid to what someone brings to the conversation?

When there is a really good relationship and a lot of trust, I almost always start by letting them set the tone for what they want to talk about that day. And then I have in my back pocket a set of things for me to talk about if they don't bring any structure. But mostly my clients will start by telling me what's on the top of their mind for their work that week. If they don't have anything, I'll ask what's top of mind and usually, that will get them talking about a bunch of things. If they do say, "Everything's fine, I'm not really sure what to talk about" — which does happen — that's when I start to go directly to those things that I did to prepare. I'll look at the challenges and assignments from the last session, and I'll ask about them. I ask, "How did that project go? Did it ship? Was that bug resolved? Did that new person start on the team? How did that go?" Whatever it was that we were talking about in the last session. That almost always gets them talking about those things that will lead to great things to highlight or things to talk about or further challenges to discuss.

If they do have something to say right away when I ask what's top of mind, then it becomes more of a challenge of balancing what their priorities are right now with creating continuity from prior sessions and with their goals. I want to avoid a situation where every session we talk about something completely different and there's no continuity between the sessions. When they do have a lot to talk about, if we get 20 or 30 minutes into the session and I haven't had a chance to connect what we're talking about back to the prior goals or the prior challenges, I find myself at a stopping point saying something like, "I have some threads that I want to pull on from the prior session," or "I have some prompts that I want to give you, but is there anything else that you want to make sure that we talk about in this session?" So I have some ways to try to get prior sessions and their goals into the discussion.

Of course, if there's something so burning and urgent that they just want to talk about that for the whole hour, that's okay, too. I had a client recently where there was a major departure from the team that caused a lot of challenges that were very immediate, and we spent the entire hour talking about how to best address the challenges and learn from the situation. And in that session, we didn't talk about longer-term goals or even short-term goals. And we didn't get to talk about the previous sessions’ discussions either. And I think that's okay because I always want to keep in mind, like, how do I make this person better at their job today? And sometimes that means a hyper-focus on one current problem.

It sounds like it’s about using your discretion and trying to pull the thread through, but if there's something that you can tell will be helpful to really dive into for an hour, sometimes it's better to go in that direction.

Right — It has to do with getting to know somebody and learning more about their work situation and what their work priorities are. You'll know when there's something that's really burning that is worth prioritizing over continuity or focusing on long-term goals.

How do you think about balancing active listening and questions vs. providing your own guidance and expertise?

As domain-specific coaches, we pride ourselves on offering a mixture of those two things. We often describe BestPracticer as a mixture of coaching and mentorship, which is not exactly a mixture of listening and talking, but I think that's a reasonable comparison because coaching involves a lot of listening, a lot of validating, a lot of motivating, and a lot of holding your client accountable to their goals. And mentorship much more comes from a place of expertise and knowledge. And we believe that combining these two things and using the right one at the time leads to the best possible on-the-job, in-the-flow-of-work learning experience. Balancing those two things is a core part of what makes BestPracticer unique.

I don't actually find it hard to balance because for me it's very clear when I do have something to offer in the mentorship dimension. Like sometimes your client is talking about a problem that you actually have extensive experience solving. So for me, that might be, "If I'm an engineering lead of a product development team, how do I collaborate with product managers and designers that I'm working with?" If somebody is talking to me about those kinds of challenges, that's something that I'm really well versed in and experienced. I've done a lot of that in my career. And so that's when I get more into mentorship mode. But if somebody is talking to me about challenges that I've never faced before, I'm not tempted to fake mentorship mode, and I enter more of a listening and brainstorming partner type of mode, rather than an authoritative mentor.

I guess one thing that might be hard to balance is if you have a client where you can enter mentorship mode too much. And I don't think this happens all that much on BestPracticer, because we try to match coaches with learners that are close to their level, but not that far behind them. So you may have encountered many situations that your client is encountering. I definitely have had some situations that are more mentorship heavy. And in those, I need to make sure to carve out space for coaching. I can think of one example where my client and I worked together on their code almost exclusively. Every session was just like a pair programming session, which was really valuable. It was really fun, and I got to teach that person a lot. I remember asynchronous JavaScript and debugging and thinking about client versus server and how to debug on your development server versus how to debug in the production server and migrations and all these awesome technical subjects that are really useful.

But I did have to be mindful to make sure that at least once every few sessions, we had some time to zoom out and talk about goals and make sure that the kinds of things we're taking on at work and the way we're feeling about work and motivation and ownership and autonomy and all of those dimensions — we're feeling like we're moving in the right direction too. So I think in that type of situation it can be too easy to get into the mentorship mode. And it's too tempting because you can get really quick wins and it's really productive. You have to make sure to prioritize some of the longer-term directional conversations, which are much more in the coaching mode.

It didn't occur to me that pairing on work could be more in mentorship mode whereas zooming out could be more in coaching mode.

Totally, although I'm definitely oversimplifying it. Coaching can be more of a listening activity and more of a zoomed-out activity. And mentorship is more of a talking activity and more of a zoomed-in activity. It's an interesting way to think about it. And I do think that's an oversimplification, but they feel related to me.

I was talking to a coach about how work can be a window into understanding someone’s soft skills and what's coming up for them. So maybe it's about how you're approaching a co-working type of session. Maybe there’s a way to approach it from more of a coaching side.

That's a great way to put it. One thing that brings to mind that's usually pretty successful is when we are zoomed-in and pair programming or talking about the details or having a more mentorship type of conversation, one way to get out of it is to identify something in there. You can find a great example of a pattern or a reusable piece of knowledge or tactic and highlight that. And then use that to zoom out and talk about the bigger skill or the bigger goal. For example, we could be pair programming. We could encounter some function that we don't understand how it works and that could lead to a discussion about, okay, how do we figure out how this function works? And if that involves maybe asking another engineer on the team for help, that could lead to a lot of discussions around, How do you recognize when you should ask another engineer on the team for help?
How do you prepare for that kind of a thing? How do you ask questions in a way that's not going to be poorly received or disruptive? And then that can, in turn, lead to even more questions about collaboration and leadership in general. Do you see yourself being in the shoes of this person that you're asking for help with someday and how can you get there? So when you're zoomed-in — looking for patterns and trends and doors to open — that can lead to those bigger discussions around direction and goals.

So it's not just about solving the specific problem...

Yeah, but it can be both. And that's something we say about what we do, which is having a BestPracticer coach makes you better at your job today and helps you build skills for the future. And I think this is a good example of that. One other example of this that comes to mind — when going from the details to zoomed-out — is to look for markers of progress in the details. So I'm thinking about one client that I've been seeing regularly for a while. In the way that they handled a certain situation, I saw the difference between how they would have handled that similar situation very differently if it had been six or nine months ago. And so I took a moment to highlight that, and it's a little less of a doorway to a bigger discussion, but it's a great time to write down a win, acknowledge progress, and celebrate that.

How do you encourage someone to actively participate in their growth?

Well, one thing is that all learners on BestPracticer are already pretty active just by the nature of them being here. They've sought coaching out or their manager has identified that they would be a good candidate and pitched them on it, and they've opted into it. So we already hear that from a lot of our coaches, especially the coaches that have experienced mentoring on other platforms, too, that our learners are the most motivated. And that's really, really awesome. So the baseline is already really high. That's not to say that somebody can't like lose that motivation or at any given moment, they don't have that motivation. I have one client who was working at a startup and they got acquired by a much bigger company and actually stayed with them through that transition. It was really interesting because at the startup, they were a big fish in a small pond. They had so much ownership and autonomy over what they were doing. And they had so much excitement for the future. They had a small engineering team of three people, but they were so excited to raise that next round of funding as a company and grow that engineering team to 10 or 12 people. And they were in a position to be the leader of that team, and it was a huge career step for them. But when the company was acquired, that huge piece of autonomy and ownership felt like it got taken away. And they felt like their career potential was postponed because they weren't going to be leading  a large engineering group because the new company already had existing leadership and layers of management.

So the way we worked through that was by setting new goals with a different frame of reference. And I believe that there are interesting challenges, motivating challenges to be found in just about any job, anywhere in any organization. It's not always the case that they're the exact right ones for you, but they're at this moment in your career. If you look and you try to find them, you can usually find something motivating. And this person who went from Head of Engineering at a tiny startup role to a senior IC engineer at a pretty large company, the prompt that I gave to him was: How can you be the best possible senior engineer that you could be?

And at first, they weren’t that motivated by this because they had been a senior IC engineer before at different companies and felt like they already knew how to be a good senior IC engineer. But through repeatedly bringing up this prompt and an obsessive examination of it — and also leaning on the BestPracticer curriculum, as there's lots of content there about what it means to be a great senior IC engineer — we were able to come up with new areas for growth. One good example was building cross-functional leadership skills in a complex organization. This client had a lot of ideas for how to change things in the larger org. They saw things that were not so much broken, but just processes that didn't work very well in the new org. But from their startup, they had figured out great ways to solve them.

And so learning how to identify those solutions and drive them in the much larger, more complicated organization brings this whole new set of skills that — once we were able to label it that way — started to feel really motivating. And I see that as a pretty powerful thing because this person had been building leadership skills at the startup for a long time. And at first, it wasn't really clear how to apply those to the new role. But once it became clear how to apply those leadership skills to the new role, the motivation came back and they were reengaged again.

I love that question... How can you be the best possible [insert your role] you can be?  And maybe it was the same senior IC role they’ve held before, but it came with a completely new set of challenges.

Right. Because they were a different person than in those prior roles. They had grown a lot in between, so it was about how do you do it again, but with your new self?

I’ve noticed a pattern across clients that people almost always are more focused on their title at first than what they're actually doing. They felt that because their title was the same as one that he had had in the past that it wasn't an opportunity for growth, but that couldn't have been further from the truth. It's what you're doing now, not what your title is. And I've worked through that with a lot of my clients where they see themselves as what their title is. And that could be very de-motivating. But once we start focusing on the actual challenges of the work and looking around us in the organization and trying to seize challenges and opportunities, it's really clear that it doesn't matter.

What advice would you give to a new software engineering coach?

Remind yourself that there is a good reason for the people that you're going to be matched with. The BestPracticer team has been really thoughtful about the match so that you are set up for success. The person that you're going to be coaching will be facing challenges that you are comfortable with and that you’ve faced yourself before. It might not be true for all of their challenges, but we aim to make that true for the majority of their current challenges. And so what that means is that, especially in the first few months, in the early sessions of your relationship, you can lean much more heavily on your experience and on mentorship rather than the coaching aspect of it, which can take time to develop those skills and take practice to develop those skills. So be okay with just being, just listening, and offering your guidance in a way that may not be perfectly structured or perfectly by the coaching book in the first few sessions.

And one other piece of advice, and this is along similar lines, at the risk of sounding too cheesy: Just be yourself and get to know your client as BestPracticer provides you with a lot of materials and a lot of guidance on how to run an onboarding session, and what a successful session looks like, and to create a magic moment by the sixth session or however we put it. But what I often tell coaches is you've met a lot of people in your field before. You've met a lot of colleagues. You've met a lot of people at other companies and you know what it's like to talk to somebody who's a software engineer or whatever field you might be. And you can just come back to that. Just be curious about what they're doing, ask them questions about their team and their work and their tools.

And just like when you're trying to get to know somebody at your company, or if you're reconnecting with a friend who works at a different company and you want to understand more about their work and their world, you can very much just get back to the basics of trying to get to know somebody and talking to somebody who is like-minded and has similar interests and works in the same field as you. There's so much to talk about. So just be curious about them and ask them questions about their work and their world, and that will start to lead towards goals, skills, challenges, and all of that.