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Jean Hsu: Hi Cate, thanks for joining me for Lead Time Chats.
Cate Hudson: Hey Jean, thanks for having me.
Jean: So good to see you. The topic I want to talk to you about today is something that I think a lot of engineering leaders face at some point, which is the question of, should I work with an external coach? People have a lot of questions about, what do you get out of it? What's it good for? What it’s not good for? As someone who has worked with different external coaches, I know you're also going through coach training so I thought this would be the perfect topic for us to chat about.
Cate: Yeah. I feel strongly that everyone will benefit from coaching. It can be hard to find the right coach to work with, but if you're not getting enough out of it, then it's probably a sign that you haven't found the right coach yet. It's been really valuable to me.
Jean: You probably have a sense of, if you were to find a coach now—and same for me—you actually have some calibration of what the right coach looks like.What does that look like for other people who may have not worked with a coach before?
Cate: I think the most important thing with a coach is somebody who you can build a relationship of trust with so that you can take to them the things that are maybe harder or inadvisable to talk to your manager or your peers about. Somebody who you can have a sufficient trust with that they can lovingly push you and call you on your shit.
Jean: What are some of the things that you found useful to work with a coach on versus working with someone internally at a company?
Cate: I think it's much easier for me to take to my coach a bunch of like random nonsense and overwhelm and then have them help me sort through it and then by the time I talk to say my boss about it then my thinking is more structured and I know what I'm asking for, so that's a big help.
I think the other thing is situations where I feel like I'm failing. Going to the coach with those so that, again, they can help me sort through it and feel more empowered or more able to address it. Whereas if I went to my boss with something that I felt like I was failing at, he might feel like he needed to fix it for me or what have you.
The other thing that I think is really valuable is being able to create continuity across workplaces. I've been working with my coach for a long time, like I’ve had three different jobs in the time that we've been working together.
So firstly, we have a high level of trust and context, but also, in those kinds of transition points between jobs, she's been really able to support me, especially when I'm not sure. The two sides that's most helpful is when I was in the place where I was thinking , is it time for me to look for my next job? That's not something that I'm necessarily going to want to talk to my boss about.
Jean: Or they may be biased and they want to keep you.
Cate: Yeah and, if they don't, that’s a different problem, isn't it? My last manager just never had one-on-ones with me. Then the other side is like coming afterwards. If I am in my new job and am still carrying some amount of trauma say, from my previous job, my coach can help me pick through what's important now, and what's not.
Jean: So your coach is someone who has that long-term context and it sounds like you've built up a relationship with your coach, such that you can come to them with something like, “Okay, I’m super overwhelmed and I feel like I'm failing. Let me just brain dump everything out and then we can sort through that together. Whereas you, depending on your job and your manager, you may not feel comfortable doing that because that can carry like, “oh, what if now because I said I think I'm failing they think I'm failing or they feel like I'm struggling because I came to them in this like pretty unfiltered state.”
Cate: Yeah, exactly. It's I might not feel comfortable with it, but also maybe it’s not helpful, like I have an hour a week. I used to report to a CEO and he had no time. He had no time for anything. Right now I report to the CTO and he would make a lot of time for me, but I didn't want to waste his time when I'm a ball of crazy. I want to take that to my coach and then I want to use the time I have with my manager effectively.
Then as a manager who has had people I report to working with external coaches, it's also been really valuable because it gives me space to say you know what, maybe I'm not the best person to help you with this? And like an external support can be helpful to you. I think, with the best will in the world, you might really care about the long-term success of your directs and want to really help them as people, but I think part of, being good at that is accepting that sometimes that sometimes you're not the best person to help them with certain situations and pushing them to find something else.
Jean: Yeah. So when you've had people that report to you work with a coach, how did that start? Was it that you recommended it to them? Cause I know one question people have is how do you suggest other people get coaching?
Cate: I was really lucky. At DuckDuckGo everyone at a certain level gets a budget for coaching. So, for my peers and above it's expected that we're in coaching and it's seen as valuable. Automatic, where I was before, had a very extensive coaching program where coaching was available to everybody down to the IC level and the amount of it that you could get varied. In both environments the thing that's good about it is it's very normalized that people expect to be working with a coach. The company values that the company pays for it.
And so then it's varied, but For coaching, it's the same with a lot of things, right? Like we have professional development budgets, we have whatever, like EAP groups, like there's a bunch of resources that get provided by companies.
Not everybody takes full advantage of them. So I just tend to treat coaching is like a neutral thing in that set to be like, okay we have this list of things available to you based on what you're trying to do, what you're struggling with, whatever. This could be a good option to take, I think, to come back to the kind of first thing of like, how do you find a coach to work with people do find that difficult.
And so one thing that I've done lately, whether it's like a friend and I'm like, maybe it's time for you to try this. Or somebody I work with is to give them a starting point and say Hey. I think this coach could be a good person to talk to you first. Like, why don't you just have a chat with them?
And if they decide to chat with the people that's great, I'm not invested in it, over time, especially automatic prior, we worked through this set of coaches. I had a good idea of which profile matches to which purpose, and I have a few coaches who I think are really good, who I'm happy to recommend.
Jean: What are some of those, like what did some of those fits look like?
Cate: My coach, she's very zero bullshit. She has a lot of experience and so I sent one of my friends to work with her lately. I was like, “I think you should talk to Danny. I think she could be good for you.” I felt like my friend really needed to come to the first point and be lovingly called on her shit. She had spouted off a bunch of things to me that she'd previously communicated to her boss, which is perhaps not the best move, and I was like, if you want to stop doing this you can call me anytime. I'm always happy to hear about these things, but maybe this can really help you with the thing that you're trying to work on.
Jean: It seems like you're matchmaking based more on people. I know some people are also like, “Oh, I'm a first time engineering manager. I'm a new CTO and I don't know what I'm doing,” and want some general coaching and some engineering specific stuff and they want someone who's been in their shoes before. Do you know what I mean?
Cate: Yeah. I think there's more and more of that. Like there's a couple of organizations that do it. It's about matching people who are a few years ahead in their career and then it's like this mix of coaching and mentoring. Or in some ways I think it's almost like looking like a manager that's not weighed down by your organization. That's what you're getting from these kinds of relationships, which is fine. In co-active coaching, there's this idea that the client is capable, resourceful and whole, and I really love that idea because it posits the premise that the person has the answers that they need and that your role as a coach is to help them find them.
If people are looking more for advice or support, or feel a need to like, have somebody that gets it, I think that's understandable, but I think for coaches in that situation, like one of the things I've seen is, and I have not worked with this kind of coach, but I've had people working with this kind of coach and I'm like, Oh, this person is like, giving you that playbook, but it's not actually really like that.
You just have somebody else's plate cool. Like these are useful tools, but I don't see that person growing in a way that I think they could have. If they had a coach who was truly. Like challenging them and trying to get them to come up with their own answers and so that's one of the things that, when I was taking coaching and he was like, do you want to take coaching training?
Because you want to be better at coaching. And for whatever reason, or do you want to take coaching training? Because you see it as a useful mechanism for giving advice to people.
Jean: I think that can be one of the risks of getting a coach who’s someone who's been there done that a few years ahead is that it's way too easy without proper training and practice to slip into that, “oh, when I was at this company and we ran into that problem, this is what we did” even in the most well-intentioned cases. What I've seen and I found this challenging too, when I was coaching engineering leaders full-time. So what I, when people message me and they're like, Hey, I'm looking for a coach.
And I try to refer them out to people. I really try to get a sense of what is it they're looking for it? Cause people are like, Oh, I really want to work with someone. Who's been an engineering manager and engineering director before, but then when you dig into what they actually want to work on, it's more about interpersonal issues or like their confidence.
And I don't think that those are things you necessarily need someone who has an engineering background can actually be useful to have someone who's worked with a wide range of people and not just engineers because people are people.
Cate: I think that's true, but also Does this fallacy that we're going to get what we need from one person, and then it's like, Oh, I don't get everything I need from my manager so I need a coach now. He's no, like you get some stuff from your monitor. Hopefully you get some stuff from my car. It was really important to have. For example, a work BFF, right? Like that somebody who can really help you to have like a wide network of people in comparable roles who you talk to regularly.
Then, to your point like people are looking for a coach, but they don't necessarily know what they hear, but like the answer might not just be one person, the answer might be a coach and more participation in some kind of group, like more investment in a mentoring relationship.
Like more time, like for example, like there's a whole slate of options available. Two people, but they're not necessarily taking them all. And I think this is particularly relevant in the kind of dark time that we live in now, because people do feel more isolated. And a lot of the ways that people would get passive support through networking events or through the office or whatever, like those things of God.
And so you need to be a little bit more deliberate from what are you getting in and who you're getting it from?
Jean: What are some situations, topics or situations, where working with an external coach is not such a good fit?
Cate: That's an interesting question. I think an external coach should be, like this is why a good relationship and the quality of the coach is so important, right? I think the topic is probably the one you're most not ready to take to an external coach, for example.
Or where you take the wrong topic, like you take what should I do? But you actually don't have a choice about what you do because it's been decided. It’s really a question of like, how do I manage my feelings about what I'm doing? Sometimes I think it's also a question of what piece of the problem and how do you frame it to my coach?
Then as a coach, it's your job to understand, why is this coming up? Why is this a big topic of conversation? What does this person need to move forward and be effective?
Jean: Yeah. I think a lot of times coaches don't read behind what, like anyone can bring a topic to a coach and be like, hey, I want to be better at X. Perhaps there's something behind that or there's some other issue that everyone's like “oh, thank God this person's getting coaching. We can finally get them help with Z.” But then they're working with their coach on X the whole time and the coaching is usually confidential so then how do you get that?
You really want a good coach to either dig in and figure out, okay, what's actually going on in this situation. Or I know some companies will, if they do have a full blown coaching program, make you write out some of your goals, say these are the things I intend to work with my coach on, and get some feedback from your manager and those sort of things.
But I think that with coaching in the workplace, there's some connective tissue between the coach and the rest of the company.
Cate: We used to fill in that kind of format at Automatic and I didn't find it super valuable. To be honest, I was just like, I don't know, whatever catastrophe comes onto my plate each week. That's what I'm going to be like. It wasn't a knowable thing for me, which I think it's different when you are in a senior leadership role and getting coaching on an ongoing way just to manage the way that you need to work versus when like, “oh, I'm getting coaching because I'm a new manager and I need to work through these things” or “oh, I got this difficult feedback and to work through it, I'm going to work with a coach on it.” That might be like a tactical time-boxed coaching engagement and it's different from an ongoing investment in myself.
Jean: Like I just need more support. I need ongoing support.
Jean: I think those forms can be useful when it's less “Hey, I got this feedback. I'm also aware of it and I want to go work on it with someone.” So then you would come to the coach with that issue, but sometimes there are people who the company or their manager feels could use coaching, but perhaps they need a little bit of structure around what to talk to their coach about because they've never had coaching before.
Cate: I think that's true. But often, I think that gap comes down to individual self-awareness. If they have high self-awareness, then there's a match between what people think they need and what they think they need and if they have low self-awareness, for example, it's like oh, I need to get into coaching to truly earn my leadership space or whatever. Then their perception is oh, this person is in fact bullying their teammates.
Jean: I think it becomes more important to figure out how everyone works together when it's someone with low self-awareness and I'm curious if you've seen some way to make that work or have that all fit together.
Cate: I don't think I've seen a good way to be honest. One of the things I worry about with coaching is you send somebody toxic to coaching and, if the coach doesn't pick up on that, and a lot of people—particularly like narcissistic people—hide that very well. Then the coach just supports them in becoming even more toxic.
Jean: Right. Cause they only work with what they bring.
Cate: Yeah. They work with what the client brings them. I've seen people with a very coherent narrative way about, whatever and I've also been like, “oh, I'll take you at face value, help you, mentor you or whatever I like suggesting to you.” And then later I find out a more holistic picture and I'm like, damn. I don't know if like overtime as a coach, you would get more tuned into it, but I think, you might not because it is your job as a coach to show up for the person as they come to you and like really believe in their capacity.
Jean: I guess that's why a lot of coaches I've seen are doing like feedback or 360 feedback that people close to you will fill out, but I don't know how honest it is. It’s different than actually seeing how someone interacts in the workplace. I've also seen coaches like to sit down and talk to people at the more executive levels. They sit down and talk to a bunch of people one-on-one or have quick phone interviews with folks and aggregate that and get a more full picture of what's going on with this person at work.
Cate: I think that's great, but it's quite a significant time undertaking. Like a 360 assessment is incredibly expensive. It’s not something that every individual can do. The level of engagement with those things is really valuable as well.
Jean: So it sounds like, overall, you think it's generally useful for everyone, especially if they feel like they need additional support that they're maybe not getting internally. And some level of self-awareness around what they want to work on would be helpful as well.
Cate: Yeah. I just think self-awareness is one of the things that dramatically contributes to people's coachability and ability to grow in any way. And perhaps that it’s a warning sign, as a coach, that if the way somebody is being treated continually doesn't match up to how they see themselves that’s probably a sign that there might be a self-awareness gap there. Yeah. Cool. Yeah. Self-awareness helps for everything, but coaching is good, but not for narcissists.
Jean: [laughs] Coaching is good, but not for narcissists that's the TLDR of this chat.
Cate: Yeah. I think so. I think so.
Jean: All right. Cool. Thank you so much, Kate, for joining me today. I hope you have a good rest of your day.
Cate: You too. Lovely to see you.
Jean: Happy to see you too.