S1E11: Inside a Coaching Session

Show Notes

Summary

What actually happens inside a coaching session? In this episode of The Intentional Organization Podcast, Sara Hicks and Mathias Meyer look back at their own experiences as coaching clients. Sara sought help while navigating co-founder tension after raising a Series A. Mathias started when he became the sole CEO of his company and realized he wasn't sure what the role was supposed to look like. Both found a place to work through decisions, relationships, and the loneliness that can come with leadership.

They share the practical details: introductory calls, preparation questions, homework, and the check-ins that turn a conversation into action. Mathias remembers sorting his work into what belonged above and below the waterline, and the discomfort of asking his team for two things he was doing well. Sara recalls a question on her intake form that opened up a deeply personal conversation about her parents' health.

The conversation explores what it feels like to have someone hold up a mirror, notice recurring patterns, and ask the question you've been avoiding. Sara and Mathias discuss rehearsing difficult conversations, building confidence through practice, and recognizing growth that can be hard to see in yourself. They also reflect on how they approach coaching alongside mentoring and sharing their own experience, and on the distinction they draw between coaching and therapy.

They close by considering what makes a coaching relationship work: trust built over time, a willingness to do uncomfortable work, and a coach whose approach fits what you need. Sometimes the value is a new perspective. Sometimes it's a question that helps you say out loud what you already know, and decide what to do next.

Keywords

executive coaching, leadership, startup founders, CEO, co-founder relationships, vulnerability, feedback, difficult conversations, confidence, accountability, personal growth, finding a coach

Takeaways

• Coaching can start with a crisis, a new role, or a desire to strengthen a working relationship before problems develop.

• The CEO role changes as a company grows. Looking closely at how you spend your time can help you decide where your attention is most useful.

• Preparation can go beyond business goals. Personal circumstances may shape how you show up at work and what support you need.

• A coach can help you see patterns, explore options, and recognize your own contribution to a difficult situation.

• Asking what you're doing well can feel just as uncomfortable as hearing what needs to change. Both can be part of learning.

• Practicing a difficult conversation gives you a place to try the words, experience pushback, and prepare to act, even if the nerves remain.

• Reflection becomes more useful when it leads to a concrete next step: what will you do, when will you do it, and what support will help?

• Working with someone over time gives them a chance to notice progress you might overlook and remind you of challenges you've already handled.

• A coach may sometimes offer perspective from their own experience. The decision about what to do with it remains yours.

• Introductory conversations with a few coaches can help you explore fit, while trust in the relationship takes time to build.

Resources mentioned

• The Reboot Podcast — Mathias recalls how listening to coaching conversations helped him feel more willing to have his own.

• S1E8: What Makes for a Productive Offsite? — their earlier conversation about offsites and making time for working relationships.

• The Intentional Organization by Sara Hicks and Mathias Meyer — including questions and considerations for finding a coach.

Chapters

00:44 The Journey to Coaching

04:26 Navigating Challenges as a CEO

09:05 The Role of Coaching in Leadership

11:28 Preparing for Coaching Sessions

17:29 Vulnerability in Coaching

21:30 Embracing Feedback and Growth

23:18 Navigating the Awkwardness of Professional Relationships

24:54 The Distinction Between Coaching and Therapy

27:06 Facing Difficult Conversations

29:32 Building Confidence Through Practice

32:08 The Emotional Landscape of Leadership

40:33 The Role of Experience in Coaching

43:06 Finding the Right Coach

Transcript

Sara (00:00) So, what actually happens inside a coaching session? Today, Matthias and I pull back the curtain and we get a bit personal. We share our own stories of what brought each of us to seek out coaching in the first place. It started from a co-founder crisis to just not knowing what a CEO is even supposed to do. We're talking about the awkward homework, the uncomfortable

role play conversations, and the questions that are gonna stick with you for years and years. So if you've ever wondered whether coaching is worth it or what you're actually supposed to get out of it, this episode is for you.

Sara Hicks (00:45) Here we are.

Mathias Meyer (00:46) Here we

are. This time unstructured. There is very little research for this topic because today we're talking about what it's like to be in a coaching session. And we're talking about it from our perspectives. So there will be some reminiscing, there will be remembering.

reliving some potentially uncomfortable moments. Because I mean, now we both of us work as coaches and it's sometimes easy to forget how we even got to this point, But yeah.

So shall we get into it?

Sara Hicks (01:26) We shall, we shall, yes, yes.

Mathias Meyer (01:28) So when did you start working with a coach?

Sara Hicks (01:30) I started working with a coach.

Probably in.

2018 to

Mathias Meyer (01:37) Mm-hmm.

Sara Hicks (01:37) was right around the time of our series A.

which I think was 2018, so.

I had done a boot camp, I had done a long CEO startup founder weekend couple years prior and that was really profound. We'd just raised the Series A and I was going through, well, some co-founder tension. Yeah,

Mathias Meyer (02:00) Mm-hmm. Yeah.

Sara Hicks (02:03) some really just hard stuff and I...

Got to the place. I remember thinking to myself like so just not sustainable either I have to step away I have to leave or Something has to change because I'm I'm part of the problem here. Like I am I was disengaging I just wasn't I stuck totally stuck and We had this I'm just jumping in I'm just gonna remember I'm just going down the path.

Mathias Meyer (02:27) Yeah, go for it, go for it.

Sara Hicks (02:30) I Remember we had this

Meeting was in our office in Santa Monica and one of our investors, one of our board members was at the meeting and we were working through a particularly project with a client and the other client was also part of the

the venture portfolio. So the board member knew that, you know, I was like, he was there to help us to try

Mathias Meyer (02:54) Uggh.

Sara Hicks (02:54) to help us navigate this project and all this tension and frustrations that had been brewing in this project. anyway, it was a terrible meeting. You know, there was a lot of tension that was very visible and palpable. And remember reaching out to him after I said, could we meet up for coffee the next morning? And we met up.

that next morning and I just was like, well, I'm kind of glad you got to see all that frustration and all, you know, feel it. I need help. And he was like, Yep, I got it. going to reach out. Here's who you should talk to. And he introduced me to the person who would become my coach.

Mathias Meyer (03:30) Uhhh...

Sara Hicks (03:31) And, you know, so a lot of my very first sessions were about, all of that.

all about the co-founder tension, all about the situation, kind of what my patterns were. And it was really, this is part of coaching. It's my what I was bringing to the situation and to the company and to how I was showing up and

Mathias Meyer (03:54) Hmm.

Sara Hicks (03:55) deeply difficult.

Mathias Meyer (03:58) Yeah.

Sara Hicks (03:59) yeah, it was...

Exactly what I needed, know, lot of coaching and a of what I do and I think you do too, Mathias, is a lot of what my coach did is just kind of help hold up a mirror, so to speak, to help to

Mathias Meyer (04:10) Hmm.

Sara Hicks (04:11) show me myself and show me, you know, more clearly the situation. You know, an accountability partner and ultimately he helped me navigate, parting ways with the co-founder. We'll get into all

Mathias Meyer (04:24) Yeah.

Sara Hicks (04:24) that, but that's a long answer.

say, yeah, I was in a crisis. needed support. And it was, we worked through that. And then I worked with that coach all the way through the acquisition of the company. you know,

Mathias Meyer (04:38) Hmm.

Sara Hicks (04:39) I don't know, three, four years of weekly conversations, navigating everything from selling the company to co-founder transition to

layoffs to, you know, good times as well. So all of the above.

Mathias Meyer (04:57) Yeah, and trying to figure out how to work with the German probably as well.

Sara Hicks (05:02) Right, and

then bringing on board this German. I mean, there's so much stuff, right, that goes into people decisions and culture and I'd never been in that position. It was my first time being

Mathias Meyer (05:16) Hmm.

Sara Hicks (05:16) a startup founder, startup CEO, first time ever raising venture capital, millions of dollars and trying to figure out.

how to run the business, build a team, build a culture in a sustainable way, and all while going through

Mathias Meyer (05:29) Uh-uh.

Yeah.

Sara Hicks (05:32) so I'm sure that triggers some stuff for you too, because I know we have some parallels.

Mathias Meyer (05:36) A little bit, a little bit. But it's

interesting that for you, as you were describing this, I also thought about like, this is, so this came out of a crisis, is, you know, not an uncommon thing for, you know, seeking out external help. For me, it was not a crisis, maybe a personal one in that I didn't know what to do

like for me, this happened when, in our group of founders just split up responsibilities more. And I was suddenly the sole CEO of the company and I didn't actually know what that meant. What do I actually do in this role?

Sara Hicks (06:16) Thank

Mathias Meyer (06:17) That's when I talked to a good friend about this and that's then when I learned, there are people who can help you with this. And then he introduced me to two coaches and one of them, clicked very well for me. And we also then started working for...

When did we start? End of 2014? I think the last conversations we had were maybe 2019 or something. So it was also, it was quite a while. And yeah, it's like, oh, there's someone I can talk to about all of this, which I think is like, even though there's, you know, all of the discomfort that happens in many of these conversations, there's something about being in the

in the CEO seat or maybe even any executive seat or maybe even being part of a group of founders where you still feel alone in some ways, like

Sara Hicks (07:07) Yep.

Mathias Meyer (07:09) because everybody's always rushing, everybody's busy in their stuff. And I this is what I also what I like to talk to my co-founders about is like, Not enough.

co-founders or executives, executive teams, pay enough attention to the relationships, right? and to doing the work that helps nurture and maintain the relationships. And I mean, that it also includes me. It's started this too

Sara Hicks (07:33) Yeah, so true.

Mathias Meyer (07:35) late. We talked about like off-sites recently for another pod. And, you know, that slightly came up there

but yeah, I had some wild conversations throughout the years and not wild and like they were outrageous or anything. They were deeply uncomfortable. But yeah, for me, for me, it was just really trying to understand is my role in the company. And then also

Sara Hicks (07:58) Yeah.

Mathias Meyer (07:58) over time, understanding that that role doesn't actually, you know, it's not fixed.

the role actually changes or can change every couple of months.

Sara Hicks (08:11) Right. Yeah, that reminded me. mean, I think I went to Google and was like, what does a startup CEO do? know?

Mathias Meyer (08:19) Yeah, and the answers

are very, very much not satisfying.

Sara Hicks (08:23) No,

I was like, what help? I'm like, what do I do? It's Monday. you know, like I might as well just ask who am I? What? You also made me remember, Mathias that we also worked with the coach together. Right.

Mathias Meyer (08:36) That is true, that is true. Speaking

of maintaining relationships.

Sara Hicks (08:42) Right. And I don't think that was in crisis. I think that was more of a proactive

Mathias Meyer (08:46) Mm-hmm.

Sara Hicks (08:46) move on our part to say, you know, as part of the business partnership and wanting to show up differently as leaders. And we didn't work with that coach for too long, but it certainly was helpful to have a party, a person that we could, you know, check in with and connect with and work through.

Mathias Meyer (09:05) Yeah. I mean, I've been, I just, it's been interesting over the years as I've been brought in to founder leadership teams for similar situations where, I mean, you know, either a crisis or a relationship that needed to be mended. think the difference for us was like where we started working, with our Joint Coach, like we...

We didn't feel like things weren't in bad place. We just didn't want it to get there. I've been in the coach seat for situations where was already dire. And I do, I've got to say, even throughout my own past and my own experience,

find that it's not joyful work per se. Maybe rewarding is the better word. And

Sara Hicks (09:53) That's a good word.

Mathias Meyer (09:55) also when at least people are ready to put in the work. They don't feel like they need to be there, for example, because the board forced them to, which is never a productive starting point for coaching anyway.

Sara Hicks (10:09) Yeah.

Mathias Meyer (10:09) But when they're there and ready,

to do the work as uncomfortable as it can be. As you said, like it's about getting a mirror held up and it's even more uncomfortable when, you it's not just a third more neutral person or a person that is, you know, ideally somewhere on your side, in your corner. But when it's a person who is there for the third person in the relationship, which is the relationship, right? Which is very...

There's something

Sara Hicks (10:38) Right.

Mathias Meyer (10:38) very airy-fairy and metaphorical, but it's still like... I found that it does help people to think about it in a slightly different way.

Sara Hicks (10:47) Right.

Mathias Meyer (10:48) Anyway, wow, yeah, that's... Wow.

Sara Hicks (10:51) Little

remembrance, a trip down memory lane there, yeah?

Mathias Meyer (10:54) Yeah. In a way, I was just thinking about this. think part of it was also like listening to the Reboot podcast, like when it first came out, about those uncomfortable conversations public,

And it helped. It's like, if people can actually do this on a podcast, I can probably do this as well.

Sara Hicks (11:17) Yeah, it was like listening to a coaching session. Yeah.

Mathias Meyer (11:20) Yeah, it felt wrong in some ways, but sometimes it is awkward.

Sara Hicks (11:23) Sometimes, sometimes it's awkward. Yes, yes.

Let's get to some of the practical. Did for your first coaching session, was there any preparation that your coach had you do?

Mathias Meyer (11:38) Probably. we had an intro call where I talked about where I'm at, what I'm struggling with. And I think out of that came like, I mean, if we then count like the first actual coaching call we had, know, then yes, there was homework. I think this was the very point where I was trying to figure out like, what does the CEO do?

like beyond what you find on the internet, which is usually a mix of fundraising, hiring, and either strategy or product or something else. Like usually it's that list,

Sara Hicks (12:11) Yep.

Mathias Meyer (12:12) but it just in very vague terms, very not satisfying. And we were like that company who weren't fundraising. So I was like, so what else am I going to do if that's not what we're doing? And

also, was, you we just got a new office and I, for some reason, because maybe, you know, I am or was a little bit too controlling or I didn't want to make anybody else do this work, I also assembled office furniture in that office. Like I even planned with, you know, one of the early employees, planned the kitchen together.

But I was assembling office furniture and was also hiring a few folks at the same time, which I got, you know, found very enjoyable. felt like there was a lot of stuff that I was doing that wasn't, I don't want to use the word impact, but maybe the more recent terminology

Sara Hicks (13:00) Yeah. You

Mathias Meyer (13:07) that I started using.

is that wasn't the right lever, right? It wasn't the good lever for me. And I'm not using, I'm not leverage, I'm avoiding that. But

Sara Hicks (13:17) Right, right, right.

Mathias Meyer (13:18) you know, if you think about lever, it's more for me, like work that has high impact. But where you

Sara Hicks (13:26) Right.

Mathias Meyer (13:27) put in some of the work and ideally in the longer term, you get a higher reward, right? Like something like that. And so, but.

You know, back then we put it, she put it differently. It was like, there was some work that felt like I was under the water line. So almost drowning in a way, but not,

Sara Hicks (13:43) Yep. Yep.

Mathias Meyer (13:45) that's not the terminology we use. Although it sometimes might've felt like, exactly. And then.

Sara Hicks (13:48) Yeah, above water, below water, yeah. Above

the line, below the line, yeah.

Mathias Meyer (13:53) So she had me do an exercise where I was supposed to collect all the work I'm doing that is below the water line, or that I think is below the water line, because it's always, it's a relative thing. And then also think about what is the work that from my view is above the water.

And this, know, in some ways it wasn't entirely different from, Googling and trying to figure out what does a CEO do, but in some ways, you know, the framing is a different one. It gives you

Sara Hicks (14:19) Right.

Mathias Meyer (14:19) also permission to think beyond that. And that's what I found helpful about that exercise. And so I had a really long list, list in the end, and came out with a few things where, Oh, this is what I could actually do. Like, and hiring was a part of that.

This is like this, least at this stage of the company, me being involved in hiring is a good leverage point. you know, maybe I'm the best person to hire for these specific roles because we're hiring for them for the first time and nobody else has done it before. I don't know. There's all, all kinds of reasons, but I found,

Sara Hicks (14:48) Right, right.

Mathias Meyer (14:50) I mean, I sometimes still do that with, you know, my clients today because like people who, you know, like us land in the

in the founder and then executive and then people management seat for the first time. I think that transition is always difficult and also just trying to figure out what am I actually doing here?

Sara Hicks (15:10) Yeah, it comes up often with managers or people who are promoted into people manager roles. You know, just different seats, like becoming a startup CEO, right? Yeah.

Mathias Meyer (15:21) What was it for you? The first piece of homework?

Sara Hicks (15:24) first coaching sesh, got a bunch of questions, a document to complete prior to the session. It kind of answered a bunch of the questions that you had of, you know, what's going on. It also went into, you know,

what are some of the top three, top five pivotal moments of your life? Yeah,

Mathias Meyer (15:43) interesting.

Sara Hicks (15:44) there were some ones where I was like, I have to dig deep here.

Mathias Meyer (15:49) No.

Sara Hicks (15:50) trying to think of some of the other ones, but similar to that, just trying to understand personal motivations and little bit of history and.

And then got into the team, the business, who, who's my leadership It was sort of like it was about me and about my past and my history and all of my motivations and what drives me. then shifting it to, what's going on right now? What's happening? What's the team? What's the situation?

there was one question. I'll go back. There's one question in the homework. was like the last question. was like, is there anything else you know that last like, is there something else you want your

Mathias Meyer (16:26) Yeah.

Sara Hicks (16:27) coach to know? And, you know, I'd filled out all this paperwork, you know, I was like being a good student and I went really tried to like be really deep and thorough and

That question just like got me. was like, oh, oh, right. Mathias, you know the story, but I was going through a very challenging time. My parents were

Mathias Meyer (16:52) No.

Sara Hicks (16:52) ill just paused and I was like, oh, I should probably tell my coach that, you my parents are quite ill and we're going through.

a really challenging time with their health and and I put that in there and I just remember like, feeling so vulnerable and raw like, you know, I and I just I sent it off, you know, and that's where we started. The first session was like talking about my mom in particular, and it was just so beautiful and scary as a heck and hard

Mathias Meyer (17:21) Hmm... Yeah.

Sara Hicks (17:25) because I was vulnerable to, you know, someone who I was just getting to know.

yeah, one thing that my coach was really good at or is really good at is, and you kind of described it, was just, what's going on right now? Like every session was like, what would be helpful today? You know, where do you want to let's do a check in

Mathias Meyer (17:41) Yeah

Sara Hicks (17:42) what's happening right now? And then it quickly shifts to this second layer lever. I love that word lever of, OK, you know,

you do about this? How do you tend to operate? What are your options?

Mathias Meyer (17:55) Hmm.

Sara Hicks (17:56) And he would have me outline talk through all options, even if they were didn't make sense or there was no way I was going to do something, I was just very sort of like giving me agency and sort of clarity to be like, okay, I have all these options in front of me. And then

Mathias Meyer (18:12) Yeah.

Sara Hicks (18:14) it shifted to, okay.

Well, what am I going to do about it? What will I do differently? Or what can I do to shift it? And often he would be like, OK, can you do that by the next week or next two weeks? Or when will you be able to do that? And let's

Mathias Meyer (18:29) Mmm.

Sara Hicks (18:30) check in on it next week just to have someone to hold me accountable.

Mathias Meyer (18:34) Yeah, the homework was my favorite part usually. not just because I not because I love homework, but more it was nice to keep a thread through this whole thing. And didn't necessarily mean that we always follow up on the homework the next time around. But it was from my benefit. Yeah, I mean, that extra field in your or that extra question of anything else feels like this is the

awkward pause in written form. Like it's just... What else is there? Yeah.

Sara Hicks (19:02) Totally. It's that

like, it's that so important when you there's that silence and it happens

Mathias Meyer (19:08) Yeah.

Sara Hicks (19:08) all the time. You're like, just, I just have to fill the void. And that was that in a question. was like, what one more thing, you know.

Mathias Meyer (19:18) Yeah, I mean, I was lucky I didn't, I didn't have like personal circumstances contribute much. I do remember one time where, it was close talking about maybe my parents and how they, inevitably shaped me and, you know, wondering is it worth looking at that?

And then I also appreciated this, you know, in a way it felt like a very German response from her. it's like, I don't think that's useful. Like just, you know, let's focus on what you do from here on out rather than, you know, spend too much time on the past. Like you could tell that she didn't, you know, might've not been

Sara Hicks (19:57) Yep.

Mathias Meyer (19:59) a big fan of Sigmund Freud or Carl Jung in this, you know, trying to tie everything back to your mother in this case.

I did appreciate it. will say that in life, even just having something of an understanding of what I took with me from my childhood and how that might be holding me back, I found that useful every now and then. But then again, the

Sara Hicks (20:24) Yeah. Yeah.

Mathias Meyer (20:25) more useful part is always, now that I know, what do I do with that?

Sara Hicks (20:29) Yeah. Right. Right.

Mathias Meyer (20:32) That was always the more interesting challenge. And I think that was to me always the...

the nice part about coaching, about having this, this other person that was the challenge, like to me, stepping into the CEO role, trying to lead a company, I kind of took it as a personal learning and growth challenge. I was like, I want to see if I can do this. Right. and then I will, you know, I will stop writing code. I will stop doing this and that I will focus only on.

being the best I can be, whether I am, or I was, at what point, it was not necessarily for me to judge, but that was the challenge for me, for myself, going into it, and it was just nice to have somebody push this challenge. To me, it's like today, working with a personal trainer, it feels similar. I'm being pushed without getting yelled at, which is nice.

Sara Hicks (21:28) Yeah, being coached.

Mathias Meyer (21:30) It

feels similar. But part of it is like you have to push yourself. Or at least that's what it is for me. I wanna push more. And that's what

Sara Hicks (21:39) Yep. Yeah.

Mathias Meyer (21:40) I've always appreciated. And sometimes just even I try to think like making me go through some really uncomfortable things. Like, you know me as a German, like there's some stuff where I'm just like, don't, or traditionally I might not have cared.

like what is any good or positive feedback? And it's not really, like my assumption was always, even when it was like the feedback was about me, I just want to know am I doing wrong, right? Those kinds of things. Because supposedly this is what everybody tells you, you learn from failure, you grow from failure. And that is true. There's learning opportunities in all of that. And

Sara Hicks (22:21) Right, right.

Mathias Meyer (22:23) one of the...

one piece of homework she had for me was to send an email to the entire team and ask them to send me back two things that I'm doing well.

I was like, I can't do that. Like, this is like,

Sara Hicks (22:41) Yeah.

Mathias Meyer (22:42) I'm gonna look like I'm just, I'm fishing for compliments or,

Sara Hicks (22:46) You

Mathias Meyer (22:47) you know, shouldn't I also ask like what I'm doing wrong or, you know, there was always this longing for fixing things. And I guess maybe there's, you know, some of this goes back to my engineering past where fixing is, somewhat ingrained.

Sara Hicks (23:04) Yeah.

Mathias Meyer (23:05) But this was like, I could think of two really uncomfortable things. And even though this was just an email, this is like one line in that email, nothing more.

Sara Hicks (23:17) Yep.

Mathias Meyer (23:18) And

it was so weird.

Sara Hicks (23:19) Classic.

Mathias Meyer (23:21) It was so weird. What was that for you? Like, did you have moments like that?

Sara Hicks (23:27) I'm sure I did. I was just thinking of that question that that email two things I'm doing well. I feel that way when I get requests to recommend someone on LinkedIn. It's like so I don't know LinkedIn recommendations just feel so fabricated to me.

Mathias Meyer (23:45) True, mean, yeah, I mean...

Sara Hicks (23:46) That's a whole nother rabbit hole, sorry. I just went there, but I

was like, yeah, I just feel like, yes, it's theater, it's performance theater.

Mathias Meyer (23:53) Yeah.

Sara Hicks (23:56) There was another thing you said that I just thought, like a lot of people ask me, as they're contemplating coaching, what's the difference between coaching or therapy? you

Mathias Meyer (24:04) Mm-mm.

Sara Hicks (24:05) know, coaching's not therapy. You spend more time generally in coaching.

in the now and looking forward and generally these are big generalizations generally in therapy you do look back to childhood and but clearly emotions come up so you know there are elements of therapy there's elements of consulting even though coaching is not consulting there's elements of of mentoring even though

Mathias Meyer (24:31) Mmm... yeah.

Sara Hicks (24:32) coaching isn't mentoring like like there's a blend of all that that's that's in coaching but yeah there's

not as much emphasis on some of the causes and conditions and patterns that you might have gotten from your parents or from your childhood

Mathias Meyer (24:46) Yeah.

Sara Hicks (24:46) right because as we like to say we're here now we

what are we going to do about it what's what can we do

Mathias Meyer (24:53) Yeah.

Sara Hicks (24:54) thing that we navigated with my coach that was also, hard was, and I was getting pressure from my board too. I had to make a decision to, to let someone go, someone on the leadership team, this person worked very closely with and,

God, just I was so resistant to that and I my coach,

Mathias Meyer (25:12) Hmm.

Sara Hicks (25:13) I don't you know, we spent multiple sessions that conversation, what that might look like and how to prepare and how to have that conversation. just it helped. Once I got through it, I think I I learned so much about how to navigate that. But

Mathias Meyer (25:30) Yeah.

Sara Hicks (25:31) yeah, super awkward and hard to like

work through my own doubts and insecurities and challenges about doing that and fears. I was afraid.

Mathias Meyer (25:44) Yeah. I was just thinking that At times I was also looking to my coach, maybe just for permission to do a thing. Right. And,

Sara Hicks (25:52) Yes.

Mathias Meyer (25:54) and sometimes, I mean, I find this even today, sometimes the most helpful answer, that I also today sometimes give to clients is

one, know, when they, when, when I reflect everything to my coach or they reflect everything to me, you already know what you need to do.

Like the the whatever the decision or the response is some it's already happened. It's already in here But you know, there are times when I was waiting for something to say a difficult conversation or how I go about it Just like in your example Or do I bring up a certain topic that's going to be touchy or riddle with past

conflict and fissures and Sometimes that was the most useful thing I got from my coach is just that already know what you already know what you need to do or maybe just asking back like just Now turn that what what needs to happen? I just having this external party who again buys no stake in the outcome

I like they're only there to help you make a decision it doesn't matter what decision it is to them.

It's

Sara Hicks (27:06) Yep. Right.

Mathias Meyer (27:07) just a decision that gets you out of whatever cycle or loop you are in because they will see it. They will see it because it's come up in the last three sessions and somehow still nothing is out.

And this is like the accountability partner that you talked about where it's just, sometimes the most helpful thing is for somebody to point this out to you. this has come up like a few times or even, know, some rewarding sessions that surprise my clients even is when I can connect a conversation today to something we talked about maybe more than a year ago, which is also sometimes nice when it's about the individual growth.

Like maybe a year ago we talked about a problem like this and everything seemed like a complete crisis. And today there's a level of calm because it's not the first time anymore.

Sara Hicks (27:57) one of the most, one of the joys I get as a coach especially working with folks for a longer period of time. I've had some clients I've been working with for several years and I get to kind of be that person who says, you know, I just want to point out a pattern here that I'm seeing or I remember back to here, like,

You used to not know how to do this and look at you here. Now you're leading this, driving this, know, like, know, or they'll be stuck here and I'm like, hey, you've done this before. You know how to do this.

Mathias Meyer (28:30) Yeah.

Sara Hicks (28:30) You're actually good at this now, you know? I love being able to do that and to be that mirror back to that person.

Mathias Meyer (28:38) Yeah, yeah, same. also like, you know, when you talk about, you know, letting somebody go, that's never an easy and easy conversation. And maybe it shouldn't come easy at like at any point, right? But I've had conversations like this many times when somebody was, struggling with what they what they should do.

And then, you know, sometimes the useful thing is first like walk them through, like as your coach did for you. Like, so what are the options? What are, what is, what's the worst that could happen and what's the best that could happen? and then you give them a different framing. for how to think about, is this person harmful to my team?

they can't quite maybe put a finger on You can give them a tool or a framing to think about is, are they actually or just harmful or not performing, whatever that means.

Sara Hicks (29:32) Great.

Mathias Meyer (29:32) And then they get to a different point of clarity because are stuck just like we were once this.

whatever the fear is of what might happen and also of the just incredible and again, like warranted discomfort of having

Sara Hicks (29:47) Yep.

Mathias Meyer (29:48) to have that conversation with somebody and

Sara Hicks (29:51) Yep.

Mathias Meyer (29:51) telling them somebody that something that impacts their life definitely for the worse.

Sara Hicks (29:57) I remember that question

that our coach asked us. I've used versions of it. what's not being said that needs to be said or

Mathias Meyer (30:04) you

Sara Hicks (30:05) something like that. Such a good one.

Mathias Meyer (30:07) Yeah.

Sara Hicks (30:07) Another one of those like awkward silence, like, that last question. Yeah.

Mathias Meyer (30:14) Yeah, is like that last question. It opens up a space

Well, it gives permission to say the things that you don't want to say or that you're afraid to

Sara Hicks (30:24) Right, right.

Mathias Meyer (30:25) say because of consequences and things like that. That does remind me of, yeah,

Sara Hicks (30:29) Right, creates a container.

Mathias Meyer (30:31) you know, and you get to practice it in a safe space with a coach first, like, which is, you know, reminds me of one of my more uncomfortable coaching sessions where, like with my coach, like,

We always did video because I I was in Berlin, still am, and she was first on the East Coast and then moved to the U.S. West Coast. at one point, she had me like really practice a difficult conversation. Just like, you know, sitting like this in front of the camera and then swapping seats. And then just really had me

Sara Hicks (31:05) Thank

Mathias Meyer (31:07) really say everything I wanted to say.

or I felt like I needed to say. That was so weird. But again, like the point is, you know, the point of working with a coach like that is to push you, to help you through these really uncomfortable situations.

Sara Hicks (31:25) Yeah. Yeah, we did. We

Mathias Meyer (31:27) good.

Sara Hicks (31:28) did several of those with I've done several of those with my coach, the role playing, like actually

Mathias Meyer (31:33) role-playing.

Sara Hicks (31:34) practicing those. you know, sometimes he would take on the role of someone who was an interrupter or someone who's got to

someone who got defensive and like really try to like be combative. And So hard because I just don't.

That's my fear. It's like someone's gonna get defensive or combative or Interrupt me So many of the people I work with are kind of more early stage. I have a few that are more scaling or growth stage, whatever you would call it but like so much of the the folks I work with it comes down to helping to build confidence right and helping

them to

Mathias Meyer (32:08) Yeah.

Sara Hicks (32:09) make decisions

about delegation, which is really about surviving.

Mathias Meyer (32:16) That is true. That

is true. interesting framing.

Sara Hicks (32:19) And then as I think

work with more mature companies and founders maybe who have been doing that role or executives who have been in the role for a while, it becomes maybe more about letting go or delegation

Mathias Meyer (32:31) WHAAAAT

Sara Hicks (32:32) or.

How do they, build? Is it building? don't know, building and kind becoming a leader, I guess is the way to put it. I hadn't really thought about that. Yeah, the different kind of stages of the company and the stages of

Mathias Meyer (32:44) Yeah.

Sara Hicks (32:45) the individual. And certainly as folks who are more mature in their leadership skills or leadership and management, it becomes more about strategy and helping them to think about strategic.

planning just different stages of the individual and of the company.

Mathias Meyer (33:01) Yeah, very true. Yeah, you mentioned confidence earlier that just you need the kind of confidence to go in that personal growth and taking on these challenges. But that confidence only comes from actually doing the work. And some of that confidence you might be able to get from doing a practice run, it certainly helps. But that conversation is not gonna.

make go away, that racing pulse, that, you know, dry mouth or whatever else you might be feeling before you go into the conversation. Maybe that never goes away and maybe that's a good thing, just like, you know, in public speaking, there might always be a level of nervousness and maybe that's okay. You just understand over time

Sara Hicks (33:47) and I'll you time.

Mathias Meyer (33:48) that it's just there.

and it'll be gone as soon as you start talking on stage. And so you just, over time you just walk on stage and do your thing and that's it. But the nervousness is still there. And I think it's maybe similar in this case, but anyway, the confidence only comes from actually doing the work. And sometimes it is nice to have this form to practice it. And then also to someone who pushes you to do the work.

I think that's maybe where the biggest growth opportunities have come from for me, working with a coach.

Sara Hicks (34:23) Yeah. Yeah. Yeah, I agree

that pushing to to action or this is where like coaching to me is there is a lot of reflection in coaching, certainly in the way I coach. But there is also point almost in every coaching session or with every coaching client where it shifts towards that accountability or

towards action. My coach would often ask me, and always near the end of the coaching session, kind of like, okay, conversation do you need to have what's going to happen next and when or, know, what will you do differently this time?

Mathias Meyer (34:58) Yeah.

Sara Hicks (34:59) you know, where might this be challenging? Where might you fall back into your old patterns just to name it and talk about it?

Mathias Meyer (35:05) Yeah.

Sara Hicks (35:06) And always like, can I help you? What support or structure would help do I need to follow through on this? And often that would just be like, it be helpful you could text me or I could text you. Like, Mathias you would often text me if I was going into a venture capital meeting or an important conversation and you'd be, you would just say this, you got this. And it usually was the muscle emoji. You got this. And it would just like,

Mathias Meyer (35:29) Muscle emerging.

Sara Hicks (35:31) It's that power pose that you should take in, that I often take before I get on stage or before I go into a scary conversation or big meeting. It's

Mathias Meyer (35:39) yeah.

Sara Hicks (35:40) like, you got this. And I just know that like Mathias over there in Berlin, helping me. Give me a little confidence.

Mathias Meyer (35:46) as much as I can from this distance. yeah, way you just described it, even the follow-up with your coach, I think, and this is, again, like what some of my coaches or my clients are sometimes surprised by is sometimes just the most useful thing is for somebody to ask you questions, you know, whether they're the right questions or not.

even when you say, I don't know what to do with this question. They ask another question and you started verbalizing things, right? You started putting into words, whatever you've thought about for the weeks prior, for the hours prior or forever, how long and

you know, the realization is already in there. Right? Like it is this when, when you can say as a, as an external party, as a coach, I think you already know the answer where it's, it's clear when we listen to it. And it also becomes clear to you as a person verbalizing it that, the conclusion is already in there. It's just, this is just the first time where you've put all the pieces together into some narrative.

And suddenly it becomes obvious. Those are kind of my favorite, my favorite coaching sessions in a way, because like you're just, and also I guess it's like somewhat of the classic definition of coaching, even though in my experience, in practice, usually what's what my, what my clients are not looking for, just getting asked questions and assuming they know all of the answers. Because as you were saying, like as you go through different stages of scale, you, you

Sara Hicks (37:09) Yep.

Mathias Meyer (37:17) come across entirely new challenges. It's like, how are you supposed to know? I

Sara Hicks (37:22) Yeah.

Mathias Meyer (37:22) that very rewarding as even just former coachee myself and now in those types of conversations where you get people to talk and talk and talk and suddenly everything clicks.

It's very nice.

Sara Hicks (37:37) Very nice. Yeah, I do love that. when it clicks or when it really starts to come together.

this made me think of.

There's so much. I don't know how to say this, It's not just executive, I was just saying, being an executive or startup founders like there's so many emotions that are connected

Mathias Meyer (37:51) Yeah.

Sara Hicks (37:51) to it, but it's it's being a human really that. it's emotionally loaded and even if again, it's not therapy, so it's not like leaders are coming to me or or in a coaching session and we're.

out loud talking about feelings. But always listen to patterns and I always listen to my clients and there's every session there's these emotions that are underneath maybe what is being talked about. So like one we've already talked about which is that feeling frustration with some sort of team or people dynamic.

Mathias Meyer (38:25) Yeah.

Sara Hicks (38:26) we've already talked about feeling lonely in the role of a CEO. And so there's frustration, there's loneliness, or fear of failure, letting folks down, letting the team down, fear of the business failing.

I actually just had a session last week and the client was just really struggling the trade-offs that have to happen between work and life and

Mathias Meyer (38:49) Hmm.

Sara Hicks (38:50) feeling some guilt even about not having the time that she felt like she needed to have to be present in her life. And

that emotional processing, all those things that are coming up are just so real, right? Like, I don't

Mathias Meyer (39:01) Yeah.

Sara Hicks (39:01) know where I'm going with this. just may, I don't know what triggered me to think about that, but it is part of our role is just to understand and also to have some empathy, like, just to

Mathias Meyer (39:09) Yeah.

Sara Hicks (39:10) be someone like, yeah, I felt that. Yeah, you're not alone.

Mathias Meyer (39:13) Yeah.

Sara Hicks (39:14) That's hard. Just sometimes my coach would just say, yeah, that sounds hard.

Mathias Meyer (39:19) Yeah, sometimes just that is difficult or that not difficult. is, that is useful. I had to just have somebody else say this to you. And it's like, yes, it is. But yeah, I think going through the years and coaching, was really the time where I learned sit with the emotions that are underneath and, uh, I mean, you know, as a hyper rational German, or at least that's what I like to think of myself, but

you know, underneath this just there's,

Sara Hicks (39:48) I can confirm some of that.

Mathias Meyer (39:51) there's still, you know, a chocolatey gooey center. It was weird and unusual to have this kind of experience. But it was still nice. It was like was this moment when you realize like, maybe the trajectory, the path where

it's you know, the personal growth that you need to go through as you move into these roles isn't just about like the work, right? It's about understanding the trades of management, which you can read books about, you can read our book about it. But it really also is like challenge that comes from these difficult or new situations and also from

like

the personal growth that you go through because you push yourself not just uncomfortable situations with you know other people but also with yourself and that this is entirely new to me i have no idea what i'm doing here and still for some reason i am responsible for the livelihood of however many people

Sara Hicks (40:56) hard stuff. I this is this is the work, right? This is the work of

Mathias Meyer (40:59) It is the work, yeah.

Sara Hicks (41:01) of growing of the leadership of coaching. Sometimes I I don't know if you experienced this, Mathias but sometimes. Like I'm an operator, you know, I have been a startup founder, I'm a product person through and through and coaches generally. Again, I'm making a big generalization.

We generally don't say, here's what you should do. We try not to be prescriptive.

Mathias Meyer (41:21) Yeah.

Sara Hicks (41:22) But there are a lot of times, I must confess, in a coaching session where I will say, hey, I'm going to take off my coaching hat for a second.

Mathias Meyer (41:29) Mm-hmm.

Sara Hicks (41:30) And I'm going to put on my, you know, just Sara former chief product officer, CEO hat. And here's what that person would do. And I just, I don't know, I just

Mathias Meyer (41:40) Yeah.

Sara Hicks (41:41) can't stop myself sometimes. But more often than not, like

I try to not do that and I try to just

Mathias Meyer (41:46) Yeah.

Sara Hicks (41:46) step back and suggest Or ask questions that we've talked about around like Let's just look at you know what are some of the options you know what would a different version of what you could do here or? What decision would you make if you could if you weren't afraid of kind of the consequences or.

Or what's

Mathias Meyer (42:02) Yeah.

Sara Hicks (42:03) my one of my favorite ones is like, what's the cost of not doing this of not addressing

Mathias Meyer (42:06) the

Sara Hicks (42:07) this? Yeah. Anyway, I just wanted to I do actually sometimes jump in and

Mathias Meyer (42:13) Yeah?

Sara Hicks (42:14) and say, hey, this is what Sara the product person would do. It's pretty normal.

Mathias Meyer (42:19) And I mean, sometimes,

sometimes clients ask me straight, like, what is what would you do? And then you say, like, well, given this or that, you know, within my experience, because I mean, that is where, I find this about many of my clients, they, don't come for me, or only for having to answer questions, or having just to come up with the solutions on their own, and the traditional

coaching style, you know, they come for a level of likeness and for, know, for the knowledge or understanding that you, or in this case, I have been through, those challenges myself. I, they want to learn from somebody who's done the work already and get their perspective also other than like, don't.

just

like you, don't do that a lot. But it is, part of the conversation usually when they ask me straight out, like I respond with, you know, my thing. But then again, the agency for what they do with that is still on them, right? It's like, I make that clear from the very get-go, whatever I tell you, I'm saying this as Mathias whatever you do with it, you do as you.

Sara Hicks (43:29) Yep,

Mathias Meyer (43:30) I'm not the one where you

Sara Hicks (43:30) yep, absolutely.

Mathias Meyer (43:31) can say, well, my tea has told me. Like, I'm serious.

Sara Hicks (43:34) Yeah.

I know we should wrap up. one.

Mathias Meyer (43:36) We should, This was a great,

great coaching session, Sara I'm just.

Sara Hicks (43:41) It was kind of like

a mini coaching session and very meta. do a free intro call, Mathias think you do too. look, I often say not be the right person for you. Like you only really kind of know once you,

Mathias Meyer (43:52) No.

Sara Hicks (43:53) you kind of get started after a month, three months of weekly conversation. You know, just takes some time to build that.

trust and build that relationship. But

Mathias Meyer (44:03) for sure. Yeah.

Sara Hicks (44:05) if you're thinking about coaching, have that intro conversation. I do know that in our book we have some suggestions for questions to ask and things to think about if you are looking for a coach. And and talk to a few

Mathias Meyer (44:15) Yeah, I will also say

Sara Hicks (44:17) people.

Mathias Meyer (44:18) for sure. Like for me, actually, like speaking of likeness, like I liked in my coach that she was not a startup founder in any way. Like she, wasn't specifically looking for somebody or maybe it didn't cross my mind back then, but it made her more, maybe more neutral or maybe just, don't.

struggling to find the right word, but it never bothered me.

Sara Hicks (44:41) makes sense. Yeah.

Mathias Meyer (44:44) I needed the pushes and the mirror in the conversation. I didn't need the solutions. an engineer, could probably figure out some of these mess. I just needed to be asked the really difficult questions. And she was working with other startup founders, so this was not an entirely new thing.

I personally appreciated that a lot, like that it wasn't necessarily somebody was utterly familiar with the ups and downs of the startup world. She was actually a studied psychologist, which was, I found

Sara Hicks (45:18) Nice.

Mathias Meyer (45:19) extra helpful in many regards.

Sara Hicks (45:21) yeah, that is nice. alrighty, with that, I think we will wrap it up.

• #Leadership
• #Coaching
• #Communication