CTO Coaching: How to Choose a Coach and What to Expect

David's Notes:

Peter Bell and I answer a few important questions for CTOs to consider when hiring a coach.

1. Why would you consider hiring a coach?

   1. Personal skills? Behavior?

   2. What do you need a coach for? Company? Career/Position? Department? Technology? Communications?

2. What should you look for in a coach?

   1. What are outcomes going to look like? What can we expect that might happen? Are these sessions confidential?

   2. What kind of questions would you ask a coach to determine their competence?

3. How long might a coaching engagement typically be? What is the contractual commitment?

   1. What is the right amount of time to give a coaching relationship to determine whether this has the chance to add value?

4. How do you talk to your boss about needing more support?

5. As a coach, how do you build trust with someone who didn’t initially think of getting a coach?

6. What outcomes might be the goal of a few months of coaching?

   1. What is a CTO, and what must a CTO be good at?

   2. How do you make a distinction between something which would be a good fit for a coaching relationship versus a pure technical consult?

7. Is it important for coaching relationships to be in-person?

8. What are coaching anti-patterns?

---

Transcript

Peter Bell:

Hi there, my name is Peter Bell. Today, I'm talking with David Subar, managing director at Interna. David, thanks so much for joining me today. We're going to be talking about CTO coaching: how to choose one and what to expect. So maybe to jump right into it, why would-- you're an engineering leader-- why would you consider hiring a CTO coach?

David Subar:

Well, you'd get one if you're in a challenging or new situation that you haven't been in and you need some perspective. Maybe, you're in a new position. You don't have someone in the organization who's done it before, who you trust, and you need someone to help you think about the situation and lead you through it.

The key with a coach is that you want to have a person that you can speak to completely freely, that you can get feedback from. You don't want somebody who's going to tell you what to do, but to help you think through problems. If you're in a situation where you're on new ground, and there's no one that you can trust to help you through, then a coach can be very helpful there.

Peter Bell:

That makes sense. So, what would you look for in a coach? And, I'd imagine it's a function of the kinds of problems that you're trying to face.

David Subar:

Yeah. And then-- look, the problem with coaching is anyone can say they're a coach. Someone might say, "Hey, I'm a life coach." Or, you know, any number of coaches. I think about-- and in the stuff that we do at Interna, coaching is one of the things we do for technology and product managers and executives-- you have to consider, do you have a life problem? That's a certain kind of person, and that's not the kind of coaches that we are. Are you focused on something about your company or career or department? Then you want to understand that, and then you might want to dig down. Which of those is it? Is it your position? Is it your department? Is it communications that you are looking for help with? And it might be several of those. Find someone who has done that as a coach. Maybe even who has done that, sat in that seat, that can help you through those things.

Peter Bell:

So that brings up a great point, which is: if you think about it, how long might a coaching engagement typically be? Is this something where you come in, you solve a problem in six weeks, and you're out? You know, you meet once a week or whatever. Or is this potentially a longer term relationship where you're working with somebody throughout their tenure on a job, or even across companies?

David Subar:

They tend to be longer term. If someone says, "Hey, I'm going to coach you for three weeks and everything's going to be perfect." Unless you have a small tactical problem, you probably want to avoid that person. Particularly if you're talking about career or broad management or communication. It probably is a longer term thing. We typically work with people every week or every other week. Less frequently than that tends not to be that useful. And it can last, you know, six months, it could last a year, it could last longer. I think you should expect longer, but I think you want to have the option to make it short. "Hey, I tried this person as a coach. This one's not working for me. I want to jump out and try someone else."

Peter Bell:

Now, what's the magic timeframe for that? I mean, if somebody just speaks to somebody for 50 minutes. "Well, the problem isn't solved, time to try the next coach." They're probably never going to get a good outcome from anyone. Equally, spending six months with somebody and getting absolutely no traction is probably a waste of time and money. What's the right amount of time to give a coaching relationship to determine whether this has the chance to add value?

David Subar:

I think there's two steps to that answer. I would say, "Let's just do a one-hour session." Most coaches will just give you a free one-hour session to see if you can understand. Well, actually, interview the coach first. If the interview goes well and there's some attributes you like, do the one-hour session. Just see how the chemistry feels. Then you can go into a contractual relationship and that kind of thing. I would give it two, three, or four sessions. If you're not feeling it after four sessions, certainly I would go find someone else.

The thing about these things is what's right and what's not right. Some of it's just subjective. If it's not feeling right after four sessions, it's probably not going to feel right. And by the way, there's a lot of good coaches out there. So don't try to force-fit one. Look for somebody else.

Peter Bell:

Makes perfect sense. Now, you talked about interviewing them before you even start with those first sessions. What would be some kind of questions you would ask a coach to determine competence, fit, or anything else?

David Subar:

First thing I would do is ask about their experience. I would ask about their experience as a coach and what they did before being a coach, particularly for technologists, CTOs, product managers, and CPOs. Those are the things that I know about. This may be true for other areas as well. Having experience in the seat gives a coach perspective. So, I think you want experience in a similar role and experiences coaching. So, I'd ask about that. I would ask about those two kinds of experiences first.

I might ask about what kind of companies you've been involved with. B2C companies and B2B companies are different from each other. The kind of needs and some of the interactions are different from each other. I might ask about that.

I might ask about the methodology. We might start an engagement. What are we going to do? Do we just sit for an hour at a time and just talk? Do you have a way that we start from some state and go to another state? Are there ways that you learn about me and know about me? Who do you talk to? I would ask about that. I would want to feel comfortable with it.

One of the things that we do-- and not everybody does this-- is we do a 360. And so, we will talk to the person we're coaching about what the issues are, what their goals are, and where they're trying to get to. And we'll talk to their peers-- the people that work for them, the people they report to-- and get an idea of where those people think the person we're coaching is at. We'll triangulate and use a series of steps after that. Not everybody does that. You should be comfortable with the methodology. You might, with a 360, make a person uncomfortable. And, if that's the primary methodology, then don't use that coach. It's fine; there are other ones. You should just feel comfortable with it. And, you know, there's still a few other things you can ask as well, but go ahead.

Peter Bell:

What would be some of the other things you can ask?

David Subar:

What are outcomes going to look like? What can we expect that might happen? You should ask about confidentiality. For us, confidentiality is critical. We want to create an environment where the person that we're coaching feels free to talk about anything because we're here to get them to the next state, which means that-- typically, companies will pay for the coaching. Even though the company's paying and we have some kind of responsibility to the company, there's a lot of stuff we're not going to tell the company because we can't create a great coaching relationship. You should ask about that.

And then I would ask, "What is my commitment to the coach contractually?" Some coaches say, "Well, you have to commit to six months or a year." Those aren't necessarily bad ideas because there is work that they need to do upfront. They're frankly looking to make sure that they get renumerated for that upfront work. We don't do that. We just say, anytime you want to get out, give us 30 days notice. You should ask about what the contractual commitment is as well.

Peter Bell:

Something that came up is this idea that the company may well pay for it. And possibly, the methodology could include something like a 360 when you're speaking to bosses and subordinates. Before that kind of coaching engagement, obviously you need some kind of organizational buy-in, both for the check and for the access to the rest of the team. How, as a CTO, especially if you've got a little bit of imposter syndrome-- "I really don't know how to do this." How do you have that conversation with your boss to say, "I could do with some support to do a better job"? Without making it sound like, "I don't know what I'm doing. Fire me and hire somebody more competent."

David Subar:

No one's actually asked that question of me before, and that's a great question. Sometimes you get an easy out. Sometimes the CEO has a coach. The board has coaches for different executives.

We've been called in sometimes by CEOs that say, "We want to invest in this CTO. Can you help coach them?" It often might happen after review, after an annual or semi-annual review, whatever your cadence is, where something comes up. Maybe it's communication patterns or alignment to strategy. And that often provides an opportunity to say, "Oh, I heard what you said in the review. And I'd like to get better at this. What do you think about having a coach of someone who's sat in the seat before?" So as opposed to walking up to the CEO and saying, "I have a weakness here I need to address." Leverage a weakness that might have been brought up, and then it feels like a win-win.

Peter Bell:

That makes sense. Just to turn it the other way around, so, I'd been asking about what happens if you want a coach and, you're like, "How do you approach your boss?" What happens if your boss comes in and says, "Hey, you're doing great at this VP of Engineering role. In fact, you're doing so well, we want to bring somebody else in to tell you how to do your job." How do you start to build trust with somebody who maybe didn't initially come up with the idea of getting a coach for themselves?

David Subar:

A couple of things: one is, if someone fundamentally doesn't want a coach, we won't take the assignment. If you fundamentally don't want a coach, we're not going to be helpful. We have been in situations where people have said, "It's been recommended I get a coach. I don't know what that means. Can we sit and talk." Glad to do that; glad to do that every day. Our thing is, we're not going to make you Superman. We're going to help you become Superman-- if you want to-- in the areas you're interested in.

So if we can have a conversation with someone who was told, "Hey, we're going to bring a coach in for you." The first question we ask is, "What are things that you are interested in working on? What are areas that you think can be helpful?" And sometimes we hear, "I have this weakness", "I don't like to do this", "This I find troublesome", or "I don't understand this." Sometimes we're told, "I've been told this about myself." Then my next question is, "Do you think that's true?" If the answer is: "No, fundamentally it's not true." The next question might be, "Why do you think people perceive that?" And then there's the answer there. Then we go, "Great. Is that something that we should work on? Or you're just not interested?" And once again, if they're just not interested, then let's not do it. Not only are there plenty of coaches, there's plenty of places to coach, and plenty of people to coach. It's not fun to spend time with someone who doesn't want to spend time with you.

Peter Bell:

I love how you bring up this idea of weaknesses and maybe they don't want to work on it. There are two schools of thought. There's the "We want well-rounded executives," and clearly it's important to have a range of skills. Then there's the "Play to your strengths, rather than one day becoming average at everything."

How do you think about that from a coaching environment in terms of leveraging somebody's strength, and possibly looking to backfill high or delegate responsibilities? Do you have any opinions on what things a CTO has to be good at or are there absolutely areas where somebody can be weak?

David Subar:

I have a two-part answer to your question. The first part of the answer is a question itself. "What is a CTO?" A CTO at one company and a CTO at another -- same title-- could mean a very different thing. "I am the co-founder and I am the chief architect. That's who I am as CTO." Or, "I'm responsible for everything technology." Or "I'm responsible for technology and product management." There's a bunch of or's."

So the first questions are, "What is your role?", "What does the company expect of you?", and "What do you want your role to be in the company?" In the case where I am responsible for all of the technology development in the company-- by the way, you probably should be good at that-- and being good at it doesn't mean you don't need coaching at it. That's something the company will expect you to be good at, but you need to do that in a way that's aligned to company values and company mission.

One of the things that we talk about a lot is creating value for customers. By creating value for customers, the side effect is revenue; and the side effect of that is profitability. I'm oversimplifying it. That implies that your job is not just to have your teams write code, but they have to write it to align with sales and marketing and strategy and all those other things.

Oftentimes, CTOs who've found themselves coming up from the developer, manager, director, and eventually CTO or something like that don't have backgrounds in some of those areas and don't know how to talk about those areas. And maybe don't have the right metrics when they're talking with the CEO about this. How do you go from being an expert in the thing that you grew up in to providing value and alignment and good communication to your peers?

And then looking down, some people grew up doing this, and they might not have had proper training with managing teams of tens or hundreds of people. How do you think about that differently from being an individual contributor or from managing teams of five or ten? You're thrust into these positions with all of these new requirements and no owner's manual. Those are the things that people generally are not very good at and they generally need help with.

Peter Bell:

Makes sense. Now you've talked a fair bit about what a coach is. I'd love to figure out where the edges are. Where it stops becoming coaching. How do you think about the distinction between something which would be a good fit for a coaching relationship versus a pure technical consult?

"We've got to make a rearchitecture decision." "We're moving to microservices." "We're thinking about CAFCA, and all I've ever done is build rails or Django monolith."

David Subar:

Coaching will extend a little bit into that area, but you don't want to get that far. I've been CTO of a bunch of companies, personally. I've seen a lot of these things and I can talk about those things. When you're talking about: "What is our specific stack going to look like?" "What's our specific architecture going to look like?" "Oh, we're going to use microservices." "We're going to use Lambda." "What about the cold-start problem?" I could talk about that, but what you really want is someone who's working on a particular kind of thing today. You will want to talk about that, but that's not what a coach is for. A coach is for management, maybe to help a little bit with architecture, communication, organizational design, and personal skills. There's a bunch of other places to find the people that are technology-- if you want a technology consultant, there's people that do that. And there are a lot of really good ones. You should not expect your coach to do that. A coach is not a therapist.

Peter Bell:

That was my next question. Could you talk about personal skills? What happens if-- "Ever since I was six, I've been uncomfortable with X"? How far do you go down that road? Because I feel like sometimes it might start as "I'm having trouble prioritizing the backlog," but it actually becomes a very personal issue that is perhaps driving that behavior.

David Subar:

This is also kind of in the penumbra of what coaching is. I might give some personal advice, but I'm not a therapist. I'm not trained as a therapist, and I'm not trying to be a therapist. And there'll be some things I'll say like, "This is not something that I can help you with. And here are some suggestions." Now, you have to say that carefully.

I try to set boundaries upfront in the coaching relationships. "Here are the places that we can be helpful, and here are the places that we can't." During the coaching sessions, we start out with a goal. "Here are the things we want to work on." We do a 360. "Here is the view of it. Here is your view of it." We come back, and we will triangulate on what might be a better representation of what the world is. "Great. Here is where our goal is." "Here is some stuff we're going to talk about." We tend to do this every other session and then the sessions in between we ad hoc things that came up. We can have kind of a set regimen of the things that we're looking at and trying to work on. If something falls out of that, if it's in the context of being a technology executive, then we're glad to address it. If it's outside of that, then we'll say, "We'd love to help you with this, but it's not what we're good at." And to the extent that we can suggest other resources, we will. It's again, low-level architecture algorithm stuff. By the way, I code every so often. I know that stuff, but there's people that are better at that, you know? And so, there's things that will fall out of that.

Peter Bell:

So, you mentioned outcomes. Could you maybe just give some concrete, tangible examples? What might be some kinds of engagements that you've seen and some of the kinds of outcomes that might be the goal of a few months of coaching?

David Subar:

I'm going to state these generically, just so not to reveal... there've been several situations we've been in with co-founders, whose companies were scaling. We were there in two cases, that I'm thinking about, where the companies were scaling quite quickly. And the person we're coaching felt a little lost and maybe the team had doubled in size and the CEO was complaining. "I'm not sure if this is the right person." "Person got us from step A to step B, but now the person is not aligned." In both of the cases I'm thinking about, we had conversations about: "Who do you need to be talking with among your peers, and about what?", "How do you talk with the CEO?", "How do you talk with the board of directors?", "What do you not talk about?" Nothing that you're trying to hide, but things that are just not interesting to them and they'll feel like it's a waste of time.

In both cases, the teams both doubled again. And then, there was much better alignment between the CEO and the CTO. Both of them really started with CEO/CTO friction that was caused by a misalignment of expectations and a misalignment with communication patterns.

And what you find is: "Oh, this is what you want!" "This is the way we should communicate." "Here's why I'm doing this." And then that flow tends to flow down into the organization. It's, "Oh, you know what? We're not going to build a super elegant architecture right now. We're going to build half of it and we're going to build half of it because this is what we need to prove as a business to get us to the next step." "We need to lower churn. Why do we need to lower churn? Oh, here's the business reason? What does that mean from an architectural standpoint? What does that mean we're not going to do now?"

What does that mean to your team? "Oh, we're going to be introducing tech debt. How do I talk to my team about that, and what tech debt we're going to accept and what tech debt we're not going to accept." "How do I think about that, and how to make my team feel comfortable about that? And how has that all aligned with the business, and how do I describe that to my team?"

And then how do I come back to the CEO and say, "By the way, we're going to have to refactor this stuff and you're going to get no business benefit that I can measure."

Having been able to talk about those things in a way that creates effectiveness for the team, creates effectiveness for the company as a whole, and creates alignment. In both those cases, the CTOs came out saying, "Okay, I feel a lot better about this." And, "I don't always win everything, but in places that I lose, I understand why." And, "Even if I'm still not comfortable, I don't feel like I was railroaded." And the CEOs come out and say, "I have a more effective CTO, and I like hanging out with this person in a business setting. This person feels like part of my team now."

Peter Bell:

That's great. One small aside, which is: it's so obviously COVID times, everything has been online for awhile. Do you feel that it's important for coaching relationships to be in-person? You know, once we are post-pandemic and people are back in offices... or do you feel that you can absolutely coach on zoom?

David Subar:

I think you can absolutely coach on zoom. Every one of the people that I've coached, I have met at some point in the coaching relationship face-to-face. But, there's someone I coach in London, for instance, and there's someone I coach in New York. I'm in Los Angeles. There's people that I coach in LA and in other places, but I've always found a time to meet face-to-face.

Peter Bell:

And then finally, maybe just to wrap us up, I know we're getting a little short on time. Any coaching anti-patterns? Anything that a coach or a coaching relationship should not be covering?

David Subar:

Yeah. We talked about some of them already. Your coach isn't your therapist. Your coach can sometimes give you specific advice and tell you how to do things; but, in general, you want your coach asking questions of you and not telling you what to do. There's a big difference between coaching and teaching. Teaching is when someone doesn't know how to do something and you just tell them how. Coaching is when someone has the fundamental skills to do something, but maybe has not thought it through; or maybe it's not a hundred percent efficient, and you're much better off asking questions to have that person be thoughtful about what might or might not work.

A coach also isn't your cheerleader to say everything is happy and rosy, right? You want your coach to sometimes give you some hard news. The good news about your coach giving you hard news, your coach isn't going to fire you. Your coach has given you hard news because you know that the coach thinks it would be helpful. Your coach shouldn't be like a shadow manager or someone who executes your boss's wishes, right? Your coach is there for you. If you find that your coach is just an echo of the CEO, that's an anti-pattern. You should probably stop that relationship. But, if you have a coach who really listens, really asks hard questions when needed, gives good advice, is confidential, and has some experience in what you're doing, you're probably in a good relationship.

Peter Bell:

David, thank you so much for taking the time to talk.

David Subar:

Thank you.