How do you Exec Coach? / May Samali
Learning from Executive Coaches.
Good morning! This is the sequel of my “How do you CEO” series.
I’ve been working with an Executive Coach for 3+ years - he will be the final interview of this series. I love the way we can unpack big problems and work on strengths. So, naturally, I had to understand how that magic works to become a better manager and coach myself.
~ Batko, CEO @ Startmate, Founder @ Puddle Pod
Do you have an Executive Coach?
If you do and can recommend him/her - please leave their detail here (1 min).
I have yet to find a good place to find reliable Exec Coaches
👉 so here is the list of the above recommendations.
#2 May Samali
Website // LinkedIn // Instagram
How do you executive coach?
I think that executive coaching is something you do, not someone you are. It's a modality, rather than an identity per se.
The most important aspect is holding and creating a space that's not only safe but also challenges the individual. If we want to push people outside their comfort zones, we need to build psychologically safe spaces and trusting relationships from the start. Otherwise, we risk coachees bringing a filtered version of themselves to the table.
My approach to executive coaching is to coach the body, mind and spirit. The most effective way to reach peak performance, especially for executives and startup founders, is to coach the thinking brain and the feeling brain. Being in tune with the body is also really powerful, touching on what emotions are coming up, identifying where is there stuck energy, and where inspiration is coming from.
You mentioned executive coaching is for the body, the mind and the spirit. How do you look at the spiritual coaching?
Spirit is an interesting word. I think some people tune in more naturally to their gut instincts or their inner truth. For others, “spirit” is a synonym for what's in their heart or what feelings are coming up. A good way to ground someone at the start of a session is with deep breathing and mindfulness exercises to really tune into what's coming up at the body level. This is usually a signpost for what’s happening at a spirit level.
I ask questions like: What's coming up? What's on your mind? What do you notice in your energy? What's here right now? Energy is a good word for it. Sometimes people might notice they're frustrated or feeling a bit antsy or maybe feeling really empowered and so that gives us a bit of a glimpse as to what's happening at the spirit, energy or heart level.
How did you become an executive coach?
I still don't know what I want to be when I grow up, but we're here now, aren't we? I love this question about how we got to where we are because it's an indication of how fluid I think this career journey is.
I became an executive coach and I would say I don't identify with that label very closely. I see myself more so as a founder. I founded the Human Leadership Lab where we are on a mission to grow and develop human leadership in organizations, teams and individuals.
How did I get into coaching specifically? When I was working as a venture capital investor in Silicon Valley at the Urban Innovation Fund, I wanted to be the best possible value-add investor for our portfolio companies. And the thing that I kept noticing was that the biggest indicator of success for our portfolio companies was not so much the outer game of entrepreneurship (questions such as: Are they an effective communicator? Are they hiring the right CTO? Are they effectively pitching for that next round?).
Rather, it was the inner game of entrepreneurship that mattered most: founders’ mindsets, values, personal operating systems, and level of mental fitness. I was asked a couple of times by our portfolio companies whether I knew any startup coaches and this question got me curious about the profession.
Fast forward a couple of years, I was then CEO of an edtech organization and was managing global teams, trying to fly the plane as we were building it. And one of the things that I noticed again is that I got a lot of energy from helping my direct reports be as successful as possible. I became really interested in how to unlock their true potential.
I then bit the bullet and started my formal coaching certification process. I did about a year of training - 200 hours, 100 hours of mentorship and a six-course program to become the best investor and CEO possible. I thought the coaching skills would help me show up as a better investor and manager. And the more I leaned into coaching, the more it became my main thing. So, I stopped moonlighting with the coaching and instead made it my main thing. I was also having founders approach me asking me to coach them during this time, so it all came together in an organic way.
In your role as CEO, how did you create that space for your direct reports? Did you create extra meetings or was it part of your weekly 1:1s?
I was still a CEO when I started my formal coaching training, so the first forum in which I practised my coaching skills was in my regular 1:1s with my direct reports at the time. I started to make my 1:1s more open and fluid in terms of their structure. I would lead with real inquiries. Questions like: What has been the most energizing part of your week? Or if you weren't in this role, where would you be?
I created a safe space for direct reports to imagine and not have to people-please.
What do clients ask you most often?
Before we kick off, when we're getting to know each other, the question I get asked the most often is: How will we measure success? How will we know that the coaching has worked? These are super fair questions.
The other question I get asked a lot is: Why did you become a coach? I think people are genuinely curious if you've been a full-time CEO, or full-time investor, then why this, why now? Why do you care so much about coaching?
In the coaching relationship, I always get asked: what should I do? What's the right way to do this? CEOs are always curious about what others are doing. Most of the time it's sense checking because it can get really lonely at the top, as you would know. And so often you think you're the only one that's experiencing whatever you are. And a coach has that bird's eye view because they’re in touch with a lot of executives. And sometimes it's just wanting that validation, acknowledgement and to be seen.
You mentioned clients ask you - what does success look like? What does it look like?
It's a really good question to ask. For me, success is defined on a very practical level. I usually work with folks for 6 months or more. What we first do is set out the areas of focus for a coaching relationship. And so when you think of areas of focus it is about the areas of your life or leadership that you want to see growth and progress in. Then we develop some measurable outcomes for each of these areas.
If I was a fly on the wall watching Batko in 6 month’s time, what would I see? What are you saying, doing, thinking, eating, breathing? How would we know that Batko’s developed? So it's very iterative, just like the entrepreneurial process. We have a V1 of your areas of focus. After a couple of sessions, we might have a V2. Then we touch base on your areas of focus every couple of months.
As the person develops, and their capacity and understanding of themselves develops, the areas of focus develop and what's possible expands. And so that's what I see as one measure of success - that the areas of focus themselves evolve and often the individual “graduates” beyond that area of focus and can go to the next level.
The other measure of success is that we see consistent systems and habits in their day-to-day practice. So we are looking for deep transformation, not quick fixes. Anyone can google “the 5 traits of a toxic team” or the “5 ways to build mental resilience”. There are a lot of frameworks and tools out there. The resources and tools are amazing, but they are not the focus. They simply augment our work. The focus of the work is the individual themselves and how they’re living their lives.
I also think of success as the moment I feel I'm ready to graduate people out of the coaching relationship. Because what we're doing is we're building an empowered relationship. It's not about dependency.
Do you only ask questions or sometimes give answers?
Asking empowering questions is a really important tool in our coaching toolbox, but it's not the only tool.
When I was early in my coaching career, I was perhaps more purist. I’ve since evolved my approach. I’m more fluid in how I partner with individuals. I’ve learnt that we can do our clients a disservice if we stay purists for the sake of being purists and not offer them all that we can in the spirit of moving them forward.
For example, if an executive is stuck on a particular question relating to raising a round of capital, I will explicitly ask, “in this situation, do I have permission to wear my fellow entrepreneur hat or my investor hat?” And I will make it very clear that anything that I'm saying after that is with a specific hat, for example, my investor hat.
This might involve me saying, “As someone who served on a board of a company, my sense is the board might be looking for X.” I will offer my perspective and experience as just another data point, not as the source of truth. Another place I’m more instructive is in relation to resources. I'll tell people what resources they should read to watch to get to their own answers if they're not able to in real-time. As a coach most of the time you're asking questions. However, I think there are exceptions to the rule.
Every session will have multiple commitments coming out of it. I will make a request. For example, “I want you to go and have X number of conversations about X topic.” Or I'll give them an inquiry, something to think about and reflect on. Or I'll give them a challenge, something so wild that it pushes them outside their comfort zones and their initial reaction might be Hell No. But as I always say, you get to decide. So you can say yes, no, or give me a counteroffer. It's not a demand. It's a request. And that's what makes this a coaching relationship. People don't need another mother or project manager. They need an accountability buddy and champion.
Do you have a mental model for asking great questions?
There's a real art and science to asking questions.
A good question is one where, as a coach, you're not presupposing the answer, and where you genuinely are coming from a place of curiosity. Now I might have an instinct around what might be holding you back, but if I put my instincts out there, I shouldn't be attached to it. So good questions are trying to traverse new territory together. Really being a guide on the side, not a sage on the stage. What I’m signalling to clients is “You know yourself better than anyone will know you, but I'm an expert with the tools to help you navigate.”
I think a great question gets to the question behind the question. For example, we often get asked, “Where do you want to be next year?” or “What do you want to achieve by next year?” They’re good questions. But what about deeper questions such as: What will happen when you achieve that? How will your life change? Who will you become? What values is that then honouring? What if you could honour those values now? What would you do differently?
So behind every question is a question that gets even deeper and ultimately you can get to the bottom of what’s really happening.
What are they not saying but needs to be brought out and made explicit?
Questions that are open-ended, goes without saying, are ones that are effective, one at a time. Questions that often start with “what” or “how.” Most questions that start with “why” put the client on the defensive, when we're building relationships. So I don’t like to use too many of them initially.
For example, instead of asking you,“Batko, why are we doing this interview?”, it’s much more effective for me to ask, “What do you hope to get out of this interview?”
When should someone get an executive coach?
I think that coaching is a resource that should be available to everyone throughout the different seasons of their career and life. So I would say the question is less, “when should you get it?” but rather “who is the right coach for the season you're in?” If you have generally a growth mindset, if you love learning, if you love moving through the stages of adult development, you should absolutely go for coaching.
Be clear on what it is that you want to stretch or expand, or where you feel stuck. I think coaching during transitional moments can be very impactful. If you're new to a role, if you're looking to leave a role, if you're looking to get promoted, if you're looking to start a company, expand your company, raise your next round of capital, or navigate any other change, then a different type of leadership is required. Coaching can serve as a powerful partnership to help you move through these moments with purpose, confidence and courage.