Questions to Ask A Prospective CEO Coach with Jessica Wolf

Announcer: Welcome to The Daily Bolster. Each day we welcome transformational executives to share their real- world experiences and practical advice about scaling yourself, your team, and your business.

Matt Blumberg: Welcome to The Daily Bolster. I'm Matt Blumberg, co- founder and CEO of Bolster, and I'm here today with Jessica Wolf. Jessica is the co- founder and CEO of Skye, S- K- Y- E, which is a platform for accelerating personal goals with one- to- one coaching. Jessica, welcome to The Daily Bolster.

Jessica Wolf: Thank you. Happy to be here.

Matt Blumberg: So you live in the world of coaches, and part of Bolster lives in the world of coaches as well. So my question for you today is, for all the CEOs or CXOs out there who are contemplating getting a coach, what are the top three questions that someone should ask a prospective coach when they're interviewing them?

Jessica Wolf: Sure. I'd say the first is, What is your coaching philosophy and approach? So understanding their approach is critical to determine if their style aligns with your needs and preferences. So some coaches might focus on motivation and accountability. Others might emphasize deep introspection. So asking about the methodologies, tools, techniques they use to see if it resonates with you and what you're looking for. I'd say two, what's your experience and expertise in my specific area of interest concern? I think there's one camp that believes a coach does not necessarily need to have functional industry or experience expertise to be a good coach could be the case. I prefer to work with a coach who has been in my shoes and can have that perspective, so they can straddle that line between holistic coaching and strategic advisory where appropriate. So understanding their past credentials, their past outcomes, how they have supported individuals in certain or similar challenges would be important to ask. And then I think lastly-

Matt Blumberg: Do you care about experience with the function, experience with the sector, both? Do you care about one more than the other?

Jessica Wolf: So at Skye we care about both, and I think that coaching is typically not sharing advice, it's helping the individual uncover their own answers. But when you head in towards that more advisory or consulting work, of course, you can give pointed advice or strategic support. And so Skye offers both. And most of our coaches, because they are tenured operators, have that experience to share. And so we match based on industry and function.

Matt Blumberg: And then what is number three?

Jessica Wolf: I'd say number three is, how do you structure coaching sessions and measure progress? So some people prefer almost a deep talk therapy. I don't want to call it therapy, but approach to coaching. And others prefer a really structured, outcome- driven approach with homework and goals per session. So you first need to reflect and understand what you're looking for and see if the coach's approach aligns with what you need. And so I think that's really up to you just to dive deep on whether it's a systematic approach and then how they measure that progress over time.

Matt Blumberg: And how does that differ from the first question? What's your philosophy?

Jessica Wolf: So actually most coaching schools have their own unique philosophy around coaching. Some are a whole- person model, so it takes a more holistic approach and starts first with you before you get into anything work- related. Others are very structure- based and are a six- month model and are goals- oriented. So I think a lot of coaches carry a philosophy from where they went to coaching school, and so that informs their work. And then I'd say that is very much related to question three. So whatever their philosophy is probably is mixed into their structure and how they like to measure progress. But a coach will take their training and then imbue it with some of their own experiences and come up with their own approach.

Matt Blumberg: Right. Those are all great tips. I find when picking a coach, there's also this intangible of, do the two of you click? And I think you only get that by having lots of conversations, not by looking for very specific things, but maybe you get to that through these questions as well. But I think all three questions are spot on.

Jessica Wolf: Totally. We think of it like speed dating. So when you come to Skye, we match you with three coaches, and you have the opportunity to assess for that chemistry fit. We say you have to want to look forward to working with your coach. Otherwise, it's going to be really hard to hear what they have to say. So that chemistry and personality alignment is critical.

Matt Blumberg: All right. Jessica Wolf from Skye, thanks for being here.

Jessica Wolf: Thanks.