The Art (& Power) of Asking Questions with Shola Kaye

So I asked Shola for her to share situations where she wished that she asked questions, and in those specific situations, what are the questions that she wished she asked and why. We also cover sort of common reasons why people shy away from asking questions, and we also get into practical strategies to deal with not getting the answer that you want,

So if you enjoy what me and Tazmin are doing, why not give us a one-off donation? We are set up on buy me a coffee link in the show notes to do that. And please, please, please help spread the word of the podcast. Word of mouth is still one of the best ways to grow. Podcast listeners and visibility and all that lovely stuff.

So the next time you're listening to an episode and you know someone who would very much enjoy, very much, get a lot out of the the podcast episode, why not share it to them? Find the link and open up WhatsApp, whatever message a service you're using and send them a link. We'd be so appreciative of that.

Hello Shola and welcome to the podcast.

Shola: Hi, Sarah, great to be with you today.

Sarah: Great to be with you too. And I am loving the vibrant yellow you've got on today.

Shola: I can hear the birds chirping outside the door, figured. Oh, okay. Put some bright colors on to to be spring-like so, here we go.

Sarah: It does make me laugh in the UK that any hint of sunshine and we are out there, aren't we?

With the sunglasses, the shorts, the summer wear.

Shola: Absolutely. You gotta make the most of it.

Sarah: Exactly. Exactly. Um, so we met, so to give our listeners context of how we know each other. So you were the fabulous keynote speaker at WTS Fest in London, weren't you?

Shola: I was. I was. That was back in, well, yeah, about six weeks ago now.

Yeah, I mean, life is just a bit of a blur. I dunno about you, but I think it was in February, if I, if I remember rightly. And, um, yeah. What, remind me and tell the audience what the title of your talk was.

Shola: So the title of the talk was The Art of the Ask. And it's all about how to ask for things that you want and what kind of questions you should be asking and, and of who.

Shola: Absolutely. Absolutely. I mean, one of the things that, um, goes down quite well in that particular talk is the time we spend on how to deal with rejection, because so many people don't ask in case they get that no.

Sarah: And that is possibly one of the biggest reasons would you say that people don't ask?

Shola: Yeah, I think it's a big one. I think often we don't, certainly, you know, my own career, very early on, I just didn't really have enough experience and even confidence to think that I could ask for things. So it wasn't even that I feared rejection, but just I didn't

contemplate that I could ask for stuff that I needed. I just thought you'd just get dolled, whatever anyone wants to give you, and that's the end of it.

Shola: Yeah, absolutely. And I think it's, so many things come into play here. It could have been the way that you were raised, it could have been the, you know, you've been in an environment before where you weren't encouraged to sort of share your opinions or to share your, your needs.

So conditioning, history, et cetera, can all play a role in, in how much we ask for the things that we, we, we need to help us.

Sarah: Exactly. And would you be able to share an experience from your past where you wished you asked questions and what questions you wish that you would've asked?

um, I, you know, I hadn't had much work experience apart from working in, you know, shops and things like that when I was a, a, a teenager. Um, and so then I got my first corporate job and I just thought, well, if you keep really quiet and just do the work behind the scenes, then that's good enough to, you know, um, help you progress.

And it was a consulting role. Of course, as a consultant, you're supposed to speak up, you're supposed to, uh, you know, show people that you have information, valuable information, good ideas, and so of course my. Strategy of just keeping, keeping my nose clean and being really quiet in the corner was not a very successful one.

What, what's next in terms of, you know, what, what do you need for us to, um, help you move forward? But then on the other hand as well, I mean, it didn't occur to me early in that role to, to ask my manager, well you, what, what, what are you looking for? Or if I want to succeed in this role, what should I be doing?

Or I don't feel like I'm making much of a contribution. Can I get a bit more developmental feedback from you? So that I, you know, make, make some progress. So ask questions.

If I could change anything about that role, I think I would, or that time, I think I would've been asking more questions.

And even if deep down and in our gut, we can feel that something's not quite right or we are not performing to, um, the standard that we want or anything, 'cause I, I think sometimes listening to your gut and if something doesn't feel quite right or you, you just wanna ask a question, it's having that confidence to ask questions and actually asking questions is okay.

And every time that I've asked a question, the person that I've asked that question to, whether it's a manager, a client, anyone who I'm working with on a project, um, we've then been able to have a really good conversation, but also make sure that we're on the same page as well.

So at least if I'd have started asking it would've probably freed him up as well to to be a little bit more honest and open about my performance and what he was looking for. So I think that whoever it is, sometimes we feel it's not our role to ask first it should be somebody else. But you know what?

Maybe for all sorts of reasons, that person feels reluctant, so just grab the ball by the horns and go for it.

you've gotta be proactive, right? You've gotta, you've gotta, be the one who is asking those questions, being proactive, suggesting 'cause if you don't and you just keep quiet and carry on doing what you're doing, you don't know how you're performing and you don't know if you are in the, even in the right sort of direction. Right?

Shola: Absolutely, absolutely. And I think it's, um, I mean I know that in that role I was deeply unhappy as well, so. Even if, uh, I mean when, when you're feeling unhappy with a situation that's telling you something, it's telling you that there's some kind of action required maybe on your part or that the circumstance has to change.

So even a well-placed question, even if you know what's wrong, right? Or you know where you're trying to get to with this, but you ask a question instead that can often be taken. In a much more, it, it, it sometimes it's not seen as so challenging. When people ask us, when they say, right, this is wrong, this needs to change.

And the more that you'll feel less scared and actually empowered to ask questions, right?

Shola: Absolutely. Absolutely. And, and I really like that sort of reframe of, of that expression, because all too often we feel like. We should get it perfectly right. And it's so funny 'cause when I do this talk, I often give people a, a feedback form to fill out afterwards to let me know how it, the content went down.

And there's always one or two people that say things like, Shola give me the exact language to use so that I always get a yes from every question. And, and it's like, well, hold on. I think I said this in the talk. You know, this isn't magic.

You might still get a no. But at least now there's clarity for everyone concerned, right?

Sarah: Shola this first half has been such a great conversation. We are gonna take a short break now, but after the break, I'd really love to pick your brains and get some really actionable strategies from you that our listeners can start implementing to help them ask questions.

Does that sound good? Yeah, sounds amazing, Sarah. Wonderful. All right, so join us for part two.

Shola, are you still with us?

Shola: I'm still here.

Shola: Yeah. So, um, I wanna give you a couple of. Well, actually three different things to keep in mind.

So the first one is, and these are specific asking strategies. So the first one is, um. How to ask for a mentor, and a lot of people, you know, would love to have a mentor, but if you go to someone and you say, oh, can you please be my mentor? Quite often they'll say no because it obviously, it just sounds like it's a lot of responsibility and effort, and everyone today is so busy.

You know, do your research on them, and then you approach 'em and you say, oh, uh, you know, I love your content, or I love that you did X, Y, and Z the other day, or, I saw you in that meeting. I loved what you said, can I ask you a question? And then you ask them something very specific that you genuinely want their advice on.

And so then when they give you the advice, you say, oh, thank you so much. That's great. And you go and you put it into practice. And so then when you've got some results, you then return to that person and you say, uh oh, thank you so much for your advice last time. This is what I did. This is how it worked.

And then they will likely feel really pleased that you took their advice. And then at that point you can say to them, well, and you know, I've got another question. Do you mind? And so, although. They're not your formal mentor, they're still in this position where they're giving you advice and, and giving you sort of strategies and so on.

So instead of you saying. Is my performance good enough to be promoted? You're saying what would it take? And so you are presuming that you have the skills, the knowhow, the whatever it is to, to be promoted, but you just need a little bit of a, the edge, you know, from your manager giving you these extra tips.

Um, and so you're now enrolling them to be on your team to support you. The third strategy is okay. Yeah. So the third one is, this one is to make your request a bit more juicy, and quite often in the workplace we tend to strip away emotion from. Requests that we are making because we feel that it's inappropriate to, to sort of use emotion to help us.

But quite often if you share a reason or share a feeling attached to your request, that is much more compelling for the person than just a very dry kind of. Ask. Um, so for example, you might be approaching somebody for, I don't know, let's say a pay rise, right? So you might be, pay rise is a tough one.

Try my hands at a, a, a bigger challenge or a different project. So I'm wondering if it's possible for me to join project A, B, C, uh, for three months. And I think if I got to join project A, B, C, that would really advance my skills. It would really let me see. What impact I can have in this company. And I think I'd find it really exciting and very motivating, and it would just help me, uh, you know, add even more to, to what's going on here in the team and in the, in the role.

So there's three little frameworks that you can use for asking.

Sarah: Amazing, amazing. I can definitely see myself implementing all three of them. So with the emotion and making sure that you reflect how you're feeling, should it always be a positive emotion?

Shola: That's a good question. I think there's times where it might not be a positive one.

So, yeah, I don't see why you can't, um, put in, you know, sort of some more negative emotions in the right place.

Sarah: Yeah. I suppose it's all about context and what your question is and why, and also just being a bit mindful about your boundaries as well, because obviously you've gotta be comfortable. Talking about certain things that you feel comfortable with, with your boss.

So if that is all aligned, then yeah, I can see how that works. A question that I feel like I really need to ask is, and we alluded, it, alluded to it earlier about rejection, so Yeah, how, how would you suggest our listeners best prepare for that?

Shola: Yeah, so I think you. Prepare in a number of ways. So I think you can think about, think a few steps ahead.

So it might be that you start to cultivate relationships with other people in case you don't get the response that you wanted. So you do have alternatives. Also, some people, when they get a no, they get terribly tense. They get really. Upset, frustrated. And so for some people, just this idea of relaxing after hearing a no can be really transformative and, and recognizing that there is life after the no, you know, it's not gonna ruin everything.

Space, the way that you view yourself on somebody else's response to your no, uh, to your request, because you know, if anything, you should be patting yourself on the back and say, you know what? I, I had the guts to ask this time I didn't get what I wanted. But, you know, I, I'm, I'm gonna go from strength to strength here because I did the thing I did, I did the difficult thing.

Once you've asked, and you've gotta know, just be prepared to keep the relationship going. Be, you know, don't act as though you are. Super upset or you're never gonna talk to them again or whatever, because that person might be someone that you return to later on. Maybe you ask them again in six months, or you say, well, you've said no.

Sarah: I remember you sharing like an example of that.

When you were doing your talk, 'cause you were like you, um, someone might reach out to you and you can't facilitate it at that time. And then if they go super quiet or if there's no response, when the opportunity then arises, if you've burnt that bridge and you've not even responded, then why should that person spend their time?

Responding to you or like following up with an opportunity. So yeah, it's, I get that there might be a bit of pride that's getting in the way, but I think sometimes you need to put your pride aside and just be like, and, and respond. Just respond and, yeah.

Right. So I could have just. Not ignored their, their question, but I got back to them and then they completely went silent. And I was thinking, well, are they upset or are they angry? And so then when something did come up that I could have given to them, I thought, oh, you know what it sounds, it seems like it's too much hassle to get back in touch with this person, so just keep.

Keep the lines of communication open there. There's no harm in doing that at all. I love that. I love that. Right.

Sarah: I'm very sorry, Shola, but we are rapidly, rapidly running out of time and there are always three questions that we squeeze in and we ask all of our guests, are you ready for them?

Shola: Go for it.

Sarah: What is the main takeaway from this episode?

Why not? Why not? Best career advice. Um, gosh, I think that, look at, I was, I was reading Elizabeth Gilbert's Big Magic the other day. She's the person that wrote, eat, pray, love, which was a massive film success a few years back. And she talks about the creative process and that you can either create with a sort of martyr.

With lightness and with with fun, rather than with too much seriousness.

Sarah: I've never heard of that before. And I love it. I love the trickster. And it's that that shift in mindset, isn't it? And actually embracing it and being like, how wonderful I get to do all these wonderful things, I get to take on a challenge.

Right? And yeah, I love that. I absolutely love that. And then my last question is someone. Awesome to follow right now and why?

Shola: Um, books by this, a guy called Oliver Berkman who writes about he productivity, but in a kind of different way. So he's got a book called, I think it's called 4,000 Weeks. And it's fact if you, if you read that've, uh, it's, it's on my list.

Try to use every spare moment to get things done so that there's a lot there in that book. Lots of like really great nuggets to take away.

Sarah: Amazing. Amazing. Well, I'm very sorry that that is the end of our conversation, but can I just say a huge thank you for coming on the podcast, having this conversation with you, uh, having this conversation with me and sharing your wonderful knowledge, experience, and strategies around the power of the ask.

Shola: Thank you, Sarah. It's been a real pleasure. It's been great to chat to you. I've really enjoyed this half an hour.

Sarah: Thanks so much. It's amazing. It's gone too fast, hasn't it? Too fast. And before we wrap up, just a reminder of how you can support the podcast. So if you like what me and Tazmin are doing, we are set up on Buy Me A Coffee.

Right. That is it. That is time, and the only thing left to say is look after yourselves and until next time.