
Stepsero · 2026-05-11
Key moments - from our scoring
Substance score
42 / 100
Five dimensions, 20 points each
How do modern leaders navigate organizational decisions without complete information? Costas, drawing from nearly 20 years in banking and his current coaching practice, challenges the notion that ambiguity is merely a contemporary problem - it's always existed, but how we respond matters enormously. The episode dissects the gap between the linear decision-making model many were taught (collect data, apply precedent, conclude) and today's reality: leaders must move forward through fog with incomplete datasets, unclear implementation paths, and teams anxious about making wrong moves. Matteo and Costas explore practical tactics: clarifying objectives upfront while remaining open to good questions, checking in frequently rather than disappearing for days, and distinguishing between unclear objectives (poor management) and unclear implementation paths (natural ambiguity). For executives and managers, the conversation addresses a central paradox - admitting uncertainty without appearing indecisive - and argues that sharing the burden of decision-making through psychological safety and ego management actually strengthens rather than weakens leadership credibility. Costas reveals his own process: investing time in stakeholder relationships, building trust across decision-making groups, and resisting the urge to rush, especially when navigating resistance or competing organizational voices.
Leaders should provide a high-level objective while remaining open to clarifying questions and feedback from their teams. Rather than disappearing to work in isolation, they should check in frequently - after a day or two - to confirm direction of travel aligns with the original ask, enabling teams to comment on tangible work rather than abstract guidance.
Clarity refers to the objective itself - what needs to be accomplished and why. Ambiguity resides in the implementation - the specific steps and data interpretation needed to reach that clear objective. A leader can be crystal clear about the goal (e.g., value this company) but the path forward remains ambiguous because data interpretation requires contextual filtering and judgment.
Good clarifying questions come after you've done your own thinking and unpacked what you can independently. Leaders respect questions that challenge the premise or reveal logical gaps (like asking whether a methodology applies to all regions equally), but they lose patience with frequent, vague questions asked before demonstrating personal effort to understand the ask.
Yes - managing your ego and empowering others to contribute actually strengthens credibility. When leaders say 'I know our direction, but how we get there is a team sport,' teams perceive security and confidence rather than incompetence. Sharing the burden of finding answers through coaching, mentorship, or internal facilitation reduces the isolation of leadership while building psychological safety.
He reflects on desired outcomes and invests significant time building trust with stakeholders and decision-makers before committing fully. Rather than pushing hard with 100% intensity (his former banker instinct), he's learned to be patient with the people side of negotiations, recognizing that organizational decisions often involve multiple invisible stakeholders and require time to establish credibility across groups.
Our reviewer’s read on each dimension, with quotes from the episode.
The episode contains a handful of genuinely useful operational points - especially on clarifying objectives early and checking in incrementally rather than disappearing into a dark room - but they are buried under extended conversational filler and leadership platitudes. Insight rate is low relative to runtime.
not to then withdraw. Go into a dark room and work on something for five days and then present it
People are much more able to comment on something than to give specific guidance or clarity in a vacuum at the beginning
The distinction between ambiguity and lack of clarity is the episode's most interesting intellectual move and mildly counterintuitive; everything else recycles well-worn leadership tropes about psychological safety, ego management, and coaching. No genuinely contrarian or first-principles framing.
I don't think ambiguity and lack of clarity are the same
How we get there is a team sport
Costas has real practitioner credibility - roughly 20 years in banking and now executive coaching - but he presents as a mid-tier coach rather than a proven operator at scale; there is no named firm, no disclosed seniority level, and no landmark achievement to anchor his authority.
I don't think I would have survived in banking for almost 20 years
I've done a talk on negotiation at Nottingham, uh, business school
The company-valuation walkthrough (comparable companies, stripping out defaults and profit warnings) is the episode's lone concrete example and does add texture, but there are zero named companies, no dollar figures, no timelines, and no measurable outcomes anywhere in the conversation.
Ignore the companies that have just had a, uh, trading default or a, uh, profit warning. Ignore the companies that have just gone through an acquisition
we think these are the comparable companies to this company. Which means what are the companies that have businesses like this one and how are they valued
The host makes a genuine intellectual contribution by distinguishing ambiguity from lack of clarity and frames a real paradox around leader vulnerability, but he rarely follows through with hard pushback or challenges unsubstantiated claims; most exchanges end with the guest's answer accepted without further probing.
Let me challenge you with this question, then
I think that sometimes we conflate ambiguity with, um, lack of clarity, which to me speaks of, in a way, bad management
Computed from the transcript - who did the talking, and the words that came up most.
Ambiguity at work is not new. Yet, it feels harder than ever, and it's one of the most underrated sources of anxiety for knowledge workers and leaders alike. Costas (executive coach and former banker) has navigated plenty of uncertainty across his career. In this conversation, we explore how to move forward when the information is incomplete, why the best leaders share the burden of uncertainty rather than carrying it alone, and why ambiguity and lack of clarity are not the same thing, even if they feel identical in the moment. One short conversation. A little more clarity on one of the foggiest parts of modern work. Our Guest: Costas Kalisperas Costas is the Founder & CEO of In Tune Executive Coaching. His focus is on helping leaders to be in tune with themselves and their environment, tap into their inner resourcefulness and manage their interactions with others more effectively. To know more about Costas, please visit any of the links below. References: Costas Kalisperas LinkedIn profile Listen to the next Episode All Podcast Episodes
Transcribed and scored by The B2B Podcast Index.
Speaker A: Costas, good to see you again and welcome to the Stepsero podcast.
Speaker B: Thank you, Matteo. It's good to see you too.
Speaker A: We used to be told a version of work that was linear. You collect data, you fall back on precedents, you get to a conclusion. And these days I feel that the reality of work is very different. It's a lot more complex, a lot more chaotic, a lot more ambiguous. We work in, um, an environment where I feel you rarely have the luxury to make decisions while having all the information at your disposal. So you essentially need to move forward through this fog, sometimes they call it. And that's what I'd like to talk to you about. How do we deal with this? Since I feel it's an underrated topic and also, in my opinion, one of the main causes for anxiety these days at work. So I don't want to corner you right away into a question. I'd rather ask you what your thoughts are on ambiguity at work and, uh, whether you've come across it in your banking career or coaching career.
Speaker B: Sure. Uh, I think you're asking the right guy, uh, because in some ways I'm on my sixth career, so the idea that that was in any way linear, as I look back on it all clear, I think is quite an interesting observation. So I think the answer is that you can always join the dots backwards in a career, but you can't foresee the future, you can't really join them forward. So you are right to point out that when you start your career, or even when you're in the middle of your career, you're not only trying to make sure you understand what's expected of you, what the mission or vision of the company you work for is, but also what the deliverable is. Yeah, that you're asked to deliver, but you're also trying to work out, well, what does this kind of do for me? Yeah, how does this progress my thinking? How does this develop my skillset? So I think ambiguity, to be honest, is not just a recent thing. I think there's been ambiguity, uh, you know, always. Certainly I felt it from the age of, you know, 18, 19, when I had to apply to a university. In those days without social media, I'd never even seen the university. I'd never even visited it. I didn't really know what studying law meant. I had no other ideas at the time. So my point is that you have to deal with what you know, uh, and then we can talk about how you sort of reduce ambiguity along the journey. Mhm.
Speaker A: Let me dive into that Right away. Because the way I see ambiguity, for example, in decision making, right, we are taught in a way to be data driven. That's a big thing these days, especially in the, in the tech scene where I come from. So, so you, you want to make data informed decisions, but you also know that the, uh, reality is that the data is rarely complete or you rarely have, again, the luxury of having all that data available. Otherwise, you know, the job would be a lot easier than what it actually is. How do you help yourself or, or the leaders you coach or the people you manage move forward rather than wait for the perfect moment? How do you create that momentum? How do you get somebody to start and get that confidence over time without waiting for the perfect information, the perfect data? So basically navigating this ambiguity, going through this fog.
Speaker B: Yeah, I'm trying to understand the question, but let me tell you how it landed with me. I think as a leader, uh, often you give a sense of direction about what you would like to happen, but you don't always know the specific steps that get you there. And I'm not being unkind to leaders. I'm simply saying that they usually are the guys with the vision or with the strategy or with the focus on the target goal for the business, right? But when they are, uh, rushed or short of time and under pressure, they give a high level view of what's expected. So I think that from a leader's perspective, it's important not only to give the high level view, but to be open to, at least in the initial stages, to good questions, to good questions and to feedback. So in the banking, um, example, I remember if somebody, if a boss gave me some generic directional objectives for a particular client, I think it was important A, to listen very carefully to begin with, B, to kind of clarify early what the objective of the deliverable was. But more importantly, not to then withdraw. Go into a dark room and work on something for five days and then present it, you know, with some ambiguity that you knew you had lived through with the answer. That's not what I wanted, Costas. Yeah, so clarify up front, ask questions about the objective, but also check in along the way. It was always better after a data say, this is what this thing looks like. This is how we progressing towards your objective. Are we on the right path? And people are much more able to comment on something than to give specific guidance or clarity in a vacuum at the beginning. So clarify what's needed. Start doing what you think is clear, but check in quickly to make sure the direction of travel is Consistent with the ask.
Speaker A: I wonder how you make space for that. So what I'm getting at is, and I'm touching maybe a little bit on psychological safety here, if you will, as a leader, how do you prove to your team that they won't be punished for doing something wrong or making the wrong move or the wrong step in an ambiguous situation? How do you make space for them to ask questions, clarify things early, and not make them feel that maybe they didn't understand the assignment in the first place?
Speaker B: That's a really difficult question to answer, Mattel, Uh, because unfortunately, that comes down to leadership. And we've talked a lot about leadership and creating thinking environments. Right. Where people feel comfortable doing that. But the only thing I would say is, however difficult a leader, and as you know, I don't believe people are difficult. I think behavior is difficult. But however, let's, let's say less accepting, some leaders might see over this openness to clarify, to ask questions. If they are good questions, they are good questions. Even the most defensive leaders will respond to them because if they are questions that actually challenge the premise of what they thought they wanted, they will realize because they're intellectually smart enough to do so, that actually, that's a really good clarifying question. Kos, I'm glad you asked me that. In fact, you're right. This doesn't apply to Europe. It only applies to the United States. Thanks for asking that question. If you're saying, well, actually we're having a global presentation here and we're applying the same methodology to three regions, should I be applying the same methodology to all three? Oh, that's actually a really good question. So it's not about. So even if you feel that some leaders will not be receptive to clarification, uh, questions early, if they are too many and too soon is the point. Before you've done your own thinking, before you've unpacked what you can, before you've really asked yourself, what's the key question I really need to know to move forward here? Yeah. If that question is a good one, most leaders will understand it and will respect it because you've done some thinking that led to that question. If it's. What do you mean, how do I do it? When it. Do you see what I'm saying? If it's too soon and too often without thought ahead of time, I think that's when, uh, leaders perhaps, uh, don't have the patience, uh, to, uh, deal with your clarification requests.
Speaker A: Let me challenge you with this question, then. Let Me address a different angle. Maybe the flip side of the situation where you're an executive, you're the leader, you are the manager. You have to somehow admit in a way that you don't have a crystal ball. You don't know the future. At the same time, you don't want to sound indecisive towards your team. You still want to guide them, you still want them to trust you and to feel comfortable that you will be able to make the right decision. How do you deal with, um, this paradox? You being the leader but not having all the answers, you navigating the ambiguity but not necessarily wanting to transmit that, uh, that insecurity. And the reason why I ask you this, Costas, is because I believe you Write in your LinkedIn profile something in the lines of leadership being lonely or, ah, leadership being somehow, um, something about being lonely at the top.
Speaker B: Right.
Speaker A: Which to me also speaks about the unspoken uncertainties that some leaders go through.
Speaker B: Yeah, no, it's a very good observation of my LinkedIn profile. I, uh, think I say leadership can be lonely, but I think I have also said leadership is lonely. But there's a difference there because you're right. I think the benefit of coaching is that leaders sometimes have to make decisions or understand themselves without compromising, as you say, their presentation to their team, that they have all the answers and they have no self doubt. Right. Which no one is like that. And, uh, therefore coaching helps them kind of separate that conversation from the business. So that's, I think, where lonely leadership, I think, lends itself to coaching. But you can stop it. Being lonely is the point. If you are a more enlightened leader, again, merging all our issues together, if you manage your ego, in fact, the burden of leadership is lightened, is lightened when you ask your people to tell you what they think. When you empower them to say, listen, guys, I want us to go in that direction. I'm not sure I know how to do it. Maybe we could do it this way or that way. What do you guys think? First of all, it's an incredibly empowering thing. People don't suddenly think the guy is an idiot. He doesn't know what he's doing. He needs us to tell him. Actually, it's empowering for them. And secondly, in fact, what they'll think is, wow, that guy's pretty secure in himself because he's happy to accept that whilst he knows where he wants to go. How we get there is a team sport. So leadership can be lonely if you carry the burden on your own. And so what I suggest is you carry the burden with others, whether it's an external coach or a mentor, but you also carry the burden internally. Right. By being open, by, uh, facilitating, by encouraging challenge. Not every day, not for every decision. You know, sometimes there is no time. Yeah. But as a concept, sharing the responsibility of finding the right answers, even if you think you know the direction, you
Speaker A: know, there's something that has been sitting with me for a while, and I, I look at job descriptions, job openings, all over LinkedIn or different platforms, and there is this thing about looking for candidates that are not only comfortable with ambiguity, but they thrive in ambiguity. And, uh, my personal take sometimes is that dealing with ambiguities is crucial. Right. Especially these days. Super important. At the same time, I think that sometimes we conflate ambiguity with, um, lack of clarity, which to me speaks of, in a way, bad management. Do you feel there can be a situation where we speak about ambiguity, but the ambiguity can actually be. Or it's a lot more solvable than what it seems that maybe the answer is not to deal with ambiguity, but, uh, deal with the basics first or clarify the basics first?
Speaker B: Yeah, I mean, I don't think ambiguity and lack of clarity are the same. So somebody could be clear about where, what the objective is. We have a client meeting. You know, they want to buy our services. We want to explain to them that A, B and C is what we do differently to our competitors. And I want us to put together some materials that, uh, you know, present that position as professionally and as compellingly as we can. Fantastic. How do you do it? Right? So that is pretty clear as an objective. It's the implementation that is the challenge. It's the specific steps that is the challenge. When I was a banker, for example, let's say I wanted to value a company, and I was going to present to that company, and I spoke to my team, guys, we think these are the comparable companies to this company. Which means what are the companies that have businesses like this one and how are they valued? Let's put together. Yeah. A set of data. Yeah, set of data. You talked about data that shows us how all these other companies are valued, and then we can decide how our company's value. That sounds like a very clear, sensible thing to do if you're valuing a company. Fantastic. The leader's been clear, the mission is perfect. Makes sense. I get the data, and the valuations are all over the place. Some are valued high, some are valued low. So just the data without any understanding of the data doesn't help me get to the objective. So the objective was clear, but the steps to get there were less than clear because the steps should have said, ignore the companies that have just had a, uh, trading default or a, uh, profit warning. Ignore the companies that have just gone through an acquisition. Ignore the ones that don't do what we, you see, I'm saying, so the objective is clear, but when you receive the data you go, well, that doesn't help me at all. So this is why I think these important little check ins is really the answer. When you're receiving this, it's not ambiguous. It's important to understand how to implement the ultimate objective. And when you're receiving the objective, the objective may be clear. Frankly, the analysis in theory is clear, but we haven't adjusted for the specific things that we need to do to make it more relevant, more helpful. So, uh, I don't think there's anything ambiguous in the objective. Uh, but what had to be clarified in the example I just gave you was the specific steps we needed to make to present the objective in a compelling way.
Speaker A: Is it cool that I ask you something? On a personal note as a, uh, closing question for the conversation.
Speaker B: Yeah.
Speaker A: What about you? So you, you know, we've spoken several times now. We had several episodes. Is there a process or a structure that you rely on when deciding between a few options and the outcome is uncertain or you deal with ambiguity yourself? Are you more of a gut, um, feeling person or do you have a way of navigating that ambiguity yourself?
Speaker B: Ah, do I have a way? That's a really difficult question to answer. I think the way is often the how. Sometimes you know what needs to be done or you have a good status for what needs to be done. The biggest challenge, the biggest stress factor is how do you get there? Which is really consistent with the answer I just gave. We talked on the last podcast about some changes to a board, but what if it's to win a piece of business? You know, and I think I know what it is that the organization expects from me, but how do I go about it? Especially if there's resistance from the organization, especially if there's, uh, you know, there's some different voices in the decision making group that have different perspectives. So I think the way I do it, man, is, is I reflect on the desired outcome. We've talked about this a little bit before, but I invest time in the people, in the people who are requesting the ask of me, you know, who are, who are asking me either to provide a service and so on. And I don't rush that process anymore. I think I used to rush it. I think I used to be, because of my banker mentality, if I wanted to win a piece of business, I was all in like 100%, we got to win it. But sometimes you realize that actually navigating the decision making challenges of the counterparty of the other side takes a little bit more time. Especially when, and I've done a talk on negotiation at Nottingham, uh, business school. Especially when you're not just negotiating with one person with the person you're speaking to, you're negotiating with their whole organization with all the decision makers behind them, with their bosses, with their board. Yeah. And sometimes that takes a little bit of time to build enough trust, enough credibility with a number of them for them to converge on saying yes, that's, uh, we're going to go ahead with that. So I'm not sure if that answers your question, but I think I'm a bit more patient about the people side. I think I've always been aware of the people side. Otherwise I don't think I would have survived in banking for almost 20 years. But I think increasingly running my own business and finding and um, hopefully nurturing my clients, I give them time to reflect and for me to build trust with different decision makers without pushing too hard. I think that's what I now try to do.
Speaker A: Look, Costas, we are talking about ambiguity. I don't expect a straightforward answer.
Speaker B: Right.
Speaker A: Otherwise, what would be the point? I appreciate your time as always and I expect to see you maybe next
Speaker B: week and look forward to it. Thanks, Mattel.
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